dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bcd201cd2bdd4de7a33cabe5dea03260 | Nc1cccc(C(F)(F)F)c1.O=C1C(=O)N(c2ccsc2)c2ccccc21>>O=C1C(=Nc2cccc(C(F)(F)F)c2)c2ccccc2N1c1ccsc1 | S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=O)=O.FC(C=1C=C(N)C=CC1)(F)F>>S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=NC1=CC(=CC=C1)C(F)(F)F)=O | [NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1.O=[C:3]1[C:2](=[O:1])[N:21]([c:22]2[cH:23][cH:24][s:25][cH:26]2)[c:20]2[c:15]1[cH:16][cH:17][cH:18][cH:19]2>>[O:1]=[C:2]1[C:3](=[N:4][c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[N... | Nc1cccc(C(F)(F)F)c1.O=C1C(=O)N(c2ccsc2)c2ccccc21 | O=C1C(=Nc2cccc(C(F)(F)F)c2)c2ccccc2N1c1ccsc1 | null | null | null | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | 561e2daf1aa504fe4e7a04c4a24377b070a888e3731bdc015219988535a1cb4e | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | O=C1C(=Nc2ccccc2)c2ccccc2N1c1ccsc1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5]:[c:6]:[#16;a:7])-[c:8]:[c:9]-1:[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[#16;a:7]:[c:6]:[c:5]-[#7:4]1-[c:8]:[c:9](:[c:10])-[C;H0;D3;+0:1](=[N;H0;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:2]-1=[O;D1;H0:3] | 22 | [{"value": 22.0, "product": "S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=NC1=CC(=CC=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.2, "product": "S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=NC1=CC(=CC=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of 1-(3-thienyl)-2H-indole-2,3-dione (25 mg, 0.11 mmol) (prepared as described below) and 3-trifluoromethylaniline (14 uL, 0.11 mmol) was heated neat at 140° C. for 2 h. The crude material was purified by preparative TLC using a mixture of 3:7 ethyl acetate and hexane as the eluent, giving the desired product... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2.c1ccsc1 | HO- | null | 140 | null | Nc1cccc(C(F)(F)F)c1.O=C1C(=O)N(c2ccsc2)c2ccccc21>>O=C1C(=Nc2cccc(C(F)(F)F)c2)c2ccccc2N1c1ccsc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-88c257a92db94d31902826796464a259 | O=C1Nc2ccccc2C1=O.OB(O)c1ccsc1>>O=C1C(=O)N(c2ccsc2)c2ccccc21 | ClCCl.N1C(=O)C(=O)C2=CC=CC=C12.S1C=C(C=C1)B(O)O.S1C=C(C=C1)B(O)O.C(C)N(CC)CC>>S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=O)=O | [O:1]=[C:2]1[C:3](=[O:4])[NH:5][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21.OB(O)[c:6]1[cH:7][cH:8][s:9][cH:10]1>>[O:1]=[C:2]1[C:3](=[O:4])[N:5]([c:6]2[cH:7][cH:8][s:9][cH:10]2)[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | O=C1Nc2ccccc2C1=O.OB(O)c1ccsc1 | O=C1C(=O)N(c2ccsc2)c2ccccc21 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)N(CC)CC.O.C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | C(C)(=O)OC(C)=O | Heteroatom Alkylation and Arylation | Petasis reaction with amines and boronic acids | be3d88681ac45276609ee88d2d0617d0b24c7e5449c029bdbdb9b91a4d91e9d8 | d8988f95994c3a53b8581714df91fdcf58fce7c875a9f3af0fd1011694639d17 | O=C1C(=O)N(c2ccsc2)c2ccccc21 | O-B(-O)-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c:5]:1.[O;D1;H0:6]=[C:7]1-[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-[C:12]-1=[O;D1;H0:13]>>[O;D1;H0:6]=[C:7]1-[c:8]:[c:9](:[c:10])-[N;H0;D3;+0:11](-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4]:[c:5]:2)-[C:12]-1=[O;D1;H0:13] | 33 | [{"value": 33.0, "product": "S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.4, "product": "S1C=C(C=C1)N1C(C(C2=CC=CC=C12)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Copper(II) acetate monohydrate (4.25 g, 23.4 mmol) was heated at reflux in acetic anhydride (30 mL) for 2 h. The mixture was filtered and washed with anhydrous ether (500 mL). The solid was dried in vacuo at 55° C. for 16 h. Dichloromethane (1 mL) was added to a mixture of copper(II) acetate (62 mg, 0.34 mmol), isatin ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Boronic acid | Tertiary amide | c1ccc2c(c1)CCN2.c1ccsc1 | c1ccsc1.c1ccc2c(c1)CC[NH]2 | c1ccsc1.c1ccc2c(c1)CC[NH]2 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)N(CC)CC.O.C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)(=O)OC(C)=O | null | 16 | O=C1Nc2ccccc2C1=O.OB(O)c1ccsc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)N(CC)CC.O.C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].C(C)(=O)OC(C)=O>O=C1C(=O)N(c2ccsc2)c2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9df4502829734d918fa049bfcbebe25a | Nc1cccc(C(F)(F)F)c1.O=C1C(=O)N(Cc2csc3ccc(Cl)cc23)c2ccccc21>>O=C1C(=Nc2cccc(C(F)(F)F)c2)c2ccccc2N1Cc1csc2ccc(Cl)cc12 | ClC=1C=CC2=C(C(=CS2)CN2C(C(C3=CC=CC=C23)=O)=O)C1.FC(C=1C=C(N)C=CC1)(F)F>>ClC=1C=CC2=C(C(=CS2)CN2C(C(C3=CC=CC=C23)=NC2=CC(=CC=C2)C(F)(F)F)=O)C1 | [NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1.O=[C:3]1[C:2](=[O:1])[N:21]([CH2:22][c:23]2[cH:24][s:25][c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][c:32]23)[c:20]2[c:15]1[cH:16][cH:17][cH:18][cH:19]2>>[O:1]=[C:2]1[C:3](=[N:4][c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]2)... | Nc1cccc(C(F)(F)F)c1.O=C1C(=O)N(Cc2csc3ccc(Cl)cc23)c2ccccc21 | O=C1C(=Nc2cccc(C(F)(F)F)c2)c2ccccc2N1Cc1csc2ccc(Cl)cc12 | null | null | null | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | 561e2daf1aa504fe4e7a04c4a24377b070a888e3731bdc015219988535a1cb4e | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | O=C1C(=Nc2ccccc2)c2ccccc2N1Cc1csc2ccccc12 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[c:6]:[c:7]-1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:5]-[#7:4]1-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:1](=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12])-[C:2]-1=[O;D1;H0:3] | 20 | [{"value": 18.0, "product": "ClC=1C=CC2=C(C(=CS2)CN2C(C(C3=CC=CC=C23)=NC2=CC(=CC=C2)C(F)(F)F)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.0, "product": "ClC=1C=CC2=C(C(=CS2)CN2C(C(C3=CC=CC=C23)=NC2=CC(=CC=C2)C(F)(F)F)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of 1-[(5-chloro-1-benzothien-3-yl)methyl]-2H-indole-2,3-dione (50 mg, 0.15 mmol) (prepared as described below) and 3-trifluoromethylaniline (0.020 mL, 0.15 mmol) was heated neat at 140° C. for 2 h. The crude material was purified by preparative TLC using a mixture of 1:3 ethyl acetate and hexane as the eluent... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccccc1.c1ccc2c(c1)CC[NH]2.c1ccc2sccc2c1 | HO- | null | 140 | null | Nc1cccc(C(F)(F)F)c1.O=C1C(=O)N(Cc2csc3ccc(Cl)cc23)c2ccccc21>>O=C1C(=Nc2cccc(C(F)(F)F)c2)c2ccccc2N1Cc1csc2ccc(Cl)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d327e019b1b044a48ebe861108e36ba4 | Clc1ccc2scc(CBr)c2c1.O=C1Nc2ccccc2C1=O>>O=C1C(=O)N(Cc2csc3ccc(Cl)cc23)c2ccccc21 | N1C(=O)C(=O)C2=CC=CC=C12.[H-].[Na+].BrCC=1C2=C(SC1)C=CC(=C2)Cl>>ClC=1C=CC2=C(C(=CS2)CN2C(C(C3=CC=CC=C23)=O)=O)C1 | Br[CH2:6][c:7]1[cH:8][s:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]12.[O:1]=[C:2]1[C:3](=[O:4])[NH:5][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[O:1]=[C:2]1[C:3](=[O:4])[N:5]([CH2:6][c:7]2[cH:8][s:9][c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]23)[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21 | Clc1ccc2scc(CBr)c2c1.O=C1Nc2ccccc2C1=O | O=C1C(=O)N(Cc2csc3ccc(Cl)cc23)c2ccccc21 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c168ddb7803c893ec5334f16b8c2262b487eff0908e05ac9b9feab6bfceb9bd3 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1C(=O)N(Cc2csc3ccccc23)c2ccccc21 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1.[O;D1;H0:7]=[C:8]1-[c:9]:[c:10](:[c:11])-[NH;D2;+0:12]-[C:13]-1=[O;D1;H0:14]>>[O;D1;H0:7]=[C:8]1-[c:9]:[c:10](:[c:11])-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[c:2]2:[c:3]:[c:4]:[#16;a:5]:[c:6]:2)-[C:13]-1=[O;D1;H0:14] | 45 | [{"value": 45.0, "product": "ClC=1C=CC2=C(C(=CS2)CN2C(C(C3=CC=CC=C23)=O)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.7, "product": "ClC=1C=CC2=C(C(=CS2)CN2C(C(C3=CC=CC=C23)=O)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A solution of isatin (125 mg, 0.85 mmol) in anhydrous dioxane (10 mL) was added dropwise to a solution of sodium hydride (60% dispersion in mineral oil, 25 mg, 0.62 mmol) in anhydrous dioxane (10 mL) at 0° C. under argon. The mixture was allowed to stir for 5 minutes and then a solution of 3-(bromomethyl)-5-chlorobenzo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2sccc2c1.c1ccc2c(c1)CC[NH]2 | HBr | O1CCOCC1 | null | 0.083333 | Clc1ccc2scc(CBr)c2c1.O=C1Nc2ccccc2C1=O>O1CCOCC1>O=C1C(=O)N(Cc2csc3ccc(Cl)cc23)c2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-772d953501794ab3ae8d8eda15faa2b4 | Nc1ccc2[nH]ccc2c1.O=C1C(=O)N(c2ccccc2)c2ccccc21>>O=C1C(=Nc2ccc3[nH]ccc3c2)c2ccccc2N1c1ccccc1 | C1(=CC=CC=C1)N1C(=O)C(=O)C2=CC=CC=C12.NC=1C=C2C=CNC2=CC1>>N1C=CC2=CC(=CC=C12)N=C1C(N(C2=CC=CC=C12)C1=CC=CC=C1)=O | [NH2:4][c:5]1[cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]2[cH:13]1.O=[C:3]1[C:2](=[O:1])[N:20]([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:19]2[c:14]1[cH:15][cH:16][cH:17][cH:18]2>>[O:1]=[C:2]1[C:3](=[N:4][c:5]2[cH:6][cH:7][c:8]3[nH:9][cH:10][cH:11][c:12]3[cH:13]2)[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[N:20]1[c:... | Nc1ccc2[nH]ccc2c1.O=C1C(=O)N(c2ccccc2)c2ccccc21 | O=C1C(=Nc2ccc3[nH]ccc3c2)c2ccccc2N1c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | 561e2daf1aa504fe4e7a04c4a24377b070a888e3731bdc015219988535a1cb4e | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | O=C1C(=Nc2ccc3[nH]ccc3c2)c2ccccc2N1c1ccccc1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[c:6]:[c:7]-1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:3]=[C:2]1-[#7:4](-[c:5])-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:1]-1=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | 14 | [{"value": 14.0, "product": "N1C=CC2=CC(=CC=C12)N=C1C(N(C2=CC=CC=C12)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.9, "product": "N1C=CC2=CC(=CC=C12)N=C1C(N(C2=CC=CC=C12)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | 1-phenylisatin (51.8 mg, 0.23 mmol) and 5-aminoindole (31 mg, 0.23 mmol) were mixed and heated at 140° C. for 2 h. The resulting crude product was purified by preparative TLC using ethyl acetate/hexane (6:4) as the eluent, giving the desired product as a yellow solid (10.8 mg, 14%). 1H NMR (400 MHz): δ 8.28 (s, 1H), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HO- | null | 140 | null | Nc1ccc2[nH]ccc2c1.O=C1C(=O)N(c2ccccc2)c2ccccc21>>O=C1C(=Nc2ccc3[nH]ccc3c2)c2ccccc2N1c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-feec89b91f5545d8860da6e7fb9ba390 | Nc1ccc(Cl)nc1.O=C1C(=O)N(c2ccccc2)c2ccccc21>>O=C1C(=Nc2ccc(Cl)nc2)c2ccccc2N1c1ccccc1 | C1(=CC=CC=C1)N1C(=O)C(=O)C2=CC=CC=C12.NC=1C=CC(=NC1)Cl>>ClC1=CC=C(C=N1)N=C1C(N(C2=CC=CC=C12)C1=CC=CC=C1)=O | [NH2:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[n:10][cH:11]1.O=[C:3]1[C:2](=[O:1])[N:18]([c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[c:17]2[c:12]1[cH:13][cH:14][cH:15][cH:16]2>>[O:1]=[C:2]1[C:3](=[N:4][c:5]2[cH:6][cH:7][c:8]([Cl:9])[n:10][cH:11]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[N:18]1[c:19]1[cH:20][cH:21][cH:22][cH... | Nc1ccc(Cl)nc1.O=C1C(=O)N(c2ccccc2)c2ccccc21 | O=C1C(=Nc2ccc(Cl)nc2)c2ccccc2N1c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | 561e2daf1aa504fe4e7a04c4a24377b070a888e3731bdc015219988535a1cb4e | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | O=C1C(=Nc2cccnc2)c2ccccc2N1c1ccccc1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[c:6]:[c:7]-1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]:[#7;a:13]:[c:14]>>[O;D1;H0:3]=[C:2]1-[#7:4](-[c:5])-[c:6]:[c:7](:[c:8])-[C;H0;D3;+0:1]-1=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]:[#7;a:13]:[c:14] | 59 | [{"value": 59.0, "product": "ClC1=CC=C(C=N1)N=C1C(N(C2=CC=CC=C12)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.0, "product": "ClC1=CC=C(C=N1)N=C1C(N(C2=CC=CC=C12)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | 1-phenylisatin (23.0 mg, 0.10 mmol) and 5-amino-2-chloropyridine (12.8 mg, 0.10 mmol) were mixed and heated at 140° C. for 7 h. The resulting crude product was purified by preparative TLC using hexane/ethyl acetate (8:2) as the eluent, giving the desired product as a yellow solid (19.7 mg, 59%). 1H NMR (400 MHz) δ 8.15... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccncc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HO- | null | 140 | null | Nc1ccc(Cl)nc1.O=C1C(=O)N(c2ccccc2)c2ccccc21>>O=C1C(=Nc2ccc(Cl)nc2)c2ccccc2N1c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-207181d19e484bbaa07c19a722783cb4 | Cc1nc2cc(N)ccc2s1.O=C1C(=O)N(c2ccccc2)c2ccccc21>>Cc1nc2cc(N=C3C(=O)N(c4ccccc4)c4ccccc43)ccc2s1 | NC=1C=CC2=C(N=C(S2)C)C1.C1(=CC=CC=C1)N1C(=O)C(=O)C2=CC=CC=C12>>CC=1SC2=C(N1)C=C(C=C2)N=C2C(N(C1=CC=CC=C21)C2=CC=CC=C2)=O | [CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([NH2:7])[cH:24][cH:25][c:26]2[s:27]1.O=[C:8]1[C:9](=[O:10])[N:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([N:7]=[C:8]3[C:9](=[O:10])[N:11]([c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[c:18]4[cH:19][c... | Cc1nc2cc(N)ccc2s1.O=C1C(=O)N(c2ccccc2)c2ccccc21 | Cc1nc2cc(N=C3C(=O)N(c4ccccc4)c4ccccc43)ccc2s1 | null | null | null | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | 561e2daf1aa504fe4e7a04c4a24377b070a888e3731bdc015219988535a1cb4e | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | O=C1C(=Nc2ccc3scnc3c2)c2ccccc2N1c1ccccc1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[c:6]:[c:7]-1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[N;H0;D2;+0:13]=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[c:6]:[c:7]-1:[c:8]):[c:14] | 32.3 | [{"value": 32.3, "product": "CC=1SC2=C(N1)C=C(C=C2)N=C2C(N(C1=CC=CC=C21)C2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.2, "product": "CC=1SC2=C(N1)C=C(C=C2)N=C2C(N(C1=CC=CC=C21)C2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | 5-amino-2-methylbenzothiazole (52.2 mg, 0.31 mmol) was mixed with 1-phenylisatin (69.7 mg, 0.31 mmol) and heated at 140° C. for 3 h. The resulting crude product was purified by preparative TLC using ethyl acetate/hexane (6:4) as the eluent to give the desired product as a yellow solid (36.9 mg, 32.3%). 1H NMR Data: δ 7... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | c1ccc2scnc2c1.c1ccccc1.c1ccc2c(c1)CC[NH]2 | HO- | null | 140 | null | Cc1nc2cc(N)ccc2s1.O=C1C(=O)N(c2ccccc2)c2ccccc21>>Cc1nc2cc(N=C3C(=O)N(c4ccccc4)c4ccccc43)ccc2s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e037e31718604301905587b44988ae37 | C[Si](C)(C)CCOCCl.Cc1ccc(S(=O)(=O)c2[nH]cnc2-c2ccccn2)cc1>>C[Si](C)(C)CCOCn1cnc(-c2ccccn2)c1 | [H-].[Na+].C1=CC=CC2=CC=CC=C12.C[Si](C)(C)CCOCCl.C1(=CC=C(C=C1)S(=O)(=O)C1=C(N=CN1)C1=NC=CC=C1)C>>C[Si](CCOCN1C=NC(=C1)C1=NC=CC=C1)(C)C | Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].Cc1ccc(S(=O)(=O)[c:19]2[nH:9][cH:10][n:11][c:12]2-[c:13]2[cH:14][cH:15][cH:16][cH:17][n:18]2)cc1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[cH:10][n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][n:18]2)[cH:19]1 | C[Si](C)(C)CCOCCl.Cc1ccc(S(=O)(=O)c2[nH]cnc2-c2ccccn2)cc1 | C[Si](C)(C)CCOCn1cnc(-c2ccccn2)c1 | null | null | O.CN(C)C=O.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 845808e6b3e35ce4ec39553792793212778b97299c5f5f2dc9695651e4c571da | 1502a7de07e81aa5c4c9fb94e798252eccfeaaf15ef0c0ef1af8f3f5987a2267 | c1ccc(-c2c[nH]cn2)nc1 | C-c1:c:c:c(-S(=O)(=O)-[c;H0;D3;+0:1]2:[nH;D2;+0:2]:[c:3]:[#7;a:4]:[c:5]:2-[c:6]:[#7;a:7]):c:c:1.Cl-[CH2;D2;+0:8]-[#8:9]-[C:10]>>[#7;a:7]:[c:6]-[c:5]1:[#7;a:4]:[c:3]:[n;H0;D3;+0:2](-[CH2;D2;+0:8]-[#8:9]-[C:10]):[cH;D2;+0:1]:1 | 2.2 | [{"value": 2.1, "product": "C[Si](CCOCN1C=NC(=C1)C1=NC=CC=C1)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 2.2, "product": "C[Si](CCOCN1C=NC(=C1)C1=NC=CC=C1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred solution of naphthalene (5.8 g, 45.3 mmol) in dry THF (20 mL) was added Na (0.85 g, 37.0 mmol) under N2. After 15 minutes stirring at room temperature, the resultant green suspension was cooled to −78° C. A cooled (−78° C.) solution of 2-[5-(Toluene-4-sulfonyl)-1H-imidazol-4-yl]-pyridine (Tetrahedron Lett.... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary halide.Ether | Ether | c1ccccc1.c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccncc1 | TsOH.HCl | O.CN(C)C=O.C1CCOC1 | null | 0.25 | C[Si](C)(C)CCOCCl.Cc1ccc(S(=O)(=O)c2[nH]cnc2-c2ccccn2)cc1>O.CN(C)C=O.C1CCOC1>C[Si](C)(C)CCOCn1cnc(-c2ccccn2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff412a054c254907a8636742a26e0441 | C[Si](C)(C)CCOCn1cnc(-c2ccccn2)c1.O=Cc1cn(Cc2ccc(Cl)cc2)c2ccccc12>>C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | C(C)(C)[N-]C(C)C.[Li+].C(C)C1=CC=CC=C1.C1CCOC1.C[Si](CCOCN1C=NC(=C1)C1=NC=CC=C1)(C)C.ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C=O)C=C1>>ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(O)C=2N(C=C(N2)C2=NC=CC=C2)COCC[Si](C)(C)C)C=C1 | [CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][n:17]2)[n:18][cH:19]1.[CH:20](=[O:21])[c:22]1[cH:23][n:24]([CH2:25][c:26]2[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]12>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2... | C[Si](C)(C)CCOCn1cnc(-c2ccccn2)c1.O=Cc1cn(Cc2ccc(Cl)cc2)c2ccccc12 | C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 1429ad5c64747667b11a35a9b6ee20c6ea95d82b5bbcef33ff8f15f573964c71 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1ccc(Cn2cc(Cc3nc(-c4ccccn4)c[nH]3)c3ccccc32)cc1 | [C:1]-[#7;a:2]1:[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7]:[c:8]:1.[C:9]-[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[cH;D2;+0:14]:1>>[C:1]-[#7;a:2]1:[c:3]:[c:4](-[CH;D3;+0:5](-[OH;D1;+0:6])-[c;H0;D3;+0:14]2:[#7;a:13]:[c:12]:[c:11]:[#7;a:10]:2-[C:9]):[c:7]:[c:8]:1 | 87 | [{"value": 87.0, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(O)C=2N(C=C(N2)C2=NC=CC=C2)COCC[Si](C)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(O)C=2N(C=C(N2)C2=NC=CC=C2)COCC[Si](C)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | -78 | CELSIUS | 1 | HOUR | Lithium diisopropylamide (2 M solution in petane/ethylbenzene/THF, 57 uL, 0.12 mmol) was added to a stirred solution of 2-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-pyridine (10.5 mg, 0.038 mmol) in dry THF (3 mL) at −78° C. under N2. After 1 hour at this temperature, a solution of N-4-chlorobenzylindole-3-... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccncc1.c1ccccc1.c1c[nH]c2ccccc12 | null | C1CCOC1 | -78 | 1 | C[Si](C)(C)CCOCn1cnc(-c2ccccn2)c1.O=Cc1cn(Cc2ccc(Cl)cc2)c2ccccc12>C1CCOC1>C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ed383daff64b4fd5b60b3b126b8aaf5a | C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12>>C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(=O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | CCCCCC.C(C)(=O)OCC.ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(O)C=2N(C=C(N2)C2=NC=CC=C2)COCC[Si](C)(C)C)C=C1>>ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2N(C=C(N2)C2=NC=CC=C2)COCC[Si](C)(C)C)C=C1 | [CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][n:17]2)[n:18][c:19]1[CH:20]([OH:21])[c:22]1[cH:23][n:24]([CH2:25][c:26]2[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]2)[c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]12>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6... | C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(=O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | null | O=[Mn]=O | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1nc(-c2ccccn2)c[nH]1)c1cn(Cc2ccccc2)c2ccccc12 | [C:1]-[#7;a:2]1:[c:3]:[c:4](-[CH;D3;+0:5](-[OH;D1;+0:6])-[c:7]2:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:2-[C:12]):[c:13]:[c:14]:1>>[C:1]-[#7;a:2]1:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[c:7]2:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:2-[C:12]):[c:13]:[c:14]:1 | 100 | [{"value": 100.0, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2N(C=C(N2)C2=NC=CC=C2)COCC[Si](C)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2N(C=C(N2)C2=NC=CC=C2)COCC[Si](C)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 2 | HOUR | A mixture of [1-(4-chloro-benzyl)-1H-indol-3-yl]-[4-pyridin-2-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanol (10 mg, 18.4 mmol) and (10 mg, 18.4 mmol) and MnO2 (0.2 g, 2.3 mmol) in dichloromethane (5 mL) was stirred at room temperature for two hours. Flash silica gel chromatography (2:1 hexane/ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1c[nH]cn1.c1ccncc1.c1ccccc1.c1c[nH]c2ccccc12 | null | O=[Mn]=O.ClCCl | null | 2 | C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12>O=[Mn]=O.ClCCl>C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(=O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d42d62dfba464ca38ebb2a68e6f7aad6 | C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(=O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12>>O=C(c1nc(-c2ccccn2)c[nH]1)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2N(C=C(N2)C2=NC=CC=C2)COCC[Si](C)(C)C)C=C1>>ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2NC=C(N2)C2=NC=CC=C2)C=C1 | C[Si](C)(C)CCOC[n:13]1[c:3]([C:2](=[O:1])[c:14]2[cH:15][n:16]([CH2:17][c:18]3[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]3)[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]23)[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[cH:12]1>>[O:1]=[C:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[cH:12][nH:13]1)[c:14]1[... | C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(=O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | O=C(c1nc(-c2ccccn2)c[nH]1)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | null | Cl | C(C)O | Reduction | OtherReaction | 22457429d65073759ef3e1f3cb6703668c081ddbc38609f3e2cac12929d01451 | d646edd3b1165ce8eea24b0587d24c565cf6371928b4879100704e7b3cd85ed9 | O=C(c1nc(-c2ccccn2)c[nH]1)c1cn(Cc2ccccc2)c2ccccc12 | C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]:[#7;a:5]):[#7;a:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[c:10]:[c:11]:[#7;a:12]>>[#7;a:5]:[c:4]-[c:3]1:[#7;a:6]:[c:7](-[C:8](=[O;D1;H0:9])-[c:10]:[c:11]:[#7;a:12]):[nH;D2;+0:1]:[c:2]:1 | null | [] | null | null | null | null | To a stirred solution of [1-(4-Chloro-benzyl)-1H-indol-3-yl]-[4-pyridin-2-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanone (10 mg, 18.4 mmol) in ethanol (3 mL) was added 5 drops of concentrated HCl. The resultant solution was heated to 70° C. for 10 hours. Volatile components were then removed under r... