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-0387783899c642a8b7eb4ba379bcdf5d | ord-a640596bee56439294189a305e34ca1b | FC(F)(F)Oc1ccc(CBr)cc1Cl.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(OC(F)(F)F)c(Cl)c1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@H](CCCC1)C(=O)N.BrCC1=CC(=C(C=C1)OC(F)(F)F)Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@H](CCCC1)C(=O)N)CC1=CC(=C(C=C1)OC(F)(F)F)Cl | Br[CH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][C:17]([F:18])([F:19])[F:20])[c:21]([Cl:22])[cH:23]1.[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[NH:10][S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]1>>[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[N:10]([CH2... | FC(F)(F)Oc1ccc(CBr)cc1Cl.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(OC(F)(F)F)c(Cl)c1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 59 | [{"value": 59.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@H](CCCC1)C(=O)N)CC1=CC(=C(C=C1)OC(F)(F)F)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound was prepared in 59% yield from (1S,2R)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (75 mg, 0.237 mmol) and 4-bromomethyl-2-chloro-1-trifluoromethoxy-benzene (72 mg, 0.249 mmol) according to the procedure described for Example 3: 1H NMR (500 Mz, DMSO) δ 7.81 (d, 2 H, J=8.5), 7.6... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | FC(F)(F)Oc1ccc(CBr)cc1Cl.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(OC(F)(F)F)c(Cl)c1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc5d1a3ab1bd44959d062ec02630b953 | Fc1ccc(CBr)cc1Cl.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(F)c(Cl)c1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@H](CCCC1)C(=O)N.BrCC1=CC(=C(C=C1)F)Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@H](CCCC1)C(=O)N)CC1=CC(=C(C=C1)F)Cl | Br[CH2:11][c:12]1[cH:13][cH:14][c:15]([F:16])[c:17]([Cl:18])[cH:19]1.[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[NH:10][S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1>>[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[N:10]([CH2:11][c:12]1[cH:13][cH:14][c:... | Fc1ccc(CBr)cc1Cl.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(F)c(Cl)c1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 43 | [{"value": 43.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@H](CCCC1)C(=O)N)CC1=CC(=C(C=C1)F)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound was prepared in 43% yield from (1S,2R)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (75 mg, 0.237 mmol) and 4-bromomethyl-2-chloro-1-fluoro-benzene (56 mg, 0.249 mmol) according to the procedure described for Example 3: 1H NMR (500 Mz, DMSO) δ 7.80 (d, 2 H, J=8.5), 7.63 (d, 2 H,... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | Fc1ccc(CBr)cc1Cl.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(F)c(Cl)c1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-062c4fdfd57a4121b3baf971cd0c07cc | Clc1ccc(CBr)s1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(Cl)s1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@H](CCCC1)C(=O)N.BrCC=1SC(=CC1)Cl>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@H](CCCC1)C(=O)N)CC=1SC(=CC1)Cl | Br[CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[s:17]1.[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[NH:10][S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]1>>[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[N:10]([CH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[s:... | Clc1ccc(CBr)s1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(Cl)s1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1cccs1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5].[C:6]-[C:7](-[NH;D2;+0:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12])-[C:13]-[C:14](-[N;D1;H2:15])=[O;D1;H0:16]>>[C:6]-[C:7](-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5])-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12])-[C:13]-[C:14](-[N;D1;H2:15])=[O;D1;H0:... | 38 | [{"value": 38.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@H](CCCC1)C(=O)N)CC=1SC(=CC1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound was prepared in 38% yield from (1S,2R)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (75 mg, 0.237 mmol) and 2-bromomethyl-5-chloro-thiophene (83 mg, 0.498 mmol) according to the procedure described in Example 3: 1H NMR (400 Mz, CDCl3) δ 7.72 (d, 2 H, J=6.6), 7.59 (d, 2 H, J=8.9)... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCC1.c1ccsc1.c1ccccc1 | HBr | null | null | null | Clc1ccc(CBr)s1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(Cl)s1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aaa12cfaca7042c7bba0cb2fba7fe154 | FC(F)(F)Sc1ccc(CBr)cc1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(SC(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@H](CCCC1)C(=O)N.BrCC1=CC=C(C=C1)SC(F)(F)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)SC(F)(F)F | Br[CH2:11][c:12]1[cH:13][cH:14][c:15]([S:16][C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1.[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[NH:10][S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]1>>[NH2:1][C:2](=[O:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[N:10]([CH2:11][c:1... | FC(F)(F)Sc1ccc(CBr)cc1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(SC(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 64 | [{"value": 64.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)SC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound was prepared in 64% yield from (1S,2R)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (100 mg, 0.316 mmol) and 1-bromomethyl-4-trifluoromethylsulfanyl-benzene (90 mg, 0.332 mmol) according to the procedure described in Example 3: 1H NMR (400 Mz, DMSO-d6) δ 7.79 (d, 2 H, J=8.8), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr | CO | null | null | FC(F)(F)Sc1ccc(CBr)cc1.NC(=O)[C@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>CO>NC(=O)[C@H]1CCCC[C@H]1N(Cc1ccc(SC(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed10b2c70d2b47c3a62ee8f7be7d71c0 | FC(F)(F)Oc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCC[C@@H]1N(Cc1ccc(OC(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)N.BrCC1=CC=C(C=C1)OC(F)(F)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)OC(F)(F)F | Br[CH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1.[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH:10][S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]1>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[N:10]([CH2:11]... | FC(F)(F)Oc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@@H]1CCCC[C@@H]1N(Cc1ccc(OC(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | CCOC(=O)C.C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 67 | [{"value": 67.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.3, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)OC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | cis-2-(4-Chloro-benzenesulfonylamino)-cyclohexanecarboxylic acid amide (200 mg, 0.63 mmol), CsCO3 (250 mg, 0.76 mmol), and 1-bromomethyl-4-trifluoromethoxy-benzene (155 mg, 0.69 mmol) was stirred in acetonitrile (15 mL) at room temperature for 18 h. The reaction was then diluted with EtOAc (150 mL) and washed with H2O,... