From b8ca10066ebbbd91ac53b0299c1628da92aa1a80 Mon Sep 17 00:00:00 2001 From: Ben Deadman Date: Mon, 16 Sep 2024 17:18:51 +0100 Subject: [PATCH] updated the minisci dataset --- ...set-c1e2bd4243aa49448b1e61636463c7cf.pb.gz | 3 - ...set-c1e2bd4243aa49448b1e61636463c7cf.pbtxt | 28281 ++++++++++++++++ 2 files changed, 28281 insertions(+), 3 deletions(-) delete mode 100644 data/c1/ord_dataset-c1e2bd4243aa49448b1e61636463c7cf.pb.gz create mode 100644 data/c1/ord_dataset-c1e2bd4243aa49448b1e61636463c7cf.pbtxt diff --git a/data/c1/ord_dataset-c1e2bd4243aa49448b1e61636463c7cf.pb.gz b/data/c1/ord_dataset-c1e2bd4243aa49448b1e61636463c7cf.pb.gz deleted file mode 100644 index cea7e8b8..00000000 --- a/data/c1/ord_dataset-c1e2bd4243aa49448b1e61636463c7cf.pb.gz +++ /dev/null @@ -1,3 +0,0 @@ -version https://git-lfs.github.com/spec/v1 -oid sha256:72f8546ce94de1d1caaed16187d71ef891439ebfdcea9e45588f6e15fac32d94 -size 22687 diff --git a/data/c1/ord_dataset-c1e2bd4243aa49448b1e61636463c7cf.pbtxt b/data/c1/ord_dataset-c1e2bd4243aa49448b1e61636463c7cf.pbtxt new file mode 100644 index 00000000..0269fbfd --- /dev/null +++ b/data/c1/ord_dataset-c1e2bd4243aa49448b1e61636463c7cf.pbtxt @@ -0,0 +1,28281 @@ +name: "Minisci dataset from Roche" +description: "Minisci reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)" +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_1" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)OOS(=O)(=O)O.N" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7727-54-0" + } + amount { + moles { + value: 0.45 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 2.99995 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.005001 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=CC(=C2C=CC=CC12)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "491-35-0" + } + amount { + moles { + value: 0.15 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(O)C1CCCCC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "98-89-5" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 40.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: ARGON + } + } + } + outcomes { + reaction_time { + value: 16.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2C(=CC1C3CCCCC3)C" + } + identifiers { + type: CAS_NUMBER + value: "56947-80-9" + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 82.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1HNMR(CDCl3,300MHz) \316\264 8.04(1H,ddd,J=8.4,1.3,0.6Hz,Ar\342\200\220H),7.94(1H,dm,J=8.2Hz,Ar\342\200\220H),7.66(1H,ddd,J=8.4,6.9,1.5Hz,Ar\342\200\220H),7.49(1H,ddd,J=8.2,6.9,1.3Hz,Ar\342\200\220H),7.17(1H,q,J=0.9Hz,Ar\342\200\220H),2.87(1H,tt,J=11.9,3.4Hz,alkylCH),2.68(3H,d,J=0.9Hz,CH3),2.07\342\200\2231.74(5H,m,alkylCHs),1.66\342\200\2231.23(5H,m,alkylCHs);13CNMR(75MHz,CDCl3) \316\264 166.7,147.7,144.4,129.6,129.1,127.2,125.5,123.7,120.4,47.7,33.0,26.7,26.3,19.0" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/acs.orglett.8b02988" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_2" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)OOS(=O)(=O)O.N" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7727-54-0" + } + amount { + moles { + value: 0.45 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 2.99995 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.005001 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2C=CC1C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "91-63-4" + } + amount { + moles { + value: 0.15 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(O)C1CCCCC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "98-89-5" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 40.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: ARGON + } + } + } + outcomes { + reaction_time { + value: 16.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2C(=CC1C)C3CCCCC3" + } + identifiers { + type: CAS_NUMBER + value: "37597-46-9" + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 80.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1HNMR (CDCl3, 300 MHz) \316\264 8.10 \342\200\223 7.94 (2H, m, Ar\342\200\220H), 7.65 (1H, ddd, J=8.4, 6.8, 1.4 Hz, Ar\342\200\220H), 7.48 (1H,ddd, J=8.3, 6.8, 1.3 Hz, Ar\342\200\220H), 7.17 (1H, s, Ar\342\200\220H), 3.39 \342\200\223 3.20 (1H, m, alkyl CH), 2.72 (3H, s, CH3), 2.08 \342\200\223 1.80 (5H, m, alkyl CHs), 1.66 \342\200\223 1.44 (4H, m, alkyl CHs), 1.41 \342\200\223 1.28 (1H, m, alkyl CH); 13C NMR (75 MHz, CDCl3) \316\264 159.0, 153.4, 148.3, 129.7, 128.9, 125.4, 125.3, 123.0, 118.5, 38.9, 33.7, 27.1, 26.5,25.7" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/acs.orglett.8b02988" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_3" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)OOS(=O)(=O)O.N" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7727-54-0" + } + amount { + moles { + value: 10.5 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 69.99883 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.11669 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2C=CC1C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "91-63-4" + } + amount { + moles { + value: 3.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(O)C1CCCCC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "98-89-5" + } + amount { + moles { + value: 35.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 40.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: ARGON + } + } + } + outcomes { + reaction_time { + value: 16.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2C(=CC1C)C3CCCCC3" + } + identifiers { + type: CAS_NUMBER + value: "37597-46-9" + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 78.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1HNMR (CDCl3, 300 MHz) \316\264 8.10 \342\200\223 7.94 (2H, m, Ar\342\200\220H), 7.65 (1H, ddd, J=8.4, 6.8, 1.4 Hz, Ar\342\200\220H), 7.48 (1H,ddd, J=8.3, 6.8, 1.3 Hz, Ar\342\200\220H), 7.17 (1H, s, Ar\342\200\220H), 3.39 \342\200\223 3.20 (1H, m, alkyl CH), 2.72 (3H, s, CH3), 2.08 \342\200\223 1.80 (5H, m, alkyl CHs), 1.66 \342\200\223 1.44 (4H, m, alkyl CHs), 1.41 \342\200\223 1.28 (1H, m, alkyl CH); 13C NMR (75 MHz, CDCl3) \316\264 159.0, 153.4, 148.3, 129.7, 128.9, 125.4, 125.3, 123.0, 118.5, 38.9, 33.7, 27.1, 26.5,25.7" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/acs.orglett.8b02988" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_4" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)OOS(=O)(=O)O.N" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7727-54-0" + } + amount { + moles { + value: 0.45 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 2.99995 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.005001 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "FC=1C=CC=2N=C(C=CC2C1)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "1128-61-6" + } + amount { + moles { + value: 0.15 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(O)C1CCCCC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "98-89-5" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 40.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: ARGON + } + } + } + outcomes { + reaction_time { + value: 16.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "FC=1C=CC=2N=C(C=C(C2C1)C3CCCCC3)C" + } + identifiers { + type: CAS_NUMBER + value: "2248050-76-0" + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 62.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/acs.orglett.8b02988" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_5" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)OOS(=O)(=O)O.N" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7727-54-0" + } + amount { + moles { + value: 0.45 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 2.99995 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.005001 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=2C=CC(OC)=CC2C=CC1C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "1078-28-0" + } + amount { + moles { + value: 0.15 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(O)C1CCCCC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "98-89-5" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 40.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: ARGON + } + } + } + outcomes { + reaction_time { + value: 16.