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Silyl protective group | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccncc1.c1ccccc1.c1c[nH]c2ccccc12 | HO- | Cl.C(C)O | null | null | C[Si](C)(C)CCOCn1cc(-c2ccccn2)nc1C(=O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12>Cl.C(C)O>O=C(c1nc(-c2ccccn2)c[nH]1)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbbb2b9f1e29472da3da9ca8a042618d | C[Si](C)(C)CCOCCl.Cc1ccc(S(=O)(=O)c2[nH]cnc2-c2ccccn2)cc1>>Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)ncn2COCC[Si](C)(C)C)cc1 | O.C[Si](C)(C)CCOCCl.C1(=CC=C(C=C1)S(=O)(=O)C1=C(N=CN1)C1=NC=CC=C1)C.[H-].[Na+]>>C1(=CC=C(C=C1)S(=O)(=O)C1=C(N=CN1COCC[Si](C)(C)C)C1=NC=CC=C1)C | Cl[CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:26])[CH3:27].[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[c:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][n:16]3)[n:17][cH:18][nH:19]2)[cH:28][cH:29]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[c:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][n:... | C[Si](C)(C)CCOCCl.Cc1ccc(S(=O)(=O)c2[nH]cnc2-c2ccccn2)cc1 | Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)ncn2COCC[Si](C)(C)C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | O=S(=O)(c1ccccc1)c1[nH]cnc1-c1ccccn1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[#16:4]-[c:5]1:[nH;D2;+0:6]:[c:7]:[#7;a:8]:[c:9]:1-[c:10]:[#7;a:11]>>[#16:4]-[c:5]1:[c:9](-[c:10]:[#7;a:11]):[#7;a:8]:[c:7]:[n;H0;D3;+0:6]:1-[CH2;D2;+0:1]-[#8:2]-[C:3] | null | [] | null | null | 30 | MINUTE | To a stirred solution of 2-[5-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-pyridine (Tetrahedron Lett. 1976, 285) (1.65 g, 5.51 mmol) in dry DMF (15 mL) was added NaH (60% in mineral oil, 0.36 g, 9.0 mmol) at room temperature under N2. After 30 minutes stirring, SEM-Cl (1.21 mL, 6.83 mmol) was added through a syringe. The sl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccncc1.c1c[nH]cn1 | HCl | CN(C)C=O | null | 0.5 | C[Si](C)(C)CCOCCl.Cc1ccc(S(=O)(=O)c2[nH]cnc2-c2ccccn2)cc1>CN(C)C=O>Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)ncn2COCC[Si](C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bc17dbd7d8ca41a3b3c7c7c6e9e646f3 | Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)ncn2COCC[Si](C)(C)C)cc1.O=Cc1cn(Cc2ccc(Cl)cc2)c2ccccc12>>Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)nc(C(O)c3cn(Cc4ccc(Cl)cc4)c4ccccc34)n2COCC[Si](C)(C)C)cc1 | ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C=O)C=C1.C1(=CC=C(C=C1)S(=O)(=O)C1=C(N=CN1COCC[Si](C)(C)C)C1=NC=CC=C1)C.[Li]CCCC.CCCCCC>>ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(O)C=2N(C(=C(N2)C2=NC=CC=C2)S(=O)(=O)C2=CC=C(C=C2)C)COCC[Si](C)(C)C)C=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[c:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][n:16]3)[n:17][cH:18][n:38]2[CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:44])([CH3:45])[CH3:46])[cH:47][cH:48]1.[CH:19](=[O:20])[c:21]1[cH:22][n:23]([CH2:24][c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[c:32]2[cH:3... | Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)ncn2COCC[Si](C)(C)C)cc1.O=Cc1cn(Cc2ccc(Cl)cc2)c2ccccc12 | Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)nc(C(O)c3cn(Cc4ccc(Cl)cc4)c4ccccc34)n2COCC[Si](C)(C)C)cc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 1429ad5c64747667b11a35a9b6ee20c6ea95d82b5bbcef33ff8f15f573964c71 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | O=S(=O)(c1ccccc1)c1[nH]c(Cc2cn(Cc3ccccc3)c3ccccc23)nc1-c1ccccn1 | [C:1]-[#7;a:2]1:[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7]:[c:8]:1.[C:9]-[#7;a:10]1:[c:11]:[c:12]:[#7;a:13]:[cH;D2;+0:14]:1>>[C:1]-[#7;a:2]1:[c:3]:[c:4](-[CH;D3;+0:5](-[OH;D1;+0:6])-[c;H0;D3;+0:14]2:[#7;a:13]:[c:12]:[c:11]:[#7;a:10]:2-[C:9]):[c:7]:[c:8]:1 | 30 | [{"value": 30.0, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(O)C=2N(C(=C(N2)C2=NC=CC=C2)S(=O)(=O)C2=CC=C(C=C2)C)COCC[Si](C)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.6, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(O)C=2N(C(=C(N2)C2=NC=CC=C2)S(=O)(=O)C2=CC=C(C=C2)C)COCC[Si](C)(C)C)C=C1", "d... | null | null | 20 | MINUTE | To a stirred solution of 2-[5-(toluene-4-sulfonyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-pyridine (0.15 g, 0.35 mmol) in dry THF (10 mL) was added 2.5 M n-BuLi solution in hexane (0.21 mL, 0.525 mmol) under N2 at −78° C. After 20 minutes at this temperature, a solution of N-4-chlorobenzylindole-3-carbox... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccncc1.c1c[nH]cn1.c1ccccc1.c1c[nH]c2ccccc12 | null | C1CCOC1 | null | 0.333333 | Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)ncn2COCC[Si](C)(C)C)cc1.O=Cc1cn(Cc2ccc(Cl)cc2)c2ccccc12>C1CCOC1>Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)nc(C(O)c3cn(Cc4ccc(Cl)cc4)c4ccccc34)n2COCC[Si](C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d976bc6859134fbdb59bda0093445708 | Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)nc(C(=O)c3cn(Cc4ccc(Cl)cc4)c4ccccc34)n2COCC[Si](C)(C)C)cc1>>Cc1ccc(S(=O)(=O)c2[nH]c(C(=O)c3cn(Cc4ccc(Cl)cc4)c4ccccc34)nc2-c2ccccn2)cc1 | ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2N(C(=C(N2)C2=NC=CC=C2)S(=O)(=O)C2=CC=C(C=C2)C)COCC[Si](C)(C)C)C=C1.Cl>>ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2NC(=C(N2)C2=NC=CC=C2)S(=O)(=O)C2=CC=C(C=C2)C)C=C1 | C[Si](C)(C)CCOC[n:10]1[c:9]([S:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:40][cH:39]2)(=[O:7])=[O:8])[c:32](-[c:33]2[cH:34][cH:35][cH:36][cH:37][n:38]2)[n:31][c:11]1[C:12](=[O:13])[c:14]1[cH:15][n:16]([CH2:17][c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]2)[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]12>>[CH3:1][c:2]1[cH:3... | Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)nc(C(=O)c3cn(Cc4ccc(Cl)cc4)c4ccccc34)n2COCC[Si](C)(C)C)cc1 | Cc1ccc(S(=O)(=O)c2[nH]c(C(=O)c3cn(Cc4ccc(Cl)cc4)c4ccccc34)nc2-c2ccccn2)cc1 | null | Cl | CCOCC.C(C)O | Functional Group Interconversion | OtherReaction | 4453229f5d52ab9263f2a1b95ef2960a17d25fe01b1763198b4e3825e08bb196 | 2f92ceb47a2c5f0a05014164c6c0cc7321f1835340f738b5a91e9951d7ee0060 | O=C(c1nc(-c2ccccn2)c(S(=O)(=O)c2ccccc2)[nH]1)c1cn(Cc2ccccc2)c2ccccc12 | C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:1]1:[c:2](-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7]):[#7;a:8]:[c:9](-[c:10]:[#7;a:11]):[c:12]:1-[#16:13]>>[#16:13]-[c:12]1:[nH;D2;+0:1]:[c:2](-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7]):[#7;a:8]:[c:9]:1-[c:10]:[#7;a:11] | 98 | [{"value": 98.0, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2NC(=C(N2)C2=NC=CC=C2)S(=O)(=O)C2=CC=C(C=C2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2NC(=C(N2)C2=NC=CC=C2)S(=O)(=O)C2=CC=C(C=C2)C)C=C1", "details": "CALCULATEDPERCENTYIELD"... | null | null | 18 | HOUR | To a solution of [1-(4-chloro-benzyl)-1H-indol-3-yl]-[4-pyridin-2-yl-5-(toluene-4-sulfonyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanone (15 mg, 21.5 mmol) in ethanol (1 mL) was added 5 drops of 2N HCl. The solution was stirred at room temperature for 18 hours. A solution of 1 M HCl in ether (0.5 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Silyl protective group | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.c1ccccc1.c1c[nH]c2ccccc12.c1ccncc1 | HO- | Cl.CCOCC.C(C)O | null | 18 | Cc1ccc(S(=O)(=O)c2c(-c3ccccn3)nc(C(=O)c3cn(Cc4ccc(Cl)cc4)c4ccccc34)n2COCC[Si](C)(C)C)cc1>Cl.CCOCC.C(C)O>Cc1ccc(S(=O)(=O)c2[nH]c(C(=O)c3cn(Cc4ccc(Cl)cc4)c4ccccc34)nc2-c2ccccn2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-20413ce04b154f219c25441a909e3dde | Brc1cccnc1.C[Si](C)(C)CCOCn1cnc(C=O)c1>>C[Si](C)(C)CCOCn1cnc(C(O)c2cccnc2)c1 | C(C)(=O)OCC.C[Si](CCOCN1C=NC(=C1)C=O)(C)C.BrC=1C=NC=CC1.[Li]CCCC>>N1=CC(=CC=C1)C(O)C=1N=CN(C1)COCC[Si](C)(C)C | Br[c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1.[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[cH:10][n:11][c:12]([CH:13]=[O:14])[cH:21]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[cH:10][n:11][c:12]([CH:13]([OH:14])[c:15]2[cH:16][cH:17][cH:18][n:19][cH:20]2)[cH:21]1 | Brc1cccnc1.C[Si](C)(C)CCOCn1cnc(C=O)c1 | C[Si](C)(C)CCOCn1cnc(C(O)c2cccnc2)c1 | null | null | CCOCC | C-C Coupling | Grignard_alcohol | b19854b2eef93f01734a1ce1e1a8bde192af0da0e7ae2b2f44efcbe0d23365f0 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1cncc(Cc2c[nH]cn2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11](-[CH;D2;+0:12]=[O;H0;D1;+0:13]):[c:14]:1>>[C:7]-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11](-[CH;D3;+0:12](-[OH;D1;+0:13])-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2):[c:14]:1 | null | [] | null | null | 15 | MINUTE | A solution of 3-bromopyridine (1.0 g, 6.33×10−3 mol) was cooled to −78° in a dry ice/acetone bath. To this solution, BuLi (3.48 mL, 6.96×10−3 mol, 2M solution in cyclohexane) was added dropwise and the reaction was stirred for 15 minutes. A solution of 1-(2-trimethylsilanylethoxymethyl)-1H-imidazole-4-carbaldehyde (0.9... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccncc1 | c1ccncc1 | c1c[nH]cn1.c1ccncc1 | Br- | CCOCC | null | 0.25 | Brc1cccnc1.C[Si](C)(C)CCOCn1cnc(C=O)c1>CCOCC>C[Si](C)(C)CCOCn1cnc(C(O)c2cccnc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2308b8a30d7d463382b10ef392265f9a | O=C(c1nc(C(O)c2cccnc2)c[nH]1)c1cn(Cc2ccc(Cl)cc2)c2ccccc12>>O=C(c1cccnc1)c1c[nH]c(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)n1 | ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2NC=C(N2)C(C=2C=NC=CC2)O)C=C1>>ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2NC=C(N2)C(=O)C=2C=NC=CC2)C=C1 | [OH:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1)[c:9]1[cH:10][nH:11][c:12]([C:13](=[O:14])[c:15]2[cH:16][n:17]([CH2:18][c:19]3[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]3)[c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]23)[n:32]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1)[c:9]1[cH:10][nH:11][c:12]([C:13](=[O:14])[c:... | O=C(c1nc(C(O)c2cccnc2)c[nH]1)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | O=C(c1cccnc1)c1c[nH]c(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)n1 | null | O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1cccnc1)c1c[nH]c(C(=O)c2cn(Cc3ccccc3)c3ccccc23)n1 | [O;D1;H0:1]=[C:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6](-[CH;D3;+0:7](-[OH;D1;+0:8])-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]):[#7;a:14]:1>>[O;D1;H0:1]=[C:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13]):[#7;a:14]:1 | 75.6 | [{"value": 75.0, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2NC=C(N2)C(=O)C=2C=NC=CC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.6, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C=2NC=C(N2)C(=O)C=2C=NC=CC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of [1-(4-chlorobenzyl)-1H-indol-3-yl-[4-(hydroxypyridin-3-yl-methyl)-1H-imidazol-2-yl]methanone (20 mg, 4.5×10−5 mol) in CH2Cl2 (5 mL) was added MnO2 (50 mg). The reaction was stirred for 1 hour at room temperature and filtered through celite to produce the desired product as a white solid (yield 15 mg, 7... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccncc1.c1c[nH]cn1.c1ccccc1.c1c[nH]c2ccccc12 | null | O=[Mn]=O.C(Cl)Cl | null | 1 | O=C(c1nc(C(O)c2cccnc2)c[nH]1)c1cn(Cc2ccc(Cl)cc2)c2ccccc12>O=[Mn]=O.C(Cl)Cl>O=C(c1cccnc1)c1c[nH]c(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fd6f0c326a9148ff934b57bc2c62cb8d | CC(C)(N)CO.O=C(O)c1c[nH]cn1>>CC1(C)COC(c2c[nH]cn2)=N1 | NC(CO)(C)C.C(C)N(CC)CC.S(=O)(Cl)Cl.N1C=NC(=C1)C(=O)O.S(=O)(Cl)Cl>>N1C=NC(=C1)C=1OCC(N1)(C)C | [CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[NH2:12].O=[C:6](O)[c:7]1[cH:8][nH:9][cH:10][n:11]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][O:5][C:6]([c:7]2[cH:8][nH:9][cH:10][n:11]2)=[N:12]1 | CC(C)(N)CO.O=C(O)c1c[nH]cn1 | CC1(C)COC(c2c[nH]cn2)=N1 | null | null | C(C)#N | Acylation | OtherReaction | 8349e8085b37b550a682e762f0e69acedc45072a14a4107a16ab0b6fe107183a | ce8f445f68adbc5a0620bff5b5f5a7094d4b1ccc0eb9436ecabaa60f89a0b6d3 | c1nc(C2=NCCO2)c[nH]1 | O-[C;H0;D3;+0:1](=O)-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[NH2;D1;+0:10])-[C:11]-[OH;D1;+0:12]>>[C;D1;H3:7]-[C:8]1(-[C;D1;H3:9])-[C:11]-[O;H0;D2;+0:12]-[C;H0;D3;+0:1](-[c:2]2:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:2)=[N;H0;D2;+0:10]-1 | 60 | [{"value": 60.0, "product": "N1C=NC(=C1)C=1OCC(N1)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 4-Imidazolecarboxylic acid (2 grams, 17.9 mmol) and thionyl chloride (5 mL, 68.5 mmol) were heated to reflux in anhydrous acetonitrile (50 mL) under nitrogen for 1 hour. Then all volatile was removed under vacuum. The conversion to acid chloride is almost quantitative. To a solution of imidazole acid chloride in anhydr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Primary amine | Ether | null | C1=NCCO1 | C1=NCCO1.c1c[nH]cn1 | HO- | C(C)#N | null | 5 | CC(C)(N)CO.O=C(O)c1c[nH]cn1>C(C)#N>CC1(C)COC(c2c[nH]cn2)=N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5f531b14c93e416ba95778738417275e | CO.O=C(O)c1cnc(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)[nH]1>>COC(=O)c1cnc(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)[nH]1 | ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C2=NC=C(N2)C(=O)O)C=C1.S(O)(O)(=O)=O.CO>>COC(=O)C=1NC(=NC1)C(=O)C1=CN(C2=CC=CC=C12)CC1=CC=C(C=C1)Cl | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][n:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]3)[c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]23)[nH:28]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][c:8]([C:9](=[O:10])[c:11]2[cH:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][c:18]([... | CO.O=C(O)c1cnc(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)[nH]1 | COC(=O)c1cnc(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)[nH]1 | null | null | CCCCCC.C(C)(=O)OCC | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | O=C(c1ncc[nH]1)c1cn(Cc2ccccc2)c2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-[C:6]=[O;D1;H0:7]):[#7;a:8]:[c:9]:1.[C;D1;H3:10]-[OH;D1;+0:11]>>[C;D1;H3:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-[C:6]=[O;D1;H0:7]):[#7;a:8]:[c:9]:1 | 89 | [{"value": 89.0, "product": "COC(=O)C=1NC(=NC1)C(=O)C1=CN(C2=CC=CC=C12)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-[1-(4-chloro-benzyl)-1H-indole-3-carbonyl]-3H-imidazole-4-carboxylic acid (60 mg) and concentrated sulfuric acid (1 mL) in methanol (100 mL) was heated to reflux overnight. After removal of solvent, the mixture was dissolved in ethyl acetate and washed with 5% sodium hydroxide solution. The organic laye... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1c[nH]cn1.c1ccccc1.c1c[nH]c2ccccc12 | HO- | CCCCCC.C(C)(=O)OCC | null | null | CO.O=C(O)c1cnc(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)[nH]1>CCCCCC.C(C)(=O)OCC>COC(=O)c1cnc(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4064ef06fe44843a44aa1d2a81431ba | C1COCCN1.O=C(O)c1cnc(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)[nH]1>>O=C(c1ncc(C(=O)N2CCOCC2)[nH]1)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C2=NC=C(N2)C(=O)O)C=C1.Cl.CN(CCCN=C=NCC)C.N1CCOCC1>>ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C2=NC=C(N2)C(=O)N2CCOCC2)C=C1 | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.O[C:7]([c:6]1[cH:5][n:4][c:3]([C:2](=[O:1])[c:16]2[cH:17][n:18]([CH2:19][c:20]3[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]3)[c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]23)[nH:15]1)=[O:8]>>[O:1]=[C:2]([c:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2... | C1COCCN1.O=C(O)c1cnc(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)[nH]1 | O=C(c1ncc(C(=O)N2CCOCC2)[nH]1)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ncc(C(=O)N2CCOCC2)[nH]1)c1cn(Cc2ccccc2)c2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](-[C:6]=[O;D1;H0:7]):[#7;a:8]:[c:9]:1.[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[O;D1;H0:7]=[C:6]-[c:5]1:[#7;a:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-2):[c:9]:[#7;a:8]:1 | 68 | [{"value": 68.0, "product": "ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C(=O)C2=NC=C(N2)C(=O)N2CCOCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 2-[1-(4-chloro-benzyl)-1H-indole-3-carbonyl]-3H-imidazole-4-carboxylic acid (10 mg, 0.026 mmol), 4-(dimethylamino)pyridine (DMAP) (30 mg, 0.25 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (30 mg, 0.16 mmol) in CH2Cl2 (2 mL) was stirred at room temperature under N2 for 1 hour.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1c[nH]cn1.C1COCC[NH]1.c1ccccc1.c1c[nH]c2ccccc12 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | 1 | C1COCCN1.O=C(O)c1cnc(C(=O)c2cn(Cc3ccc(Cl)cc3)c3ccccc23)[nH]1>CN(C1=CC=NC=C1)C.C(Cl)Cl>O=C(c1ncc(C(=O)N2CCOCC2)[nH]1)c1cn(Cc2ccc(Cl)cc2)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ab737bf159040288af138309c872f14 | CCOC(=O)C1C2CCC(=O)C21.O=C(OO)c1cccc(Cl)c1>>CCOC(=O)C1C2CCOC(=O)C21 | ClC1=CC(=CC=C1)C(=O)OO.O=C1C2C(C2CC1)C(=O)OCC.ClC1=CC(=CC=C1)C(=O)OO>>O=C1C2C(C2CCO1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]2[CH2:8][CH2:9][C:11](=[O:12])[CH:13]12.O=C(O[OH:10])c1cccc(Cl)c1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]2[CH2:8][CH2:9][O:10][C:11](=[O:12])[CH:13]12 | CCOC(=O)C1C2CCC(=O)C21.O=C(OO)c1cccc(Cl)c1 | CCOC(=O)C1C2CCOC(=O)C21 | null | null | ClCCl | Acylation | OtherReaction | a8e8469e3623064606fe1b9fd2c891a6a6a63477615e20cd14c3c38c33abfaba | 080a648f0857c5de1d01246bda2c02ea163b62a2a8afe5b93ac413f4b3f0aa2f | O=C1OCCC2CC12 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]1-[C:6]2-[C:7]-1-[C:8]-[CH2;D2;+0:9]-[C;H0;D3;+0:10]-2=[O;D1;H0:11]>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]1-[C:6]2-[C:7]-1-[C:8]-[CH2;D2;+0:9]-[O;H0;D2;+0:1]-[C;H0;D3;+0:10]-2=[O;D1;H0:11] | 60 | [{"value": 60.0, "product": "O=C1C2C(C2CCO1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "O=C1C2C(C2CCO1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To a stirred solution of ethyl (1SR,5RS,6SR)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylate (34.8 g, 207.2 mmol) in dichloromethane (300 mL), 70% m-chloroperbenzoic acid (51.1 g, 207.2 mmol) was added and refluxed overnight. The following day, additional 70% m-chloroperbenzoic acid (51.1 g, 207.2 mmol) was added and reflux c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Peroxide | Ester | C1CC2CC2C1.c1ccccc1 | C1CC2CC2CO1 | C1CC2CC2CO1 | HCl | ClCCl | null | 15 | CCOC(=O)C1C2CCC(=O)C21.O=C(OO)c1cccc(Cl)c1>ClCCl>CCOC(=O)C1C2CCOC(=O)C21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0bf367d4bf6a4f398d1a8705dba7e9f6 | CCOC(=O)C1C2CCOC(=O)C21>>CCOC(=O)C1C2CCOC(O)C21 | O=C1C2C(C2CCO1)C(=O)OCC.