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr | CCOC(=O)C.C(C)#N | null | null | FC(F)(F)Oc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>CCOC(=O)C.C(C)#N>NC(=O)[C@@H]1CCCC[C@@H]1N(Cc1ccc(OC(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b2ead5687a14a758587e33ca9a9ec93 | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)N.BrCC1=CC=C(C=C1)C(F)(F)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)C(F)(F)F | Br[CH2:11][c:12]1[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1.[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH:10][S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]1>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[N:10]([CH2:11][c:12]... | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@@H]1CCCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 52 | [{"value": 52.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (155 mg) was prepared in 52% yield from cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide and 1-bromomethyl-4-trifluoromethyl-benzene according to the procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.80 (d, 2 H, J=8.6 Hz), 7.61 (m, 4 H), 7.49 (d, 2 H,J=8.0 Hz), 7.32 (s, 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7d9b6a42ebc047d0a4e928f40c44ea67 | Fc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCC[C@@H]1N(Cc1ccc(F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)N.BrCC1=CC=C(C=C1)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)F | Br[CH2:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1.[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[NH:10][S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[N:10]([CH2:11][c:12]1[cH:13][cH:14][c:15](... | Fc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@@H]1CCCC[C@@H]1N(Cc1ccc(F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 67 | [{"value": 67.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (178 mg) was prepared in 67% yield from cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide and 1-bromomethyl-4-fluoro-benzene according to the procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.74 (d, 2 H, J=8.0 Hz), 7.60 (d, 2 H, J=8.0 Hz), 7.28 (m, 3 H), 7.05 (m, 2 H), 6.67... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | Fc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCC[C@@H]1N(Cc1ccc(F)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83b1b572c4fe4e0f8bef16bc986afbb0 | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>N#Cc1ccc(CN([C@H]2CCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)N.BrCC1=CC=C(C#N)C=C1>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)C#N | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:29][cH:28]1.[NH:8]([C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[C:15]([NH2:16])=[O:17])[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([C@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]2[C:15... | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | N#Cc1ccc(CN([C@H]2CCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 49 | [{"value": 49.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (133 mg) was prepared in 49% yield from cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide and 4-bromomethyl-benzonitrile according to the procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.84 (d, 2 H, J=8.0 Hz), 7.73 (d, 2 H, J=8.0 Hz), 7.66 (d, 2 H,J=8.0 Hz), 7.48 (d, 2 H,J... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HBr | null | null | null | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>N#Cc1ccc(CN([C@H]2CCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-474b07b4ecb54a2f8dd335b22ee451cf | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)N.BrCC1=CC=C(C(=O)OC)C=C1>>COC(C1=CC=C(C=C1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1[C@H](CCCC1)C(N)=O)=O | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:31][cH:30]1.[NH:10]([C@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]1[C:17]([NH2:18])=[O:19])[S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([C@@H:11]2[CH2:12][CH2:... | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | COC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 61 | [{"value": 61.0, "product": "COC(C1=CC=C(C=C1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1[C@H](CCCC1)C(N)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (90 mg) was prepared in 61% yield from cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide and methyl 4-(bromomethyl)benzoate according to the procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.83 (m, 4 H), 7.64 (d, 2 H, J=8.0 Hz), 7.42 (d, 2 H,J=8.0 Hz), 7.28 (s, 1 H), 6.61 (... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HBr | null | null | null | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c400ad91b144176b231fe597fdc5691 | FC(F)(F)Oc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCC[C@H]1N(Cc1ccc(OC(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@@H](CCCC1)C(=O)N.BrCC1=CC=C(C=C1)OC(F)(F)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)OC(F)(F)F | Br[CH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1.[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[NH:10][S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]1>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[N:10]([CH2:11][c... | FC(F)(F)Oc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@@H]1CCCC[C@H]1N(Cc1ccc(OC(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 20 | [{"value": 20.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound was prepared in 20% yield from trans-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide and 1-bromomethyl-4-trifluoromethoxy-benzene according to the procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.63 (d, 2 H, J=8.0 Hz), 7.43 (m, 4 H), 7.37 (s br, 1 H), 7.18 (d, 2 H, J=8.0 Hz)... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | FC(F)(F)Oc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCC[C@H]1N(Cc1ccc(OC(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-58448d7f5a0d42338e8645028949ddee | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCC[C@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@@H](CCCC1)C(=O)N.BrCC1=CC=C(C=C1)C(F)(F)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)C(F)(F)F | Br[CH2:11][c:12]1[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1.[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[NH:10][S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]1>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[N:10]([CH2:11][c:12]1[... | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@@H]1CCCC[C@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 45 | [{"value": 45.