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "CC1=NC2=CC=C(OC)C=C2C(C3CCCCC3)=C1" + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 68.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/acs.orglett.8b02988" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_6" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)OOS(=O)(=O)O.N" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7727-54-0" + } + amount { + moles { + value: 0.45 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 2.99995 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.005001 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N1=CC2=CC=CC=C2C=C1C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "1125-80-0" + } + amount { + moles { + value: 0.15 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(O)C1CCCCC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "98-89-5" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 40.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: ARGON + } + } + } + outcomes { + reaction_time { + value: 16.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C(=CC=2C=CC=CC2C1C3CCCCC3)C" + } + identifiers { + type: CAS_NUMBER + value: "2130838-00-3" + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 91.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/acs.orglett.8b02988" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. 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Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_109" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N1=CC2=CC=CC=C2C=C1C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "1125-80-0" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(I)C1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "254454-54-1" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 40.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added over 1 min to a stirred solution of 3-methylisoquinoline 1c (143 mg, 1.0 mmol), concentrated H2SO4 (107 \316\274L, 2.0 mmol), 1-Boc-3-(iodo)azetidine (566 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at 40 \302\260C. After 3 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at 40 \302\260C for 25 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred at 40 \302\260C for another 25 min, then poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous was extracted with Et2O (2 x 25 mL) and EtOAc (1 x 25 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil (617 mg). The oil was purified by column chromatography on silica gel using EtOAc / hexanes (0:1 to 1:4) as eluent to give the product contaminated with DMSO. The product was dissolved in Et2O (10 mL) and washed with brine (3 x 8 mL), dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude oil (165 mg). The oil was purified further using column chromatography on silica gel using EtOAc / hexanes (0:1 to 1:4) as eluent to give the desired product 3c (61 mg, 20%) as an oil" + } + outcomes { + reaction_time { + value: 0.8 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(C2=NC(=CC=3C=CC=CC32)C)C1" + } + identifiers { + type: CAS_NUMBER + value: "1180653-85-3" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 20.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "243.6" + data { + key: "found" + value { + float_value: 243.6 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 7.78-7.73 (m, 2H), 7.62 (t, J = 7.5 Hz, 1H), 7.50 (d, J = 7.6 Hz, 1H), 7.38 (s, 1H), 4.56-4.50 (m, 3H), 4.41-4.39 (m, 2H), 2.69 (s, 3H), 1.46 (s, 9H); 13C NMR (100 MHz; CDCl3) \316\264 158.6, 156.7, 150.6, 137.2, 130.0, 127.2, 126.4, 124.6, 124.2, 117.8, 79.5, 53.4, 32.6, 28.6, 24.4;" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_110" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N1=CN(C=2C=CC=CC12)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "1632-83-3" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(I)C1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "254454-54-1" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added to a stirred solution of 1-methylbenzimidazole 1g (100 mg, 1.0 mmol), concentrated H2SO4 (108 \316\274L, 1.0 mmol), 1-Boc-3-(iodo)azetidine (566 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (5 mL) at room temperature. The mixture was stirred at room temperature for 120 min, then diluted with EtOAc and saturated NaHCO3. The aqueous and organic layers were partitioned and the organic layer was washed with brine, dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using EtOAc / hexanes (3:7 to 7:3) as eluent to give the desired product 3f(52 mg, 17%) as a solid. " + } + outcomes { + reaction_time { + value: 2.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(C2=NC=3C=CC=CC3N2C)C1" + } + identifiers { + type: CAS_NUMBER + value: "1180653-92-2" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 17.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "288.17" + data { + key: "found" + value { + float_value: 288.17 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 7.71-7.67 (m, 1H), 7.24-7.16 (m, 3H), 4.31-4.26 (m, 4H), 3.96-3.89 (m, 1H), 3.58 (s, 3H), 1.37 (s, 9H); 13C NMR (100 MHz; CDCl3) 156.3, 153.9, 142.4, 136.2, 122.8, 122.3, 119.7, 109.1, 79.9, 53.3, 29.8, 28.5, 26.3" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_111" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.3 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 4.7 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.3 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1N=C(OC)C=CC1OC" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "4603-59-2" + } + amount { + moles { + value: 0.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(I)C1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "254454-54-1" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.15 mL, 1.5 mmol) was added over 1 min to a stirred solution of 3,6-dimethoxypyridazine 1e (67 mg, 0.5 mmol), concentrated H2SO4 (51 \316\274L, 1.0 mmol), 1-Boc-3-(iodo)azetidine (271 mg, 1.0 mmol) and iron(II) - 14 -sulfate heptahydrate (40 mg, 0.15 mmol) in DMSO (5 mL) at room temperature. The mixture was then placed in an oil bath at 60 \302\260C. After 2 min a further portion of iron(II) sulfate heptahydrate (40 mg, 0.15 mmol) was added and the mixture was stirred at 60 \302\260C for 30 min. Further H2O2 (0.15 mL, 1.5 mmol) and iron(II) sulfate heptahydrate (40 mg, 0.15 mmol) was added, and the mixture was stirred at 60 \302\260C for another 30 min. A final aliquot of H2O2 (0.15 mL, 1.5 mmol) and iron(II) sulfate heptahydrate (40 mg, 0.15 mmol) was added and the mixture was stirred at 60 \302\260C for another 30 min. After allowing to cool, the mixture was poured into a 0.2 M solution of NaOH (15 mL) and Et2O (25 mL). The aqueous and organic layers were partitioned and the aqueous was extracted with Et2O (2 x 15 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil (408 mg). The oil was purified by column chromatography on silica gel using EtOAc / hexanes (0:1 to 1:1) as eluent to give the desired product 3d (57 mg, 41%) as an oil" + } + outcomes { + reaction_time { + value: 1.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(C2=CC(=NN=C2OC)OC)C1" + } + identifiers { + type: CAS_NUMBER + value: "1180653-87-5" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 41.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "296.16" + data { + key: "found" + value { + float_value: 296.16 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 6.85 (d, J = 0.9 Hz, 1H), 4.27 (t, J = 8.7 Hz, 2H), 4.06 (s, 6H), 3.96 (t, J = 7.5 Hz, 2H), 3.83-3.76 (m, 1H), 1.45 (s, 9H); 13C NMR (100 MHz; CDCl3) \316\264 162.5, 160.5, 156.4, 135.1, 117.5, 80.0, 54.9, 53.4, 28.5, 28.2" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_112" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=CC(=C2C=CC=CC12)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "491-35-0" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(I)C1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "254454-54-1" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added to a stirred solution of lepidine 1a (132 \316\274L, 1.0 mmol), concentrated H2SO4 (53 \316\274L, 1.0 mmol), 1-Boc-3-(iodo)azetidine (849 mg, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at room temperature. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at room temperature for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred for 60 min, then poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 - 12 -mL). The aqueous and organic layers were partitioned and the organic layer was washed with H2O (1 x 30 mL) and brine (1 x 30 mL), then dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using EtOAc / hexanes (3:7) as eluent to give the desired product 3a (90 mg, 30%) as a solid and a 9:1 mixture of lepidine 1aand desired product 3a (58 mg)." + } + outcomes { + reaction_time { + value: 1.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(C2=NC=3C=CC=CC3C(=C2)C)C1" + } + identifiers { + type: CAS_NUMBER + value: "1180653-80-8" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 30.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "299.5" + data { + key: "found" + value { + float_value: 299.5 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; d6-DMSO) \316\264 8.08 (m, 1H), 8.00 (m, 1H), 7.78-7.73 (m, 1H), 7.62-7.58 (m, 1H), 7.36 (d, J = 0.5 Hz, 1H), 4.30-4.22 (m, 2H), 4.21-4.11 (m, 2H), 4.10-4.03 (m, 1H), 2.67 (d, J = 0.5 Hz, 3H), 1.42 (s, 9H); 13C NMR (100 MHz; d6-DMSO) \316\264 160.7, 155.7, 147.0, 144.9, 129.4, 129.1, 126.7, 126.0, 124.1, 120.9, 78.6, 54.5-53.7, 34.6, 28.1, 18.2" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_113" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "OC(C=1C=CN=C2C=CC(OC)=CC21)C3N4CCC(C3)C(C4)CC" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "522-66-7" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(I)C1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "254454-54-1" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 1-2 min to a stirred solution of 6-methoxy-4-methylquinoline 4a (173 mg, 1.0 mmol), concentrated H2SO4 (107 \316\274L, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at room temperature. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at room temperature for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred for 15 min, then poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 25 mL). The combined organic extracts were dried (MgSO4), filtered and the - 16 -solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using 30% EtOAc / hexanes as eluent to give recovered 6-methoxy-4-methylquinoline 4a (32 mg, 19%), a mixture of 6-methoxy-4-methylquinoline 4a and the desired product 5a (15 mg) and the desired product 5a (72 mg, 31%) as a solid. An analytical portion of the product 5a was recrystallized from hexanes for data purposes" + } + outcomes { + reaction_time { + value: 0.75 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(C2=NC=3C=CC(OC)=CC3C(=C2)C(O)C4N5CCC(C4)C(C5)CC)C1" + } + identifiers { + type: CAS_NUMBER + value: "1180653-98-8" + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 17.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 7.96 (d, J = 9.2 Hz, 1H), 7.38-7.35 (m, 2H), 7.19 (d, J = 2.6 Hz, 1H), 5.15 (dd, J = 8.3, 5.9 Hz, 2H), 5.03 (t, J = 6.2 Hz, 2H), 4.52-4.44 (m, 1H), 3.96 (s, 3H), 2.68 (s, 3H); 13C NMR (100 MHz; CDCl3) 158.1, 157.6, 143.9, 143.6, 131.2, 128.1, 121.6, 120.3, 102.1, 77.1, 55.7, 42.5, 19.2." + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_114" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 1.8 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 18.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 28.2 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 1.8 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2C=CC1C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "91-63-4" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(I)C1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "254454-54-1" + } + amount { + moles { + value: 9.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 40.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.86 mL, 9.0 mmol) was added to a stirred solution of quinaldine 1b (400 mg, 3.0 mmol), concentrated H2SO4 (298 \316\274L, 6.0 mmol), 1-Boc-3-(iodo)azetidine (1.58 g, 3.0 mmol) and iron(II) sulfate heptahydrate (200 mg, 0.8 mmol) in DMSO (30 mL) at room temperature. After 30 min a further portion of iron(II) sulfate heptahydrate (200 mg, 0.8 mmol) and H2O2 (30% in H2O; 0.86 mL, 9.0 mmol) was added and the mixture was stirred at room temperature for 30 min. Further H2O2 (0.86 mL, 9.0 mmol) and iron(II) sulfate heptahydrate (200 mg, 0.8 mmol) was added, and the mixture was stirred for 120 min, then poured into an ice-cold solution of NaOH and adjusted to pH >10. The aqueous was extracted with Et2O. The aqueous layer was then saturated with solid NaCl, and extracted with CHCl3 until all the product was removed from the aqueous layer. The combined organic extracts were dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using EtOAc / hexanes (1:1 to 1:0) as eluent to give the desired product 3b (450 mg, 50%) as an oil that crystallized on standing." + } + outcomes { + reaction_time { + value: 1.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(C2=CC(=NC=3C=CC=CC32)C)C1" + } + identifiers { + type: CAS_NUMBER + value: "1180653-83-1" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 50.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "299.0" + data { + key: "found" + value { + float_value: 299.0 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 8.07 (d, J = 8.3 Hz, 1H), 7.70-7.67 (q, J = 7.4 Hz, 2H), 7.51 (t, J = 7.5 Hz, 1H), 7.28 (s, 1H), 4.49 (t, J = 8.2 Hz, 2H), 4.44-4.38 (m, 1H), 4.17 (br. s, 2H), 2.77 (s, 3H), 1.46 (s, 9H); 13C NMR (100 MHz; CDCl3) \316\264 - 13 -159.0, 156.4, 148.1, 146.8, 129.8, 129.5, 126.1, 125.0, 122.8, 118.9, 80.0, 54.1, 30.1, 28.5, 25.6" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_115" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N1=CSC=2C=CC=CC12" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "95-16-9" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(I)C1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "254454-54-1" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added to a stirred solution of benzothiazole 1f (108 \316\274L, 1.0 mmol), concentrated H2SO4 (53 \316\274L, 1.0 mmol), 1-Boc-3-(iodo)azetidine (849 mg, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at room temperature. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at room temperature for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred for overnight, then poured into a 0.2 M solution of NaOH (30 mL) and EtOAc (50 mL). The aqueous and organic layers were partitioned and the organic layer was dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using EtOAc / hexanes (1:4) as eluent to give a mixture of recovered benzothiazole 1f and 1-BOC-3-(iodo)azetidine, and the desired product 3e (45 mg, 15%)" + } + outcomes { + reaction_time { + value: 18.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(C2=NC=3C=CC=CC3S2)C1" + } + identifiers { + type: CAS_NUMBER + value: "1180653-89-7" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 15.