[H-].C(C(C)C)[Al+]CC(C)C.C1(=CC=CC=C1)C>>OC1C2C(C2CCO1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]2[CH2:8][CH2:9][O:10][C:11](=[O:12])[CH:13]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH:7]2[CH2:8][CH2:9][O:10][CH:11]([OH:12])[CH:13]12 | CCOC(=O)C1C2CCOC(=O)C21 | CCOC(=O)C1C2CCOC(O)C21 | null | null | O1CCCC1.C(C)(=O)OCC | Reduction | OtherReaction | d7e6ba6b60e184669e950cc4ab06628c2fa554c0c73e10bcc375ae26d30034cb | 2884a5654446a5b733e7d59f144021b82bebc5565dd0ff9b32ffa054af42d6b4 | C1CC2CC2CO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[C:6]-1-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[#8:9]-[C:10]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[C:6]-1-[CH;D3;+0:7](-[OH;D1;+0:8])-[#8:9]-[C:10] | 85 | [{"value": 85.0, "product": "OC1C2C(C2CCO1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a solution of ethyl (1SR,6SR,7SR)-2-oxo-3-oxa-bicyclo[4.1.0]heptane-7-carboxylate (15.2 g, 82.8 mmol) in anhydrous tetrahydrofuran (300 mL) at −78° C. and under argon, a 1.5 M solution of diisobutylaluminium hydride in toluene (82.8 mL, 124.2 mmol) in anhydrous tetrahydrofuran (150 mL) at −78° C. under an argon atmo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ether.Secondary alcohol | C1CC2CC2CO1 | C1CC2CC2CO1 | C1CC2CC2CO1 | null | O1CCCC1.C(C)(=O)OCC | null | 6 | CCOC(=O)C1C2CCOC(=O)C21>O1CCCC1.C(C)(=O)OCC>CCOC(=O)C1C2CCOC(O)C21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-62d3050d48154ceb954c41bb923105d6 | FC(F)(I)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I.Fc1ccc(I)cc1>>Fc1ccc(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)c2ccc(F)cc2)cc1 | FC1=CC=C(C=C1)I.IC(C(C(C(C(C(I)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F>>FC1=CC=C(C=C1)C(C(C(C(C(C(C1=CC=C(C=C1)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F | I[C:2]([F:1])([C:9]([F:10])([F:11])[C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[C:18]([C:6](I)([F:7])[F:8])([F:19])[F:20])[F:22].I[c:5]1[cH:4][cH:3][c:27]([F:28])[cH:32][cH:31]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[C:18]([F:19])([F:20])[C:21]... | FC(F)(I)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I.Fc1ccc(I)cc1 | Fc1ccc(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)c2ccc(F)cc2)cc1 | null | [Cu] | CS(=O)C | C-C Coupling | OtherReaction | 9fd11cda55c2951fcf118877daeae2dabb10ab72374cd9d1cb2b92e436728239 | 9f6c1d75f363da4c528b3a61db2b18c6fe45e3a05a2ecc7409f5ba4bee13846f | c1ccc(CCCCCCc2ccccc2)cc1 | I-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;H0;D1;+0:3])-[C;H0;D4;+0:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[C;H0;D4;+0:13](-[F;D1;H0:14])(-[F;D1;H0:15])-[C;H0;D4;+0:16](-I)(-[F;D1;H0:17])-[F;D1;H0:18].I-[c;H0;D3;+0:19]1:[c:20]:[cH;D2;+0:21]:[c;H0;D3;+0:22](-[F;D1;H... | 74.2 | [{"value": 74.2, "product": "FC1=CC=C(C=C1)C(C(C(C(C(C(C1=CC=C(C=C1)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | 26.64 g of p-fluoroiodobenzene, 100 ml of DMSO and 15.24 g of copper powder were put in a flask under an atmosphere of nitrogen to be sufficiently stirred at a temperature of 110° C. Next, 30.46 g of 1,6-diiodoperfluorohexane was slowly dropped and stirred at a temperature of 120° C. for 20 hours. Then, the reaction so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Aromatic halide.Aromatic halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | I- | [Cu].CS(=O)C | 110 | null | FC(F)(I)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I.Fc1ccc(I)cc1>[Cu].CS(=O)C>Fc1ccc(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)c2ccc(F)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc334cf1803347089b5785dbe2a67908 | CO[Si](CCCSC(C)=O)(OC)OC>>CCC(=O)SCCC[Si](OC)(OC)OC | SCCC[Si](OC)(OC)OC.CSCCC[Si](OC)(OC)OC.[Na+].[Cl-].SCCC[Si](OC)(OC)OC.C[O-].[Na+].C(C)(=O)SCCC[Si](OC)(OC)OC.C[O-].[Na+]>>C(CC)(=O)SCCC[Si](OC)(OC)OC | [CH3:2][C:3](=[O:4])[S:5][CH2:6][CH2:7][CH2:8][Si:9]([O:10][CH3:11])([O:12][CH3:13])[O:14][CH3:15]>>[CH3:1][CH2:2][C:3](=[O:4])[S:5][CH2:6][CH2:7][CH2:8][Si:9]([O:10][CH3:11])([O:12][CH3:13])[O:14][CH3:15] | CO[Si](CCCSC(C)=O)(OC)OC | CCC(=O)SCCC[Si](OC)(OC)OC | null | null | C1(=CC=CC=C1)C | Miscellaneous | Methylation | 6c60a9cd65097a25ff428f775d481db4c10e3c53e07ccd584b19300ed77d7f30 | 6fca8ee80f3da8b18e15687d90afe45d5380c3d17d460e62b59adecbfd8cae6a | null | [#16:1]-[C:2](-[CH3;D1;+0:3])=[O;D1;H0:4]>>[#16:1]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:3]-[C;D1;H3:5] | null | [] | null | null | null | null | 816 grams of 3-mercapto-1-propyltrimethoxysilane, 871 grams of 25 weight percent methanolic solution of sodium methoxide, and 1,724 grams of toluene were charged to a 5-liter flask under an atmosphere of nitrogen. The stirred mixture developed a pinkish color. Methanol was removed from the flask by distilling off a met... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Carbo-thioester | null | null | null | Other | C1(=CC=CC=C1)C | null | null | CO[Si](CCCSC(C)=O)(OC)OC>C1(=CC=CC=C1)C>CCC(=O)SCCC[Si](OC)(OC)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85c466b3af4a4814a936e332c3e38034 | CCC(=O)Cl.CO[Si](CCCS)(OC)OC>>CCC(=O)SCCC[Si](OC)(OC)OC | C(CC)(=O)Cl.[Na+].[Cl-].SCCC[Si](OC)(OC)OC.SCCC[Si](OC)(OC)OC.C[O-].[Na+].CSCCC[Si](OC)(OC)OC.C(C)(=O)SCCC[Si](OC)(OC)OC.C[O-].[Na+]>>C(CC)(=O)SCCC[Si](OC)(OC)OC | Cl[C:3]([CH2:2][CH3:1])=[O:4].[SH:5][CH2:6][CH2:7][CH2:8][Si:9]([O:10][CH3:11])([O:12][CH3:13])[O:14][CH3:15]>>[CH3:1][CH2:2][C:3](=[O:4])[S:5][CH2:6][CH2:7][CH2:8][Si:9]([O:10][CH3:11])([O:12][CH3:13])[O:14][CH3:15] | CCC(=O)Cl.CO[Si](CCCS)(OC)OC | CCC(=O)SCCC[Si](OC)(OC)OC | null | null | C1(=CC=CC=C1)C | Acylation | thioether_nucl_sub | 774e8f449f87493fdbd93fdbbfef7c7bc086966dfce8806abcb487630046ef59 | cf70b55890699bc889b230d5ae9783daf8be8d20d1ad4c06197ffaf659088f4e | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[C:5]-[C:6]-[SH;D1;+0:7]>>[C:5]-[C:6]-[S;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4] | null | [] | null | null | null | null | 1,035 grams of 3-mercapto-1-propyltrimethoxysilane, 1,096 grams of a 25 weight percent methanolic solution of sodium methoxide, and 1,764 grams of toluene were charged to a 5-liter flask under an atmosphere of nitrogen. The stirred mixture developed a pinkish color. The flask was placed into a water bath at 64° C. Meth... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aliphatic thiol | Carbo-thioester | null | null | null | HCl | C1(=CC=CC=C1)C | null | null | CCC(=O)Cl.CO[Si](CCCS)(OC)OC>C1(=CC=CC=C1)C>CCC(=O)SCCC[Si](OC)(OC)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-286bfd62f5834868b927a82799eba4c3 | CCCCCCCC(=O)Cl.CCO[Si](CCCS)(OCC)OCC>>CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC | C(CCCCCCC)(=O)Cl.N#N.SCCC[Si](OCC)(OCC)OCC.[SiH4]>>C(CCCCCCC)(=O)SCCC[Si](OCC)(OCC)OCC | Cl[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:9].[SH:10][CH2:11][CH2:12][CH2:13][Si:14]([O:15][CH2:16][CH3:17])([O:18][CH2:19][CH3:20])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[S:10][CH2:11][CH2:12][CH2:13][Si:14]([O:15][CH2:16][CH3:17])([O:18][CH2:19][CH3:20... | CCCCCCCC(=O)Cl.CCO[Si](CCCS)(OCC)OCC | CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC | null | null | CCCCCC.C(C)N(CC)CC | Acylation | thioether_nucl_sub | 774e8f449f87493fdbd93fdbbfef7c7bc086966dfce8806abcb487630046ef59 | cf70b55890699bc889b230d5ae9783daf8be8d20d1ad4c06197ffaf659088f4e | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[SH;D1;+0:7]>>[C:5]-[C:6]-[S;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 87 | [{"value": 87.0, "product": "C(CCCCCCC)(=O)SCCC[Si](OCC)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.8, "product": "C(CCCCCCC)(=O)SCCC[Si](OCC)(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a 12-liter, three-necked round bottom flask equipped with mechanical stirrer, addition funnel, thermocouple, heating mantle, N2 inlet, and temperature controller were charged 1,021 grams of 3-mercaptopropyltriethoxysilane (SILQUEST® A-1891 silane from OSi Specialties, Inc., a subsidiary of Crompton Corp. of Greenw... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aliphatic thiol | Carbo-thioester | null | null | null | HCl | CCCCCC.C(C)N(CC)CC | null | null | CCCCCCCC(=O)Cl.CCO[Si](CCCS)(OCC)OCC>CCCCCC.C(C)N(CC)CC>CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1825c6f452cb4f8d85e5060a2e2ef1f6 | CCO[Si](CCCCl)(OCC)OCC.O=C(O)Cc1cccs1>>CCO[Si](CCCSC(C)=O)(OCC)OCC | S1C(=CC=C1)CC(=O)O.[O-]CC.[Na+].ClCCC[Si](OCC)(OCC)OCC>>C(C)(=O)SCCC[Si](OCC)(OCC)OCC | Cl[CH2:7][CH2:6][CH2:5][Si:4]([O:3][CH2:2][CH3:1])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17].O[C:9]([CH2:10]c1ccc[s:8]1)=[O:11]>>[CH3:1][CH2:2][O:3][Si:4]([CH2:5][CH2:6][CH2:7][S:8][C:9]([CH3:10])=[O:11])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17] | CCO[Si](CCCCl)(OCC)OCC.O=C(O)Cc1cccs1 | CCO[Si](CCCSC(C)=O)(OCC)OCC | null | null | S1C(=CC=C1)C(=O)O.C(C)O | Acylation | OtherReaction | 63c844c1ec474495593d771b062be3364adf503c0822f2fd1bfb69f229709474 | dfe9fe1a6355f40a3f716cb9a21cc73ccd389fac1a8bf4766414c46a9aa66845 | null | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-c1:[s;H0;D2;+0:7]:c:c:c:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[C;H0;D3;+0:4](-[CH3;D1;+0:6])=[O;D1;H0:5] | 78 | [{"value": 78.0, "product": "C(C)(=O)SCCC[Si](OCC)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This example illustrates the preparation of a thiocarboxylate alkoxysilane from a salt of a thiolcarboxylic acid using as a solvent the alcohol corresponding to the silane alkoxy group. Into a 250 ml, three-neck round bottomed flask equipped with magnetic stir bar, temperature probe/controller, heating mantle, addition... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Carbo-thioester | c1ccsc1 | null | null | HCl | S1C(=CC=C1)C(=O)O.C(C)O | null | null | CCO[Si](CCCCl)(OCC)OCC.O=C(O)Cc1cccs1>S1C(=CC=C1)C(=O)O.C(C)O>CCO[Si](CCCSC(C)=O)(OCC)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3a45e62220434afaa39c76bbec24a902 | CCO[Si](CCl)(OCC)OCC.O=C(O)Cc1cccs1>>CCO[Si](CSC(C)=O)(OCC)OCC | S1C(=CC=C1)CC(=O)O.[O-]CC.[Na+].S1C(=CC=C1)C(=O)O.ClC[Si](OCC)(OCC)OCC>>C(C)(=O)SC[Si](OCC)(OCC)OCC | Cl[CH2:5][Si:4]([O:3][CH2:2][CH3:1])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15].O[C:7]([CH2:8]c1ccc[s:6]1)=[O:9]>>[CH3:1][CH2:2][O:3][Si:4]([CH2:5][S:6][C:7]([CH3:8])=[O:9])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15] | CCO[Si](CCl)(OCC)OCC.O=C(O)Cc1cccs1 | CCO[Si](CSC(C)=O)(OCC)OCC | null | null | COCCOCCOC | Acylation | OtherReaction | 63c844c1ec474495593d771b062be3364adf503c0822f2fd1bfb69f229709474 | dfe9fe1a6355f40a3f716cb9a21cc73ccd389fac1a8bf4766414c46a9aa66845 | null | Cl-[CH2;D2;+0:1]-[#14:2](-[#8:3]-[C:4]-[C;D1;H3:5])(-[#8:6]-[C:7]-[C;D1;H3:8])-[#8:9]-[C:10]-[C;D1;H3:11].O-[C;H0;D3;+0:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-c1:[s;H0;D2;+0:15]:c:c:c:1>>[C;D1;H3:5]-[C:4]-[#8:3]-[#14:2](-[#8:6]-[C:7]-[C;D1;H3:8])(-[#8:9]-[C:10]-[C;D1;H3:11])-[CH2;D2;+0:1]-[S;H0;D2;+0:15]-[C;H0;D3;+0:12](-[C... | 55 | [{"value": 55.0, "product": "C(C)(=O)SC[Si](OCC)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 8 | CELSIUS | null | null | This example illustrates the preparation of a thiocarboxylate alkoxysilane from a salt of a thiolcarboxylic acid using a nonprotic solvent. 88 grams of powdered sodium ethoxide and 600 ml diglyme were charged into a one-liter, three-neck round bottomed flask equipped with magnetic stir bar, temperature probe/controller... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Carbo-thioester | c1ccsc1 | null | null | HCl | COCCOCCOC | 8 | null | CCO[Si](CCl)(OCC)OCC.O=C(O)Cc1cccs1>COCCOCCOC>CCO[Si](CSC(C)=O)(OCC)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-74d4123d0b44420aa4af94621d981895 | OC1(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2-c2c(F)c(F)c(F)c(F)c21>>Fc1c(F)c(F)c(C2c3c(F)c(F)c(F)c(F)c3-c3c(F)c(F)c(F)c(F)c32)c(F)c1F | FC1=C(C(=C(C=2C3=C(C(=C(C(=C3C(C12)(C1=C(C(=C(C(=C1F)F)F)F)F)O)F)F)F)F)F)F)F.P(Br)(Br)Br>>FC1=C(C(=C(C=2C3=C(C(=C(C(=C3C(C12)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F)F)F)F | O[C:8]1([c:7]2[c:5]([F:6])[c:3]([F:4])[c:2]([F:1])[c:31]([F:32])[c:29]2[F:30])[c:9]2[c:10]([F:11])[c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[c:18]2-[c:19]2[c:20]([F:21])[c:22]([F:23])[c:24]([F:25])[c:26]([F:27])[c:28]21>>[F:1][c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([CH:8]2[c:9]3[c:10]([F:11])[c:12]([F:13])[c:14]([F:15])[c:... | OC1(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2-c2c(F)c(F)c(F)c(F)c21 | Fc1c(F)c(F)c(C2c3c(F)c(F)c(F)c(F)c3-c3c(F)c(F)c(F)c(F)c32)c(F)c1F | null | null | null | Reduction | OtherReaction | 195eac6611f3aae2595ed04043ee173b5e8b0ef82ed1c26368fea7acea9768d3 | dfa71f841ee148297c95b5d95b7150768ab9356304fca8dbfde20c6dadd639d3 | c1ccc(C2c3ccccc3-c3ccccc32)cc1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]-[c:8]:[c:9]-1:[c:10]>>[c:10]:[c:9]1:[c:8]-[c:7]:[c:5](:[c:6])-[CH;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 84 | [{"value": 84.0, "product": "FC1=C(C(=C(C=2C3=C(C(=C(C(=C3C(C12)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.5 g (0.009 moles) of 1,2,3,4,5,6,7,8-octafluoro-9-hydroxy-9-(pentafluorophenyl)fluorene thus prepared, are added to 25 ml (0.26 moles) of PBr3 and heated to 1100C for 30 minutes in an inert atmosphere. The reaction mass is hydrolyzed in ice, extracted with ethyl ether, the extract is washed with an aqueous solution (... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccc2c(c1)Cc1ccccc12 | c1ccc2c(c1)Cc1ccccc12 | c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | Other | null | null | null | OC1(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2-c2c(F)c(F)c(F)c(F)c21>>Fc1c(F)c(F)c(C2c3c(F)c(F)c(F)c(F)c3-c3c(F)c(F)c(F)c(F)c32)c(F)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aa57b35910cb4d42b28c1f5616ac8b8a | Nc1cccc2ccccc12.O=C(c1ccccc1)c1cccnc1C(=O)c1ccccc1>>O=C(C1=C(C(=O)c2ccccc2)C(=Nc2cccc3ccccc23)C(=Nc2cccc3ccccc23)N=C1)c1ccccc1 | C(C1=CC=CC=C1)(=O)C=1C(=NC=CC1)C(C1=CC=CC=C1)=O.C1(=CC=CC2=CC=CC=C12)N>>C(C1=CC=CC=C1)(=O)C1=C(C(C(N=C1)=NC1=CC=CC2=CC=CC=C12)=NC1=CC=CC2=CC=CC=C12)C(C1=CC=CC=C1)=O | [NH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12.[O:1]=[C:2]([c:25]1[c:13]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:4][cH:3][cH:38][n:37]1)[c:39]1[cH:40][cH:27][cH:42][cH:43][cH:44]1>>[O:1]=[C:2]([C:3]1=[C:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[C:13](=[... | Nc1cccc2ccccc12.O=C(c1ccccc1)c1cccnc1C(=O)c1ccccc1 | O=C(C1=C(C(=O)c2ccccc2)C(=Nc2cccc3ccccc23)C(=Nc2cccc3ccccc23)N=C1)c1ccccc1 | null | Cl[Ti](Cl)(Cl)Cl | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 81a6ccb3cda3296d33283e168e4be981f2dc4081046fa5f5cf9b53fb1bf47b83 | 2019bdab2c1d3c2433800a65c6a077da0fcbaf1353302aed80ef226b181b1632 | O=C(C1=C(C(=O)c2ccccc2)C(=Nc2cccc3ccccc23)C(=Nc2cccc3ccccc23)N=C1)c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D3;+0:6](-[c:7]1:[c:8]:[c:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:1)-[c;H0;D3;+0:13]1:[n;H0;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:[c;H0;D3;+0:18]:1-[C;H0;D3;+0:19](=[O;D1;H0:20])-[c:21](:[c:22]):[c:23]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[C;H0;D3;+0:16]1=[... | null | [] | null | null | 1 | HOUR | TiCl4 (0.4 ml, 3.5 mmol) in toluene (20 ml) was added to a mixture of dibenzoylpyridine (0.91 g, 3.2 mmol) and 1-naphthylamine (2.90 g, 17 mmol) in toluene (50 ml) at 0° C. After the addition was complete, the reaction was stirred at room temperature for 1 hour and then under refluxed for 3 hours. The solid was filtere... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | Ketone.Ketone.Substituted imine.Substituted imine | c1ccncc1.c1ccccc1 | c1ccc2ccccc2c1.C1=CCCN=C1.c1ccccc1 | c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1.C1=CCCN=C1.c1ccccc1 | Other | Cl[Ti](Cl)(Cl)Cl.C1(=CC=CC=C1)C | null | 1 | Nc1cccc2ccccc12.O=C(c1ccccc1)c1cccnc1C(=O)c1ccccc1>Cl[Ti](Cl)(Cl)Cl.C1(=CC=CC=C1)C>O=C(C1=C(C(=O)c2ccccc2)C(=Nc2cccc3ccccc23)C(=Nc2cccc3ccccc23)N=C1)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fce53349e32d4b5f88198b78c4676895 | CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O.O>>C1CCOC1.CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C... | CC[C@@H]1[C@@]([C@@H]([C@H](N(C[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O.O>>CC[C@@H]1[C@@]([C@@H]([C@H](N(C[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]... | [CH3:1][N:37]([CH3:5])[C@H:36]1[CH2:35][C@@H:33]([CH3:34])[O:32][C@@H:31]([O:30][C@@H:29]2[C@@H:27]([CH3:28])[C@H:14]([O:15][C@H:16]3[CH2:17][C@@:18]([CH3:19])([O:20][CH3:21])[C@@H:22]([OH:23])[C@H:24]([CH3:25])[O:26]3)[C@@H:12]([CH3:13])[C:10](=[O:11])[O:9][C@H:8]([CH2:7][CH3:6])[C@@:55]([CH3:56])([OH:57])[C@H:53]([OH... | CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O.O | C1CCOC1.CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 59eee240871e248dd8776710490902b02362f4d5c232ad403383a07d492f3332 | 82c63b51c39309b197c513db770150d34231b1b511075cf9b084dd6a184c3729 | C1CCOC1.O=C1C[C@@H](O[C@H]2CCCCO2)C[C@@H](O[C@H]2CCCCO2)CCCCNCCCCO1 | [C:1]-[C:2](-[N;H0;D3;+0:3](-[CH3;D1;+0:4])-[CH3;D1;+0:5])-[C:6].[OH2;D0;+0:7]>>[C:1]-[C:2](-[N;H0;D3;+0:3](-[C;D1;H3:8])-[C;D1;H3:9])-[C:6].[C:10]1-[C:11]-[O;H0;D2;+0:7]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-1 | null | [] | null | null | null | null | Form E is prepared by dissolving azithromycin in THF (tetrahydrofuran). Diffusing water vapor through saturated azithromycin THF solution over time yields crystals of Form E.
Conditions: See reaction.notes.procedure_details.
Workup: Form E is prepared | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Ether.Tertiary amine | null | C1CCOC1 | C1CCOC1.C1CCCC[NH]CCCCOCCCC1.C1CCOCC1.C1CCOCC1 | Other | O1CCCC1 | null | null | CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O.O>O1CCCC1>C1CCOC1.CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b0e2dc13002843e39e1710ef993f97c6 | COC(=O)C1CCC(N)CC1O>>O=C1NC2CCC1C(O)C2 | COC(=O)C1C(CC(CC1)N)O.C1(=CC(=CC(=C1)C)C)C>>OC1C2C(NC(C1)CC2)=O | CO[C:2](=[O:1])[CH:7]1[CH2:6][CH2:5][CH:4]([NH2:3])[CH2:10][CH:8]1[OH:9]>>[O:1]=[C:2]1[NH:3][CH:4]2[CH2:5][CH2:6][CH:7]1[CH:8]([OH:9])[CH2:10]2 | COC(=O)C1CCC(N)CC1O | O=C1NC2CCC1C(O)C2 | null | null | null | Miscellaneous | OtherReaction | 1917e3d93e44ef0b9aeacacc3133ab280345b893bc8ff2c2c97f46ea3d611512 | 92bd4402d90a419a2f8338f9414db9222f74d64e606e4b1a47fea24edc8b3ea6 | O=C1NC2CCC1CC2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]-[C:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:7]-[C:6]2-[C:8]-[C:9]-[C:3]-1-[C:4]-[C:5]-2 | null | [] | null | null | null | null | Reaction of compound (3) with mesitylene at elevated temperature (e.g., 165° C.) followed by cooling to rt yields 5-hydroxy-2-aza-bicyclo[2.2.2]octan-3-one (4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | C1CC2CCC1CN2 | C1CC2CCC1CN2 | HO- | null | null | null | COC(=O)C1CCC(N)CC1O>>O=C1NC2CCC1C(O)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b503178708944433a3d3b688745efb78 | O=C1NC2CCC1C(O)C2>>OC1CC2CCC1CN2 | OC1C2C(NC(C1)CC2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C12NCC(C(C1)O)CC2 | O=[C:8]1[CH:7]2[CH:2]([OH:1])[CH2:3][CH:4]([CH2:5][CH2:6]2)[NH:9]1>>[OH:1][CH:2]1[CH2:3][CH:4]2[CH2:5][CH2:6][CH:7]1[CH2:8][NH:9]2 | O=C1NC2CCC1C(O)C2 | OC1CC2CCC1CN2 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | e3912a60e07420dceedf81cc9ae23025efa08e25e9b7d3ebc14126ea63818a24 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | C1CC2CCC1CN2 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](-[C:6])-[CH2;D2;+0:1]-[#7:2]-[C:3] | null | [] | null | null | null | null | Compound (4) can be reacted with LAH in solvent (such as THF), with reflux under nitrogen to yield 2-aza-bicyclo[2.2.2]octane-5-ol (5).
Conditions: See reaction.notes.procedure_details.