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (34 mg) was prepared in 45% yield from trans-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide and 1-bromomethyl-4-trifluoromethyl-benzene according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.77 (d, 2 H, J=8.0 Hz), 7.65 (d, 2 H, J=8.0 Hz), 7.57 (m, 3 ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCC[C@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-386f48eba40548c182cc938b1a8dd1e7 | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>N#Cc1ccc(CN([C@@H]2CCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@H]1[C@@H](CCCC1)C(=O)N.BrCC1=CC=C(C#N)C=C1>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)C#N | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:29][cH:28]1.[NH:8]([C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[C:15]([NH2:16])=[O:17])[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]2[C:... | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1 | N#Cc1ccc(CN([C@@H]2CCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 43 | [{"value": 43.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@H]1[C@@H](CCCC1)C(=O)N)CC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound was prepared in 43% yield from trans-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide and 4-bromomethyl-benzonitrile according to the procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.71(m, 4 H), 7.53 (m, 4 H), 7.29 (s, 1 H), 6.76 (s, 1 H), 4.44 (AB2,2 H,Δv=16,Jab=84 Hz), 3.96... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HBr | null | null | null | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCC[C@H]1NS(=O)(=O)c1ccc(Cl)cc1>>N#Cc1ccc(CN([C@@H]2CCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d22981a7dc349ca9113c23a40cea26a | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COC(=O)c1ccc(CN([C@@H]2CCCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCCC1)C(=O)N.BrCC1=CC=C(C(=O)OC)C=C1>>COC(C1=CC=C(C=C1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1[C@H](CCCCC1)C(N)=O)=O | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:32][cH:31]1.[NH:10]([C@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]1[C:18]([NH2:19])=[O:20])[S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([C@@H:11]2[CH2:... | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | COC(=O)c1ccc(CN([C@@H]2CCCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 28 | [{"value": 28.0, "product": "COC(C1=CC=C(C=C1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1[C@H](CCCCC1)C(N)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (321 mg) was prepared in 28% yield from cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide (800 mg, 2.42 mmol) and methyl 4-(bromomethyl)benzoate according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.83 (m, 4 H), 7.65 (d, 2 H,J=8.0 Hz), 7.45 (d, 2 ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCCCC1.c1ccccc1 | HBr | null | null | null | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COC(=O)c1ccc(CN([C@@H]2CCCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e612694473f4566a194a7e5b40d97a4 | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>N#Cc1ccc(CN([C@H]2CCCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCCC1)C(=O)N.BrCC1=CC=C(C#N)C=C1>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCCC1)C(=O)N)CC1=CC=C(C=C1)C#N | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:30][cH:29]1.[NH:8]([C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[C:16]([NH2:17])=[O:18])[S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([C@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:1... | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | N#Cc1ccc(CN([C@H]2CCCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 3 | [{"value": 3.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCCC1)C(=O)N)CC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (6.4 mg) was prepared in 3% yield from cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide (150 mg, 0.45 mmol) and 4-bromomethyl-benzonitrile according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.84 (m, 3 H), 7.69 (m, 4 H), 7.50 (d, 1 H, J=8.0 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCCCC1.c1ccccc1 | HBr | null | null | null | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>N#Cc1ccc(CN([C@H]2CCCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6b5454ca797445e19ec258975c3d6f82 | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCCC1)C(=O)N.BrCC1=CC=C(C=C1)C(F)(F)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCCC1)C(=O)N)CC1=CC=C(C=C1)C(F)(F)F | Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1.[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[NH:11][S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]1>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[N:11... | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@@H]1CCCCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 58 | [{"value": 58.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCCC1)C(=O)N)CC1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (127 mg) was prepared in 58% yield from cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide (150 mg, 0.45 mmol) and 1-bromomethyl-4-trifluoromethyl-benzene according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.80 (m, 2 H, J=8.0 Hz), 7.62 (m, 4 H), 7... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b44d5fef2bba4dd9be0b0a503504bc04 | BrCc1ccc(-n2cccn2)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCCC[C@@H]1N(Cc1ccc(-n2cccn2)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCCC1)C(=O)N.BrCC1=CC=C(C=C1)N1N=CC=C1>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCCC1)C(=O)N)CC1=CC=C(C=C1)N1N=CC=C1 | Br[CH2:12][c:13]1[cH:14][cH:15][c:16](-[n:17]2[cH:18][cH:19][cH:20][n:21]2)[cH:22][cH:23]1.[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[NH:11][S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][c:30]([Cl:31])[cH:32][cH:33]1>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:1... | BrCc1ccc(-n2cccn2)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@@H]1CCCCC[C@@H]1N(Cc1ccc(-n2cccn2)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccc(-n2cccn2)cc1)C1CCCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 18 | [{"value": 18.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCCC1)C(=O)N)CC1=CC=C(C=C1)N1N=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (40 mg) was prepared in 18% yield from cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide (150 mg, 0.45 mmol) and 1-(4-bromomethyl-phenyl)-1H-pyrazole according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 8.46 (s, 1 H), 7.79 (d, 2 H, J=12.0 Hz), 7.71... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCCCC1.c1ccccc1.c1cn[nH]c1.c1ccccc1 | HBr | null | null | null | BrCc1ccc(-n2cccn2)cc1.NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCCCC[C@@H]1N(Cc1ccc(-n2cccn2)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-075826d4fe38408cb9e4371c687d2ac0 | CCN.COC(=O)c1ccc(CN([C@@H]2CCCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1>>CCNC(=O)c1ccc(CN([C@H]2CCCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | COC(C1=CC=C(C=C1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1[C@H](CCCCC1)C(N)=O)=O.C(C)N>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCCC1)C(=O)N)CC1=CC=C(C=C1)C(NCC)=O | [CH3:1][CH2:2][NH2:3].CO[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][N:11]([C@@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C@@H:18]2[C:19]([NH2:20])=[O:21])[S:22](=[O:23])(=[O:24])[c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[cH:32][cH:33]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][N... | CCN.COC(=O)c1ccc(CN([C@@H]2CCCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | CCNC(=O)c1ccc(CN([C@H]2CCCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[NH2;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 18 | [{"value": 18.