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "291.11" + data { + key: "found" + value { + float_value: 291.11 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 - 15 -MHz; CDCl3) \316\264 8.02 (d, J = 8.2 Hz, 1H), 7.89 (dd, J = 9.0, 0.4 Hz, 1H), 7.49 (dt, J = 7.7, 1.1 Hz, 1H), 7.40 (dt, J = 7.7, 1.1 Hz, 1H), 4.42 (t, J = 8.6 Hz, 2H), 4.30 (dd, J = 8.5, 6.0 Hz, 2H), 4.23-4.16 (m, 1H), 1.47 (s, 9H); 13C NMR (100 MHz; CDCl3) 171.4, 156.3, 153.2, 135.1, 126.4, 125.4, 123.1, 121.8, 80.1, 55.4, 32.7, 28.5" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_116" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 0.7 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.21 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 2.1 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 3.29 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.21 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=NC=2C=C(OC)C(OC)=CC2C1OC=3C=CC=CC3" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "1180653-47-7" + } + amount { + moles { + value: 0.35 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 0.7 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 110 \316\274L, 1.1 mmol) was added dropwise over 1-2 min to a stirred solution of 6,7-dimethoxy-4-phenoxyquinazoline 1k (100 mg, 0.35 mmol), concentrated H2SO4 (38 \316\274L, 0.71 mmol), 3-iodooxetane (130 mg, 0.71 mmol) and iron(II) sulfate heptahydrate (30 mg, 0.11 mmol) in DMSO (3.5 mL) at 60 \302\260C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (30 mg, 0.11 mmol) was added and the mixture was stirred at 60 \302\260C for 30 min. Further H2O2 (110 \316\274L, 1.1 mmol) and iron(II) sulfate heptahydrate (30 mg, 0.11 mmol) was added, and the mixture was stirred at 60 \302\260C for 20 min. After allowing to cool, the mixture was poured into a 0.2 M solution of NaOH (50 mL) and Et2O (30 mL). The aqueous and organic layers were partitioned and the organic layer was dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by column chromatography on silica gel using EtOAc as eluent to give the desired product 2k (11 mg, 9%) as a solid. Also isolated from the column was a mixture of starting 6,7-dimethoxy-4-phenoxyquinazoline 1k and desired product 2k (17 mg). The mixture of 1k and 2k (17 mg) was purified further by preparative high-performance liquid chromatography (column: Gemini C18; size: 150 x 21.2 mm; eluent: 20-90% CH3CN in 10 mM aqueous Et2NH; run time: 20 min; detection: UV at 254 nM) to give recovered 6,7-dimethoxy-4-phenoxyquinazoline 1k (7 mg, 7%) and the desired product 2k (6 mg, 5%). The aqueous layer from the workup above was saturated with solid NaCl and extracted with EtOAc (3 x 30 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude solid (ca. 110 mg). The solid was purified by high-performance liquid chromatography to give 6,7-dimethoxy-2-(oxetan-3-yl)quinazolin-4(3H)-one 2j (13 mg, 14%). Also recovered from the high-performance liquid chromatography column was 6,7-dimethoxy-quinazolin-4(3H)-one. Total yield of desired product 2k = 17 mg (14%); Total yield of 6,7-dimethoxy-2-(oxetan-3-yl)quinazolin-4(3H)-one 2j = 13 mg (14%)." + } + outcomes { + reaction_time { + value: 0.8 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C1N=C(NC2=CC(OC)=C(OC)C=C12)C3COC3" + } + identifiers { + type: CAS_NUMBER + value: "1180653-74-0" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 14.0 + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "N=1C(=NC=2C=C(OC)C(OC)=CC2C1OC=3C=CC=CC3)C4COC4" + } + identifiers { + type: CAS_NUMBER + value: "1180653-75-1" + } + measurements { + analysis_key: "product_2_isolated" + type: YIELD + percentage { + value: 14.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "339.13" + data { + key: "found" + value { + float_value: 339.13 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 7.55 (s, 1H), 7.49-7.44 (m, 2H), 7.31-7.26 (m, 4H), 4.98-4.92 (m, 4H), 4.40 - 11 -(quint., J = 7.7 Hz, 1H), 4.07 (s, 3H), 4.06 (s, 3H); 13C NMR (100 MHz; CDCl3) \316\264 165.7, 163.3, 156.1, 152.8, 150.1, 129.6, 125.7, 122.0, 109.2, 106.7, 101.3, 76.0, 56.6, 56.5, 42.6" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + analyses { + key: "product_2_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_117" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.3 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 4.7 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.3 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "FC1=CC=C(C=C1Cl)NC=2N=CN=C3C=C(OC)C(OCCCN4CCOCC4)=CC32" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "184475-35-2" + } + amount { + moles { + value: 0.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 153 \316\274L, 1.5 mmol) was added to a stirred solution of gefitinib 4d (223 mg, 0.5 mmol), concentrated H2SO4 (80 \316\274L, 1.5 mmol), 3-iodooxetane (183 mg, 1.0 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) in DMSO (5 mL) at 60 \302\260C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (50 mg, 0.18 mmol) was added, followed by dropwise addition of further H2O2 (30% in H2O; 153 \316\274L, 1.5 mmol) over 5 min. The mixture was stirred at 60 \302\260C for 30 min. After allowing to cool, the mixture was poured into a 0.2 M solution of NaOH which had been saturated with solid NaCl (30 mL) and EtOAc (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with EtOAc (1 x 30 mL). The combined organic layers were dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude residue (ca. 300 mg). The residue was purified by high-performance liquid chromatography (column: Gemini C18; size: 250 x 21.2 mm; eluent: 70-90% MeOH in 10 mM aqueous Et2NH or 75% MeOH in 10 mM aqueous Et2NH; run time: 25 min; detection: UV at 254 nM) to give the desired product 5f (35 mg, 93% pure, 13% yield adjusted for purity). An analytical portion of the product 5f was triturated with hot EtOAc / hexanes to - 21 -give material for data purposes" + } + outcomes { + reaction_time { + value: 0.5 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "FC1=CC=C(C=C1Cl)NC=2N=C(N=C3C=C(OC)C(OCCCN4CCOCC4)=CC32)C5COC5" + } + identifiers { + type: CAS_NUMBER + value: "1180654-05-0" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 13.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "503.18" + data { + key: "found" + value { + float_value: 503.18 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 8.01 (dd, J = 6.5, 2.7 Hz, 1H), 7.70-7.66 (m, 1H), 7.32 (br. s, 1H), 7.23 (s, 1H), 7.19 (t, J = 8.7 Hz, 1H), 7.09 (s, 1H), 5.13 (t, J = 6.3 Hz, 2H), 5.08 (dd, J = 8.5, 5.8 Hz, 2H), 4.49-4.41 (m, 1H), 4.21 (t, J = 6.6 Hz, 2H), 4.00 (s, 3H), 3.75 (t, J = 4.6 Hz, 4H), 2.60 (t, J = 7.0 Hz, 2H), 2.51 (br. s, 4H), 2.17-2.20 (m, 2H); 13C NMR (100 MHz; CDCl3) 162.9, 156.4, 155.5, 152.4 (d, J = 244 Hz), 147.0, 146.2, 135.7 (d, J = 5 Hz), 123.5, 121.1, 121.0 (d, J = 7 Hz), 116.8 (d, J = 22 Hz), 108.0, 107.2, 100.7, 76.1, 67.8, 67.0, 56.4, 55.5, 52.9, 43.0, 26.2" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_118" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N1=CC2=CC=CC=C2C=C1C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "1125-80-0" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 40.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 3 min to a stirred solution of 3-methylisoquinoline 1c (143 mg, 1.0 mmol), concentrated H2SO4(107 \316\274L, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at 40 \302\260C. After 3 min a further portion of iron(II) sulfate heptahydrate (80 mg, - 5 -(80 mg, 0.3 mmol) was added and the mixture was stirred at 40 \302\260C for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added over 2 min, and the mixture was stirred at 40 \302\260C for 20 min, then poured into 0.2 M solution of NaOH (20 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 25 mL). The combined organic extracts were washed with brine (25 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil (364 mg). The oil was dry-loaded on to silica (750 mg) and purified by column chromatography on silica gel using EtOAc / hexanes (0:1 to 3:7) to give the desired product 2c (99 mg, ca. 93% purity, 46% yield adjusted for purity) as a solid. The solid was purified further by column chromatography on silica gel using EtOAc / hexanes (0:1 to 1:4 slow gradient then to 3:7) as eluent (to give 67 mg, 96% purity), then by recrystallization from methylcyclohexane to give material for data purposes. " + } + outcomes { + reaction_time { + value: 0.8 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C(=CC=2C=CC=CC2C1C3COC3)C" + } + identifiers { + type: CAS_NUMBER + value: "1180653-58-0" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 46.