Workup: with reflux under nitrogen | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | C1CC2CCC1CN2 | C1CC2CCC1CN2 | C1CC2CCC1CN2 | Other | C1CCOC1 | null | null | O=C1NC2CCC1C(O)C2>C1CCOC1>OC1CC2CCC1CN2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cf1e71fe4c904007a09048112539d7b5 | COc1cc([N+](=O)[O-])ccc1C(=O)O>>O=C(O)c1ccc([N+](=O)[O-])cc1O | CO.COC1=C(C(=O)O)C=CC(=C1)[N+](=O)[O-].B(Br)(Br)Br>>OC1=C(C(=O)O)C=CC(=C1)[N+](=O)[O-] | C[O:13][c:12]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12]1[OH:13] | COc1cc([N+](=O)[O-])ccc1C(=O)O | O=C(O)c1ccc([N+](=O)[O-])cc1O | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 96.4 | [{"value": 96.4, "product": "OC1=C(C(=O)O)C=CC(=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2-methoxy-4-nitro-benzoic acid (20 g, 0.102 mol) in 80 ml of CH2Cl2 at 0° C. was added BBr3 (1.0 M, 150 ml, 1.5 eq.). The resulting mixture was allowed to warm to rt and stirred for 2 h. MeOH was then added dropwise to quench the reaction at 0° C. and the volatile fraction was removed in vacuo. The res... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 2 | COc1cc([N+](=O)[O-])ccc1C(=O)O>C(Cl)Cl>O=C(O)c1ccc([N+](=O)[O-])cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1912afb005594a808886ebd13ae297f1 | CO.O=C(O)c1ccc([N+](=O)[O-])cc1O>>COC(=O)c1ccc([N+](=O)[O-])cc1O | OC1=C(C(=O)O)C=CC(=C1)[N+](=O)[O-].S(O)(O)(=O)=O.CO>>COC(C1=C(C=C(C=C1)[N+](=O)[O-])O)=O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[OH:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[OH:14] | CO.O=C(O)c1ccc([N+](=O)[O-])cc1O | COC(=O)c1ccc([N+](=O)[O-])cc1O | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To a MeOH solution (200 ml) of 2-hydroxy-4-nitro-benzoic acid (18 g) was added concentrated sulfuric acid. The resulting mixture was heated to reflux for 24 h. After it was cooled to rt, volatile was removed in vacuo. The residue was then partitioned between water and EtOAc. The EtOAc layer was washed with water (2×), ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.O=C(O)c1ccc([N+](=O)[O-])cc1O>>COC(=O)c1ccc([N+](=O)[O-])cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b45bffd7f014cd48f64d60f2efc62db | COC(=O)c1ccc([N+](=O)[O-])cc1O>>COC(=O)c1ccc(N)cc1O | COC(C1=C(C=C(C=C1)[N+](=O)[O-])O)=O.C1CCOC1>>COC(C1=C(C=C(C=C1)N)O)=O | O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]([OH:12])[cH:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]1[OH:12] | COC(=O)c1ccc([N+](=O)[O-])cc1O | COC(=O)c1ccc(N)cc1O | null | O=[Pt]=O | CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 101.1 | [{"value": 101.1, "product": "COC(C1=C(C=C(C=C1)N)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Hydroxy-4-nitro-benzoic acid methyl ester (14 g) was dissolved in EtOH (100 ml) and THF (10 ml) and stirred under hydrogen (1 atm) in the presence of PtO2 for 24 h. The reaction mixture was then filtered through a celite bed. The filtrate was concentrated to give 12 g of 4-Amino-2-hydroxy-benzoic acid methyl ester as... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | O=[Pt]=O.CCO | null | null | COC(=O)c1ccc([N+](=O)[O-])cc1O>O=[Pt]=O.CCO>COC(=O)c1ccc(N)cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fa821c7b1b7e410cb3219170c5f20484 | COC(=O)c1ccc(N)cc1O>>CC(=O)O.COC(=O)C1CCC(N)CC1O | COC(C1=C(C=C(C=C1)N)O)=O>>C(C)(=O)O.COC(=O)C1C(CC(CC1)N)O | [cH:1]1[c:9]([C:7](=[O:3])[O:6][CH3:5])[c:15]([OH:16])[cH:14][c:12]([NH2:13])[cH:11]1>>[CH3:1][C:2](=[O:3])[OH:4].[CH3:5][O:6][C:7](=[O:8])[CH:9]1[CH2:10][CH2:11][CH:12]([NH2:13])[CH2:14][CH:15]1[OH:16] | COC(=O)c1ccc(N)cc1O | CC(=O)O.COC(=O)C1CCC(N)CC1O | null | null | CC(=O)O | Functional Group Addition | Arene hydrogenation | f016c105648a33d3cff64e844522022f27224329dd0134929cbd01928d7f53f1 | 6a4ae61b6ded7400fe1119f95023081d237c6ae2706cb77bd73364875f7447a0 | C1CCCCC1 | [C;D1;H3:1]-[#8:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[N;D1;H2:9]):[cH;D2;+0:10]:[c;H0;D3;+0:11]:1-[O;D1;H1:12]>>[C;D1;H3:1]-[#8:2]-[C;H0;D3;+0:3](=[O;D1;H0:13])-[CH;D3;+0:5]1-[C:14]-[CH2;D2;+0:7]-[CH;D3;+0:8](-[N;D1;H2:9])-[CH2;D2;+0:10]-[CH;D3;+0:11]-1-[O;D1;H1:1... | 93.2 | [{"value": 93.2, "product": "C(C)(=O)O.COC(=O)C1C(CC(CC1)N)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Amino-2-hydroxy-benzoic acid methyl ester (10 g) in 200 ml of HOAc was hydrogenated under 56 psi pressure at 60° C. for 42 h. The volatile was then removed. The residue was stirred in 50 ml of 4/1 of ether/EtOH and precipitate formed. Filtration gave 6.5 g of 4-amino-2-hydroxy-cyclohexanecarboxylic acid methyl ester ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic alcohol | Carboxylic acid.Ester.Secondary alcohol | c1ccccc1 | C1CCCCC1 | C1CCCCC1 | Other | CC(=O)O | null | null | COC(=O)c1ccc(N)cc1O>CC(=O)O>CC(=O)O.COC(=O)C1CCC(N)CC1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ee14ef9802374bb18184286fb77e884c | COC(=O)C1CCC(N)CC1O>>O=C1NC2CCC1C(O)C2 | C(C)(=O)O.COC(=O)C1C(CC(CC1)N)O>>OC1C2C(NC(C1)CC2)=O | CO[C:2](=[O:1])[CH:7]1[CH2:6][CH2:5][CH:4]([NH2:3])[CH2:10][CH:8]1[OH:9]>>[O:1]=[C:2]1[NH:3][CH:4]2[CH2:5][CH2:6][CH:7]1[CH:8]([OH:9])[CH2:10]2 | COC(=O)C1CCC(N)CC1O | O=C1NC2CCC1C(O)C2 | null | null | C1(=CC(=CC(=C1)C)C)C | Miscellaneous | OtherReaction | 1917e3d93e44ef0b9aeacacc3133ab280345b893bc8ff2c2c97f46ea3d611512 | 92bd4402d90a419a2f8338f9414db9222f74d64e606e4b1a47fea24edc8b3ea6 | O=C1NC2CCC1CC2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]-[C:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:7]-[C:6]2-[C:8]-[C:9]-[C:3]-1-[C:4]-[C:5]-2 | 72.6 | [{"value": 72.6, "product": "OC1C2C(NC(C1)CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Amino-2-hydroxy-cyclohexanecarboxylic acid methyl ester acetic acid salt (6.6 g) was heated to reflux in mesitylene (60 ml) for 3 h. After cooling to rt, solvent was decanted and the crystals were washed with hexane three times to provide 2.9 g of 5-hydroxy-2-aza-bicyclo[2.2.2]octan-3-one (M+: 141).
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | C1CC2CCC1CN2 | C1CC2CCC1CN2 | HO- | C1(=CC(=CC(=C1)C)C)C | null | null | COC(=O)C1CCC(N)CC1O>C1(=CC(=CC(=C1)C)C)C>O=C1NC2CCC1C(O)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-48de3044de514cad8592433ee383241a | O=C1NC2CCC1C(O)C2>>OC1CC2CCC1CN2 | OC1C2C(NC(C1)CC2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C12NCC(C(C1)O)CC2 | O=[C:8]1[CH:7]2[CH:2]([OH:1])[CH2:3][CH:4]([CH2:5][CH2:6]2)[NH:9]1>>[OH:1][CH:2]1[CH2:3][CH:4]2[CH2:5][CH2:6][CH:7]1[CH2:8][NH:9]2 | O=C1NC2CCC1C(O)C2 | OC1CC2CCC1CN2 | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | e3912a60e07420dceedf81cc9ae23025efa08e25e9b7d3ebc14126ea63818a24 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | C1CC2CCC1CN2 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](-[C:6])-[CH2;D2;+0:1]-[#7:2]-[C:3] | 139.8 | [{"value": 139.8, "product": "C12NCC(C(C1)O)CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-hydroxy-2-aza-bicyclo[2.2.2]octan-3-one (2.6 g, 18 mmol) in 60 ml of anhydrous THF was added 55 ml of LAH (1.0 M in THF). After the mixture was refluxed under N2 for 24 h, it was cooled to rt and quenched with 2 ml of water, followed by 2 ml of 15% NaOH and 6 ml of water. The suspension was then stir... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | C1CC2CCC1CN2 | C1CC2CCC1CN2 | C1CC2CCC1CN2 | Other | C1CCOC1 | null | null | O=C1NC2CCC1C(O)C2>C1CCOC1>OC1CC2CCC1CN2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9206c04afd5e46ee8b918e129e7dcd7a | CCOP(OCC)OCC.Clc1ccc(CBr)cc1Cl>>CCOP(=O)(Cc1ccc(Cl)c(Cl)c1)OCC | P([O-])([O-])[O-].C(C)OP(OCC)OCC.ClC=1C=C(CBr)C=CC1Cl.C(C)OP(OCC)OCC>>C(C)OP(OCC)(=O)CC1=CC(=C(C=C1)Cl)Cl | CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:15][CH2:16][CH3:17].Br[CH2:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14]1)[O:15][CH2:16][CH3:17] | CCOP(OCC)OCC.Clc1ccc(CBr)cc1Cl | CCOP(=O)(Cc1ccc(Cl)c(Cl)c1)OCC | null | null | null | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C-[O;H0;D2;+0:5]-[P;H0;D3;+0:6](-[#8:7]-[C:8])-[#8:9]-[C:10]>>[C:8]-[#8:7]-[P;H0;D4;+0:6](=[O;H0;D1;+0:5])(-[#8:9]-[C:10])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 80 | CELSIUS | null | null | Triethylphosphite (4.28 ml) was added dropwise to 3,4-dichlorobenzylbromide (6.0 g, 25 mmol) at rt with stirring. After 1 ml of triethylphosphite was added, the mixture was heated to 80° C. until an exothermic reaction was started. The remaining phosphite was added at a rate sufficient to maintain the reflux. After the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1 | HBr | null | 80 | null | CCOP(OCC)OCC.Clc1ccc(CBr)cc1Cl>>CCOP(=O)(Cc1ccc(Cl)c(Cl)c1)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce628456443e443baa5b2213a7275376 | CC(C)(C)OC(=O)N1CC2CCC1CC2=Cc1ccc(Cl)c(Cl)c1>>CC(C)(C)OC(=O)N1CC2CCC1CC2Cc1ccc(Cl)c(Cl)c1 | C(C)(C)(C)OC(=O)N1C2CC(C(C1)CC2)=CC2=CC(=C(C=C2)Cl)Cl.CCO>>C(C)(C)(C)OC(=O)N1C2CC(C(C1)CC2)CC2=CC(=C(C=C2)Cl)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]2[CH2:11][CH2:12][CH:13]1[CH2:14][C:15]2=[CH:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[c:22]([Cl:23])[cH:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]2[CH2:11][CH2:12][CH:13]1[CH2:14][CH:15]2[CH2:16][c:17]1[cH:18][cH:19][c:20... | CC(C)(C)OC(=O)N1CC2CCC1CC2=Cc1ccc(Cl)c(Cl)c1 | CC(C)(C)OC(=O)N1CC2CCC1CC2Cc1ccc(Cl)c(Cl)c1 | null | O=[Pt]=O | CCOC(=O)C | Reduction | Hydrogenation (double to single) | 35b11a50381c784f672ad7297be3d356451f3f2517b5f5253ed3e73874f1135c | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CC2CC3CCC2CN3)cc1 | [C:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-[C:6]-[C;H0;D3;+0:7]-1=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-[C:6]-[CH;D3;+0:7]-1-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11] | 88.4 | [{"value": 88.4, "product": "C(C)(C)(C)OC(=O)N1C2CC(C(C1)CC2)CC2=CC(=C(C=C2)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-(3,4-Dichloro-benzylidene)-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester (0.45 g) was stirred under 1 atm of H2 in 20 ml of 1:1 of EtOH:EtOAc in the presence of PtO2 for 20 min. The reaction mixture was filtered through celite and concentrated to give 0.4 g of 5-(3,4-dichloro-benzyl)-2-aza-bicyclo[2.2... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CC2CCC1C[NH]2 | C1CC2CCC1C[NH]2 | c1ccccc1.C1CC2CCC1C[NH]2 | null | O=[Pt]=O.CCOC(=O)C | null | null | CC(C)(C)OC(=O)N1CC2CCC1CC2=Cc1ccc(Cl)c(Cl)c1>O=[Pt]=O.CCOC(=O)C>CC(C)(C)OC(=O)N1CC2CCC1CC2Cc1ccc(Cl)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-44ae9cae3c594257b3e75c823ab048f1 | CC(C)(C)OC(=O)N1CC2CCC1CC2Cc1ccc(Cl)c(Cl)c1>>Clc1ccc(CC2CC3CCC2CN3)cc1Cl | C(C)(C)(C)OC(=O)N1C2CC(C(C1)CC2)CC2=CC(=C(C=C2)Cl)Cl.ClCl.C(=O)(C(F)(F)F)O>>ClC=1C=C(CC2C3CNC(C2)CC3)C=CC1Cl | CC(C)(C)OC(=O)[N:14]1[CH:9]2[CH2:8][CH:7]([CH2:6][c:5]3[cH:4][cH:3][c:2]([Cl:1])[c:16]([Cl:17])[cH:15]3)[CH:12]([CH2:11][CH2:10]2)[CH2:13]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH:7]2[CH2:8][CH:9]3[CH2:10][CH2:11][CH:12]2[CH2:13][NH:14]3)[cH:15][c:16]1[Cl:17] | CC(C)(C)OC(=O)N1CC2CCC1CC2Cc1ccc(Cl)c(Cl)c1 | Clc1ccc(CC2CC3CCC2CN3)cc1Cl | null | null | null | Reduction | Boc amine deprotection | 5091de91ddb9e214175a2319ca749cd723edf44fd299461038b1f29f2d3eb7a2 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CC2CC3CCC2CN3)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4](-[C:5])-[C:6]>>[C:5]-[C:4](-[C:6])-[NH;D2;+0:1]-[C:2]-[C:3] | 96.8 | [{"value": 96.8, "product": "ClC=1C=C(CC2C3CNC(C2)CC3)C=CC1Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5-(3,4-dichloro-benzyl)-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester (0.24 g, 0.65 mmol) in 2 mL of CH2 Cl2 was added 1 mL of TFA. After the mixture was stirred at rt for 1 h, it was quenched with NaHCO3 (sat.). It was then extracted with CH2Cl2 and the organic layer was washed with Na... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC2CCC1C[NH]2 | C1CC2CCC1CN2 | c1ccccc1.C1CC2CCC1CN2 | HO- | null | null | 1 | CC(C)(C)OC(=O)N1CC2CCC1CC2Cc1ccc(Cl)c(Cl)c1>>Clc1ccc(CC2CC3CCC2CN3)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ae678e9bb372491a819577284c2f7716 | Cc1ccc(C(=O)NC(CO)C(C)C)cc1>>Cc1ccc(C(=O)NC(C=O)C(C)C)cc1 | C=1C=C[NH+]=CC1.[O-][Cr](=O)(=O)Cl.OCC(C(C)C)NC(C1=CC=C(C=C1)C)=O>>C(=O)C(C(C)C)NC(C1=CC=C(C=C1)C)=O | [CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][CH:9]([CH2:10][OH:11])[CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[NH:8][CH:9]([CH:10]=[O:11])[CH:12]([CH3:13])[CH3:14])[cH:15][cH:16]1 | Cc1ccc(C(=O)NC(CO)C(C)C)cc1 | Cc1ccc(C(=O)NC(C=O)C(C)C)cc1 | null | null | CCOCC.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH2;D2;+0:6]-[OH;D1;+0:7]>>[C:1]-[C:2](-[#7:3]-[C:4]=[O;D1;H0:5])-[CH;D2;+0:6]=[O;H0;D1;+0:7] | 34.2 | [{"value": 34.2, "product": "C(=O)C(C(C)C)NC(C1=CC=C(C=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a suspension of PCC in 20 mL of CH2Cl2 was added N-(1-hydroxymethyl-2-methyl-propyl)-4-methyl-benzamide (2.2 g, 10 mmol) in 15 mL of CH2Cl2. After the mixture was stirred for 1.5 h, it was diluted with Et2O and filtered through a celite bed. The filtrate was concentrated and the residue purified on a silica gel colu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | CCOCC.C(Cl)Cl | null | 1.5 | Cc1ccc(C(=O)NC(CO)C(C)C)cc1>CCOCC.C(Cl)Cl>Cc1ccc(C(=O)NC(C=O)C(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-55b815432aad4d159e753de12c860ab4 | CC(C)(C)OC(=O)OC(C)(C)C.O=C1CC2CCC(C1)N2>>CC(C)(C)OC(=O)N1C2CCC1CC(=O)C2 | Cl.C12CC(CC(CC1)N2)=O.C(C)(C)(C)OC(OC(C)(C)C)=O>>C(C)(C)(C)OC(=O)N1C2CC(CC1CC2)=O | CC(C)(C)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]1[CH:9]2[CH2:10][CH2:11][CH:12]1[CH2:13][C:14](=[O:15])[CH2:16]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH:9]2[CH2:10][CH2:11][CH:12]1[CH2:13][C:14](=[O:15])[CH2:16]2 | CC(C)(C)OC(=O)OC(C)(C)C.O=C1CC2CCC(C1)N2 | CC(C)(C)OC(=O)N1C2CCC1CC(=O)C2 | null | null | CCO | Protection | Boc amine protection of secondary amine | 519761b43f4cc2e3964bf4294005ce7f3bca6ecbaccc7f40bf7b7d5c48dc8bba | f0869a0b34976f381b42755ff52efacfde708ff6f8d3c39d434136b4f68fd40e | O=C1CC2CCC(C1)N2 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[O;D1;H0:8]=[C:9]1-[C:10]-[C:11]2-[C:12]-[C:13]-[C:14](-[C:15]-1)-[NH;D2;+0:16]-2>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:16]1-[C:11]2-[C:12]-[C:13]-[C:14]-1-[C:15]-[C:9... | 99.1 | [{"value": 99.1, "product": "C(C)(C)(C)OC(=O)N1C2CC(CC1CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of 8-aza-bicyclo[3.2.1]octan-3-one hydrochloride (4.5 g, 0.028 mol) in 100 mL of EtOH was added carbonic acid di-tert-butyl ester (12 g, 2 eq.) and 11 mL of TEA. The resulting mixture was heated at 60° C. for 3 h. The volatile fraction was removed and the residue was partitioned between EtOAc and water. T... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Secondary amine.Boc.Boc | Carbamic ester | C1CC2CCC(C1)N2 | C1CC2CCC(C1)[NH]2 | C1CC2CCC(C1)[NH]2 | HO- | CCO | 60 | null | CC(C)(C)OC(=O)OC(C)(C)C.O=C1CC2CCC(C1)N2>CCO>CC(C)(C)OC(=O)N1C2CCC1CC(=O)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ebee6e095942447a958113ac2ece4f20 | CC(C)(C)OC(=O)N1C2CCC1CC(=Cc1ccc(Cl)c(Cl)c1)C2>>CC(C)(C)OC(=O)N1C2CCC1CC(Cc1ccc(Cl)c(Cl)c1)C2 | C(C)(C)(C)OC(=O)N1C2CC(CC1CC2)=CC2=CC(=C(C=C2)Cl)Cl>>C(C)(C)(C)OC(=O)N1C2CC(CC1CC2)CC2=CC(=C(C=C2)Cl)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH:9]2[CH2:10][CH2:11][CH:12]1[CH2:13][C:14](=[CH:15][c:16]1[cH:17][cH:18][c:19]([Cl:20])[c:21]([Cl:22])[cH:23]1)[CH2:24]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH:9]2[CH2:10][CH2:11][CH:12]1[CH2:13][CH:14]([CH2:15][c:16]1[cH:17][cH:18][c:19]([Cl:... | CC(C)(C)OC(=O)N1C2CCC1CC(=Cc1ccc(Cl)c(Cl)c1)C2 | CC(C)(C)OC(=O)N1C2CCC1CC(Cc1ccc(Cl)c(Cl)c1)C2 | null | O=[Pt]=O | CCO.CCOC(=O)C | Reduction | Hydrogenation (double to single) | 61359dbf105e04824331d15315b59607f568509a6885b5623edd9a28008b713e | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CC2CC3CCC(C2)N3)cc1 | [c:1]:[c:2](-[CH;D2;+0:3]=[C;H0;D3;+0:4]1-[C:5]-[C:6]-[#7:7]-[C:8]-[C:9]-1):[c:10]>>[c:1]:[c:2](-[CH2;D2;+0:3]-[CH;D3;+0:4]1-[C:5]-[C:6]-[#7:7]-[C:8]-[C:9]-1):[c:10] | 84 | [{"value": 84.0, "product": "C(C)(C)(C)OC(=O)N1C2CC(CC1CC2)CC2=CC(=C(C=C2)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3,4-Dichloro-benzylidene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (1.0 g, 2.7 mmol) in 10 mL of EtOH and 10 mL of EtOAc was stirred with 25 mg of PtO2 under 1 atm of H2 at rt for 3 h. It was then filtered through a celite bed and the filtrate was concentrated. The residue was purified on a sili... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CC2CCC(C1)[NH]2 | C1CC2CCC(C1)[NH]2 | C1CC2CCC(C1)[NH]2.c1ccccc1 | null | O=[Pt]=O.CCO.CCOC(=O)C | null | null | CC(C)(C)OC(=O)N1C2CCC1CC(=Cc1ccc(Cl)c(Cl)c1)C2>O=[Pt]=O.CCO.CCOC(=O)C>CC(C)(C)OC(=O)N1C2CCC1CC(Cc1ccc(Cl)c(Cl)c1)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc5d6d3efe544eaeb49452f7c8ca9b47 | CC(C)(C)OC(=O)N1C2CCC1CC(Cc1ccc(Cl)c(Cl)c1)C2>>Clc1ccc(CC2CC3CCC(C2)N3)cc1Cl | C(C)(C)(C)OC(=O)N1C2CC(CC1CC2)CC2=CC(=C(C=C2)Cl)Cl.C(=O)(C(F)(F)F)O>>ClC=1C=C(CC2CC3CCC(C2)N3)C=CC1Cl | CC(C)(C)OC(=O)[N:14]1[CH:9]2[CH2:8][CH:7]([CH2:6][c:5]3[cH:4][cH:3][c:2]([Cl:1])[c:16]([Cl:17])[cH:15]3)[CH2:13][CH:12]1[CH2:11][CH2:10]2>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH:7]2[CH2:8][CH:9]3[CH2:10][CH2:11][CH:12]([CH2:13]2)[NH:14]3)[cH:15][c:16]1[Cl:17] | CC(C)(C)OC(=O)N1C2CCC1CC(Cc1ccc(Cl)c(Cl)c1)C2 | Clc1ccc(CC2CC3CCC(C2)N3)cc1Cl | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bc1078c51d2c1bcda18d21ba95df06b7f944f6a8c8cb6b8b6cf32743c1438d87 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CC2CC3CCC(C2)N3)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2](-[C:3])-[C:4]-[C:5]-[C:6]-1-[C:7]>>[C:3]-[C:2]1-[C:4]-[C:5]-[C:6](-[C:7])-[NH;D2;+0:1]-1 | 98.4 | [{"value": 98.4, "product": "ClC=1C=C(CC2CC3CCC(C2)N3)C=CC1Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3,4-Dichloro-benzyl)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.35 g, 0.94 mmol) was stirred in 2 mL of CH2Cl2 with 0.5 mL of TFA at rt for 3 h. After being quenched with 20% NaOH to basic medium, the mixture was extracted with EtOAc. The organic layer was washed with NaCl (sat.), dried over Na... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC2CCC(C1)[NH]2 | C1CC2CCC(C1)N2 | c1ccccc1.C1CC2CCC(C1)N2 | HO- | C(Cl)Cl | null | null | CC(C)(C)OC(=O)N1C2CCC1CC(Cc1ccc(Cl)c(Cl)c1)C2>C(Cl)Cl>Clc1ccc(CC2CC3CCC(C2)N3)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb248a4f42a842708b15e43336f8ae83 | COP(OC)OC.Clc1ccc(CBr)cc1>>COP(=O)(Cc1ccc(Cl)cc1)OC | COP(OC)OC.ClC1=CC=C(CBr)C=C1>>COP(OC)(=O)CC1=CC=C(C=C1)Cl | C[O:4][P:3]([O:2][CH3:1])[O:13][CH3:14].Br[CH2:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[CH3:1][O:2][P:3](=[O:4])([CH2:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[O:13][CH3:14] | COP(OC)OC.Clc1ccc(CBr)cc1 | COP(=O)(Cc1ccc(Cl)cc1)OC | null | null | null | Miscellaneous | OtherReaction | 0cee6f48ecb82f0bf47fd5d9d42e2dd8fcb51b36e7641d6549e2ebcac266a3bf | 60e0209a3e01281b77ea7e07e181a846736713b5a4a90ae8d47a0480f9ce79e5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[P;H0;D3;+0:6](-[#8:7]-[C;D1;H3:8])-[#8:9]-[C;D1;H3:10]>>[C;D1;H3:8]-[#8:7]-[P;H0;D4;+0:6](=[O;H0;D1;+0:5])(-[#8:9]-[C;D1;H3:10])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 93 | [{"value": 93.0, "product": "COP(OC)(=O)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.3, "product": "COP(OC)(=O)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a stirred solution of trimethylphosphite (0.57 ml, 4.9 mmol) was added 4-chlorobenzylbromide (1.0 g, 4.9 mmol) at rt. The resulting mixture was stirred at rt for 5 min. and then heated in an oil bath at 80° C. for 20 min. It was cooled to rt and the product purified on a silica-gel column with 25% EtOAc in hexane to... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1 | HBr | null | null | 0.083333 | COP(OC)OC.Clc1ccc(CBr)cc1>>COP(=O)(Cc1ccc(Cl)cc1)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4d774f7c7a4402abeb9dbcc1620b356 | CC(N)CN1C2CCC1CC(Cc1ccc(Cl)cc1)C2.COc1cc(N=C=O)cc(OC)c1OC>>O=C1NC2CCC1C(O)C2 | ClC1=CC=C(CC2CC3CCC(C2)N3CC(C)N)C=C1.COC=1C=C(C=C(C1OC)OC)N=C=O>>OC1C2C(NC(C1)CC2)=O | CC(N)CN1[CH:4]2[CH2:5][CH2:6][CH:7]1C[CH:8](Cc1ccc(Cl)cc1)[CH2:10]2.COc1cc([N:3]=[C:2]=[O:1])cc([O:9]C)c1OC>>[O:1]=[C:2]1[NH:3][CH:4]2[CH2:5][CH2:6][CH:7]1[CH:8]([OH:9])[CH2:10]2 | CC(N)CN1C2CCC1CC(Cc1ccc(Cl)cc1)C2.COc1cc(N=C=O)cc(OC)c1OC | O=C1NC2CCC1C(O)C2 | null | null | C(Cl)Cl | Acylation | OtherReaction | 091d79ae60e53bf682d6f02055f116e435ae9d3019f1b815fc646d7ce20da705 | 7faaae824a78ddff6f18f31143dc1edf7b4a33d6eb2adde89738aa67c9f01932 | O=C1NC2CCC1CC2 | C-C(-N)-C-N1-[CH;D3;+0:1]2-[C:2]-[CH;D3;+0:3](-C-c3:c:c:c(-Cl):c:c:3)-C-[CH;D3;+0:4]-1-[C:5]-[C:6]-2.C-O-c1:c:c(-[N;H0;D2;+0:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]):c:c(-[O;H0;D2;+0:10]-C):c:1-O-C>>[O;D1;H0:9]=[C;H0;D3;+0:8]1-[NH;D2;+0:7]-[CH;D3;+0:1]2-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:10])-[CH;D3;+0:4]-1-[C:5]-[C:6]-2 | 55 | [{"value": 55.0, "product": "OC1C2C(NC(C1)CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 2-[3-(4-chlorobenzyl)-8-aza-bicyclo[3.2.1]oct-8-yl]-1-methyl-ethylamine in CH2Cl2 was added 3,4,5-trimethoxyphenylisocyanate at −78° C. After the addition, it was allowed to warm up to rt where it was stirred for 4 h. It was then diluted with CH2Cl2. The organic layer was washed with NaCl (sat.) and dr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Ether.Isocyanate.Primary amine.Tertiary amine | Secondary amide.Secondary alcohol | C1CC2CCC(C1)N2.c1ccccc1.c1ccccc1 | C1CC2CCC1CN2 | C1CC2CCC1CN2 | HCl | C(Cl)Cl | null | 4 | CC(N)CN1C2CCC1CC(Cc1ccc(Cl)cc1)C2.COc1cc(N=C=O)cc(OC)c1OC>C(Cl)Cl>O=C1NC2CCC1C(O)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-23f198ef4e9e47f1a2a8dd10acbcbbba | CC(N)CN1C2CCC1CC(Cc1ccc(Cl)cc1)C2>>OC1CC2CCC1CN2 | ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.Cl.CS(=O)(=O)C=1C=C(C=CC1)N.