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCCCC1)C(=O)N)CC1=CC=C(C=C1)C(NCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 16 | HOUR | cis-4-[[(2-Carbamoyl-cycloheptyl)-(4-chlorobenzenesulfonyl)-amino]-methyl]-benzoic acid methyl ester (50 mg, 0.10 mmol) and ethylamine (1.0 M in MeOH, 6 mL) were heated with stirring at 60° C. for 16 h. The solution was concentrated to dryness and the product purified by silica-gel column chromatography (20%–90% EtOAc/... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCCCCC1.c1ccccc1 | HO- | null | 60 | 16 | CCN.COC(=O)c1ccc(CN([C@@H]2CCCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1>>CCNC(=O)c1ccc(CN([C@H]2CCCCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d45019bce59c47efb688bac5cb18f0b1 | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCC1)C(=O)N.BrCC1=CC=C(C=C1)C(F)(F)F>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCC1)C(=O)N)CC1=CC=C(C=C1)C(F)(F)F | Br[CH2:10][c:11]1[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1.[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]1[NH:9][S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]1>>[NH2:1][C:2](=[O:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]1[N:9]([CH2:10][c:11]1[cH:12][cH:13][... | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | NC(=O)[C@@H]1CCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 50 | [{"value": 50.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCC1)C(=O)N)CC1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (191 mg) was prepared in 50% yield from cis-2-(4-chlorobenzenesulfonylamino)-cyclopentanecarboxylic acid amide (250 mg, 0.83 mmol) and 1-bromomethyl-4-trifluoromethyl-benzene according to the N-alkylation procedure described in Example 11: 1 H NMR (DMSO-d6) δ 7.73 (d, 2 H, J=8.0 Hz), 7.56 (m, 4 H), ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | C1CCCC1.c1ccccc1.c1ccccc1 | HBr | null | null | null | FC(F)(F)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>NC(=O)[C@@H]1CCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63c4080b79dd478793eef49f45dbf3a0 | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>N#Cc1ccc(CN([C@H]2CCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCC1)C(=O)N.BrCC1=CC=C(C#N)C=C1>>ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCC1)C(=O)N)CC1=CC=C(C=C1)C#N | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:28][cH:27]1.[NH:8]([C@H:9]1[CH2:10][CH2:11][CH2:12][C@H:13]1[C:14]([NH2:15])=[O:16])[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([C@H:9]2[CH2:10][CH2:11][CH2:12][C@H:13]2[C:14]([NH2:15])=[O:1... | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | N#Cc1ccc(CN([C@H]2CCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 20 | [{"value": 20.0, "product": "ClC1=CC=C(C=C1)S(=O)(=O)N([C@@H]1[C@@H](CCC1)C(=O)N)CC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (68 mg) was prepared in 20% yield from cis-2-(4-Chlorobenzenesulfonylamino)-cyclopentanecarboxylic acid amide (250 mg, 0.83 mmol) and 4-bromomethyl-benzonitrile according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.70 (d, 2 H, J=8.0 Hz), 7.71 (d, 2 H, J=12.0 Hz), 7.60... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCC1.c1ccccc1 | HBr | null | null | null | N#Cc1ccc(CBr)cc1.NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>N#Cc1ccc(CN([C@H]2CCC[C@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8e371e35fc1e435e8257067758daaf41 | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COC(=O)c1ccc(CN([C@@H]2CCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCC1)C(=O)N.BrCC1=CC=C(C(=O)OC)C=C1>>COC(C1=CC=C(C=C1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1[C@H](CCC1)C(N)=O)=O | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:30][cH:29]1.[NH:10]([C@H:11]1[CH2:12][CH2:13][CH2:14][C@H:15]1[C:16]([NH2:17])=[O:18])[S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([C@@H:11]2[CH2:12][CH2:13][CH2:... | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | COC(=O)c1ccc(CN([C@@H]2CCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 43 | [{"value": 43.0, "product": "COC(C1=CC=C(C=C1)CN(S(=O)(=O)C1=CC=C(C=C1)Cl)[C@H]1[C@H](CCC1)C(N)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The titled compound (161 mg) was prepared in 43% yield from cis-2-(4-chlorobenzenesulfonylamino)-cyclopentanecarboxylic acid amide (250 mg, 0.83 mmol) and methyl 4-(bromomethyl)benzoate according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.82 (d, 2 H, J=8.0 Hz), 7.75 (d, 2 H, J=8.0 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCC1.c1ccccc1 | HBr | null | null | null | COC(=O)c1ccc(CBr)cc1.NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>COC(=O)c1ccc(CN([C@@H]2CCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ccb572f47204e98991b3ed20fabe162 | CCNC(=O)c1ccc(CCl)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>>CCNC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | [I-].[K+].C([O-])([O-])=O.[Cs+].[Cs+].ClC1=CC=C(C=C1)S(=O)(=O)N[C@@H]1[C@@H](CCCC1)C(=O)N.ClCC1=CC=C(C(=O)NCC)C=C1>>C(N)(=O)[C@@H]1[C@@H](CCCC1)N(S(=O)(=O)C1=CC=C(C=C1)Cl)CC1=CC=C(C(=O)NCC)C=C1 | Cl[CH2:10][c:9]1[cH:8][cH:7][c:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[cH:32][cH:31]1.[NH:11]([C@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]1[C:18]([NH2:19])=[O:20])[S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][N:11]([C@@H... | CCNC(=O)c1ccc(CCl)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1 | CCNC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 | null | null | C(C)(=O)OCC.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(c1ccccc1)N(Cc1ccccc1)C1CCCCC1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]>>[C:5]-[C:6](-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C:12]-[C:13](-[N;D1;H2:14])=[O;D1;H0:15] | 40.5 | [{"value": 40.0, "product": "C(N)(=O)[C@@H]1[C@@H](CCCC1)N(S(=O)(=O)C1=CC=C(C=C1)Cl)CC1=CC=C(C(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.5, "product": "C(N)(=O)[C@@H]1[C@@H](CCCC1)N(S(=O)(=O)C1=CC=C(C=C1)Cl)CC1=CC=C(C(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 8 | HOUR | Cesium carbonate (1.4 mmol) was added to a solution of (1R,2S)-2-(4-Chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (0.62 mmol) in DMF (7 mL). 4-Chloromethyl-N-ethylbenzamide (0.76 mmol) was added to the mixture followed by potassium iodide (0.75 mmol). Reaction was stirred at room temperature overnight. R... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.C1CCCCC1.c1ccccc1 | HCl | C(C)(=O)OCC.CN(C)C=O | null | 8 | CCNC(=O)c1ccc(CCl)cc1.NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1>C(C)(=O)OCC.CN(C)C=O>CCNC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31e32b715b4240b3acd76a37764f4545 | O=C1CCC(=O)O1.O=C1CCC(=O)O1>>O=C(O)CCC(=O)O | C(C1=CC=CC=C1)(=O)O.C1(CCC(=O)O1)=O.C1(CCC(=O)O1)=O.C(C1=CC=CC=C1)(=O)O>>C(C1=CC=CC=C1)(=O)O.C(CCC(=O)O)(=O)O | [O:1]=[C:2]1[CH2:4][CH2:5][C:6](=[O:7])[O:8]1.O=C1CCC(=O)[O:3]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[OH:8] | O=C1CCC(=O)O1.O=C1CCC(=O)O1 | O=C(O)CCC(=O)O | null | null | CC=1C=CC=CC1C | Protection | OtherReaction | da0c9c1398230b7f57f60c6dc4f1e2d7ac1d64333a725db73b018b10abdb3365 | ea81bfe55c61aaad1c8b89e11728f1a9a966874b18077baa8eefc78dbdc7f105 | null | O=C1-C-C-C(=O)-[O;H0;D2;+0:1]-1.[O;D1;H0:2]=[C;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-1>>[O;D1;H0:2]=[C;H0;D3;+0:3](-[OH;D1;+0:1])-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | null | [] | 165 | CELSIUS | 6 | HOUR | This Example describes a process used for making reaction product 6 as indicated in Table 2, namely a reaction product of di-isopropanolamine, benzoic acid and succinic acid anhydride. A 1 liter reaction flask was provided with a mechanical agitator, a thermometer and a DeanStark arrangement. 261.06 g (1.960 mol) of di... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Anhydride | Carboxylic acid.Carboxylic acid | C1CCOC1.C1CCOC1 | null | null | HO- | CC=1C=CC=CC1C | 165 | 6 | O=C1CCC(=O)O1.O=C1CCC(=O)O1>CC=1C=CC=CC1C>O=C(O)CCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2a4ac5e1aac4e2bbc9b719031e51886 | COc1cc(CC(=O)O)ccc1O.Oc1c(F)c(F)c(F)c(F)c1F>>COc1cc(CC(=O)Oc2c(F)c(F)c(F)c(F)c2F)ccc1O | OC1=C(C=C(C=C1)CC(=O)O)OC.FC1=C(C(=C(C(=C1O)F)F)F)F.Cl.C(C)N=C=NCCCN(C)C>>FC1=C(C(=C(C(=C1OC(CC1=CC(=C(C=C1)O)OC)=O)F)F)F)F | O[C:7]([CH2:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:23]([OH:24])[cH:22][cH:21]1)=[O:8].[OH:9][c:10]1[c:11]([F:12])[c:13]([F:14])[c:15]([F:16])[c:17]([F:18])[c:19]1[F:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[O:9][c:10]2[c:11]([F:12])[c:13]([F:14])[c:15]([F:16])[c:17]([F:18])[c:19]2[F:20])[cH:21][cH:22][c:23]1... | COc1cc(CC(=O)O)ccc1O.Oc1c(F)c(F)c(F)c(F)c1F | COc1cc(CC(=O)Oc2c(F)c(F)c(F)c(F)c2F)ccc1O | null | null | C(Cl)Cl | Acylation | Mitsunobu esterification | f18451ac648b00cb7c6684a3e64bee855b0320c7eb0f62b757b29d5fb6745560 | 1489fe0065c6531b60fda87a3857d7da1cd21873868856f058c20706f927fa08 | O=C(Cc1ccccc1)Oc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 98.2 | [{"value": 98.2, "product": "FC1=C(C(=C(C(=C1OC(CC1=CC(=C(C=C1)O)OC)=O)F)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 4-hydroxy-3-methoxyphenylacetic acid (4.65 g), pentafluorophenol (4.2 g), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (4.9 g) and methylene chloride (50 ml) was stirred at room temperature for 18 hours. The reaction solution was washed with water, and the organic layer was dried over sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 18 | COc1cc(CC(=O)O)ccc1O.Oc1c(F)c(F)c(F)c(F)c1F>C(Cl)Cl>COc1cc(CC(=O)Oc2c(F)c(F)c(F)c(F)c2F)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-64dd8aed2e704a5db3218f40da5b57c0 | CCOC(C)=O.O=[N+]([O-])c1cccc(B(O)O)c1>>O=[N+]([O-])c1cccc(C2=CCCCC2)c1 | [N+](=O)([O-])C=1C=C(C=CC1)B(O)O.[Cl-].[Li+].C([O-])([O-])=O.[Na+].[Na+].C(C)(=O)OCC>>C1(=CCCCC1)C=1C=C(C=CC1)[N+](=O)[O-] | O=[C:10](O[CH2:14][CH3:13])[CH3:11].OB(O)[c:8]1[cH:7][cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]2=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15]1 | CCOC(C)=O.O=[N+]([O-])c1cccc(B(O)O)c1 | O=[N+]([O-])c1cccc(C2=CCCCC2)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | OtherReaction | 16ef4b3265e74ef361382716ba0cf0b1730c1372f7f6bd1c9f1cded169f6e724 | 6c61a8d8087cf66a44b1bdd3b2cae66e4998841668591a424c6b7b8464aca09e | C1=C(c2ccccc2)CCCC1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=[C;H0;D3;+0:6](-[CH3;D1;+0:7])-O-[CH2;D2;+0:8]-[CH3;D1;+0:9]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[C:10]1=[CH;D2;+0:6]-[CH2;D2;+0:7]-[C:11]-[CH2;D2;+0:9]-[CH2;D2;+0:8]-1):[c:4]:[c:5] | null | [] | null | null | null | null | The above product (1.3 g) is dissolved in ethylene glycol dimethyl ether (10 ml), and thereto are added 3-nitrophenylboronic acid (1.3 g), tetrakis(triphenylphosphine)palladium (0) (330 mg), lithium chloride (720 mg) and 2M aqueous sodium carbonate (8 ml), and the mixture is heated under reflux for 3 hours. To the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boronic acid | null | c1ccccc1 | c1ccccc1.C1=CCCCC1 | c1ccccc1.C1=CCCCC1 | HO-.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | null | null | CCOC(C)=O.O=[N+]([O-])c1cccc(B(O)O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>O=[N+]([O-])c1cccc(C2=CCCCC2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-12d171e79ec8486d858f0a836123bd8b | O=[N+]([O-])c1cccc(C2=CCCCC2)c1>>Nc1cccc(C2CCCCC2)c1 | C1(=CCCCC1)C=1C=C(C=CC1)[N+](=O)[O-]>>C1(CCCCC1)C=1C=C(N)C=CC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([C:7]2=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13]1 | O=[N+]([O-])c1cccc(C2=CCCCC2)c1 | Nc1cccc(C2CCCCC2)c1 | null | [Pd] | C(C)O | Reduction | OtherReaction | aedbe3d2ebd0427caa3930e585ae8e4dc8f542b0b55db013139a0615a6de4c38 | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(C2CCCCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5](-[C;H0;D3;+0:6]1=[CH;D2;+0:7]-[C:8]-[C:9]-[C:10]-[C:11]-1):[c:12]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[CH;D3;+0:6]1-[C:11]-[C:10]-[C:9]-[C:8]-[CH2;D2;+0:7]-1):[c:12] | 78.9 | [{"value": 78.9, "product": "C1(CCCCC1)C=1C=C(N)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(Cyclohexen-1-yl)-1-nitrobenzene(7.5 g) is dissolved in ethanol (150 ml), and thereto is added 10% palladium on carbon (750 mg), and the mixture is subjected to catalytic hydrogenation at 25° C. The catalyst is removed by filtration, and the solvent is evaporated under reduced pressure. The residue is purified by sil... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | C1=CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | Other | [Pd].C(C)O | null | null | O=[N+]([O-])c1cccc(C2=CCCCC2)c1>[Pd].C(C)O>Nc1cccc(C2CCCCC2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd7b4d64b7d94c7185fa396d68006275 | CCCC[N+](CCCC)(CCCC)CCCC.COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.[OH-].[OH-]>>COc1cc(CC(=O)Nc2cccc(I)c2)ccc1OCCNC(=O)OC(C)(C)C | OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)I)OC.[OH-].[K+].[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C)(C)(C)OC(=O)NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)I)OC | CCCC[N+:23](CCC[CH3:29])([CH2:22][CH2:21][CH2:27][CH3:28])[CH2:24]CC[CH3:30].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([I:15])[cH:16]2)[cH:17][cH:18][c:19]1[OH:20].[OH-:26].[OH-:25]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:1... | CCCC[N+](CCCC)(CCCC)CCCC.COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.[OH-].[OH-] | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1OCCNC(=O)OC(C)(C)C | null | null | BrCCBr | C-C Coupling | OtherReaction | 757fa7843a163165783de92f1a885d2b0352e6afe60a0c4bfef0e44a2451f764 | 72df38691547ba592811bbfb775d3279d4c21ebe48b2858cb2f61d0534b16a23 | O=C(Cc1ccccc1)Nc1ccccc1 | C-C-C-C-[N+;H0;D4:1](-C-C-C-[CH3;D1;+0:2])(-[C:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;D1;H3:6])-[CH2;D2;+0:7]-C-C-[CH3;D1;+0:8].