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "200.6" + data { + key: "found" + value { + float_value: 200.6 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 7.76 (d, J = 8.2 Hz, 1H), 7.67-7.60 (m, 2H), 7.48 (t, J = 7.5 Hz, 1H), 7.39 (s, 1H), 5.29-5.26 (m, 2H), 5.21-5.17 (m, 2H), 5.08-5.00 (m, 1H), 2.70 (s, 3H); 13C NMR (100 MHz; CDCl3) \316\264 158.7, 150.7, 137.2, 130.0, 127.2, 126.4, 124.4, 124.2, 117.7, 75.8, 39.0, 24.4" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_119" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "ClC1=NC=NC=2C=C(OC)C(OC)=CC12" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "13790-39-1" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 153 \316\274L, 1.5 mmol) was added dropwise over 1-2 min to a stirred solution of 4-chloro-6,7-dimethoxyquinazoline 1j (112 mg, 0.5 mmol), concentrated H2SO4 (54 \316\274L, 1.0 mmol), 3-iodooxetane (183 mg, 1.0 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) in DMSO (5 mL) at 60 \302\260C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) was added and the mixture was stirred at 60 \302\260C for 30 min. Further H2O2 (153 \316\274L, 1.5 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) was added, and the mixture was stirred at 60 \302\260C for 30 min. After allowing to cool, the mixture was poured into a 0.2 M solution of NaOH saturated with solid NaCl (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 25 mL). The combined organic extracts were washed with brine (1 x 30 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using MeOH / EtOAc (1:9) as eluent to give the desired product 2j (47 mg, 36%). " + } + outcomes { + reaction_time { + value: 1.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C1N=C(NC2=CC(OC)=C(OC)C=C12)C3COC3" + } + identifiers { + type: CAS_NUMBER + value: "1180653-74-0" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 36.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "263.1" + data { + key: "found" + value { + float_value: 263.1 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; d6-DMSO) \316\264 12.01 (br. s, 1H), 7.42 (s, 1H), 7.17 (s, 1H), 4.87 (t, J = 6.2 Hz, 2H), 4.81 (dd, J = 8.4, 5.8 Hz, 2H), 4.26-4.18 (m, 1H), 3.92 (s, 3H), 3.87 (s, 3H); 13C NMR (100 MHz; d6-DMSO) \316\264 161.1, 154.6, - 10 -154.6, 148.3, 144.7, 113.9, 108.0, 104.9, 73.1, 56.0, 55.7, 37.7" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_120" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "O=C(OCC)C=1C=CN=CC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "1570-45-2" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 40.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 2 min to a stirred solution of ethyl isonicotinate 1d (151 mg, 1.0 mmol), concentrated H2SO4 (107 \316\274L, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at 40 \302\260C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at 40 \302\260C for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred at 40 \302\260C for 60 min, then diluted with EtOAc (50 mL). The mixture was poured in to saturated NaHCO3 (5 mL) and brine (100 mL). The aqueous and organic layers were partitioned and the organic layer was washed with brine (3 x 20 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by column chromatography on silica gel using EtOAc / hexanes (1:19 to 2:3) to give the desired product 2d (49 mg, 24%) as an oil." + } + outcomes { + reaction_time { + value: 1.5 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C(OCC)C=1C=CN=C(C1)C2COC2" + } + identifiers { + type: CAS_NUMBER + value: "1180653-60-4" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 24.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "208.09" + data { + key: "found" + value { + float_value: 208.09 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 8.80 (d, J = 5.0 Hz, - 6 -1H), 7.82 (s, 1H), 7.76 (dd, J = 5.0, 1.5 Hz, 1H), 5.09 (dd, J = 8.4, 5.9 Hz, 2H), 4.98 (app. t, J = 6.2 Hz, 2H), 4.47 (tt, J = 8.4, 6.7 Hz, 1H), 4.43 (q, J = 7.1 Hz, 2H), 1.43 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz; CDCl3) \316\264 165.1, 161.6, 150.6, 138.4, 121.2, 120.9, 76.8, 61.9, 41.8, 14.2;" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_121" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N1=CN(C=2C=CC=CC12)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "1632-83-3" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 1-2 min to a stirred solution of 1-methylbenzimidazole 1g (100 mg, 1.0 mmol), concentrated H2SO4 (107 \316\274L, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at room temperature. After 30 min a further portion of iron(II) sulfate heptahydrate (200 mg, 0.75 mmol) and H2O2 (0.31 mL, 3.0 mmol) was added, and the mixture was stirred at room temperature for 30 min. Further iron(II) sulfate heptahydrate (200 mg, 0.75 mmol) and H2O2 (0.31 mL, 3.0 mmol) was added and the mixture stirred at room temperature for 120 min, then heated to 60 \302\260C and stirred for 60 min. After allowing to cool, the mixture was poured into a solution of NaOH and ice (to pH > 10) and it was then extracted with Et2O. The aqueous layer was saturated with solid NaCl and extracted with CHCl3. The combined organic extracts were dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using EtOAc / MeOH (1:0 to 4:1) to give impure product (40 mg). The impure product was purified further by preparative thin-layer chromatography using EtOAc / MeOH (19:1) as eluent to give product (25 mg). The product was purified further using preparative high-performance liquid chromatography using 0.1% aqueous formic acid / MeCN (19:1 to 9:1) as eluent to give the desired product 2g (12 mg, 6%) as a solid." + } + outcomes { + reaction_time { + value: 3.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2N(C1C3COC3)C" + } + identifiers { + type: CAS_NUMBER + value: "1180653-66-0" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 6.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "189.1" + data { + key: "found" + value { + float_value: 189.1 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 7.80-7.78 (m, 1H), 7.31-7.29 (m, 3H), 5.21 (t, J = 5.8 Hz, 2H), 5.08 (dd, J = 8.4, 5.5 Hz, 2H), 4.63-4.55 (m, 1H), 3.65 (s, 3H); 13C NMR (100 MHz; CDCl3) \316\264 153.5, 142.4, 136.0, 122.9, 122.5, 119.7, 109.2, 75.0, - 8 -75.0, 32.9, 29.7;" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_122" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.45 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 4.5 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 7.05 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.45 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1N=C(OC)C=2C=CC=CC2C1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "24953-56-8" + } + amount { + moles { + value: 0.75 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.23 mL, 2.25 mmol) was added dropwise over 5 min to a stirred solution of 1-methoxyphthalazine 1l (120 mg, 0.75 mmol), concentrated H2SO4 (80 \316\274L, 1.5 mmol), 3-iodooxetane (276 mg, 1.5 mmol) and iron(II) sulfate heptahydrate (63 mg, 0.225 mmol) in DMSO (7.5 mL) at 60 \302\260C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (50 mg, 0.19 mmol) was added and the mixture was stirred at 60 \302\260C for 60 min. Ater allowing to cool, the mixture was poured into a 0.2 M solution of NaOH which has been saturated with solid NaCl (40 mL) and EtOAc (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with EtOAc (1 x 30 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using EtOAc / hexanes (0:1 to 3:2) to give the desired product 2l (54 mg, 34%) as a solid. An analytical sample was triturated with Et2O / EtOAc for data purposes." + } + outcomes { + reaction_time { + value: 1.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C1NN=C(C=2C=CC=CC12)C3COC3" + } + identifiers { + type: CAS_NUMBER + value: "1180653-77-3" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 34.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "203.08" + data { + key: "found" + value { + float_value: 203.08 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 10.66 (br. s, 1H), 8.52-8.50 (m, 1H), 7.86-7.80 (m, 2H), 7.44 (d, J = 8.3 Hz, 1H), 5.11 (app. s, 2H), 5.09 (app. s, 2H), 4.73-4.65 (m, 1H); 13C NMR (100 MHz; CDCl3) \316\264 160.5, 145.5, 133.9, 131.9, 129.1, 128.3, 127.6, 123.8, 74.5, 36.8" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_123" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.45 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 4.5 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 7.05 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.45 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1N=C(OC)C=CC1OC" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "4603-59-2" + } + amount { + moles { + value: 0.75 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.23 mL, 2.25 mmol) was added dropwise over 5 min to a stirred solution of 3,6-dimethoxypyridazine 1e (100 mg, 0.75 mmol), concentrated H2SO4 (80 \316\274L, 1.5 mmol), 3-iodooxetane (276 mg, 1.5 mmol) and iron(II) sulfate heptahydrate (63 mg, 0.225 mmol) in DMSO (7.5 mL) at 60 \302\260C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (50 mg, 0.19 mmol) was added and the mixture was stirred at 60 \302\260C for 60 min. Ater allowing to cool, the mixture was poured into a 0.1 M solution of NaOH (30 mL) and EtOAc (30 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with EtOAc (1 x 30 mL). The combined organic extracts were dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by column chromatography on silica gel to give the desired product 2e (33 mg, 22%) as a solid" + } + outcomes { + reaction_time { + value: 1.