[N-]=C=O.ClC1=CC=C(CC2CC3CCC(C2)N3CC(C)N)C=C1>>C12NCC(C(C1)O)CC2 | CC(N)C[N:9]1[CH:4]2[CH2:3][CH:2](Cc3ccc(Cl)cc3)[CH2:8][CH:7]1[CH2:6][CH2:5]2>>[OH:1][CH:2]1[CH2:3][CH:4]2[CH2:5][CH2:6][CH:7]1[CH2:8][NH:9]2 | CC(N)CN1C2CCC1CC(Cc1ccc(Cl)cc1)C2 | OC1CC2CCC1CN2 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 8467f5c8c6569dadff72439090ac5fb4a7b3b1d50e70fce31113e3c40a90437b | f73e452cbf9c00fc806cfb5b02d46cf1158828e998063579a6deb3fb2eef7d3c | C1CC2CCC1CN2 | C-C(-N)-C-[N;H0;D3;+0:1]1-[C:2]2-[C:3]-[CH;D3;+0:4](-C-c3:c:c:c(-Cl):c:c:3)-[CH2;D2;+0:5]-[CH;D3;+0:6]-1-[C:7]-[C:8]-2>>[O;D1;H1:9]-[CH;D3;+0:4]1-[C:3]-[C:2]2-[C:8]-[C:7]-[CH;D3;+0:6]-1-[CH2;D2;+0:5]-[NH;D2;+0:1]-2 | 55 | [{"value": 55.0, "product": "C12NCC(C(C1)O)CC2", "details": "PERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 45 | MINUTE | To a solution of triphosgene (0.22 g, 0.33 eq.) in CH2Cl2 was added 3-methane-sulfonyl-phenylamine hydrochloride (0.5 g, 2.4 mmol), followed by the dropwise addition of TEA (0.37 ml, 1.1 eq.). The mixture was heated to 40° C. for 30 min. It was allowed to cool to rt and stirred for an additional 45 min. The isocyanate ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Tertiary amine | Secondary alcohol.Secondary amine | C1CC2CCC(C1)[NH]2.c1ccccc1 | C1CC2CCC1CN2 | C1CC2CCC1CN2 | HCl | C(Cl)Cl | 40 | 0.75 | CC(N)CN1C2CCC1CC(Cc1ccc(Cl)cc1)C2>C(Cl)Cl>OC1CC2CCC1CN2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0971232d3b6d429393204000125b63f4 | CCN1CCNCC1.Cc1ccc(NC(=O)c2ccc(CCl)cc2)cc1Nc1nccc(-c2cccnc2)n1>>CCN1CCN(Cc2ccc(C(=O)Nc3ccc(C)c(Nc4nccc(-c5cccnc5)n4)c3)cc2)CC1 | Cl.ClCC1=CC=C(C(=O)NC2=CC(=C(C=C2)C)NC2=NC=CC(=N2)C=2C=NC=CC2)C=C1.C(C)N1CCNCC1>>C(C)N1CCN(CC1)CC1=CC=C(C(=O)NC2=CC(=C(C=C2)C)NC2=NC=CC(=N2)C=2C=NC=CC2)C=C1 | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:37][CH2:38]1.Cl[CH2:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[NH:14][c:15]2[cH:16][cH:17][c:18]([CH3:19])[c:20]([NH:21][c:22]3[n:23][cH:24][cH:25][c:26](-[c:27]4[cH:28][cH:29][cH:30][n:31][cH:32]4)[n:33]3)[cH:34]2)[cH:35][cH:36]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([C... | CCN1CCNCC1.Cc1ccc(NC(=O)c2ccc(CCl)cc2)cc1Nc1nccc(-c2cccnc2)n1 | CCN1CCN(Cc2ccc(C(=O)Nc3ccc(C)c(Nc4nccc(-c5cccnc5)n4)c3)cc2)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b703623ddc3b029d4716c15f5414f41773434bcc7e3f3853faf62273596bed77 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(Nc1cccc(Nc2nccc(-c3cccnc3)n2)c1)c1ccc(CN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1):[c:4] | null | [] | null | null | null | null | A suspension of 466 mg (1 mmol) of 4-chloromethyl-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide hydrochloride in 25 ml of dry ethanol is treated with 381 μl (3 mmol) N-ethylpiperazine and then heated under reflux for 16 hours. The yellow solution is cooled to room temperature and decanted from a ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1 | HCl | C(C)O | null | null | CCN1CCNCC1.Cc1ccc(NC(=O)c2ccc(CCl)cc2)cc1Nc1nccc(-c2cccnc2)n1>C(C)O>CCN1CCN(Cc2ccc(C(=O)Nc3ccc(C)c(Nc4nccc(-c5cccnc5)n4)c3)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5a591d52583e406b91b766cc7f618e39 | C1CNCCN1.Cc1ccc(NC(=O)c2ccc(CCl)cc2)cc1Nc1nccc(-c2cccnc2)n1>>Cc1ccc(NC(=O)c2ccc(CN3CCNCC3)cc2)cc1Nc1nccc(-c2cccnc2)n1 | N1CCNCC1.ClCC1=CC=C(C(=O)NC2=CC(=C(C=C2)C)NC2=NC=CC(=N2)C=2C=NC=CC2)C=C1>>CC1=C(C=C(C=C1)NC(C1=CC=C(C=C1)CN1CCNCC1)=O)NC1=NC=CC(=N1)C=1C=NC=CC1 | [NH:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1.Cl[CH2:13][c:12]1[cH:11][cH:10][c:9]([C:7]([NH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[c:23]([NH:24][c:25]3[n:26][cH:27][cH:28][c:29](-[c:30]4[cH:31][cH:32][cH:33][n:34][cH:35]4)[n:36]3)[cH:22]2)=[O:8])[cH:21][cH:20]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[... | C1CNCCN1.Cc1ccc(NC(=O)c2ccc(CCl)cc2)cc1Nc1nccc(-c2cccnc2)n1 | Cc1ccc(NC(=O)c2ccc(CN3CCNCC3)cc2)cc1Nc1nccc(-c2cccnc2)n1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61ec49e5207aa33ebff7094bb66b1d997d4af14524931a8b3643ef7a94219a9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(Nc1cccc(Nc2nccc(-c3cccnc3)n2)c1)c1ccc(CN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1):[c:4] | null | [] | null | null | null | null | 25.8 g (300 mmol) of piperazine are suspended in a mixture of 25 ml of ethanol and 25 ml of water. After almost a clear solution has formed, 12.9 g (30 mmol) of 4-chloromethyl-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide are added step by step. The yellow solution is boiled under reflux for 14 h... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1C[NH]CCN1 | c1ccccc1.c1ccccc1.C1C[NH]CCN1.c1cncnc1.c1ccncc1 | HCl | O.C(C)O | null | null | C1CNCCN1.Cc1ccc(NC(=O)c2ccc(CCl)cc2)cc1Nc1nccc(-c2cccnc2)n1>O.C(C)O>Cc1ccc(NC(=O)c2ccc(CN3CCNCC3)cc2)cc1Nc1nccc(-c2cccnc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-06c95230022b4108a66d024c80f0fd2b | Cc1ccc(NC(=O)c2ccc(CN3CCNCC3)cc2)cc1Nc1nccc(-c2cccnc2)n1>>Cc1ccc(NC(=O)c2ccc(CN3CCNCC3)cc2)cc1Nc1nccc(-c2cccnc2)n1 | CC1=C(C=C(C=C1)NC(C1=CC=C(C=C1)CN1CCNCC1)=O)NC1=NC=CC(=N1)C=1C=NC=CC1.CS(=O)(=O)O.C(C)(=O)OCC>>CS(=O)(=O)O.CC1=C(C=C(C=C1)NC(C1=CC=C(C=C1)CN1CCNCC1)=O)NC1=NC=CC(=N1)C=1C=NC=CC1 | [CH3:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]([CH2:18][N:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)[cH:25][cH:26]2)[cH:27][c:28]1[NH:29][c:30]1[n:31][cH:32][cH:33][c:34](-[c:35]2[cH:36][cH:37][cH:38][n:39][cH:40]2)[n:41]1>>[CH3:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:1... | Cc1ccc(NC(=O)c2ccc(CN3CCNCC3)cc2)cc1Nc1nccc(-c2cccnc2)n1 | Cc1ccc(NC(=O)c2ccc(CN3CCNCC3)cc2)cc1Nc1nccc(-c2cccnc2)n1 | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(Nc1cccc(Nc2nccc(-c3cccnc3)n2)c1)c1ccc(CN2CCNCC2)cc1 | null | null | [] | null | null | null | null | 4.8 g (10 mmol) of N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-4-piperazin-1-ylmethyl-benzamide are dissolved in 20 ml of ethanol under heating and 0.99 g of methanesulfonic acid are added. After addition of ethyl acetate the product cristallizes. Drying at 50 mbar and 60° C. yields N-[4-methyl-3-(4-pyri... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.C1C[NH]CCN1.c1cncnc1.c1ccncc1 | null | C(C)O | null | null | Cc1ccc(NC(=O)c2ccc(CN3CCNCC3)cc2)cc1Nc1nccc(-c2cccnc2)n1>C(C)O>Cc1ccc(NC(=O)c2ccc(CN3CCNCC3)cc2)cc1Nc1nccc(-c2cccnc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e0d738309634983917a5ab5ec75e95e | COc1c(Cl)ccnc1CO.O=S(Cl)Cl>>COc1c(Cl)ccnc1CCl | Cl.OCC1=NC=CC(=C1OC)Cl.S(=O)(Cl)Cl>>ClCC1=NC=CC(=C1OC)Cl | O[CH2:10][c:9]1[c:3]([O:2][CH3:1])[c:4]([Cl:5])[cH:6][cH:7][n:8]1.O=S(Cl)[Cl:11]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][n:8][c:9]1[CH2:10][Cl:11] | COc1c(Cl)ccnc1CO.O=S(Cl)Cl | COc1c(Cl)ccnc1CCl | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccncc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | A 1000 ml round-bottom flask is loaded with 67 g (0.319 mol) of 2-hydroxymethyl-3-methoxy-4-chloro-pyridine hydrochloride and 469 ml of toluene. 73 g (0.606 mol) of thionyl chloride are then dropped therein, under stirring and at inner temperature of about 15–25° C. After completion of the addition, the mixture is wash... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccncc1 | HCl | C1(=CC=CC=C1)C | null | null | COc1c(Cl)ccnc1CO.O=S(Cl)Cl>C1(=CC=CC=C1)C>COc1c(Cl)ccnc1CCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-10712981336d48529ad7b571d5791d5b | C1OCC2OC12.Cc1sc(C)c(Br)c1Br>>Cc1sc(C)c([C@@H]2COC[C@H]2O)c1Br | C(CCC)[Li].BrC1=C(SC(=C1Br)C)C.O1C2COCC21.B(F)(F)F.CCOCC.[Cl-].[NH4+]>>BrC=1C(=C(SC1C)C)[C@H]1[C@@H](COC1)O | [CH:7]12[CH2:8][O:9][CH2:10][CH:11]1[O:12]2.Br[c:6]1[c:4]([CH3:5])[s:3][c:2]([CH3:1])[c:13]1[Br:14]>>[CH3:1][c:2]1[s:3][c:4]([CH3:5])[c:6]([C@@H:7]2[CH2:8][O:9][CH2:10][C@H:11]2[OH:12])[c:13]1[Br:14] | C1OCC2OC12.Cc1sc(C)c(Br)c1Br | Cc1sc(C)c([C@@H]2COC[C@H]2O)c1Br | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 34ab992d0566ada1f0de348a60b1b5386b79aa4a7bf11ea78f2cf789c203b388 | 79fd712a2a6d6b4abbd49e003e84f4018bdf16c930e348b877ef642996ef6e0f | c1cc([C@H]2CCOC2)cs1 | Br-[c;H0;D3;+0:1]1:[c:2](-[Br;D1;H0:3]):[c:4](-[C;D1;H3:5]):[#16;a:6]:[c:7]:1-[C;D1;H3:8].[#8:9]1-[C:10]-[CH;D3;+0:11]2-[O;H0;D2;+0:12]-[CH;D3;+0:13]-2-[C:14]-1>>[Br;D1;H0:3]-[c:2]1:[c:4](-[C;D1;H3:5]):[#16;a:6]:[c:7](-[C;D1;H3:8]):[c;H0;D3;+0:1]:1-[C@@H;D3;+0:13]1-[C:14]-[#8:9]-[C:10]-[C@H;D3;+0:11]-1-[OH;D1;+0:12] | 64 | [{"value": 64.0, "product": "BrC=1C(=C(SC1C)C)[C@H]1[C@@H](COC1)O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | n-Butyllithium (1.6 M in hexane; 0.239 mol) is added dropwise to a solution of 3,4-dibromo-2,5-dimethylthiophene (0.239 mol) in 325 ml of THF which has been cooled to −78° C. and the mixture is stirred for 30 minutes. 3,4-Epoxytetrahydrofuran (0.217 mol) and boron trifluoride etherate (0.217 mol) are added dropwise to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Secondary alcohol | C1OCC2OC12.c1ccsc1 | c1ccsc1.C1CCOC1 | c1ccsc1.C1CCOC1 | Br- | C1CCOC1 | -78 | 0.5 | C1OCC2OC12.Cc1sc(C)c(Br)c1Br>C1CCOC1>Cc1sc(C)c([C@@H]2COC[C@H]2O)c1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2e6d7b8a1d69492fbb66425e55f40318 | Cc1sc(C)c([C@@H]2COC[C@H]2O)c1Br>>Cc1sc(C)c([C@H]2COC[C@@H]2O)c1Br | BrC=1C(=C(SC1C)C)[C@H]1[C@@H](COC1)O>>BrC=1C(=C(SC1C)C)[C@@H]1[C@H](COC1)O | [CH3:1][c:2]1[s:3][c:4]([CH3:5])[c:6]([C@@H:7]2[CH2:8][O:9][CH2:10][C@H:11]2[OH:12])[c:13]1[Br:14]>>[CH3:1][c:2]1[s:3][c:4]([CH3:5])[c:6]([C@H:7]2[CH2:8][O:9][CH2:10][C@@H:11]2[OH:12])[c:13]1[Br:14] | Cc1sc(C)c([C@@H]2COC[C@H]2O)c1Br | Cc1sc(C)c([C@H]2COC[C@@H]2O)c1Br | null | null | C(C)(=O)OC=C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cc([C@@H]2CCOC2)cs1 | null | 49 | [{"value": 49.0, "product": "BrC=1C(=C(SC1C)C)[C@@H]1[C@H](COC1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Solid Novozym 435 is added to a solution of trans-4-(4-bromo-2,5-dimethyl-3-thienyl)tetrahydro-3-furanol (0.153 mol) in 425 ml of vinyl acetate and the mixture is subsequently stirred for 24 hours. The enzyme is removed by filtration and the residue is washed with tert-butyl methyl ether. After removal of the solvent, ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccsc1.C1CCOC1 | null | C(C)(=O)OC=C | null | 24 | Cc1sc(C)c([C@@H]2COC[C@H]2O)c1Br>C(C)(=O)OC=C>Cc1sc(C)c([C@H]2COC[C@@H]2O)c1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0350bb6b14d0439995b609b641c91c4c | N.O=S(=O)([O-])Cc1noc2ccccc12>>NS(=O)(=O)Cc1noc2ccccc12 | P(=O)(Cl)(Cl)Cl.N.O1N=C(C2=C1C=CC=C2)CS(=O)(=O)[O-].[Na+]>>O1N=C(C2=C1C=CC=C2)CS(=O)(=O)N | [NH3:1].[O-][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[n:7][o:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[NH2:1][S:2](=[O:3])(=[O:4])[CH2:5][c:6]1[n:7][o:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | N.O=S(=O)([O-])Cc1noc2ccccc12 | NS(=O)(=O)Cc1noc2ccccc12 | null | null | C(C)N(CC)CC.ClCCCl | Miscellaneous | OtherReaction | f47eed3889b7e1c7487503cbd9b23ac5e2c98ed985b9c43afc1d785dd582a6d2 | e0c9535a79541a221b34be25cb1dd2b86cec670153c63c845fb668f1cf23f7ef | c1ccc2oncc2c1 | [#8;a:1]:[#7;a:2]:[c:3]-[C:4]-[S;H0;D4;+0:5](-[O-])(=[O;D1;H0:6])=[O;D1;H0:7].[NH3;D0;+0:8]>>[#8;a:1]:[#7;a:2]:[c:3]-[C:4]-[S;H0;D4;+0:5](-[NH2;D1;+0:8])(=[O;D1;H0:6])=[O;D1;H0:7] | null | [] | null | null | 90 | MINUTE | Water is removed by distillation from the above mixture of 1,2-benzisoxazole-3-acetic acid and 1,2-dichloroethane, and thereto is added dropwise chlorosulfonic acid (15.5 g) while the internal temperature is kept at 63° C.–79° C. After the addition, the mixture is stirred for 90 minutes while the reaction temperature i... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonamide | null | null | c1ccc2oncc2c1 | HO- | C(C)N(CC)CC.ClCCCl | null | 1.5 | N.O=S(=O)([O-])Cc1noc2ccccc12>C(C)N(CC)CC.ClCCCl>NS(=O)(=O)Cc1noc2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6a4f55d4da7243c497ba1cf1ccce3590 | NO.O=c1cc(O)c2ccccc2o1>>O=C(O)Cc1noc2ccccc12 | OC1=CC(OC2=CC=CC=C12)=O.S(=O)(=O)(O)O.NO.O.[OH-].[Na+]>>O1N=C(C2=C1C=CC=C2)CC(=O)O | [NH2:6][OH:7].O[c:5]1[cH:4][c:2](=[O:1])[o:3][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[n:6][o:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | NO.O=c1cc(O)c2ccccc2o1 | O=C(O)Cc1noc2ccccc12 | null | O.O.[Na+].[Na+].C(CN(CC(=O)[O-])CC(=O)[O-])N(CC(=O)O)CC(=O)O | ClCCCl | Miscellaneous | OtherReaction | 7e8c0ef2db7ee8cbd673497cf17d75c203116752546c13da49c5bc00994d2e95 | 4c6c79326fa7ceb7b50bc253dbf70ad39f8b3e19baa9d9825598ca6724d23848 | c1ccc2oncc2c1 | O-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](=[O;D1;H0:4]):[o;H0;D2;+0:5]:[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:1:[c:10].[NH2;D1;+0:11]-[OH;D1;+0:12]>>[O;D1;H0:4]=[C;H0;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:11]:[o;H0;D2;+0:12]:[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:1:[c:10] | null | [] | null | null | null | null | A mixture of hydroxylamine sulfate (344.0 g), water (904 ml) and a 25% aqueous sodium hydroxide solution (456 ml) is stirred, and thereto are added 4-hydroxycoumarin (168.0 g) and ethylenediaminetetraacetic acid disodium salt dihydrate (3.2 g), and the mixture is stirred with heating at 84° C.–86° C. for 4 hours. The r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Carboxylic acid | c1ccc2ccccc2o1 | c1ccc2oncc2c1 | c1ccc2oncc2c1 | HO- | O.O.[Na+].[Na+].C(CN(CC(=O)[O-])CC(=O)[O-])N(CC(=O)O)CC(=O)O.ClCCCl | null | null | NO.O=c1cc(O)c2ccccc2o1>O.O.[Na+].[Na+].C(CN(CC(=O)[O-])CC(=O)[O-])N(CC(=O)O)CC(=O)O.ClCCCl>O=C(O)Cc1noc2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0312240b097548b8b92e9321f813fe82 | CCOC(=O)C(=O)C(=O)C(C)C(=O)OCC>>CCOC(=O)CC(=O)C(C)C(=O)OCC | P(=O)([O-])([O-])[O-].[K+].[K+].[K+].[Na+].[Cl-].O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C(C)OC(C(C(C(C(=O)OCC)=O)=O)C)=O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>C(C)OC(C(C(CC(=O)OCC)=O)C)=O | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[CH:9]([CH3:10])[C:11](=[O:12])[O:13][CH2:14][CH3:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH:9]([CH3:10])[C:11](=[O:12])[O:13][CH2:14][CH3:15] | CCOC(=O)C(=O)C(=O)C(C)C(=O)OCC | CCOC(=O)CC(=O)C(C)C(=O)OCC | null | null | OCC(O)CO.CS(=O)C.C(C)(=O)OCC | Reduction | OtherReaction | c79d5fb7bac7eec837ba56bdf9a57f6cbc3aa865e7f94a9dcf0dd29f470fadba | b8bba43edff2dc8a2f51a23e766981b44ec41bd6be908e83b9aeb1399d621733 | null | O=[C;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[C:8]-[C:9](-[#8:10])=[O;D1;H0:11]>>[#8:10]-[C:9](=[O;D1;H0:11])-[C:8]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5] | null | [] | null | null | 48 | HOUR | To 40 mL of 300 mM potassium phosphate buffer, pH=6.5, containing NaCl (100 mM), DMSO (3% v:v), glucose (200 mM), and glycerol (10% v:v), 40 mM of 2-methyl-3-ketoketoglutarate diethyl ester was added along with 100 mg of lyophilized KRED 1008 and 30 mg of glucose dehydrogenase. The reaction mixture was incubated for 48... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | null | null | null | Other | OCC(O)CO.CS(=O)C.C(C)(=O)OCC | null | 48 | CCOC(=O)C(=O)C(=O)C(C)C(=O)OCC>OCC(O)CO.CS(=O)C.C(C)(=O)OCC>CCOC(=O)CC(=O)C(C)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cb2716e4893e47f5b420d1a47f407af7 | CCOC(=O)C(=O)C(=O)C(CC(C)C)C(=O)OCC>>CCOC(=O)CC(=O)C(CC(C)C)C(=O)OCC | P(=O)([O-])([O-])[O-].[K+].[K+].[K+].[Na+].[Cl-].O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C(C)OC(C(C(C(C(=O)OCC)=O)=O)CC(C)C)=O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>C(C)OC(C(C(CC(=O)OCC)=O)CC(C)C)=O | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[CH:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[C:14](=[O:15])[O:16][CH2:17][CH3:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[C:14](=[O:15])[O:16][CH2:17][CH3:18] | CCOC(=O)C(=O)C(=O)C(CC(C)C)C(=O)OCC | CCOC(=O)CC(=O)C(CC(C)C)C(=O)OCC | null | null | OCC(O)CO.CS(=O)C.C(C)(=O)OCC | Reduction | OtherReaction | c79d5fb7bac7eec837ba56bdf9a57f6cbc3aa865e7f94a9dcf0dd29f470fadba | b8bba43edff2dc8a2f51a23e766981b44ec41bd6be908e83b9aeb1399d621733 | null | O=[C;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[C:8]-[C:9](-[#8:10])=[O;D1;H0:11]>>[#8:10]-[C:9](=[O;D1;H0:11])-[C:8]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5] | null | [] | null | null | 48 | HOUR | To 40 mL of 300 mM potassium phosphate buffer buffer, pH=6.5, containing NaCl (100 mM), DMSO (3% v:v), glucose (200 mM), and glycerol (10% v:v), 40 mM of 2-isobutyl-3-ketoketoglutarate diethyl ester was added along with 100 mg of lyophilized KRED 1001 and 30 mg of glucose dehydrogenase. The reaction mixture was incubat... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | null | null | null | Other | OCC(O)CO.CS(=O)C.C(C)(=O)OCC | null | 48 | CCOC(=O)C(=O)C(=O)C(CC(C)C)C(=O)OCC>OCC(O)CO.CS(=O)C.C(C)(=O)OCC>CCOC(=O)CC(=O)C(CC(C)C)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe5a93f582484808a034a7efc31e9e80 | CCOC(=O)CC(=O)C(Cc1ccccc1)C(=O)OCC>>CCOC(=O)CC(O)C(Cc1ccccc1)C(=O)OCC | C(C1=CC=CC=C1)C(C(=O)[O-])C(CC(=O)[O-])=O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C=3C=CC=CC3)N)C(=O)O)C.C(C)OC(C(C(CC(=O)OCC)=O)CC1=CC=CC=C1)=O.CC(C)S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[... | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[O:19][CH2:20][CH3:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([OH:8])[CH:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[O:19][CH2:20][CH3:21] | CCOC(=O)CC(=O)C(Cc1ccccc1)C(=O)OCC | CCOC(=O)CC(O)C(Cc1ccccc1)C(=O)OCC | null | null | CS(=O)C.C(C)(=O)OCC | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccccc1 | [C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[C:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:1]-[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[CH;D3;+0:7](-[OH;D1;+0:8])-[C:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13] | null | [] | null | null | null | null | Whole cell reductions of 2-benzyl-3-ketoglutarate were carried out using E. coli cells expressing the gene encoding KRED 1008. Cells were grown overnight at 30 C in 400 mL of a Luria Broth/glucose (2 g/L)/ampicillin (100 mg/L) media. The cells were isolated by centrifugation and re-suspended in 400 mL of a minimal salt... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1 | null | CS(=O)C.C(C)(=O)OCC | null | null | CCOC(=O)CC(=O)C(Cc1ccccc1)C(=O)OCC>CS(=O)C.C(C)(=O)OCC>CCOC(=O)CC(O)C(Cc1ccccc1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-78349326ce1745d5a8f9bd4e604b64fd | CCOC(=O)CC(=O)C(Cc1ccccc1)C(=O)OCC>>CCOC(=O)C(O)C(Cc1ccccc1)C(=O)OCC | P(=O)([O-])([O-])[O-].[K+].[K+].[K+].[Cl-].[Na+].C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C4N=CN=C5N)OP(=O)(O)O)O)O)O)C(=O)N.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C(C)OC(C(C(CC(=O)OCC)=O)CC1=CC=CC=C1)=O>>C(C)OC(C(C(C(... | C([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])(=[O:7])[CH:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH3:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([OH:7])[CH:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH3:20] | CCOC(=O)CC(=O)C(Cc1ccccc1)C(=O)OCC | CCOC(=O)C(O)C(Cc1ccccc1)C(=O)OCC | null | null | null | Miscellaneous | OtherReaction | 42794165314049326ee1dffd47d8fe0d2c939e3a95e9b0e824e5ea3fa6e8969b | c6c48f97e822386f20555b91ae7345b8601049c257ff3628372f98fb0ea2791e | c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[C:6]-[c:7])-C(=[O;H0;D1;+0:8])-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[C:6]-[c:7])-[CH;D3;+0:9](-[OH;D1;+0:8])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13] | null | [] | null | null | 20 | HOUR | The procedure of Example 4 was repeated for the screening of the KRED-8000 kit with 3-benzyloxaloacetate diethyl ester. Enzymes KRED 1008 and KRED 1004 showed complete reduction to the alcohol. Both reactions were repeated in larger scale for the purpose of isolating the product and verifying the structure using 1H NMR... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ester.Ester.Secondary alcohol | null | null | c1ccccc1 | Other | null | null | 20 | CCOC(=O)CC(=O)C(Cc1ccccc1)C(=O)OCC>>CCOC(=O)C(O)C(Cc1ccccc1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b394c90f30ef4dbe873e3d28389884e7 | CN.COC(C)(C)C.O=S(=O)(F)C(F)(F)C(F)(F)F.O=S(=O)(O)O>>CN(CCO)S(=O)(=O)C(F)(F)C(F)(F)F.CNS(=O)(=O)C(F)(F)C(F)(F)F | S(O)(O)(=O)=O.C(F)(F)(C(F)(F)F)S(=O)(=O)F.CN.CC(C)(C)OC>>C(F)(F)(C(F)(F)F)S(=O)(=O)N(C)CCO.C(F)(F)(C(F)(F)F)S(=O)(=O)NC | [CH3:1][NH2:2].O([CH3:16])[C:24]([CH3:3])([CH3:4])[CH3:21].[S:6](=[O:7])(=[O:8])([C:9]([F:10])([C:12]([F:13])([F:14])[F:15])[F:27])[F:11].O[S:18]([OH:5])(=[O:19])=[O:20]>>[CH3:1][N:2]([CH2:3][CH2:4][OH:5])[S:6](=[O:7])(=[O:8])[C:9]([F:10])([F:11])[C:12]([F:13])([F:14])[F:15].[CH3:16][NH:17][S:18](=[O:19])(=[O:20])[C:21... | CN.COC(C)(C)C.O=S(=O)(F)C(F)(F)C(F)(F)F.O=S(=O)(O)O | CN(CCO)S(=O)(=O)C(F)(F)C(F)(F)F.CNS(=O)(=O)C(F)(F)C(F)(F)F | null | null | null | Acylation | OtherReaction | 32c218843c2eef4fba93b830e842717b926a63d3106553ce002f3868ddd25fe4 | d97cca2930ce3f841c78285cc306ed3dfcdd2541356a20e071545f436079d495 | null | O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[C;D1;H3:5]-[NH2;D1;+0:6].[CH3;D1;+0:7]-O-[C;H0;D4;+0:8](-[CH3;D1;+0:9])(-[CH3;D1;+0:10])-[CH3;D1;+0:11].[F;D1;H0:12]-[C;H0;D4;+0:13](-[F;H0;D1;+0:14])(-[C:15](-[F;D1;H0:16])(-[F;D1;H0:17])-[F;D1;H0:18])-[S;H0;D4;+0:19](-[F;H0;D1;+0:20])(=[O;D1;H0:21])=[O;D1;H0:... | null | [] | null | null | null | null | C2F5SO2N(CH3)CH2CH2OH was prepared from C2F5SO2F by reaction with monomethylamine in MTBE, followed by stripping of the solvent, acidification with 19% sulfuric acid, then water washing and distillation at 5.5 mm at a head temperature of 69° C. to give C2F5SO2N(CH3)H. The C2F5SO2N(CH3)H was then reacted with 3 equivale... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ether.Primary amine.Sulfonyl halide | Sulfonamide.Trifluoro group.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol.Tertiary amine | null | null | null | HO- | null | null | null | CN.COC(C)(C)C.O=S(=O)(F)C(F)(F)C(F)(F)F.O=S(=O)(O)O>>CN(CCO)S(=O)(=O)C(F)(F)C(F)(F)F.CNS(=O)(=O)C(F)(F)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7f2048978df4d2dbe4ccf298a04a8c3 | CC(C)(C)OC(=O)CBr.CS(=O)(=O)O.C[Si](C)(C)O[C@H](CCl)CC#N>>CC(C)(C)OC(=O)CC(=O)C[C@H](O)CCl | Cl.ClC[C@H](CC#N)O[Si](C)(C)C.C(C)(C)(C)OC(CBr)=O.CS(=O)(=O)O>>C(C)(C)(C)OC(CC(C[C@@H](CCl)O)=O)=O | Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].CS(=O)(O)=[O:10].C[Si](C)(C)[O:13][C@@H:12]([CH2:11][C:9]#N)[CH2:14][Cl:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[CH2:11][C@H:12]([OH:13])[CH2:14][Cl:15] | CC(C)(C)OC(=O)CBr.CS(=O)(=O)O.C[Si](C)(C)O[C@H](CCl)CC#N | CC(C)(C)OC(=O)CC(=O)C[C@H](O)CCl | null | [Zn] | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 779941a43d4bb5968b55b31d74b1c38d699161cea3051f97a6dcd28a40e7dbe2 | b4716721929ed2f87cdf47416c9420d9b1f7e0a4d8e8cf823341f9ede3b4d3c4 | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].C-S(-O)(=O)=[O;H0;D1;+0:9].C-[Si](-C)(-C)-[O;H0;D2;+0:10]-[C:11](-[C:12])-[C:13]-[C;H0;D2;+0:14]#N>>[C:12]-[C:11](-[OH;D1;+0:10])-[C:13]-[C;H0;D3;+0:14](=[O;H0;D1;+0:9])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])... | 87 | [{"value": 87.0, "product": "C(C)(C)(C)OC(CC(C[C@@H](CCl)O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Zinc dust (690 mg), tetrahydrofuran (4.0 mL), and methanesulfonic acid (10 mg) were introduced into a reaction vessel and the mixture was stirred under reflux. To the mixture was added (S)-4-chloro-3-trimethylsilanyloxybutyronitrile (1.00 g) and subsequently t-butylbromoacetate (2.04 g) over 1 hour. The mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Nitrile.Sulfonic acid.Silyl protective group | Ketone.Ester.Secondary alcohol | null | null | null | HBr | [Zn].O1CCCC1 | 0 | null | CC(C)(C)OC(=O)CBr.CS(=O)(=O)O.C[Si](C)(C)O[C@H](CCl)CC#N>[Zn].O1CCCC1>CC(C)(C)OC(=O)CC(=O)C[C@H](O)CCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c55acf361bef4b1091052b3ba3b0acef | CC(C)(C)OCl.Cc1cc([N+](=O)[O-])ccc1N>>Cc1cc([N+](=O)[O-])cc(Cl)c1N | CC1=C(N)C=CC(=C1)[N+](=O)[O-].ClOC(C)(C)C>>ClC1=C(N)C(=CC(=C1)[N+](=O)[O-])C | CC(C)(C)O[Cl:10].[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][cH:9][c:11]1[NH2:12]>>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([Cl:10])[c:11]1[NH2:12] | CC(C)(C)OCl.Cc1cc([N+](=O)[O-])ccc1N | Cc1cc([N+](=O)[O-])cc(Cl)c1N | null | null | O.C1(=CC=CC=C1)C | Functional Group Interconversion | Chlorination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | C-C(-C)(-C)-O-[Cl;H0;D1;+0:1].[N;D1;H2:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[N;D1;H2:2]):[c:4] | 80.6 | [{"value": 80.0, "product": "ClC1=C(N)C(=CC(=C1)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.6, "product": "ClC1=C(N)C(=CC(=C1)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-methyl-4-nitroaniline (56.0 g, 0.368 mol) was dispersed in toluene (430 ml) in a 1 liter four-neck flask. Tertiary butyl hypochloride (46.0 g, 0.423 mol) was added dropwise thereto, while cooled in iced water and stirred. The mixture was stirred at room temperature for 3 hours. The solids were filtered and washed thr... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O.C1(=CC=CC=C1)C | null | null | CC(C)(C)OCl.Cc1cc([N+](=O)[O-])ccc1N>O.C1(=CC=CC=C1)C>Cc1cc([N+](=O)[O-])cc(Cl)c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dfeb1845e3c64641adbb749bf3e8956f | Cc1cc(N)cc(Cl)c1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>Cc1cc(Cl)cc(N=C=O)c1 | ClC=1C=C(N)C=C(C1)C.C(C)N(CC)CC.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>ClC=1C=C(C=C(C1)C)N=C=O | [CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]([NH2:8])[cH:11]1.ClC(Cl)(Cl)O[C:9](OC(Cl)(Cl)Cl)=[O:10]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]([N:8]=[C:9]=[O:10])[cH:11]1 | Cc1cc(N)cc(Cl)c1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | Cc1cc(Cl)cc(N=C=O)c1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 38334b31448e1d8428e2cb6569eceaecc2305b2359c734a98433aa0746ff9140 | a539b8d5e65abe163774733461d6850ba8234d38df1df3c2ccdeef5ce9de389b | c1ccccc1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | 30 | MINUTE | Triphosgene (17.01 g, 0.0573 mol) was dissolved in 200 ml of toluene in a 1 liter flask. 150 ml of a toluene solution of 3-chloro-5-methylaniline (21.9 g, 0.155 mol) and triethylamine (36.0 ml) was added dropwise thereto over 30 minutes at room temperature.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Primary amine | Isocyanate | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | 0.5 | Cc1cc(N)cc(Cl)c1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>C1(=CC=CC=C1)C>Cc1cc(Cl)cc(N=C=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-235e9784afc141d3be6661cba6cb882e | C=CCBr.CC(C)(C)OC(=O)Nc1ccon1>>C=CCN1OC=CC1NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NC1=NOC=C1.[H-].[Na+].C(C=C)Br>>C(C=C)N1OC=CC1NC(=O)OC(C)(C)C | Br[CH2:3][CH:2]=[CH2:1].[n:4]1[o:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]>>[CH2:1]=[CH:2][CH2:3][N:4]1[O:5][CH:6]=[CH:7][CH:8]1[NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16] | C=CCBr.CC(C)(C)OC(=O)Nc1ccon1 | C=CCN1OC=CC1NC(=O)OC(C)(C)C | null | null | O.C(OC)COC | Heteroatom Alkylation and Arylation | OtherReaction | 7132a17ae95e3b8c6f504f9fee066c707c19d172afc370e8b416ac6b6345fabe | 5513cb5ef6b4f4059f75fd4463c40b436b61da15f056772a566098ce6491e45e | C1=CONC1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[o;H0;D2;+0:15]:[n;H0;D2;+0:16]:1>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:16]1-[O;H0;D2;+0:15]-[CH;D2;+0:14]=[CH;D2;+0:13]-[CH;D3;+0:12]-1-[#7:11]-[C:9](... | 99.6 | [{"value": 99.6, "product": "C(C=C)N1OC=CC1NC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | 3-(t-Butoxycarbonylamino)isoxazole (12 g, 65.2 mM) was dissolved in dimethoxyethane (150 ml) and cooled to 0° C. under nitrogen. To the stirred solution was added sodium hydride (60% in oil, 2.87 g, 71.7 mM), and the mixture stirred 20 minutes. Allyl bromide (8.7 g, 71.7 mM) was added dropwise, and the mixture stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Allyl | Tertiary amine.Allyl | c1cnoc1 | C1=CO[NH]C1 | C1=CO[NH]C1 | Br- | O.C(OC)COC | 0 | 0.333333 | C=CCBr.CC(C)(C)OC(=O)Nc1ccon1>O.C(OC)COC>C=CCN1OC=CC1NC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ffc1d2da8b9142a8bc7dde58751616f9 | C1=C(c2ccc(C3=NOC(CNc4ccon4)C3)cc2)CCNC1.CC1(C)OC[C@@H](C(=O)Cl)O1>>O=C([C@@H](O)CO)N1CC=C(c2ccc(C3=NOC(CNc4ccon4)C3)cc2)CC1 | Cl.Cl.N1CC=C(CC1)C1=CC=C(C=C1)C1=NOC(C1)CNC1=NOC=C1.C(C)N(CC)CC.CC1(OC[C@H](O1)C(=O)Cl)C>>O[C@H](C(=O)N1CC=C(CC1)C1=CC=C(C=C1)C1=NOC(C1)CNC1=NOC=C1)CO | [NH:7]1[CH2:8][CH:9]=[C:10]([c:11]2[cH:12][cH:13][c:14]([C:15]3=[N:16][O:17][CH:18]([CH2:19][NH:20][c:21]4[cH:22][cH:23][o:24][n:25]4)[CH2:26]3)[cH:27][cH:28]2)[CH2:29][CH2:30]1.CC1(C)[O:4][C@H:3]([C:2](Cl)=[O:1])[CH2:5][O:6]1>>[O:1]=[C:2]([C@@H:3]([OH:4])[CH2:5][OH:6])[N:7]1[CH2:8][CH:9]=[C:10]([c:11]2[cH:12][cH:13][c... | C1=C(c2ccc(C3=NOC(CNc4ccon4)C3)cc2)CCNC1.CC1(C)OC[C@@H](C(=O)Cl)O1 | O=C([C@@H](O)CO)N1CC=C(c2ccc(C3=NOC(CNc4ccon4)C3)cc2)CC1 | null | null | C(C)#N | Acylation | OtherReaction | 18bdc7daa594e2a09b3b2cf816e24c7cb7d67a2a555c640aba300b1ef33de2c8 | ee760b7d9d9b09664b9fd0edaa50b7539f880e41b8c76e125b2b75560509beff | C1=C(c2ccc(C3=NOC(CNc4ccon4)C3)cc2)CCNC1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2](-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4])-[C:5]-[O;H0;D2;+0:6]-1.[c:7]-[C:8]1=[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[O;D1;H0:4]=[C;H0;D3;+0:3](-[C:2](-[OH;D1;+0:1])-[C:5]-[OH;D1;+0:6])-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[C:8](-[c:7])=[C:9]-[C:10]-1 | 30.3 | [{"value": 30.3, "product": "O[C@H](C(=O)N1CC=C(CC1)C1=CC=C(C=C1)C1=NOC(C1)CNC1=NOC=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | (5RS)-3-(4-(1,2,5,6-Tetrahydropyrid-4-yl)phenyl)-5-(3-isoxazolylaminomethyl)-4,5-dihydro-isoxazole dihydrochloride (397 mg, 1 mM) was suspended by stirring in acetonitrile (15 ml) under nitrogen, triethylamine (404 mg, 4 mM) added, and the mixture cooled to 0° C. (4S)-2,2-Dimethyl-1,3-dioxolan-4-ylcarbonyl chloride (32... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Ether.Secondary amine | Tertiary amide.Primary alcohol.Secondary alcohol | C1=CCNCC1.C1COCO1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccccc1.C1=NOCC1.c1cnoc1 | HCl | C(C)#N | null | 0.5 | C1=C(c2ccc(C3=NOC(CNc4ccon4)C3)cc2)CCNC1.CC1(C)OC[C@@H](C(=O)Cl)O1>C(C)#N>O=C([C@@H](O)CO)N1CC=C(c2ccc(C3=NOC(CNc4ccon4)C3)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-68138597702445e8b47a15ddd363712c | C1=C(c2ccc(C3=NOC(COc4ccon4)C3)cc2)CCNC1.CC1(C)OC[C@@H](C(=O)Cl)O1>>OC[C@@H](O)CN1CC=C(c2ccc(C3=NOC(COc4ccon4)C3)cc2)CC1 | Cl.N1CC=C(CC1)C1=CC=C(C=C1)C1=NOC(C1)COC1=NOC=C1.CC1(OC[C@H](O1)C(=O)Cl)C>>O[C@@H](CN1CC=C(CC1)C1=CC=C(C=C1)C1=NOC(C1)COC1=NOC=C1)CO | [CH2:5]1[NH:6][CH2:7][CH2:28][C:9]([c:10]2[cH:11][cH:12][c:13]([C:14]3=[N:15][O:16][CH:17]([CH2:18][O:19][c:20]4[cH:21][cH:22][o:23][n:24]4)[CH2:25]3)[cH:26][cH:27]2)=[CH:8]1.C[C:29]1(C)[O:1][CH2:2][C@@H:3](C(=O)Cl)[O:4]1>>[OH:1][CH2:2][C@@H:3]([OH:4])[CH2:5][N:6]1[CH2:7][CH:8]=[C:9]([c:10]2[cH:11][cH:12][c:13]([C:14]3... | C1=C(c2ccc(C3=NOC(COc4ccon4)C3)cc2)CCNC1.CC1(C)OC[C@@H](C(=O)Cl)O1 | OC[C@@H](O)CN1CC=C(c2ccc(C3=NOC(COc4ccon4)C3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cf1f558df3b9218ce649026a7e40000b6b7b76ca970d5a433aa853f31fddcd06 | 538df750e0a08c4403b31d52f20c0e3483daf0b0095eb06d0b8124bc2c8ea9d1 | C1=C(c2ccc(C3=NOC(COc4ccon4)C3)cc2)CCNC1 | C-[C;H0;D4;+0:1]1(-C)-[O;H0;D2;+0:2]-[C:3]-[C@@H;D3;+0:4](-C(-Cl)=O)-[O;H0;D2;+0:5]-1.[c:6]-[C:7]1=[CH;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-1>>[OH;D1;+0:2]-[C:3]-[C@@H;D3;+0:4](-[OH;D1;+0:5])-[CH2;D2;+0:9]-[N;H0;D3;+0:10]1-[CH2;D2;+0:1]-[CH2;D2;+0:12]-[C:7](-[c:6])=[CH;D2;+0:8]-[CH2;D2;+0:... | null | [] | null | null | null | null | (5RS)-3-(4-(1,2,5,6-Tetrahydropyrid-4-yl)phenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydro-isoxazole hydrochloride (300 mg, 0.83 mM) was treated with (4S)-2,2-dimethyl-1,3-dioxolan-4-ylcarbonyl chloride under essentially the conditions of Example 2. Crude product was chromatographed on a 20 g silica Mega Bond Elut® column, ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Ether.Secondary amine | Primary alcohol.Secondary alcohol.Tertiary amine | C1=CCNCC1.C1COCO1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccccc1.C1=NOCC1.c1cnoc1 | HCl | null | null | null | C1=C(c2ccc(C3=NOC(COc4ccon4)C3)cc2)CCNC1.CC1(C)OC[C@@H](C(=O)Cl)O1>>OC[C@@H](O)CN1CC=C(c2ccc(C3=NOC(COc4ccon4)C3)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d2d7f0f549cb460aa3d929fdf566cbd2 | OCC1CC(c2ccc(Br)cc2)=NO1.Oc1ccon1>>Brc1ccc(C2=NOC(COc3ccon3)C2)cc1 | CC(C)OC(=O)/N=N/C(=O)OC(C)C.BrC1=CC=C(C=C1)C1=NOC(C1)CO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OC1=NOC=C1>>BrC1=CC=C(C=C1)C1=NOC(C1)COC1=NOC=C1 | O[CH2:10][CH:9]1[O:8][N:7]=[C:6]([c:5]2[cH:4][cH:3][c:2]([Br:1])[cH:19][cH:18]2)[CH2:17]1.[OH:11][c:12]1[cH:13][cH:14][o:15][n:16]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[N:7][O:8][CH:9]([CH2:10][O:11][c:12]3[cH:13][cH:14][o:15][n:16]3)[CH2:17]2)[cH:18][cH:19]1 | OCC1CC(c2ccc(Br)cc2)=NO1.Oc1ccon1 | Brc1ccc(C2=NOC(COc3ccon3)C2)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(C2=NOC(COc3ccon3)C2)cc1 | O-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[#7:4]=[C:5]-[C:6]-1.[OH;D1;+0:7]-[c:8]1:[#7;a:9]:[#8;a:10]:[c:11]:[c:12]:1>>[#7:4]1=[C:5]-[C:6]-[C:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[c:8]2:[#7;a:9]:[#8;a:10]:[c:11]:[c:12]:2)-[#8:3]-1 | 55.5 | [{"value": 55.5, "product": "BrC1=CC=C(C=C1)C1=NOC(C1)COC1=NOC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | (5RS)-3-(4-Bromophenyl)-5-hydroxymethyl-4,5-dihydro-isoxazole (3.07 g, 12 mM), triphenylphosphine (3.78 g, 14.4 mM) and 3-hydroxyisoxazole (1.02 g, 12 mM) were dissolved in anhydrous tetrahydrofuran (50 ml), cooled to 0° with stirring under nitrogen, and treated with diisopropylazodicarboxylate (2.71 g, 13.4 mM). Stirr... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.C1=NOCC1.c1cnoc1 | HO- | O1CCCC1 | null | 18 | OCC1CC(c2ccc(Br)cc2)=NO1.Oc1ccon1>O1CCCC1>Brc1ccc(C2=NOC(COc3ccon3)C2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8e277358f90547e089c61daadae3a19a | CS(=O)(=O)Cl.OCC1CC(c2ccc(F)c(F)c2)=NO1>>CS(=O)(=O)OCC1CC(c2ccc(F)c(F)c2)=NO1 | CS(=O)(=O)Cl.O.FC=1C=C(C=CC1F)C1=NOC(C1)CO.C(C)N(CC)CC>>FC=1C=C(C=CC1F)C1=NOC(C1)COS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][C:9]([c:10]2[cH:11][cH:12][c:13]([F:14])[c:15]([F:16])[cH:17]2)=[N:18][O:19]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][C:9]([c:10]2[cH:11][cH:12][c:13]([F:14])[c:15]([F:16])[cH:17]2)=[N:18][O:19]1 | CS(=O)(=O)Cl.OCC1CC(c2ccc(F)c(F)c2)=NO1 | CS(=O)(=O)OCC1CC(c2ccc(F)c(F)c2)=NO1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(C2=NOCC2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 30 | MINUTE | (5RS)-3-(3,4-Difluorophenyl)-5-hydroxymethyl-4,5-dihydroisoxazole (3.79 g, 17.8 mM) was dissolved in anhydrous dichloromethane (200 ml) under a nitrogen atmosphere, cooled to 0°, and treated with triethylamine (2.51 g, 24.9 mM). Methanesulfonyl chloride (2.45 g, 21.4 mM) was added dropwise with stirring during a period... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1=NOCC1.c1ccccc1 | HCl | ClCCl | null | 0.5 | CS(=O)(=O)Cl.OCC1CC(c2ccc(F)c(F)c2)=NO1>ClCCl>CS(=O)(=O)OCC1CC(c2ccc(F)c(F)c2)=NO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93d531d16a9747fca324270eef0b62eb | Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F.c1c[nH]cn1>>Fc1cc(C2=NOC(COc3ccon3)C2)ccc1-n1ccnc1 | [H-].[Na+].FC=1C=C(C=CC1F)C1=NOC(C1)COC1=NOC=C1.N1C=NC=C1>>FC=1C=C(C=CC1N1C=NC=C1)C1=NOC(C1)COC1=NOC=C1 | F[c:19]1[c:2]([F:1])[cH:3][c:4]([C:5]2=[N:6][O:7][CH:8]([CH2:9][O:10][c:11]3[cH:12][cH:13][o:14][n:15]3)[CH2:16]2)[cH:17][cH:18]1.[nH:20]1[cH:21][cH:22][n:23][cH:24]1>>[F:1][c:2]1[cH:3][c:4]([C:5]2=[N:6][O:7][CH:8]([CH2:9][O:10][c:11]3[cH:12][cH:13][o:14][n:15]3)[CH2:16]2)[cH:17][cH:18][c:19]1-[n:20]1[cH:21][cH:22][n:2... | Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F.c1c[nH]cn1 | Fc1cc(C2=NOC(COc3ccon3)C2)ccc1-n1ccnc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cn(-c2ccc(C3=NOC(COc4ccon4)C3)cc2)cn1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[#7;a:7]1:[c:8]:[c:9]:[nH;D2;+0:10]:[c:11]:1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[#7;a:7]:[c:11]:1):[c:2]:[c:3] | 41.5 | [{"value": 41.5, "product": "FC=1C=C(C=CC1N1C=NC=C1)C1=NOC(C1)COC1=NOC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A slurry of sodium hydride (60% in oil, 22 mg, 0.55 mM) in anhydrous N,N-dimethylformamide (0.5 ml) was stirred under an atmosphere of nitrogen and treated dropwise with a solution of imidazole (38 mg, 0.55 mM) in anhydrous N,N-dimethylformamide (0.5 ml) at 0°. The mixture was allowed to warm to ambient temperature ove... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | c1ccccc1.C1=NOCC1.c1cnoc1.c1c[nH]cn1 | HF | CN(C=O)C | null | 16 | Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F.c1c[nH]cn1>CN(C=O)C>Fc1cc(C2=NOC(COc3ccon3)C2)ccc1-n1ccnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ff5222703744bf394063e49e8e3e892 | Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F.c1cn[nH]c1>>Fc1cc(C2=NOC(COc3ccon3)C2)ccc1-n1cccn1 | FC=1C=C(C=CC1F)C1=NOC(C1)COC1=NOC=C1.N1N=CC=C1>>FC=1C=C(C=CC1N1N=CC=C1)C1=NOC(C1)COC1=NOC=C1 | F[c:19]1[c:2]([F:1])[cH:3][c:4]([C:5]2=[N:6][O:7][CH:8]([CH2:9][O:10][c:11]3[cH:12][cH:13][o:14][n:15]3)[CH2:16]2)[cH:17][cH:18]1.[nH:20]1[cH:21][cH:22][cH:23][n:24]1>>[F:1][c:2]1[cH:3][c:4]([C:5]2=[N:6][O:7][CH:8]([CH2:9][O:10][c:11]3[cH:12][cH:13][o:14][n:15]3)[CH2:16]2)[cH:17][cH:18][c:19]1-[n:20]1[cH:21][cH:22][cH:... | Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F.c1cn[nH]c1 | Fc1cc(C2=NOC(COc3ccon3)C2)ccc1-n1cccn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0326b1ac5f59f9fe82fa20e0fd38fc78c8d31082442e70f0cc0d7a023cbd5c19 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cnn(-c2ccc(C3=NOC(COc4ccon4)C3)cc2)c1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[#7;a:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[n;H0;D3;+0:11]1:[#7;a:7]:[c:8]:[c:9]:[c:10]:1):[c:2]:[c:3] | null | [] | null | null | null | null | (5RS)-3-(3,4-Difluorophenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydroisoxazole (140 mg, 0.5 mM) was treated with pyrazole using essentially the conditions of Example 5. Crude product was chromatographed on a S g silica Mega Bond Elut® column, eluting with a gradient from 0–25% ethyl acetate in dichloromethane. Relevant fra... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1 | c1ccccc1.C1=NOCC1.c1cnoc1.c1cn[nH]c1 | HF | null | null | null | Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F.c1cn[nH]c1>>Fc1cc(C2=NOC(COc3ccon3)C2)ccc1-n1cccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-526c640f7c9b4043a4aca5333df303b6 | Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F.c1nc[nH]n1>>Fc1cc(C2=NOC(COc3ccon3)C2)ccc1-n1cncn1 | FC=1C=C(C=CC1F)C1=NOC(C1)COC1=NOC=C1.N1N=CN=C1>>FC=1C=C(C=CC1N1N=CN=C1)C1=NOC(C1)COC1=NOC=C1 | F[c:19]1[c:2]([F:1])[cH:3][c:4]([C:5]2=[N:6][O:7][CH:8]([CH2:9][O:10][c:11]3[cH:12][cH:13][o:14][n:15]3)[CH2:16]2)[cH:17][cH:18]1.[nH:20]1[cH:21][n:22][cH:23][n:24]1>>[F:1][c:2]1[cH:3][c:4]([C:5]2=[N:6][O:7][CH:8]([CH2:9][O:10][c:11]3[cH:12][cH:13][o:14][n:15]3)[CH2:16]2)[cH:17][cH:18][c:19]1-[n:20]1[cH:21][n:22][cH:23... | Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F.c1nc[nH]n1 | Fc1cc(C2=NOC(COc3ccon3)C2)ccc1-n1cncn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dff1d318970a706943117b26793c51edded6a9a33120b190609ee0c5e3cf31e9 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ncn(-c2ccc(C3=NOC(COc4ccon4)C3)cc2)n1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[#7;a:7]1:[c:8]:[nH;D2;+0:9]:[#7;a:10]:[c:11]:1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[n;H0;D3;+0:9]1:[#7;a:10]:[c:11]:[#7;a:7]:[c:8]:1):[c:2]:[c:3] | null | [] | null | null | null | null | (5RS)-3-(3,4-Difluorophenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydroisoxazole (140 mg, 0.5 mM) was treated with 1,2,4-triazole using essentially the conditions of Example 5. Crude product was chromatographed on a 5 g silica Mega Bond Elut® column, eluting with a gradient from 0–25% ethyl acetate in dichloromethane. Releva... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1 | c1ccccc1.C1=NOCC1.c1cnoc1.c1nc[nH]n1 | HF | null | null | null | Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F.c1nc[nH]n1>>Fc1cc(C2=NOC(COc3ccon3)C2)ccc1-n1cncn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f4983ebb30254a8bb699350094bd6137 | Fc1cc(C2=NOC(COc3ccon3)C2)ccc1N1CCSCC1>>O=S1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1 | FC=1C=C(C=CC1N1CCSCC1)C1=NOC(C1)COC1=NOC=C1.ClC=1C=C(C(=O)OO)C=CC1.S(=O)(=O)([O-])S(=O)[O-].[Na+].[Na+]>>FC=1C=C(C=CC1N1CCS(CC1)=O)C1=NOC(C1)COC1=NOC=C1 | [S:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([C:10]3=[N:11][O:12][CH:13]([CH2:14][O:15][c:16]4[cH:17][cH:18][o:19][n:20]4)[CH2:21]3)[cH:22][c:23]2[F:24])[CH2:25][CH2:26]1>>[O:1]=[S:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([C:10]3=[N:11][O:12][CH:13]([CH2:14][O:15][c:16]4[cH:17][cH:18][o:19][n:20]4)[CH2:21]3)... | Fc1cc(C2=NOC(COc3ccon3)C2)ccc1N1CCSCC1 | O=S1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1 | null | null | ClCCl | Oxidation | Sulfanyl to sulfinyl | c85a23881a8c3a3231ed34b602ece3d962b8a98fadea32e6ade07ff31a14194b | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=S1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2)CC1 | [#7:1]1-[C:2]-[C:3]-[S;H0;D2;+0:4]-[C:5]-[C:6]-1>>[O;D1;H0:7]=[S;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 70.5 | [{"value": 70.5, "product": "FC=1C=C(C=CC1N1CCS(CC1)=O)C1=NOC(C1)COC1=NOC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred solution of (5RS)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydroisoxazole (174 mg, 0.48 mM) in dichloromethane (5 ml) was added dropwise a solution of 3-chloroperoxybenzoic acid (80%, 124 mg, 0.57 mM) in dichloromethane (5 ml) at ambient temperature, and stirring continued for... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | C1CSCC[NH]1 | C1CSCC[NH]1 | C1CSCC[NH]1.c1ccccc1.C1=NOCC1.c1cnoc1 | null | ClCCl | null | 1 | Fc1cc(C2=NOC(COc3ccon3)C2)ccc1N1CCSCC1>ClCCl>O=S1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1dc8ffc6324846a7b3c1562422dd92ff | C1CNCCN1.Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F>>Fc1cc(C2=NOC(COc3ccon3)C2)ccc1N1CCNCC1 | FC=1C=C(C=CC1F)C1=NOC(C1)COC1=NOC=C1.N1CCNCC1>>FC=1C=C(C=CC1N1CCNCC1)C1=NOC(C1)COC1=NOC=C1 | [NH:20]1[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]1.F[c:19]1[c:2]([F:1])[cH:3][c:4]([C:5]2=[N:6][O:7][CH:8]([CH2:9][O:10][c:11]3[cH:12][cH:13][o:14][n:15]3)[CH2:16]2)[cH:17][cH:18]1>>[F:1][c:2]1[cH:3][c:4]([C:5]2=[N:6][O:7][CH:8]([CH2:9][O:10][c:11]3[cH:12][cH:13][o:14][n:15]3)[CH2:16]2)[cH:17][cH:18][c:19]1[N:20]1[CH2:21... | C1CNCCN1.Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F | Fc1cc(C2=NOC(COc3ccon3)C2)ccc1N1CCNCC1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 1d452876efa46787ecd5eab4acf018720843b51fbe40244616ffd72f6a602335 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(OCC2CC(c3ccc(N4CCNCC4)cc3)=NO2)no1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | null | [] | null | null | 4 | HOUR | (5RS)-3-(3,4-Difluorophenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydroisoxazole (530 mg, 1.89 mM) was treated with piperazine using essentially the conditions of Example 4, except that the reaction conditions were 140° for 4 hours, and work-up did not include an acid wash. Crude product was chromatographed on a 50 g silica ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccccc1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1=NOCC1.c1cnoc1.C1C[NH]CCN1 | HF | null | null | 4 | C1CNCCN1.Fc1ccc(C2=NOC(COc3ccon3)C2)cc1F>>Fc1cc(C2=NOC(COc3ccon3)C2)ccc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d30f4d78e3b34e8cbf329c283d30a35d | CC(=O)OCC(=O)Cl.Fc1cc(C2=NOC(COc3ccon3)C2)ccc1N1CCNCC1>>CC(=O)OCC(=O)N1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1 | FC=1C=C(C=CC1N1CCNCC1)C1=NOC(C1)COC1=NOC=C1.C(C)(=O)OCC(=O)Cl>>FC=1C=C(C=CC1N1CCN(CC1)C(COC(C)=O)=O)C1=NOC(C1)COC1=NOC=C1 | Cl[C:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])=[O:7].[NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([C:16]3=[N:17][O:18][CH:19]([CH2:20][O:21][c:22]4[cH:23][cH:24][o:25][n:26]4)[CH2:27]3)[cH:28][c:29]2[F:30])[CH2:31][CH2:32]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][... | CC(=O)OCC(=O)Cl.Fc1cc(C2=NOC(COc3ccon3)C2)ccc1N1CCNCC1 | CC(=O)OCC(=O)N1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | 6dd420fad17fb719b6bd840e8952a8d7b2fb24721f86f8b8f9c697a36eb97ec3 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1cc(OCC2CC(c3ccc(N4CCNCC4)cc3)=NO2)no1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C;D1;H3:6]-[C:5](=[O;D1;H0:7])-[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1 | null | [] | null | null | null | null | (5RS)-3-(3-Fluoro-4-piperazin-1-ylphenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydroisoxazole (175 mg, 0.51 mM) was treated with acetoxyacetyl chloride using essentially the conditions of Example 16, to give the desired product after chromatography and precipitation (163 mg).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.C1=NOCC1.c1cnoc1 | HCl | null | null | null | CC(=O)OCC(=O)Cl.Fc1cc(C2=NOC(COc3ccon3)C2)ccc1N1CCNCC1>>CC(=O)OCC(=O)N1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-61c912b3d1694021932ca1ed5a83cc08 | CC(=O)OCC(=O)N1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1>>O=C(CO)N1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1 | FC=1C=C(C=CC1N1CCN(CC1)C(COC(C)=O)=O)C1=NOC(C1)COC1=NOC=C1.N>>FC=1C=C(C=CC1N1CCN(CC1)C(CO)=O)C1=NOC(C1)COC1=NOC=C1 | CC(=O)[O:4][CH2:3][C:2](=[O:1])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([C:13]3=[N:14][O:15][CH:16]([CH2:17][O:18][c:19]4[cH:20][cH:21][o:22][n:23]4)[CH2:24]3)[cH:25][c:26]2[F:27])[CH2:28][CH2:29]1>>[O:1]=[C:2]([CH2:3][OH:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([C:13]3=[N:14][O:15][CH:16]([C... | CC(=O)OCC(=O)N1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1 | O=C(CO)N1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1 | null | null | O1CCCC1.CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cc(OCC2CC(c3ccc(N4CCNCC4)cc3)=NO2)no1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6])-[C:7]>>[C:6]-[#7:5](-[C:3](=[O;D1;H0:4])-[C:2]-[OH;D1;+0:1])-[C:7] | 90.7 | [{"value": 90.7, "product": "FC=1C=C(C=CC1N1CCN(CC1)C(CO)=O)C1=NOC(C1)COC1=NOC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | HOUR | (5RS)-3-(3-Fluoro-4(4-(2-acetoxyacetyl)piperazin-1-yl)phenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydroisoxazole (112 mg, 0.25 mM) was suspended in a saturated solution of ammonia in methanol (8 ml), diluted with tetrahydrofuran (5 ml). The mixture was stirred at ambient temperature for 40 hours. The residue after evaporati... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1C[NH]CC[NH]1.c1ccccc1.C1=NOCC1.c1cnoc1 | HO- | O1CCCC1.CO | null | 40 | CC(=O)OCC(=O)N1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1>O1CCCC1.CO>O=C(CO)N1CCN(c2ccc(C3=NOC(COc4ccon4)C3)cc2F)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a62c224cbe324dcb99aa2eed4a2acf87 | C=NO.Nc1ccc(I)c(F)c1>>ON=Cc1ccc(I)c(F)c1 | C(C)(=O)[O-].[Na+].C=NO.C(C)(=O)[O-].[Na+].S(=O)([O-])[O-].[Na+].[Na+].N(=O)[O-].[Na+].FC=1C=C(N)C=CC1I.Cl>>FC=1C=C(C=NO)C=CC1I | [OH:1][N:2]=[CH2:3].N[c:4]1[cH:5][cH:6][c:7]([I:8])[c:9]([F:10])[cH:11]1>>[OH:1][N:2]=[CH:3][c:4]1[cH:5][cH:6][c:7]([I:8])[c:9]([F:10])[cH:11]1 | C=NO.Nc1ccc(I)c(F)c1 | ON=Cc1ccc(I)c(F)c1 | null | null | O | C-C Coupling | OtherReaction | 55b8c0fe981dbf555afb862398642dc7989c7ee6ba10759541a1cfb4518980c8 | 84dca41855125dc4e9a82934f8db40c0cf75f0ed1a57b1bed6501296b6370efc | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH2;D1;+0:6]=[#7:7]-[O;D1;H1:8]>>[O;D1;H1:8]-[#7:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 1 | HOUR | 3-Fluoro-4-iodoaniline (15.36 g, 0.069 M) and concentrated hydrochloric acid (18.51 g) were dissolved in a mixture of water (30 ml) and ice (30 g). The solution was treated at 0–5° with a solution of sodium nitrite (4.81 g, 0.07 M) in water (15 ml). The pH of the resulting red-brown solution was adjusted to 5–6 by the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Oxime | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O | null | 1 | C=NO.Nc1ccc(I)c(F)c1>O>ON=Cc1ccc(I)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4b2a98cb5fb456aba204d56b97b859e | CS(=O)(=O)Cl.OCC1CC(c2ccc(I)c(F)c2)=NO1>>CS(=O)(=O)OCC1CC(c2ccc(I)c(F)c2)=NO1 | FC=1C=C(C=CC1I)C1=NOC(C1)CO.CS(=O)(=O)Cl>>FC=1C=C(C=CC1I)C1=NOC(C1)COS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][C:9]([c:10]2[cH:11][cH:12][c:13]([I:14])[c:15]([F:16])[cH:17]2)=[N:18][O:19]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][C:9]([c:10]2[cH:11][cH:12][c:13]([I:14])[c:15]([F:16])[cH:17]2)=[N:18][O:19]1 | CS(=O)(=O)Cl.OCC1CC(c2ccc(I)c(F)c2)=NO1 | CS(=O)(=O)OCC1CC(c2ccc(I)c(F)c2)=NO1 | null | null | null | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(C2=NOCC2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | (5RS)-3-(3-Fluoro-4-iodophenyl)-5-hydroxymethyl-4,5-dihydroisoxazole (2 g, 6.2 mM) was treated with methanesulfonyl chloride under essentially the conditions of the equivalent intermediate of Example 4. Product was obtained as a white solid (2.18 g) without chromatography. MS (EI): 399 (M+) for C11H11FINO4S
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1=NOCC1.c1ccccc1 | HCl | null | null | null | CS(=O)(=O)Cl.OCC1CC(c2ccc(I)c(F)c2)=NO1>>CS(=O)(=O)OCC1CC(c2ccc(I)c(F)c2)=NO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4aabe63e35d642b59669397eee9790dc | C=CCN1OC=CC1NC(=O)OC(C)(C)C.CS(=O)(=O)OCC1CC(c2ccc(I)c(F)c2)=NO1>>CC(C)(C)OC(=O)N(CC1CC(c2ccc(I)c(F)c2)=NO1)c1ccon1 | C(C=C)N1OC=CC1NC(=O)OC(C)(C)C.FC=1C=C(C=CC1I)C1=NOC(C1)COS(=O)(=O)C.[H-].[Na+]>>FC=1C=C(C=CC1I)C1=NOC(C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1 | C=CC[N:27]1[CH:23]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:24]=[CH:25][O:26]1.CS(=O)(=O)O[CH2:9][CH:10]1[CH2:11][C:12]([c:13]2[cH:14][cH:15][c:16]([I:17])[c:18]([F:19])[cH:20]2)=[N:21][O:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH:10]1[CH2:11][C:12]([c:13]2[cH:14][cH:15][c:... | C=CCN1OC=CC1NC(=O)OC(C)(C)C.CS(=O)(=O)OCC1CC(c2ccc(I)c(F)c2)=NO1 | CC(C)(C)OC(=O)N(CC1CC(c2ccc(I)c(F)c2)=NO1)c1ccon1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | d5c1bf53c874df07b53478bae13cad45c8038e0dc3e289a776e05c9bfd1260d5 | 2d71b3049b83d922c7d3f12ca6484b598ab41524faa26d63361011954a35c8b4 | c1ccc(C2=NOC(CNc3ccon3)C2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[#7:4]=[C:5]-[C:6]-1.C=C-C-[N;H0;D3;+0:7]1-[O;H0;D2;+0:8]-[CH;D2;+0:9]=[CH;D2;+0:10]-[CH;D3;+0:11]-1-[NH;D2;+0:12]-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16](-[C;D1;H3:17])(-[C;D1;H3:18])-[C;D1;H3:19]>>[C;D1;H3:17]-[C:16](-[C;D1;H3:18])(-[C;D1;H3:19])-[#8:15]-[C:13](=[O;D1;H0:14])-[N... | 86.9 | [{"value": 86.9, "product": "FC=1C=C(C=CC1I)C1=NOC(C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A solution of (5RS)-3-(3-Fluoro-4-iodophenyl)-5-methanesulfonyloxymethyl-4,5-dihydroisoxazole (1.7 g, 4.26 mM) in dry N,N-dimethylformamide (40 ml) under nitrogen, was treated with sodium hydride (60% in oil, 0.205 g, 5.13 mM), and stirred for 5 minutes. N-Allyl-3-(t-Butoxycarbonylamino)isoxazole (0.86 g, 4.69 mM) was ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Carbamic ester.Tertiary amine.Allyl | Carbamic ester | C1=CO[NH]C1 | c1cnoc1 | C1=NOCC1.c1ccccc1.c1cnoc1 | MsOH.HO- | CN(C=O)C | null | 0.083333 | C=CCN1OC=CC1NC(=O)OC(C)(C)C.CS(=O)(=O)OCC1CC(c2ccc(I)c(F)c2)=NO1>CN(C=O)C>CC(C)(C)OC(=O)N(CC1CC(c2ccc(I)c(F)c2)=NO1)c1ccon1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5fe6025313db441eb2d02197eab1cf91 | CC(C)(C)OC(=O)N(CC1CC(c2ccc(I)c(F)c2)=NO1)c1ccon1.CC(C)(C)OC(=O)N1CC=[C]([Sn]([CH3])([CH3])[CH3])CC1>>CC(C)(C)OC(=O)N1CC=C(c2ccc(C3=NOC(CN(C(=O)OC(C)(C)C)c4ccon4)C3)cc2F)CC1 | FC=1C=C(C=CC1I)C1=NOC(C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1.C(C)(C)(C)OC(=O)N1CC=C(CC1)[Sn](C)(C)C.C1(=CC=CC=C1)[As](C1=CC=CC=C1)C1=CC=CC=C1>>FC=1C=C(C=CC1C1=CCN(CC1)C(=O)OC(C)(C)C)C1=NOC(C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1 | I[c:12]1[cH:13][cH:14][c:15]([C:16]2=[N:17][O:18][CH:19]([CH2:20][N:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[c:29]3[cH:30][cH:31][o:32][n:33]3)[CH2:34]2)[cH:35][c:36]1[F:37].[CH3][Sn]([CH3])([CH3])[C:11]1=[CH:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:39][CH2:38]1>>[CH3:1]... | CC(C)(C)OC(=O)N(CC1CC(c2ccc(I)c(F)c2)=NO1)c1ccon1.CC(C)(C)OC(=O)N1CC=[C]([Sn]([CH3])([CH3])[CH3])CC1 | CC(C)(C)OC(=O)N1CC=C(c2ccc(C3=NOC(CN(C(=O)OC(C)(C)C)c4ccon4)C3)cc2F)CC1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | CN1C(CCC1)=O | C-C Coupling | Stille reaction_other | 68c4590f05afe3a6f57ba264aa5d0c039afb25f5527da1a27e5866b619f72b30 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | C1=C(c2ccc(C3=NOC(CNc4ccon4)C3)cc2)CCNC1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[CH3]-[Sn](-[CH3])(-[CH3])-[C;H0;D3;+0:7]1=[C:8]-[C:9]-[#7:10]-[C:11]-[C:12]-1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:7]1=[C:8]-[C:9]-[#7:10]-[C:11]-[C:12]-1):[c:2]:[c:3] | 48.9 | [{"value": 48.9, "product": "FC=1C=C(C=CC1C1=CCN(CC1)C(=O)OC(C)(C)C)C1=NOC(C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Tris(dibenzylideneacetone)dipalladium (141 mg, 0.154 mM) and triphenylarsine (188 mg, 0.616 mM) were dissolved in degassed N-methylpyrrolidone (40 ml) under nitrogen, and stirred for 15 minutes. (5RS)-3-(3-Fluoro-4-iodophenyl)-5-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)-4,5-dihydro-isoxazole (1.5 g, 3.08 mM) and 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccccc1.C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccccc1 | C1=CC[NH]CC1.c1ccccc1.C1=NOCC1.c1cnoc1 | HI.Sn | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CN1C(CCC1)=O | null | 0.25 | CC(C)(C)OC(=O)N(CC1CC(c2ccc(I)c(F)c2)=NO1)c1ccon1.CC(C)(C)OC(=O)N1CC=[C]([Sn]([CH3])([CH3])[CH3])CC1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CN1C(CCC1)=O>CC(C)(C)OC(=O)N1CC=C(c2ccc(C3=NOC(CN(C(=O)OC(C)(C)C)c4ccon4)C3)cc2F)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a96cc9bd82a54b5d901a11899a87c7f3 | CC(C)(C)OC(=O)N1CC=C(c2ccc(C3=NOC(CN(C(=O)OC(C)(C)C)c4ccon4)C3)cc2F)CC1>>Fc1cc(C2=NOC(CNc3ccon3)C2)ccc1C1=CCNCC1 | FC=1C=C(C=CC1C1=CCN(CC1)C(=O)OC(C)(C)C)C1=NOC(C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1.Cl>>Cl.FC=1C=C(C=CC1C1=CCNCC1)C1=NOC(C1)CNC1=NOC=C1 | CC(C)(C)OC(=O)[N:11]([CH2:10][CH:9]1[O:8][N:7]=[C:6]([c:5]2[cH:4][c:3]([F:2])[c:20]([C:21]3=[CH:22][CH2:23][N:24](C(=O)OC(C)(C)C)[CH2:25][CH2:26]3)[cH:19][cH:18]2)[CH2:17]1)[c:12]1[cH:13][cH:14][o:15][n:16]1>>[F:2][c:3]1[cH:4][c:5]([C:6]2=[N:7][O:8][CH:9]([CH2:10][NH:11][c:12]3[cH:13][cH:14][o:15][n:16]3)[CH2:17]2)[cH:... | CC(C)(C)OC(=O)N1CC=C(c2ccc(C3=NOC(CN(C(=O)OC(C)(C)C)c4ccon4)C3)cc2F)CC1 | Fc1cc(C2=NOC(CNc3ccon3)C2)ccc1C1=CCNCC1 | null | null | null | Reduction | OtherReaction | 3aee95abaca3f5389894f7fb9396409c706f51597763b666c01a53dc019b4d79 | 62d6d161f7b7b3cc63e568e66451a46259e0e34072c373a60dd8b9591af3c67b | C1=C(c2ccc(C3=NOC(CNc4ccon4)C3)cc2)CCNC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1.C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:10]1-[C:11]-[C:12]=[C:13](-[c:14])-[C:15]-[C:16]-1>>[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1.[c:14]-[C:13]1=[C:12]-[C:11]-[NH;D2;+0:10]-[C:16]-[C:15]-1 | null | [] | null | null | null | null | (5RS)-3-(3-Fluoro-4-(1-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)-5-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)-4,5-dihydroisoxazole (817 mg, 1.51 mM) was treated with ethanolic hydrogen chloride under essentially the conditions of the equivalent intermediate of Example 1, to give the desired product dire... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine.Secondary amine | C1=CC[NH]CC1 | C1=CCNCC1 | c1ccccc1.C1=NOCC1.c1cnoc1.C1=CCNCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC=C(c2ccc(C3=NOC(CN(C(=O)OC(C)(C)C)c4ccon4)C3)cc2F)CC1>>Fc1cc(C2=NOC(CNc3ccon3)C2)ccc1C1=CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16232460f59a4ee0afb5c900b0c9458f | C[N+](=O)[O-].O=Cc1cccc(Cl)c1>>O=[N+]([O-])CC(O)c1cccc(Cl)c1 | ClC=1C=C(C=O)C=CC1.S(=O)(=O)([O-])[O-].[Mg+2].CC(C)(C)N=P(N1CCCC1)(N2CCCC2)N3CCCC3.[N+](=O)([O-])C>>ClC=1C=C(C=CC1)C(C[N+](=O)[O-])O | [O:1]=[N+:2]([O-:3])[CH3:4].[CH:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1>>[O:1]=[N+:2]([O-:3])[CH2:4][CH:5]([OH:6])[c:7]1[cH:8][cH:9][cH:10][c:11]([Cl:12])[cH:13]1 | C[N+](=O)[O-].O=Cc1cccc(Cl)c1 | O=[N+]([O-])CC(O)c1cccc(Cl)c1 | null | null | null | C-C Coupling | Henry Reaction | 2fe74ac7ac457ce8163984c7154f8a02468716ba44b0ef5f5983a0978d1cfa8c | a930e1416f4851c0cbff3b732b248e97b8b6a78afc7be2a55f7e5c8d412d0901 | c1ccccc1 | [CH3;D1;+0:1]-[#7;+:2](-[O;-;D1;H0:3])=[O;D1;H0:4].[O;H0;D1;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[O;-;D1;H0:3]-[#7;+:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[CH;D3;+0:6](-[OH;D1;+0:5])-[c:7](:[c:8]):[c:9] | 100 | [{"value": 100.0, "product": "ClC=1C=C(C=CC1)C(C[N+](=O)[O-])O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-chloro-benzaldehyde (20 g, 0.142 mol) in nitromethane (100 mL) were added magnesium sulfate (37.6 g, 0.312 mol) and phosphazene base P1-t-bu-tris(tetramethylene) (4.43 g, 0.014 mol). The reaction mixture was stirred at room temperature for 2 h. After concentration in vacuo, the residue was purified b... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Nitro group.Secondary alcohol | null | null | c1ccccc1 | null | null | null | 2 | C[N+](=O)[O-].O=Cc1cccc(Cl)c1>>O=[N+]([O-])CC(O)c1cccc(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d0e51fdf1dae4217b6d7dab0af34bc31 | CC[Si](Cl)(CC)CC.O=[N+]([O-])CC(O)c1cccc(Cl)c1>>CC[Si](CC)(CC)OC(C[N+](=O)[O-])c1cccc(Cl)c1 | ClC=1C=C(C=CC1)C(C[N+](=O)[O-])O.N1C=NC=C1.Cl[Si](CC)(CC)CC>>ClC=1C=C(C=CC1)C(C[N+](=O)[O-])O[Si](CC)(CC)CC | Cl[Si:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[CH2:6][CH3:7].[OH:8][CH:9]([CH2:10][N+:11](=[O:12])[O-:13])[c:14]1[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]1>>[CH3:1][CH2:2][Si:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[O:8][CH:9]([CH2:10][N+:11](=[O:12])[O-:13])[c:14]1[cH:15][cH:16][cH:17][c:18]([Cl:19])[cH:20]1 | CC[Si](Cl)(CC)CC.O=[N+]([O-])CC(O)c1cccc(Cl)c1 | CC[Si](CC)(CC)OC(C[N+](=O)[O-])c1cccc(Cl)c1 | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C:2]-[C;D1;H3:3])(-[C:4]-[C;D1;H3:5])-[C:6]-[C;D1;H3:7].[C:8]-[C:9](-[OH;D1;+0:10])-[c:11]>>[C:8]-[C:9](-[c:11])-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C:2]-[C;D1;H3:3])(-[C:4]-[C;D1;H3:5])-[C:6]-[C;D1;H3:7] | 91 | [{"value": 91.0, "product": "ClC=1C=C(C=CC1)C(C[N+](=O)[O-])O[Si](CC)(CC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.7, "product": "ClC=1C=C(C=CC1)C(C[N+](=O)[O-])O[Si](CC)(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 1-(3-chloro-phenyl)-2-nitro-ethanol (26 g, 0.14 mol) in DMF (50 mL) were added imidazole (28.6 g, 0.42 mol) and chlorotriethylsilane (25.3 g, 0.17 mol). The reaction mixture was stirred at room temperature for 2 h. After quenching with water, the mixture was extracted with ethyl acetate. The combined o... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | c1ccccc1 | HCl | CN(C)C=O | null | 2 | CC[Si](Cl)(CC)CC.O=[N+]([O-])CC(O)c1cccc(Cl)c1>CN(C)C=O>CC[Si](CC)(CC)OC(C[N+](=O)[O-])c1cccc(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ae3296a9b8904a4a8ed8a004b99076ce | CC[Si](CC)(CC)OC(C[N+](=O)[O-])c1cccc(Cl)c1>>CC[Si](CC)(CC)OC(CN)c1cccc(Cl)c1 | ClC=1C=C(C=CC1)C(C[N+](=O)[O-])O[Si](CC)(CC)CC>>ClC=1C=C(C=CC1)C(CN)O[Si](CC)(CC)CC | O=[N+:11]([O-])[CH2:10][CH:9]([O:8][Si:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[CH2:6][CH3:7])[c:12]1[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]1>>[CH3:1][CH2:2][Si:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[O:8][CH:9]([CH2:10][NH2:11])[c:12]1[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]1 | CC[Si](CC)(CC)OC(C[N+](=O)[O-])c1cccc(Cl)c1 | CC[Si](CC)(CC)OC(CN)c1cccc(Cl)c1 | null | [Ni] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 62 | [{"value": 62.0, "product": "ClC=1C=C(C=CC1)C(CN)O[Si](CC)(CC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.2, "product": "ClC=1C=C(C=CC1)C(CN)O[Si](CC)(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Raney nickel (1 g) was washed with distilled water five times and methanol three times. [1-(3-Chloro-phenyl)-2-nitro-ethoxy]-triethyl-silane (10 g, 0.032 mol) and Raney nickel in methanol (100 mL) was hydrogenated (35 psi) at room temperature for 14 h. The reaction mixture was filtered through a pad of celite and rinse... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].CO | null | null | CC[Si](CC)(CC)OC(C[N+](=O)[O-])c1cccc(Cl)c1>[Ni].CO>CC[Si](CC)(CC)OC(CN)c1cccc(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1c587ca20a774aef8af415f5c473206b | CC(C)(C)OC(=O)N[C@H](CO)Cc1cccc(Br)c1>>N[C@H](CO)Cc1cccc(Br)c1 | C(C)(C)(C)OC(N[C@@H](CC1=CC(=CC=C1)Br)CO)=O.Cl>>N[C@H](CO)CC1=CC(=CC=C1)Br | CC(C)(C)OC(=O)[NH:1][C@H:2]([CH2:3][OH:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Br:11])[cH:12]1>>[NH2:1][C@H:2]([CH2:3][OH:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Br:11])[cH:12]1 | CC(C)(C)OC(=O)N[C@H](CO)Cc1cccc(Br)c1 | N[C@H](CO)Cc1cccc(Br)c1 | null | null | O1CCOCC1.CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | null | [] | null | null | 14 | HOUR | To a solution of (S)-[2-(3-bromo-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester (400 mg, 1.21 mmol) in methanol (30 mL) was added 4 M HCl in dioxane (2 mL, excess). The reaction mixture was stirred at room temperature for 14 h. After concentration in vacuo, the residue was used for the next step without ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | O1CCOCC1.CO | null | 14 | CC(C)(C)OC(=O)N[C@H](CO)Cc1cccc(Br)c1>O1CCOCC1.CO>N[C@H](CO)Cc1cccc(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-388628bce0db46959552074fa18b9c22 | O=C1Cc2cc(C(=O)CCl)cc(Cl)c2N1>>O=C1C=c2cc([C@H](O)CCl)cc(Cl)c2=N1 | ClCC(=O)C=1C=C2CC(NC2=C(C1)Cl)=O.B1(N2CCC[C@H]2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C.B.C1CCOC1.B.C1CCOC1>>ClC1=CC(=CC2=CC(N=C12)=O)[C@@H](CCl)O | [O:1]=[C:2]1[CH2:3][c:4]2[cH:5][c:6]([C:7](=[O:8])[CH2:9][Cl:10])[cH:11][c:12]([Cl:13])[c:14]2[NH:15]1>>[O:1]=[C:2]1[CH:3]=[c:4]2[cH:5][c:6]([C@H:7]([OH:8])[CH2:9][Cl:10])[cH:11][c:12]([Cl:13])[c:14]2=[N:15]1 | O=C1Cc2cc(C(=O)CCl)cc(Cl)c2N1 | O=C1C=c2cc([C@H](O)CCl)cc(Cl)c2=N1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 0e23a6e145710aab8144d95bf8d39c0bd26325b51d8b99aaa9e6c352a289b0f8 | e4974a4c001df102e096679869c277028d44070b72d396fdb130a9eed1593577 | O=C1C=c2ccccc2=N1 | [Cl;D1;H0:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5]1:[c:6]:[c:7](-[Cl;D1;H0:8]):[c;H0;D3;+0:9]2:[c;H0;D3;+0:10](:[c:11]:1)-[CH2;D2;+0:12]-[C:13](=[O;D1;H0:14])-[NH;D2;+0:15]-2>>[Cl;D1;H0:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:4])-[c:5]1:[c:6]:[c:7](-[Cl;D1;H0:8]):[c;H0;D3;+0:9]2:[c;H0;D3;+0:10](:[c:11]:1)=[CH;D2;+0:12... | null | [] | null | null | 1 | HOUR | To a solution of (S)-Methyl-CBS-oxazaborolidine (1M in toluene, 0.745 mL, 0.745 mmol) and BH3-THF (8 mL, 8 mmol) is added at the same time a solution of BH3-THF (19 mL, 19 mmol) and a solution of the 5-Chloroacetyl-7-chlorooxindole (37.98 mmol) in 19 mL of THF. Both solutions are added dropwise over 30 minutes. The sol... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amide | Secondary alcohol | c1ccc2c(c1)CCN2 | C1=c2ccccc2=NC1 | C1=c2ccccc2=NC1 | null | C1CCOC1 | null | 1 | O=C1Cc2cc(C(=O)CCl)cc(Cl)c2N1>C1CCOC1>O=C1C=c2cc([C@H](O)CCl)cc(Cl)c2=N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e68f57257c354f5096eee9a9dd79a3af | O=C(CCl)c1cc(Cl)c2[nH]c(=O)oc2c1>>O=c1[nH]c2c(Cl)cc([C@H](O)CCl)cc2o1 | ClCC(=O)C1=CC2=C(NC(O2)=O)C(=C1)Cl.B1(N2CCC[C@H]2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C.B.C1CCOC1.B.C1CCOC1>>ClC[C@@H](O)C1=CC2=C(NC(O2)=O)C(=C1)Cl | [O:1]=[c:2]1[nH:3][c:4]2[c:5]([Cl:6])[cH:7][c:8]([C:9](=[O:10])[CH2:11][Cl:12])[cH:13][c:14]2[o:15]1>>[O:1]=[c:2]1[nH:3][c:4]2[c:5]([Cl:6])[cH:7][c:8]([C@H:9]([OH:10])[CH2:11][Cl:12])[cH:13][c:14]2[o:15]1 | O=C(CCl)c1cc(Cl)c2[nH]c(=O)oc2c1 | O=c1[nH]c2c(Cl)cc([C@H](O)CCl)cc2o1 | null | null | C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=c1[nH]c2ccccc2o1 | [#8;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7]-[Cl;D1;H0:8]):[c:9]>>[#8;a:1]:[c:2]:[c:3]:[c:4](-[C@H;D3;+0:5](-[OH;D1;+0:6])-[C:7]-[Cl;D1;H0:8]):[c:9] | null | [] | null | null | 1 | HOUR | To a solution of (S)-Methyl-CBS-oxazaborolidine (1M in toluene, 0.745 mL, 0.745 mmol) and BH3-THF (8 mL, 8 mmol) is added at the same time a solution of BH3-THF (19 mL, 19 mmol) and a solution of the 6-Chloroacetyl-4-chloro-2-benzooxazolinone (37.98 mmol) in 19 mL of THF. Both solutions are added dropwise over 30 minut... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccc2ncoc2c1 | null | C1CCOC1 | null | 1 | O=C(CCl)c1cc(Cl)c2[nH]c(=O)oc2c1>C1CCOC1>O=c1[nH]c2c(Cl)cc([C@H](O)CCl)cc2o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b513f6152cc04c23bca178db3193f983 | CN1CCc2cc(C(=O)CCl)cc(Cl)c21>>CN1CCc2cc([C@H](O)CCl)cc(Cl)c21 | CN1CCC2=CC(=CC(=C12)Cl)C(CCl)=O.B1(N2CCC[C@H]2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C.B.C1CCOC1.B.C1CCOC1>>CN1CCC2=CC(=CC(=C12)Cl)[C@@H](CCl)O | [CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[CH2:10][Cl:11])[cH:12][c:13]([Cl:14])[c:15]21>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([C@H:8]([OH:9])[CH2:10][Cl:11])[cH:12][c:13]([Cl:14])[c:15]21 | CN1CCc2cc(C(=O)CCl)cc(Cl)c21 | CN1CCc2cc([C@H](O)CCl)cc(Cl)c21 | null | null | C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2c(c1)CCN2 | [Cl;D1;H0:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[Cl;D1;H0:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 1 | HOUR | To a solution of (S)-Methyl-CBS-oxazaborolidine (1M in toluene, 0.745 mL, 0.745 mmol) and BH3-THF (8 mL, 8 mmol) is added at the same time a solution of BH3-THF (19 mL, 19 mmol) and a solution of N-Methyl-5-chloroacetyl-7-chloro-indoline (37.98 mmol) in 19 mL of THF. Both solutions are added dropwise over 30 minutes. T... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccc2c(c1)CC[NH]2 | null | C1CCOC1 | null | 1 | CN1CCc2cc(C(=O)CCl)cc(Cl)c21>C1CCOC1>CN1CCc2cc([C@H](O)CCl)cc(Cl)c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-572c4b05daaf4761a34d23ff16bb40d2 | CN1CCc2cc([C@H](O)CCl)cc(Cl)c21>>Cn1ccc2cc([C@H](O)CCl)cc(Cl)c21 | CN1CCC2=CC(=CC(=C12)Cl)[C@@H](CCl)O.C1(=C(C(=O)C(=O)C(=C1Cl)Cl)Cl)Cl>>ClC[C@@H](O)C=1C=C2C=CN(C2=C(C1)Cl)C | [CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([C@H:8]([OH:9])[CH2:10][Cl:11])[cH:12][c:13]([Cl:14])[c:15]21>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([C@H:8]([OH:9])[CH2:10][Cl:11])[cH:12][c:13]([Cl:14])[c:15]12 | CN1CCc2cc([C@H](O)CCl)cc(Cl)c21 | Cn1ccc2cc([C@H](O)CCl)cc(Cl)c21 | null | null | COC(C)(C)C | Oxidation | OtherReaction | e52f71b450655496f3d86d95ebb6e98299f0cbbc99b337ca618ec98c1c63efaa | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc2[nH]ccc2c1 | [C;D1;H3:1]-[N;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]-1:[c:8]>>[C;D1;H3:1]-[n;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8] | null | [] | null | null | null | null | A solution (S)-N-Methyl-5-(2-chloro-1-hydroxylethyl)-7-chloro-indoline (0.10 mmol) in 100 mL of t-butyl methyl ether is treated with o-chloroanil (0.10 mmol) at ambient temperature. The solution is concentrated and the residue chromatographed over silica gel (1:1 hexane/ethyl acetate) to provide the corresponding indol... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | null | COC(C)(C)C | null | null | CN1CCc2cc([C@H](O)CCl)cc(Cl)c21>COC(C)(C)C>Cn1ccc2cc([C@H](O)CCl)cc(Cl)c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-30ebfc903be741bf9bf3bdcb75840f8a | CC(=O)O.O=c1[nH]c2c(Cl)cccc2o1>>Cc1nc2c(Cl)cccc2o1 | C(C)(=O)O.ClC1=CC=CC2=C1NC(O2)=O.[Li+].[OH-].Cl>>ClC1=CC=CC2=C1N=C(O2)C | O=C(O)[CH3:1].O=[c:2]1[nH:3][c:4]2[c:5]([Cl:6])[cH:7][cH:8][cH:9][c:10]2[o:11]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([Cl:6])[cH:7][cH:8][cH:9][c:10]2[o:11]1 | CC(=O)O.O=c1[nH]c2c(Cl)cccc2o1 | Cc1nc2c(Cl)cccc2o1 | null | null | O.C(C)O | C-C Coupling | OtherReaction | 4faecac641dd93f98f4ce241b33d4b841415a585b4d9deedf3177dcf9778889e | f96cdbfbd3979fc19377157a3b073c6b979862e16c815ce1feb7d13f6831561f | c1ccc2ocnc2c1 | O-C(=O)-[CH3;D1;+0:1].O=[c;H0;D3;+0:2]1:[#8;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[nH;D2;+0:8]:1>>[CH3;D1;+0:1]-[c;H0;D3;+0:2]1:[#8;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[n;H0;D2;+0:8]:1 | null | [] | null | null | null | null | To a solution of the 4-chloro-2-benzooxazolinone (0.10 mol) in 200 mL ethanol is added LiOH (0.20 mol) in 100 mL of water. The solution is refluxed for 8 hr and cooled. The solution is neutralized with 1N HCl and extracted with ethyl acetate followed by drying over MgSO4. The solution is concentrated and taken up in 20... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1nc2ccccc2o1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HO- | O.C(C)O | null | null | CC(=O)O.O=c1[nH]c2c(Cl)cccc2o1>O.C(C)O>Cc1nc2c(Cl)cccc2o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7f7883d0b5364bd08c37fd40f5f0311f | Cc1nc2c(Cl)cc(C(=O)CCl)cc2o1>>Cc1nc2c(Cl)cc([C@H](O)CCl)cc2o1 | ClCC(=O)C1=CC2=C(N=C(O2)C)C(=C1)Cl.B1(N2CCC[C@H]2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C.B.C1CCOC1.B.C1CCOC1>>ClC[C@@H](O)C1=CC2=C(N=C(O2)C)C(=C1)Cl | [CH3:1][c:2]1[n:3][c:4]2[c:5]([Cl:6])[cH:7][c:8]([C:9](=[O:10])[CH2:11][Cl:12])[cH:13][c:14]2[o:15]1>>[CH3:1][c:2]1[n:3][c:4]2[c:5]([Cl:6])[cH:7][c:8]([C@H:9]([OH:10])[CH2:11][Cl:12])[cH:13][c:14]2[o:15]1 | Cc1nc2c(Cl)cc(C(=O)CCl)cc2o1 | Cc1nc2c(Cl)cc([C@H](O)CCl)cc2o1 | null | null | C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc2ocnc2c1 | [#8;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7]-[Cl;D1;H0:8]):[c:9]>>[#8;a:1]:[c:2]:[c:3]:[c:4](-[C@H;D3;+0:5](-[OH;D1;+0:6])-[C:7]-[Cl;D1;H0:8]):[c:9] | null | [] | null | null | 1 | HOUR | To a solution of (S)-Methyl-CBS-oxazaborolidine (1M in toluene, 0.745 mL, 0.745 mmol) and BH3-THF (8 mL, 8 mmol) is added at the same time a solution of BH3-THF (19 mL, 19 mmol) and a solution of 6-Chloroacetyl-4-chloro-2-methyl-benzooxazole (37.98 mmol) in 19 mL of THF. Both solutions are added dropwise over 30 minute... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccc2ocnc2c1 | null | C1CCOC1 | null | 1 | Cc1nc2c(Cl)cc(C(=O)CCl)cc2o1>C1CCOC1>Cc1nc2c(Cl)cc([C@H](O)CCl)cc2o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-26b4ff43f38b428e96196749c9914569 | Cc1cc(F)ccc1[N+](=O)[O-].c1c[nH]cn1>>Cc1cc(-n2ccnc2)ccc1[N+](=O)[O-] | FC1=CC(=C(C=C1)[N+](=O)[O-])C.[OH-].[K+].N1C=NC=C1>>CC=1C=C(C=CC1[N+](=O)[O-])N1C=NC=C1 | F[c:4]1[cH:3][c:2]([CH3:1])[c:12]([N+:13](=[O:14])[O-:15])[cH:11][cH:10]1.[nH:5]1[cH:6][cH:7][n:8][cH:9]1>>[CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][cH:11][c:12]1[N+:13](=[O:14])[O-:15] | Cc1cc(F)ccc1[N+](=O)[O-].c1c[nH]cn1 | Cc1cc(-n2ccnc2)ccc1[N+](=O)[O-] | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]1:[c:7]:[c:8]:[nH;D2;+0:9]:[c:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[n;H0;D3;+0:9]1:[c:8]:[c:7]:[#7;a:6]:[c:10]:1):[c:4]:[c:5] | 82.9 | [{"value": 80.0, "product": "CC=1C=C(C=CC1[N+](=O)[O-])N1C=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "CC=1C=C(C=CC1[N+](=O)[O-])N1C=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of 4-fluoro-2-methyl-1-nitro-benzene (300 mg, 1.84 mmol) in DMSO (2 mL) were added KOH (20 mg, 3.87 mmol) and imidazole (263 mg, 3.88 mmol). The reaction mixture was heated to 100° C. for 3.5 h, cooled to room temperature, and diluted with ice-cold water. The resulting precipitate was filtered, washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HF | CS(=O)C | 100 | null | Cc1cc(F)ccc1[N+](=O)[O-].c1c[nH]cn1>CS(=O)C>Cc1cc(-n2ccnc2)ccc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d1d6bb0cccb4aad8b03093fcbe92900 | Cc1cc(-n2ccnc2)ccc1[N+](=O)[O-]>>Cc1cc(-n2ccnc2)ccc1N | CC=1C=C(C=CC1[N+](=O)[O-])N1C=NC=C1>>N1(C=NC=C1)C1=CC(=C(C=C1)N)C | O=[N+:13]([O-])[c:12]1[c:2]([CH3:1])[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][cH:11]1>>[CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][cH:11][c:12]1[NH2:13] | Cc1cc(-n2ccnc2)ccc1[N+](=O)[O-] | Cc1cc(-n2ccnc2)ccc1N | null | [Pd] | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-n2ccnc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98 | [{"value": 98.0, "product": "N1(C=NC=C1)C1=CC(=C(C=C1)N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.8, "product": "N1(C=NC=C1)C1=CC(=C(C=C1)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To 1-(3-methyl-4-nitro-phenyl)-1H-imidazole (200 mg, 0.98 mmol) and 10% Palladium on carbon (35 mg) was added degassed methanol (3 mL). The suspension was flushed and evacuated with hydrogen/vacuum line. The suspension was allowed to stir at room temperature for 14 h under hydrogen atmosphere (hydrogen balloon). The da... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1c[nH]cn1 | Other | [Pd] | null | 14 | Cc1cc(-n2ccnc2)ccc1[N+](=O)[O-]>[Pd]>Cc1cc(-n2ccnc2)ccc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b90ce00a134f4e968668e7bf0c7d4cbe | CC(=O)OC(C)=O.Cc1cc(-n2ccnc2)ccc1N.O=[N+]([O-])O>>CC(=O)Nc1c(C)cc(-n2ccnc2)cc1[N+](=O)[O-] | [OH-].[NH4+].[N+](=O)(O)[O-].N1(C=NC=C1)C1=CC(=C(C=C1)N)C.CC(=O)OC(=O)C>>N1(C=NC=C1)C1=CC(=C(C(=C1)[N+](=O)[O-])NC(C)=O)C | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[c:6]([CH3:7])[cH:8][c:9](-[n:10]2[cH:11][cH:12][n:13][cH:14]2)[cH:15][cH:16]1.O[N+:17](=[O:18])[O-:19]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[c:6]([CH3:7])[cH:8][c:9](-[n:10]2[cH:11][cH:12][n:13][cH:14]2)[cH:15][c:16]1[N+:17](=[O:18])[O-:19] | CC(=O)OC(C)=O.Cc1cc(-n2ccnc2)ccc1N.O=[N+]([O-])O | CC(=O)Nc1c(C)cc(-n2ccnc2)cc1[N+](=O)[O-] | null | null | O.C(Cl)Cl.OS(=O)(=O)O | Acylation | OtherReaction | 5dad59d909b0adbc4da312c8e57ce586de4d339a64d615a356fa6ac17d04ca65 | 833609dd4f7e47b21405e9ebff298baf513b0578c1fe05eacf461527af0cf863 | c1ccc(-n2ccnc2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O-[N+;H0;D3:4](-[O;-;D1;H0:5])=[O;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](-[N+;H0;D3:4](-[O;-;D1;H0:5])=[O;D1;H0:6]):[c:11]:[c:12] | 41 | [{"value": 41.0, "product": "N1(C=NC=C1)C1=CC(=C(C(=C1)[N+](=O)[O-])NC(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 4-imidazol-1-yl-2-methyl-phenylamine (1 g, 5.78 mmol) in CH2Cl2 (20 mL) was added Ac2O (0.7 mL, 7.28 mmol) at 0° C. The reaction mixture was stir at room temperature for 14 h and diluted with water. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were washed with saturated N... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Nitrate.Primary amine | Nitro group.Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1c[nH]cn1 | HO- | O.C(Cl)Cl.OS(=O)(=O)O | null | 14 | CC(=O)OC(C)=O.Cc1cc(-n2ccnc2)ccc1N.O=[N+]([O-])O>O.C(Cl)Cl.OS(=O)(=O)O>CC(=O)Nc1c(C)cc(-n2ccnc2)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16361839952e4c2f9aaa29ec6e0c26d9 | CC(=O)Nc1c(C)cc(-n2ccnc2)cc1[N+](=O)[O-]>>Cc1cc(-n2ccnc2)cc([N+](=O)[O-])c1N | N1(C=NC=C1)C1=CC(=C(C(=C1)[N+](=O)[O-])NC(C)=O)C.Cl.C(=O)(O)[O-].[Na+]>>N1(C=NC=C1)C1=CC(=C(C(=C1)[N+](=O)[O-])N)C | CC(=O)[NH:16][c:15]1[c:2]([CH3:1])[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][c:11]1[N+:12](=[O:13])[O-:14]>>[CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]1[NH2:16] | CC(=O)Nc1c(C)cc(-n2ccnc2)cc1[N+](=O)[O-] | Cc1cc(-n2ccnc2)cc([N+](=O)[O-])c1N | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(-n2ccnc2)cc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 76.7 | [{"value": 76.0, "product": "N1(C=NC=C1)C1=CC(=C(C(=C1)[N+](=O)[O-])N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "N1(C=NC=C1)C1=CC(=C(C(=C1)[N+](=O)[O-])N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of N-(4-imidazol-1-yl-2-methyl-6-nitro-phenyl)-acetamide (279 mg, 1.07 mmol) in ethanol (3 mL) was added 2 N HCl (2 mL). The reaction mixture was heated to reflux for 14 h, cooled to room temperature, and neutralized with saturated NaHCO3. The resulting bright orange solid was filtered and dried under v... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.c1c[nH]cn1 | HO- | C(C)O | null | null | CC(=O)Nc1c(C)cc(-n2ccnc2)cc1[N+](=O)[O-]>C(C)O>Cc1cc(-n2ccnc2)cc([N+](=O)[O-])c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a60f404f018543bf9d9e7824bdfcf0cf | Cc1cc(-n2ccnc2)cc([N+](=O)[O-])c1N>>Cc1cc(-n2ccnc2)cc(N)c1N | N1(C=NC=C1)C1=CC(=C(C(=C1)[N+](=O)[O-])N)C>>N1(C=NC=C1)C1=CC(=C(C(=C1)N)N)C | O=[N+:12]([O-])[c:11]1[cH:10][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:3][c:2]([CH3:1])[c:13]1[NH2:14]>>[CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][c:11]([NH2:12])[c:13]1[NH2:14] | Cc1cc(-n2ccnc2)cc([N+](=O)[O-])c1N | Cc1cc(-n2ccnc2)cc(N)c1N | null | [Pd] | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-n2ccnc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 91 | [{"value": 91.0, "product": "N1(C=NC=C1)C1=CC(=C(C(=C1)N)N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "N1(C=NC=C1)C1=CC(=C(C(=C1)N)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To 4-imidazol-1-yl-2-methyl-6-nitro-phenylamine (350 mg, 1.61 mmol) and 10% Palladium on carbon (40 mg) were added degassed methanol (5 mL) and TFA (5 drops). The reaction mixture was flushed and evacuated with hydrogen/vacuum line, stirred at room temperature for 14 h under hydrogen atmosphere (hydrogen balloon). The ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1c[nH]cn1 | Other | [Pd].O | null | 14 | Cc1cc(-n2ccnc2)cc([N+](=O)[O-])c1N>[Pd].O>Cc1cc(-n2ccnc2)cc(N)c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4a43b53029b4db7bc384db26afaf96a | CN(C)CCN(C)C=O.COc1ccccn1.II>>COc1nccc(I)c1C=O | C(C)(C)(C)[Li].II.C(=O)N(CCN(C)C)C.C(CCC)[Li].COC1=NC=CC=C1.II>>IC1=C(C(=NC=C1)OC)C=O | CN(C)CCN(C)[CH:10]=[O:11].[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][cH:7][cH:9]1.I[I:8]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([I:8])[c:9]1[CH:10]=[O:11] | CN(C)CCN(C)C=O.COc1ccccn1.II | COc1nccc(I)c1C=O | null | null | COCCOC.C1CCOC1 | C-C Coupling | OtherReaction | 2b03bdb814e8ecbd28c506d4eaab0883f217c05168bdd622b46534ce0cbf2465 | 68fe05c60a2028358b72d1158b10904b150b785464c8bfa3385607b8bc4b8760 | c1ccncc1 | C-N(-C)-C-C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].I-[I;H0;D1;+0:3].[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1>>[#8:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[c;H0;D3;+0:9](-[I;H0;D1;+0:3]):[c;H0;D3;+0:10]:1-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | -78 | CELSIUS | 1 | HOUR | A 5-liter three-necked round bottom flask was equipped with an overhead mechanical stirrer under nitrogen, the flask was charged with THF (1 L) and cooled to −78° C. To this stirred solution was added tert-butyllithium (1.7 M solution in pentane) (800 mL, 1.36 mol) via canula followed by 2-methoxypyridine (132.2 g, 1.2... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amine | Aromatic halide.Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | HI | COCCOC.C1CCOC1 | -78 | 1 | CN(C)CCN(C)C=O.COc1ccccn1.II>COCCOC.C1CCOC1>COc1nccc(I)c1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1bbed1e7c096464399c0acda0973c1e0 | COc1nccc(I)c1C=O.Cc1cc(-n2ccnc2)cc(N)c1N>>COc1nccc(I)c1-c1nc2c(C)cc(-n3ccnc3)cc2[nH]1 | N1(C=NC=C1)C1=CC(=C(C(=C1)N)N)C.IC1=C(C(=NC=C1)OC)C=O>>N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(=NC=CC2I)OC)C1)C | O=[CH:10][c:9]1[c:3]([O:2][CH3:1])[n:4][cH:5][cH:6][c:7]1[I:8].[NH2:11][c:12]1[c:13]([CH3:14])[cH:15][c:16](-[n:17]2[cH:18][cH:19][n:20][cH:21]2)[cH:22][c:23]1[NH2:24]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([I:8])[c:9]1-[c:10]1[n:11][c:12]2[c:13]([CH3:14])[cH:15][c:16](-[n:17]3[cH:18][cH:19][n:20][cH:21]3)[cH:22][c:... | COc1nccc(I)c1C=O.Cc1cc(-n2ccnc2)cc(N)c1N | COc1nccc(I)c1-c1nc2c(C)cc(-n3ccnc3)cc2[nH]1 | null | null | CO | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1cncc(-c2nc3ccc(-n4ccnc4)cc3[nH]2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3](-[#8:4]):[#7;a:5]:[c:6]:[c:7]:[c:8]:1-[I;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[I;D1;H0:9]):[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:15]):[nH;D2;+0:14]:1 | 72.6 | [{"value": 60.0, "product": "N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(=NC=CC2I)OC)C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(=NC=CC2I)OC)C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | To a solution of 5-imidazol-1-yl-3-methyl-benzene-1,2-diamine (175 mg, 0.93 mmol) in methanol (8 mL) was added a solution of 4-iodo-2-methoxy-pyridine-3-carbaldehyde (245 mg, 0.93 mmol) in methanol (5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1.5 h and then at room temperature for 2 h. After concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1.c1c[nH]cn1 | HO- | CO | 0 | 1.5 | COc1nccc(I)c1C=O.Cc1cc(-n2ccnc2)cc(N)c1N>CO>COc1nccc(I)c1-c1nc2c(C)cc(-n3ccnc3)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ab4500b11a8942d39110467a871b3764 | COc1nccc(I)c1-c1nc2c(C)cc(-n3ccnc3)cc2[nH]1>>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12 | N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(=NC=CC2I)OC)C1)C>>N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2I)=O)C1)C | C[O:21][c:20]1[c:14](-[c:13]2[nH:12][c:11]3[cH:10][c:4](-[n:5]4[cH:6][cH:7][n:8][cH:9]4)[cH:3][c:2]([CH3:1])[c:23]3[n:22]2)[c:15]([I:16])[cH:17][cH:18][n:19]1>>[CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][c:11]2[nH:12][c:13](-[c:14]3[c:15]([I:16])[cH:17][cH:18][nH:19][c:20]3=[O:21])[n:22][c:23]12 | COc1nccc(I)c1-c1nc2c(C)cc(-n3ccnc3)cc2[nH]1 | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12 | null | null | Cl.C(C)(=O)OCC | Miscellaneous | OtherReaction | ffbb4288e7102e6f227d930be4a9510dc9e13ff3142954fd43347db64909ca58 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1[nH]cccc1-c1nc2ccc(-n3ccnc3)cc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5]:[c:6]:[c:7]:1-[c:8](:[#7;a:9]):[#7;a:10]>>[#7;a:9]:[c:8](-[c:7]1:[c:6]:[c:5]:[c:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1]):[#7;a:10] | 81 | [{"value": 81.0, "product": "N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2I)=O)C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | The suspension of 6-imidazol-1-yl-2-(4-iodo-2-methoxy-pyridin-3-yl)-4-methyl-1H-benzimidazole in 1 N HCl (6 mL) was heated to 70° C. for 3 days, cooled to room temperature, and diluted with ethyl acetate. After extraction, the combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The resid... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccncc1 | c1cccnc1 | c1c[nH]cn1.c1ccc2[nH]cnc2c1.c1cccnc1 | Other | Cl.C(C)(=O)OCC | 70 | null | COc1nccc(I)c1-c1nc2c(C)cc(-n3ccnc3)cc2[nH]1>Cl.C(C)(=O)OCC>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-adab9fe6d5c14f968a2ebee063d0ae4a | Cc1cc(C#N)ccc1[N+](=O)[O-]>>Cc1cc(C#N)ccc1N | CC=1C=C(C#N)C=CC1[N+](=O)[O-]>>NC1=C(C=C(C#N)C=C1)C | O=[N+:10]([O-])[c:9]1[c:2]([CH3:1])[cH:3][c:4]([C:5]#[N:6])[cH:7][cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[cH:7][cH:8][c:9]1[NH2:10] | Cc1cc(C#N)ccc1[N+](=O)[O-] | Cc1cc(C#N)ccc1N | null | [Fe] | CC(=O)O.CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 94.1 | [{"value": 92.0, "product": "NC1=C(C=C(C#N)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.1, "product": "NC1=C(C=C(C#N)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3-methyl-4-nitro-benzonitrile (20 g, 0.123 mol) in HOAc (200 mL) was added iron powder (17.55 g, 0.309 mol). After 10 min, the reaction was exothermic and turned to dark color. The reaction mixture was allowed to stir at room temperature for 14 h and then diluted with EtOAc (200 mL). The brown precipit... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Fe].CC(=O)O.CCOC(=O)C | null | 0.166667 | Cc1cc(C#N)ccc1[N+](=O)[O-]>[Fe].CC(=O)O.CCOC(=O)C>Cc1cc(C#N)ccc1N |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.