[OH-;D0:9].[OH-;D0:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:6]-[C;H0;D4;+0:5](-[CH3;D1;+0:2])(-[CH3;D1;+0:8])-[O;H0;D2;+0:9]-[C;H0;D3;+0:7](=[O;H0;D1;+0:10])-[NH;D2;+0:1]-[C:3]-[CH2;D2;+0... | null | [] | 40 | CELSIUS | 18 | HOUR | A mixture of Intermediate 1 (8.4 g), 1,2-dibromethane (160 ml), 40% aqueous potassium hydroxide solution (45 ml) and 40% aqueous tetrabutylammonium hydroxide solution (4.5 ml) is heated with stirring at 40° C. for 18 hours. The reaction solution is washed with water, and the organic layer is dried over sodium sulfate, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Carbamic ester.Ether.Ether.Boc | null | null | c1ccccc1.c1ccccc1 | Other | BrCCBr | 40 | 18 | CCCC[N+](CCCC)(CCCC)CCCC.COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.[OH-].[OH-]>BrCCBr>COc1cc(CC(=O)Nc2cccc(I)c2)ccc1OCCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9a05f2f40394d91bbdcb528d65562fd | BrCCBr.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O>>COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCBr | C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O.BrCCBr.[OH-].[K+].[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>BrCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1CCC(CC1)C(C)(C)C)OC | Br[CH2:30][CH2:31][Br:32].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([CH:15]3[CH2:16][CH2:17][CH:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]3)[cH:25]2)[cH:26][cH:27][c:28]1[OH:29]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c... | BrCCBr.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCBr | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(Cc1ccccc1)Nc1cccc(C2CCCCC2)c1 | Br-[CH2;D2;+0:1]-[C:2]-[Br;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[Br;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 50 | CELSIUS | 18 | HOUR | A mixture of N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide (the compound of Example 20) (1.5 g), 1,2-dibromethane (15 ml), 40% aqueous potassium hydroxide solution (5 ml) and 40% aqueous tetrabutylammonium hydroxide solution (0.5 ml) is stirred at 50° C. for 18 hours. The reaction solutio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | null | 50 | 18 | BrCCBr.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O>>COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8189913a89c34604a80c6e562e94b274 | O=C1CCCc2ccc([N+](=O)[O-])cc21.O=Cc1ccccn1>>O=C1C(=Cc2ccccn2)CCc2ccc([N+](=O)[O-])cc21 | [N+](=O)([O-])C1=CC=C2CCCC(C2=C1)=O.N1=C(C=CC=C1)C=O.N1CCCCC1.C(C)(=O)O>>[N+](=O)([O-])C1=CC=C2CCC(C(C2=C1)=O)=CC1=NC=CC=C1 | [O:1]=[C:2]1[CH2:3][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][c:21]21.O=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1>>[O:1]=[C:2]1[C:3](=[CH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][n:10]2)[CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][c:21]21 | O=C1CCCc2ccc([N+](=O)[O-])cc21.O=Cc1ccccn1 | O=C1C(=Cc2ccccn2)CCc2ccc([N+](=O)[O-])cc21 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Aldol condensation | cd07f60ebf87bf6a5ea60a0a56170ba2743f3105a037265dcd5d66e53d2a462f | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C1C(=Cc2ccccn2)CCc2ccccc21 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[C:6]-[C:7]-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5])-[C:9](=[O;D1;H0:10])-[c:11] | 19.1 | [{"value": 19.1, "product": "[N+](=O)([O-])C1=CC=C2CCC(C(C2=C1)=O)=CC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Nitro-1-tetralone (500 mg), pyridine-2-aldehyde (315 mg), piperidine (0.15 ml) and acetic acid (0.4 ml) are dissolved in toluene (10 ml), and the mixture is heated under reflux for 12 hours. The reaction solution is washed with water, and the organic layer is dried over sodium sulfate. The solvent is evaporated under... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccncc1.c1ccc2c(c1)CCCC2 | HO- | C1(=CC=CC=C1)C | null | null | O=C1CCCc2ccc([N+](=O)[O-])cc21.O=Cc1ccccn1>C1(=CC=CC=C1)C>O=C1C(=Cc2ccccn2)CCc2ccc([N+](=O)[O-])cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-97d243af42294beca3c2f10998f5b73c | ClCc1ccccc1.O=[N+]([O-])c1ccc2cc[nH]c2c1>>O=[N+]([O-])c1ccc2ccn(Cc3ccccc3)c2c1 | C(C)(=O)OCC.[N+](=O)([O-])C1=CC=C2C=CNC2=C1.C(C1=CC=CC=C1)Cl.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)[N+](=O)[O-] | Cl[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][nH:10][c:18]2[cH:19]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][n:10]([CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]2[cH:19]1 | ClCc1ccccc1.O=[N+]([O-])c1ccc2cc[nH]c2c1 | O=[N+]([O-])c1ccc2ccn(Cc3ccccc3)c2c1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 082ff5e2bbe1b14d00a5f44aa77c96a44849f09b23e40a195ca75be81235dc53 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[c:6]:1:[c:5]):[c:4] | 90 | [{"value": 90.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC=C(C=C12)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 6-Nitroindole (1.0 g) and benzyl chloride (2.2 g) are dissolved in dimethylsulfoxide (10 ml), and thereto is added potassium hydroxide (1.0 g), and the mixture is stirred at room temperature for 12 hours. To the mixture is added ethyl acetate, and the organic layer is washed with water, dried over sodium sulfate, and t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | HCl | CS(=O)C | null | 12 | ClCc1ccccc1.O=[N+]([O-])c1ccc2cc[nH]c2c1>CS(=O)C>O=[N+]([O-])c1ccc2ccn(Cc3ccccc3)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b59d64d91f264abeae1d4d6a9e60e2b0 | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.[Zn+][CH]1CCCCC1>>COc1cc(CC(=O)Nc2cccc(C3CCCCC3)c2)ccc1O | OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)I)OC.[Br-].C1(CCCCC1)[Zn+].[Cl-].[NH4+]>>C1(CCCCC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O | I[c:14]1[cH:13][cH:12][cH:11][c:10]([NH:9][C:7]([CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([OH:25])[cH:23][cH:22]2)=[O:8])[cH:21]1.[Zn+][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]... | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.[Zn+][CH]1CCCCC1 | COc1cc(CC(=O)Nc2cccc(C3CCCCC3)c2)ccc1O | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O1CCCC1 | C-C Coupling | OtherReaction | 77f0fcc693e9782b4cd79f902c11f89ae6e97ee5e7f63aa1dce27fa79313b7ad | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | O=C(Cc1ccccc1)Nc1cccc(C2CCCCC2)c1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[CH;D3;+0:8](-[Zn+])-[C:9]-[C:10]>>[C:6]-[C:7]-[CH;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | null | [] | null | null | 18 | HOUR | Intermediate 1 (850 mg) and tetrakis(triphenylphosphine)-palladium (0) (250 mg) are dissolved in tetrahydrofuran (16 ml), and thereto is added a 0.5 M tetrahydrofuran solution (20 ml) of cyclohexylzinc bromide under argon atmosphere at room temperature, and the mixture is stirred for 18 hours. A saturated aqueous ammon... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.C1CCCCC1 | c1ccccc1.C1CCCCC1 | c1ccccc1.c1ccccc1.C1CCCCC1 | I-.Zn | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O1CCCC1 | null | 18 | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.