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1N=C(OC)C(=CC1OC)C2COC2" + } + identifiers { + type: CAS_NUMBER + value: "1180653-63-7" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 22.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "197.09" + data { + key: "found" + value { + float_value: 197.09 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 6.89 (s, 1H), 5.01 (dd, J = 8.4, 6.0 Hz, 2H), 4.74 (t, J = 6.6 Hz, 2H), 4.38-4.32 (m, 1H), 4.30 (s, 3H), 4.04 (s, 3H); 13C NMR (100 MHz; CDCl3) \316\264 162.5, 160.3, 134.5, 117.2, 75.4, 54.8, 54.6, 34.2" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_124" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=CC(=C2C=CC=CC12)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "491-35-0" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 1-2 min to a stirred solution of lepidine 1a (132 \316\274L, 1.0 mmol), concentrated H2SO4 (107 \316\274L, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at room temperature. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at room temperature for 30 min. Further H2O2(0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred for 15 min, then poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 25 mL). The combined organic extracts were washed with brine (1 x 30 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using EtOAc / hexanes (3:7) as eluent to give a mixture of lepidine 1a and desired product 2a (25 mg), and the desired product 2a (82 mg, 40%) as a solid. An analytical portion of the product 2a was recrystallized from EtOAc / hexanes for data purposes" + } + outcomes { + reaction_time { + value: 0.75 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2C(=CC1C3COC3)C" + } + identifiers { + type: CAS_NUMBER + value: "1180653-56-8" + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 40.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 - 4 -8.07 (d, J = 8.3 Hz, 1H), 7.97 (d, J = 8.3 Hz, 1H), 7.71 (t, J = 7.6 Hz, 1H), 7.55 (t, J = 7.6 Hz, 1H), 7.38 (s, 1H), 5.19 (dd, J = 8.3, 6.0 Hz, 2H), 5.05 (t, J = 6.3 Hz, 2H), 4.51 (app. quint., J = 7.5 Hz, 1H), 2.73 (s, 3H); 13C NMR (100 MHz; CDCl3) \316\264 160.6, 147.7, 145.4, 129.8, 129.5, 127.3, 126.2, 123.8, 120.0, 76.9, 42.6, 19.0" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_125" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.3 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 4.7 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.3 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "OC(C=1C=CN=C2C=CC(OC)=CC21)C3N4CCC(C3)C(C4)CC" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "522-66-7" + } + amount { + moles { + value: 0.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 50.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.15 mL, 1.5 mmol) was added dropwise over about 1 min to a stirred solution of hydroquinine (163 mg, 0.5 mmol), 3-iodooxetane (184 mg, 1.0 mmol), concentrated H2SO4 (54 \316\274L, 1.0 mmol) and iron(II) sulfate heptahydrate (40 mg, 0.15 mmol) in DMSO (5 mL) at room temperature. After addition of the H2O2 the mixture was placed in an oil bath at 50 \302\260C. After 2 min a further portion of iron(II) sulfate heptahydrate (40 mg, 0.15 mmol) was added and the mixture was stirred at 50 \302\260C for 35 min. Further iron(II) sulfate heptahydrate (40 mg, 0.15 mmol) and H2O2 (30% in H2O; 0.15 mL, 1.5 mmol) was added and the mixture was stirred at 50 \302\260C for a further 15 min then allowed to cool. The mixture was poured into a 0.2 M solution of NaOH (15 mL) and Et2O (30 mL). Saturated NaHCO3 was added to bring the pH to 10. The aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 15 mL). The combined organic extracts were washed with brine (2 x 15 mL). The combined aqueous phases were extracted with additional Et2O (15 mL) [NB this was undertaken as some product was noted to still be in all the aqueous phase]. The combined organic extracts were dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil (186 mg). The oil was purified by preparative high-performance liquid chromatography (column: Gemini C18 10 \316\274M; size: 150 x 21.2 mm; eluent: 20-75% MeCN in 10 mM aqueous Et2NH or 35-98% MeCN in 10 mM aqueous Et2NH; run time: 17 min; flow rate: 20 mL/min; detection: UV at 254 nM) to give the desired product - 17 -5b collected as four aliquots (1st aliquot 12 mg, ca. 90% purity, 6% yield; 2nd aliquot 19 mg, ca. 80% purity, 8% yield; 3rd aliquot 17 mg, ca. 80% purity, 7% yield; 4th aliquot 12 mg, ca. 90% purity, 6% yield. All yields have been adjusted for purities). Total yield = 27% (yield adjusted for purity). The 1stand 4th aliquots were purified further by preparative high-performance liquid chromatography (column: Gemini C18 10 \316\274M; size: 150 x 21.2 mm; eluent: 55-95% MeOH in 10 mM aqueous Et2NH; run time: 20 min; flow rate: 20 mL/min; detection: UV at 254 nM) to give material for data purposes" + } + outcomes { + reaction_time { + value: 0.8 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "OC(C1=CC(=NC=2C=CC(OC)=CC21)C3COC3)C4N5CCC(C4)C(C5)CC" + } + identifiers { + type: CAS_NUMBER + value: "1180653-96-6" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 27.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "383.23" + data { + key: "found" + value { + float_value: 383.23 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 7.98 (d, J = 9.2 Hz, 1H), 7.62 (s, 1H), 7.34 (dd, J = 9.2, 2.6 Hz, 1H), 7.24 (d, J = 2.6 Hz, 1H), 5.55 (d, J = 3.8 Hz, 1H), 5.11-5.07 (m, 2H), 4.99 (d, J = 12.5, 6.2 Hz, 2H), 4.50-4.42 (m, 1H), 3.89 (s, 3H), 3.71 (br. s, 1H), 3.45-3.39 (m, 1H), 3.14-3.02 (m, 2H), 2.65-2.58 (m, 1H), 2.39-2.36 (m, 1H), 1.77 (br. s, 1H), 1.75-1.68 (m, 2H), 1.48-1.37 (m, 3H), 1.28-1.20 (m, 2H), 0.81 (t, J = 7.3 Hz, 3H); 13C NMR (100 MHz; CDCl3) \316\264 158.0, 157.7, 148.8, 144.2, 131.5, 125.6, 121.6, 116.7, 101.6, 77.1, 72.6, 59.9, 58.9, 55.9, 43.5, 42.5, 37.7, 28.5, 27.9, 25.6, 21.7, 12.2" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_126" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N1=CC(=NC2=CC=CC=C12)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7251-61-8" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (35% in H2O; 0.53 mL, 6.0 mmol) was added to a stirred solution of 2-methylquinoxaline 1h (288 mg, 2.0 mmol), concentrated H2SO4 (107 \316\274L, 1.0 mmol), 3-iodooxetane (368 mg, 1.0 mmol) and iron(II) sulfate heptahydrate (167 mg, 0.6 mmol) in DMSO (17 mL) at 60 \302\260C. The mixture was stirred at 60 \302\260C for 30 min then further H2O2 (0.53 mL, 6.0 mmol) and iron(II) sulfate heptahydrate (167 mg, 0.6 mmol) was added, and the mixture was stirred at 60 \302\260C for 30 min. One last portion of H2O2 (0.53 mL, 6.0 mmol) and iron(II) sulfate heptahydrate (167 mg, 0.6 mmol) was added, and the mixture was stirred at 60 \302\260C for 30 min. After allowing to cool, the mixture was poured into a 0.2 M solution of NaOH (50 mL) and extracted with EtOAc (3 x 30 mL). The combined organic extracts were washed with brine (3 x 50 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gels using MeOH / CH2Cl2 (0:1 to 1:19) as eluent, followed by purification by preparative high-performance liquid chromatography to give the desired product 2h (94 mg, 22%) as a solid" + } + outcomes { + reaction_time { + value: 1.5 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2N=C(C1C)C3COC3" + } + identifiers { + type: CAS_NUMBER + value: "1180653-68-2" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 22.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "201.1" + data { + key: "found" + value { + float_value: 201.1 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 8.12-8.09 (m, 1H), 8.05-8.02 (m, 1H), 7.75-7.71 (m, 2H), 5.24 (dd, J = 7.1Hz, 5.8Hz, 2H), 5.12 (dd, J = 8.4Hz, 5.7Hz, 2H), 4.76-4.68 (m, 1H), 2.61 (s, 3H); 13C NMR (100 MHz; CDCl3) \316\264 154.0, 152.2, 141.0, 129.8, 129.4, 129.1, 128.2, 74.7, 39.2, 22.2" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_127" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2C=CC1C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "91-63-4" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 1-2 min to a stirred solution of quinaldine 1b (135 \316\274L, 1.0 mmol), concentrated H2SO4 (107 \316\274L, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at room temperature. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at room temperature for 30 min. Further H2O2(0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred for 60 min, then poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 25 mL). The combined organic extracts were washed with brine (1 x 30 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using EtOAc / hexanes (3:7) as eluent to give recovered quinaldine 1b (55 mg, 39%), and the desired product 2b (64 mg, 32%) as a solid. An analytical portion of the product 2b was recrystallized from hexanes for data purposes." + } + outcomes { + reaction_time { + value: 1.5 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2C(=CC1C)C3COC3" + } + identifiers { + type: CAS_NUMBER + value: "1180653-57-9" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 32.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "200.1" + data { + key: "found" + value { + float_value: 200.1 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 8.06 (d, J = 8.4 Hz, 1H), 7.69 (m, 1H), 7.56 (d, J = 8.0 Hz, 1H), 7.49 (t, J = 7.5 Hz, 1H), 7.30 (s, 1H), 5.23 (dd, J = 8.1, 5.8 Hz, 2H), 5.00-4.90 (m, 3H), 2.78 (s, 3H); 13C NMR (100 MHz; CDCl3) \316\264 159.1, 148.1, 146.6, 129.8, 129.6, 126.1, 124.9, 122.8, 119.0, 76.5, 36.6, 25.6" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_128" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N1=CSC=2C=CC=CC12" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "95-16-9" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 1-2 min to a stirred solution of benzothiazole 1f (108 \316\274L, 1.0 mmol), concentrated H2SO4 (107 \316\274L, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at 60 \302\260C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at 60 \302\260C for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred at 60 \302\260C for 60 min. After allowing to cool, the mixture was poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted - 7 -with Et2O (2 x 25 mL). The combined organic extracts were washed with brine (1 x 30 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using EtOAc / hexanes (3:7) as eluent to give recovered benzothiazole 1f (60 mg, 44%), and the desired product 2f (58 mg, 30%)." + } + outcomes { + reaction_time { + value: 2.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C=2C=CC=CC2SC1C3COC3" + } + identifiers { + type: CAS_NUMBER + value: "1180653-65-9" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 30.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "192.4" + data { + key: "found" + value { + float_value: 192.4 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\2648.03 (d, J = 8.2 Hz, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.51-7.47 (m, 1H), 7.41-7.38 (m, 1H), 5.13 (dd, J = 8.3, 6.1 Hz, 2H), 5.04 (t, J = 6.4 Hz, 2H), 4.74-4.66 (m, 1H); 13C NMR (100 MHz; CDCl3) \316\264 170.7, 153.3, 135.0, 126.4, 125.3, 123.1, 121.9, 76.9, 39.4" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_129" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.3 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 4.7 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.3 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N#CC1=CN=C2C=C(OC)C(OC)=CC2=C1NC3=CC=C(Cl)C=C3Cl" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "331662-50-1" + } + amount { + moles { + value: 0.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "O=C(OC(C)(C)C)N1CC(I)C1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "254454-54-1" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 50.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 153 \316\274L, 1.5 mmol) was added dropwise over 5 min to a stirred solution of 4-(2,4-dichlorophenylamino)-6,7-dimethoxyquinoline-3-carbonitrile 4c (187 mg, 0.5 mmol), concentrated H2SO4 (80 \316\274L, 1.5 mmol), 1-Boc-3-(iodo)azetidine (282 mg, 1.0 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) in DMSO (5 mL) at 50 \302\260C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (50 mg, 0.18 mmol) was added and the mixture was stirred at 50 \302\260C for 45 min. Further iron(II) sulfate heptahydrate (50 mg, 0.18 mmol) was then added, followed by H2O2 (153 \316\274L, 1.5 mmol) over 5 min. The mixture was stirred at 50 \302\260C for 20 min. After allowing to cool, the - 20 -mixture was poured into a 0.1 M solution of NaOH which had been saturated with solid NaCl (50 mL) and EtOAc (50 mL). The aqueous and organic layers were partitioned and the organic layer was washed with brine (1 x 30 mL), dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography using EtOAc / hexanes (3:2) as eluent to give the desired product 5e (118 mg, 44%). An analytical portion of the product 5e was recrystallized from EtOAc / hexanes for data purposes" + } + outcomes { + reaction_time { + value: 1.1 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N#CC=1C(=NC=2C=C(OC)C(OC)=CC2C1NC3=CC=C(Cl)C=C3Cl)C4CN(C(=O)OC(C)(C)C)C4" + } + identifiers { + type: CAS_NUMBER + value: "1180654-03-8" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 44.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "529.14" + data { + key: "found" + value { + float_value: 529.14 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; d6-DMSO) \316\264 9.50 (br. s, 1H), 7.79 (s, 1H), 7.77 (s, 1H), 7.48 (s, 1H), 7.36 (s, 1H), 4.20-4.06 (m, 5H), 3.97 (s, 3H), 3.92 (s, 3H), 1.39 (s, 9H); 13C NMR (100 MHz; d6-DMSO) \316\264 159.3, 155.7, 153.8, 150.7, 149.2, 144.6, 136.2, 131.8, 131.4, 129.9, 129.3, 128.1, 115.7, 112.0, 108.8, 101.7, 86.0, 78.6, 56.2, 56.0, 53.5, 52.3, 33.4, 28.1" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_130" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.5 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.3 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 4.7 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.3 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N#CC1=CN=C2C=C(OC)C(OC)=CC2=C1NC3=CC=C(Cl)C=C3Cl" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "331662-50-1" + } + amount { + moles { + value: 0.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2(30% in H2O; 153 \316\274L, 1.5 mmol) was added dropwise over 5 min to a stirred solution of 4-(2,4- - 19 -dichlorophenylamino)-6,7-dimethoxyquinoline-3-carbonitrile 4c (187 mg, 0.5 mmol), concentrated H2SO4 (80 \316\274L, 1.5 mmol), 3-iodooxetane (183 mg, 1.0 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) in DMSO (5 mL) at 60 \302\260C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (50 mg, 0.18 mmol) was added and the mixture was stirred at 60 \302\260C for 30 min. Further H2O2 (153 \316\274L, 1.5 mmol) and iron(II) sulfate heptahydrate (100 mg, 0.36 mmol) was added, and the mixture was stirred at 60 \302\260C for 15 min. After allowing to cool, the mixture was poured into a 0.1 M solution of NaOH which had been saturated with solid NaCl (50 mL) and EtOAc (50 mL). The aqueous and organic layers were partitioned and the organic layer was washed with brine (1 x 30 mL), dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography using EtOAc / hexanes (7:3) as eluent to give the desired product 5d (86 mg, 38%). An analytical portion of the product 5d was triturated with Et2O for data purposes" + } + outcomes { + reaction_time { + value: 0.75 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N#CC=1C(=NC=2C=C(OC)C(OC)=CC2C1NC3=CC=C(Cl)C=C3Cl)C4COC4" + } + identifiers { + type: CAS_NUMBER + value: "1180654-00-5" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 38.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "430.07" + data { + key: "found" + value { + float_value: 430.07 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; d6-DMSO) \316\264 9.50 (br. s, 1H), 7.80 (s, 1H), 7.77 (t, J = 1.3 Hz, 1H), 7.47 (d, J = 1.3 Hz, 1H), 7.37 (s, 1H), 4.93 (app. t, J = 6.2 Hz, 2H), 4.85 (dd, J = 8.4, 5.6 Hz, 2H), 4.60-4.52 (m, 1H), 3.97 (s, 3H), 3.93 (s, 3H); 13C NMR (100 MHz; d6-DMSO) 159.3, 153.8, 150.7, 149.2, 144.8, 136.2, 131.9, 131.4, 130.0, 129.3, 128.1, 115.7, 112.0, 108.7, 101.7, 85.8, 73.8, 56.2, 56.0, 39.6" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_131" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.6 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 6.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 9.4 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.6 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=CC(=C2C=C(OC)C=CC12)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "41037-26-7" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 2.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 0.31 mL, 3.0 mmol) was added dropwise over 1-2 min to a stirred solution of 6-methoxy-4-methylquinoline 4a (173 mg, 1.0 mmol), concentrated H2SO4 (107 \316\274L, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at room temperature. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at room temperature for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred for 15 min, then poured into a 0.2 M solution of NaOH (30 mL) and Et2O (50 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with Et2O (2 x 25 mL). The combined organic extracts were dried (MgSO4), filtered and the - 16 -solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography using 30% EtOAc / hexanes as eluent to give recovered 6-methoxy-4-methylquinoline 4a (32 mg, 19%), a mixture of 6-methoxy-4-methylquinoline 4a and the desired product 5a (15 mg) and the desired product 5a (72 mg, 31%) as a solid. An analytical portion of the product 5a was recrystallized from hexanes for data purposes." + } + outcomes { + reaction_time { + value: 0.75 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C=2C=CC(OC)=CC2C(=CC1C3COC3)C" + } + identifiers { + type: CAS_NUMBER + value: "1180653-94-4" + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 31.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 7.96 (d, J = 9.2 Hz, 1H), 7.38-7.35 (m, 2H), 7.19 (d, J = 2.6 Hz, 1H), 5.15 (dd, J = 8.3, 5.9 Hz, 2H), 5.03 (t, J = 6.2 Hz, 2H), 4.52-4.44 (m, 1H), 3.96 (s, 3H), 2.68 (s, 3H); 13C NMR (100 MHz; CDCl3) 158.1, 157.6, 143.9, 143.6, 131.2, 128.1, 121.6, 120.3, 102.1, 77.1, 55.7, 42.5, 19.2" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +} +reactions { + identifiers { + type: CUSTOM + details: "rxn_id from SURF table" + value: "lsf_lit_minisci_132" + } + identifiers { + type: CUSTOM + details: "rxn_tech from SURF table" + value: "alkylation" + } + identifiers { + type: REACTION_TYPE + details: "alkylation minisci" + value: "alkylation minisci" + } + inputs { + key: "additive_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(=O)(O)O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7664-93-9" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "catalyst_1" + value { + components { + identifiers { + type: SMILES + value: "[Fe].O=S(=O)(O)O.O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7782-63-0" + } + amount { + moles { + value: 0.3 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + } + } + inputs { + key: "reagent_1" + value { + components { + identifiers { + type: SMILES + value: "OO" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7722-84-1" + } + amount { + moles { + value: 3.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + } + } + inputs { + key: "solvent_1" + value { + components { + identifiers { + type: SMILES + value: "O=S(C)C" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "67-68-5" + } + amount { + volume { + value: 4.7 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "solvent_2" + value { + components { + identifiers { + type: SMILES + value: "O" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "7732-18-5" + } + amount { + volume { + value: 0.3 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + } + } + inputs { + key: "startingmat_1" + value { + components { + identifiers { + type: SMILES + value: "N=1C=NC=2C=C(OC)C(OC)=CC2C1OC" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "881293-34-1" + } + amount { + moles { + value: 0.5 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + inputs { + key: "startingmat_2" + value { + components { + identifiers { + type: SMILES + value: "IC1COC1" + } + identifiers { + type: CAS_NUMBER + details: "cas number from SURF _cas column" + value: "26272-85-5" + } + amount { + moles { + value: 1.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + } + } + conditions { + temperature { + setpoint { + value: 60.0 + units: CELSIUS + } + } + pressure { + control { + type: SEALED + } + atmosphere { + type: AIR + } + } + } + notes { + procedure_details: "H2O2 (30% in H2O; 153 \316\274L, 1.50 mmol) was added dropwise to a stirred solution of 4,6,7-trimethoxyquinazoline 1i (110 mg, 0.5 mmol), concentrated H2SO4 (54 \316\274L, 1.0 mmol), 3-iodooxetane (183 mg, 1.0 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) in DMSO (5 mL) at 60 \302\260C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) was added and the mixture was stirred at 60 \302\260C for 30 min. Further H2O2 (153 \316\274L, 1.5 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) was added, and the mixture was stirred at 60 \302\260C for a further 60 min. Ater allowing to cool, the mixture was poured into a 0.2 M solution of NaOH (50 mL) and Et2O (30 mL). The aqueous and organic layers were partitioned and the aqueous layer was saturated with solid NaCl, then extracted with Et2O (2 x 25 mL). The combined organic - 9 -extracts were dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography to give a mixture of recovered 4,6,7-trimethoxyquinazoline 1i and product, followed by desired product 2i (64 mg, ca. 83% pure, 38% yield adjusted for purity). An analytical sample of the product 2i (83% purity) was purified further by perparative high-performance liquid chromatography to give material for data purposes (column: Gemini C6P (phenyl hexyl); size: 100 x 21.2 mm; particle size: 5 \316\274M; eluent: 3-70% CH3CN in 10 mM aqueous Et2NH; run time: 20 min; detection: UV at 254 nM; retention time: 7.76 min)" + } + outcomes { + reaction_time { + value: 1.5 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "N=1C(OC)=C2C=C(OC)C(OC)=CC2=NC1C3COC3" + } + identifiers { + type: CAS_NUMBER + value: "1180653-71-7" + } + measurements { + analysis_key: "MS of product_1" + type: IDENTITY + } + measurements { + analysis_key: "NMR of product_1" + type: IDENTITY + } + measurements { + analysis_key: "product_1_isolated" + type: YIELD + percentage { + value: 38.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "MS of product_1" + value { + type: MS + details: "277.6" + data { + key: "found" + value { + float_value: 277.6 + description: "Observed m/z" + } + } + } + } + analyses { + key: "NMR of product_1" + value { + type: NMR_1H + data { + key: "peaks" + value { + string_value: "1H NMR (400 MHz; CDCl3) \316\264 7.34 (s, 1H), 7.23 (s, 1H) 5.18-5.15 (m, 2H), 5.08-5.05 (m, 2H), 4.54-4.46 (m, 1H), 4.20 (d, J = 0.8 Hz, 3H), 4.02 (m, 6H); 13C NMR (100 MHz; CDCl3) \316\264 166.2, 163.6, 155.5, 149.5, 148.7, 109.2, 106.7, 101.4, 76.2, 56.4, 56.3, 54.2, 43.0" + } + } + } + } + analyses { + key: "product_1_isolated" + value { + type: WEIGHT + details: "isolated" + } + } + } + provenance { + doi: "10.1021/jo9010624" + record_created { + time { + value: "2024-09-16" + } + person { + username: "Alex T. Mueller" + orcid: "0000-0001-8063-9952" + organization: "F. Hoffmann-La Roche Ltd." + email: "alex.mueller@roche.com" + } + } + } +}