[Zn+][CH]1CCCCC1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O1CCCC1>COc1cc(CC(=O)Nc2cccc(C3CCCCC3)c2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cd1c80ce4ddb43ffb41ba233536d3992 | COc1cc(CC(=O)Oc2c(F)c(F)c(F)c(F)c2F)ccc1O.Nc1cccc(C2=CCCCC2)c1>>COc1cc(CC(=O)Nc2cccc(C3=CCCCC3)c2)ccc1O | FC1=C(C(=C(C(=C1OC(CC1=CC(=C(C=C1)O)OC)=O)F)F)F)F.C1(=CCCCC1)C=1C=C(N)C=CC1>>C1(=CCCCC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O | Fc1c(F)c(F)c(O[C:7]([CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([OH:25])[cH:23][cH:22]2)=[O:8])c(F)c1F.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([C:15]2=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]3=[CH:16][CH2:17][... | COc1cc(CC(=O)Oc2c(F)c(F)c(F)c(F)c2F)ccc1O.Nc1cccc(C2=CCCCC2)c1 | COc1cc(CC(=O)Nc2cccc(C3=CCCCC3)c2)ccc1O | null | null | C(C)(=O)OCC | Acylation | Aminolysis of esters | bee80c17ba750e5b878660daaf03b34b83cc65c10d42a24fde7726a66e741f89 | f21fd5f8c88779686ca0dcd2a6ec464a4e9cd0b9a76d99bbd673ae535081dde3 | O=C(Cc1ccccc1)Nc1cccc(C2=CCCCC2)c1 | F-c1:c(-F):c(-F):c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):c(-F):c:1-F.[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 86 | [{"value": 86.0, "product": "C1(=CCCCC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 18 | HOUR | 4-Hydroxy-3-methoxyphenylacetic acid pentafluorophenyl ester (60 mg) and Intermediate 2 (60 mg) are dissolved in ethyl acetate, and the mixture is stirred at 60° C. for 18 hours. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Ester.Primary amine | Secondary amide | c1ccccc1 | null | c1ccccc1.c1ccccc1.C1=CCCCC1 | HF | C(C)(=O)OCC | 60 | 18 | COc1cc(CC(=O)Oc2c(F)c(F)c(F)c(F)c2F)ccc1O.Nc1cccc(C2=CCCCC2)c1>C(C)(=O)OCC>COc1cc(CC(=O)Nc2cccc(C3=CCCCC3)c2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f11a7e25767446b9f431cd76e2a0831 | BrCc1ccccc1.O=C(Cc1ccc(O)c([N+](=O)[O-])c1)Nc1cccc(C2CCCCC2)c1>>O=C(Cc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1)Nc1cccc(C2CCCCC2)c1 | C1(CCCCC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)[N+](=O)[O-])=O.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+].CC(=O)C>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1CCCCC1)[N+](=O)[O-] | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[c:16]([N+:17](=[O:18])[O-:19])[cH:20]1)[NH:21][c:22]1[cH:23][cH:24][cH:25][c:26]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[cH:33]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12... | BrCc1ccccc1.O=C(Cc1ccc(O)c([N+](=O)[O-])c1)Nc1cccc(C2CCCCC2)c1 | O=C(Cc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1)Nc1cccc(C2CCCCC2)c1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc(C2CCCCC2)c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | null | null | A mixture of N-(3-cyclohexylphenyl)-4-hydroxy-3-nitrophenylacetamide (the compound of Example 29) (300 mg), benzyl bromide (287 mg), potassium carbonate (500 mg) and acetone (10 ml) is heated under reflux for 18 hours. After cooling, water is added to the mixture, and the mixture is extracted with ethyl acetate. The or... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | O | null | null | BrCc1ccccc1.O=C(Cc1ccc(O)c([N+](=O)[O-])c1)Nc1cccc(C2CCCCC2)c1>O>O=C(Cc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1)Nc1cccc(C2CCCCC2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4fca6104173e474c88751c15eb8cd6a3 | CS(=O)(=O)Cl.Nc1cc(CC(=O)Nc2cccc(C3CCCCC3)c2)ccc1OCc1ccccc1>>CS(=O)(=O)Nc1cc(CC(=O)Nc2cccc(C3CCCCC3)c2)ccc1OCc1ccccc1 | O.NC=1C=C(C=CC1OCC1=CC=CC=C1)CC(=O)NC1=CC(=CC=C1)C1CCCCC1.NC=1C=C(C=CC1OCC1=CC=CC=C1)CC(=O)NC1=CC(=CC=C1)C1CCCCC1.CS(=O)(=O)Cl>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1CCCCC1)NS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][c:6]1[cH:7][c:8]([CH2:9][C:10](=[O:11])[NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[cH:24]2)[cH:25][cH:26][c:27]1[O:28][CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]([CH2:9][C... | CS(=O)(=O)Cl.Nc1cc(CC(=O)Nc2cccc(C3CCCCC3)c2)ccc1OCc1ccccc1 | CS(=O)(=O)Nc1cc(CC(=O)Nc2cccc(C3CCCCC3)c2)ccc1OCc1ccccc1 | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc(C2CCCCC2)c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 0.5 | HOUR | 3-Amino-4-benzyloxy-N-(3-cyclohexylphenyl)phenylacetamide (the compound of Example 33) (200 mg) is dissolved in pyridine (5 ml), and thereto is added dropwise methanesulfonyl chloride (111 mg), and the mixture is stirred for 0.5 hour. Water is added to the mixture, and the mixture is extracted with ethyl acetate. The o... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.C1CCCCC1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 0.5 | CS(=O)(=O)Cl.Nc1cc(CC(=O)Nc2cccc(C3CCCCC3)c2)ccc1OCc1ccccc1>N1=CC=CC=C1>CS(=O)(=O)Nc1cc(CC(=O)Nc2cccc(C3CCCCC3)c2)ccc1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e05febe729d405e925148c7270b09cc | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.OB(O)c1ccccc1>>COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1O | OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)I)OC.C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].O>>OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1=CC=CC=C1)OC | I[c:14]1[cH:13][cH:12][cH:11][c:10]([NH:9][C:7]([CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([OH:25])[cH:23][cH:22]2)=[O:8])[cH:21]1.OB(O)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[... | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.OB(O)c1ccccc1 | COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1O | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCCC1 | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(Cc1ccccc1)Nc1cccc(-c2ccccc2)c1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 82.8 | [{"value": 82.8, "product": "OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1=CC=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Intermediate 1 (500 mg), phenylboronic acid (300 mg), tetrakis(triphenylphosphine)palladium (0) (150 mg) are dissolved in tetrahydrofuran (20 ml), and thereto are added cesium carbonate (850 mg) and water (10 ml). The mixture is heated under reflux for 18 hours under argon atmosphere. The reaction solution is extracted... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCCC1 | null | null | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.OB(O)c1ccccc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCCC1>COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-144fec4e7c764ed7b72601061fc955a2 | C#Cc1ccccc1.COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O>>COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3)c2)ccc1O | OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)I)OC.C(#C)C1=CC=CC=C1.C(C)N(CC)CC>>OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C#CC1=CC=CC=C1)OC | [CH:15]#[C:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.I[c:14]1[cH:13][cH:12][cH:11][c:10]([NH:9][C:7]([CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:26]([OH:27])[cH:25][cH:24]2)=[O:8])[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]#[C:16][c:17]3[cH:18][cH:19][cH... | C#Cc1ccccc1.COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O | COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3)c2)ccc1O | null | [Cu]I.C1([P]([Pd][P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)=CC=CC=C1 | C(C)#N | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=C(Cc1ccccc1)Nc1cccc(C#Cc2ccccc2)c1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[C;H0;D2;+0:6]#[C:7]-[c:8]):[c:2]:[c:3] | 77.2 | [{"value": 77.2, "product": "OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C#CC1=CC=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of Intermediate 1 (2.5 g), ethynylbenzene (800 mg), copper (I) iodide (124 mg), bis(triphenylphosphine)palladium (II) dichloride (1.37 g), triethylamine (19.0 g) and acetonitrile (20 ml) is heated with stirring at 50° C. under argon atmosphere. The solvent is evaporated under reduced pressure, and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HI | [Cu]I.C1([P]([Pd][P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)=CC=CC=C1.C(C)#N | 50 | null | C#Cc1ccccc1.COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O>[Cu]I.C1([P]([Pd][P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)=CC=CC=C1.C(C)#N>COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3)c2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5a3ba4d153e4ab996f6b3ba98b5134c | C#Cc1cccc(NC(=O)Cc2ccc(O)c(OC)c2)c1.FC(F)(F)c1ccccc1I>>COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3C(F)(F)F)c2)ccc1O | C(#C)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O.FC(C1=C(C=CC=C1)I)(F)F.C(C)N(CC)CC>>OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C#CC1=C(C=CC=C1)C(F)(F)F)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]#[CH:16])[cH:27]2)[cH:28][cH:29][c:30]1[OH:31].I[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[C:23]([F:24])([F:25])[F:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]#[C:16... | C#Cc1cccc(NC(=O)Cc2ccc(O)c(OC)c2)c1.FC(F)(F)c1ccccc1I | COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3C(F)(F)F)c2)ccc1O | null | [Cu]I.C1([P]([Pd][P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)=CC=CC=C1 | C(C)#N | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=C(Cc1ccccc1)Nc1cccc(C#Cc2ccccc2)c1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[CH;D1;+0:10]#[C:11]-[c:12]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[C;H0;D2;+0:10]#[C:11]-[c:12]):[c:2]:[c:3] | null | [] | 50 | CELSIUS | 18 | HOUR | A mixture of N-(3-ethynylphenyl)-4-hydroxy-3-methoxypheny-acetamide (the compound of Example 19) (200 mg), 1-trifluoromethyl-2-iodobenzene (280 mg), copper (I) iodide (19 mg), bis(triphenylphosphine)palladium (II) dichloride (70 mg), triethylamine (1 g) and acetonitrile (3 ml) is heated with stirring at 50° C. under ar... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HI | [Cu]I.C1([P]([Pd][P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)=CC=CC=C1.C(C)#N | 50 | 18 | C#Cc1cccc(NC(=O)Cc2ccc(O)c(OC)c2)c1.FC(F)(F)c1ccccc1I>[Cu]I.C1([P]([Pd][P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)=CC=CC=C1.C(C)#N>COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3C(F)(F)F)c2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-618c50e72df147e99a9b64fa3649d28f | COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3)c2)ccc1O>>COc1cc(CC(=O)Nc2cccc(CCc3ccccc3)c2)ccc1O | OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C#CC1=CC=CC=C1)OC.OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C#CC1=CC=CC=C1)OC>>OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)CCC1=CC=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]#[C:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23]2)[cH:24][cH:25][c:26]1[OH:27]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([CH2:15][CH2:16][c:17]3[cH:18][cH:19][cH:2... | COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3)c2)ccc1O | COc1cc(CC(=O)Nc2cccc(CCc3ccccc3)c2)ccc1O | null | [Pd] | C(C)(=O)OCC | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | O=C(Cc1ccccc1)Nc1cccc(CCc2ccccc2)c1 | [c:1]:[c:2](-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]>>[c:1]:[c:2](-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8] | null | [] | null | null | null | null | 4-Hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]phenylacetamide (the compound of Example 36) (250 mg) is dissolved in ethyl acetate (10 ml), and thereto is added 10% palladium on carbon (25 mg), and the mixture is subjected to catalytic hydrogenation at 25° C. The catalyst is removed by filtration, and the solvent is ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | [Pd].C(C)(=O)OCC | null | null | COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3)c2)ccc1O>[Pd].C(C)(=O)OCC>COc1cc(CC(=O)Nc2cccc(CCc3ccccc3)c2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07dd7afb520a43b7959c4a57316588b6 | COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3)c2)ccc1O>>COc1cc(CC(=O)Nc2cccc(/C=C\c3ccccc3)c2)ccc1O | OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C#CC1=CC=CC=C1)OC>>OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)\C=C/C1=CC=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]#[C:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23]2)[cH:24][cH:25][c:26]1[OH:27]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14](/[CH:15]=[CH:16]\[c:17]3[cH:18][cH:19][cH:... | COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3)c2)ccc1O | COc1cc(CC(=O)Nc2cccc(/C=C\c3ccccc3)c2)ccc1O | null | [Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2] | C(C)(=O)OCC | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | O=C(Cc1ccccc1)Nc1cccc(/C=C\c2ccccc2)c1 | [c:1]:[c:2](-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]>>[c:1]:[c:2](/[CH;D2;+0:3]=[CH;D2;+0:4]\[c:5](:[c:6]):[c:7]):[c:8] | 33.1 | [{"value": 33.1, "product": "OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)\\C=C/C1=CC=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]phenylacetamide (150 mg) obtained in Example 36 is dissolved in ethyl acetate (10 ml), and thereto is added Lindlar catalyst (5% lead-poisoned palladium-calcium carbonate) (15 mg), and the mixture is subjected to catalytic hydrogenation at 25° C. The catalyst is removed ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | [Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2].C(C)(=O)OCC | null | null | COc1cc(CC(=O)Nc2cccc(C#Cc3ccccc3)c2)ccc1O>[Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2].C(C)(=O)OCC>COc1cc(CC(=O)Nc2cccc(/C=C\c3ccccc3)c2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e923ca3883c74703a1879eb55299542a | CCN=C=NCCCN(C)C.COc1cc(CC(=O)Nc2cccc(C(=O)O)c2)ccc1O>>COc1cc(CC(=O)Nc2cccc(C(=O)NC3CCCCC3)c2)ccc1O | C(=O)(O)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O.FC1=C(C(=C(C(=C1O)F)F)F)F.Cl.C(C)N=C=NCCCN(C)C>>C1(CCCCC1)NC(=O)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O | C(C[CH2:20][N:17]=[C:18]=N[CH2:21][CH3:22])N([CH3:19])[CH3:23].O[C:15]([c:14]1[cH:13][cH:12][cH:11][c:10]([NH:9][C:7]([CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:27]([OH:28])[cH:26][cH:25]2)=[O:8])[cH:24]1)=[O:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15](=[O:16])[N... | CCN=C=NCCCN(C)C.COc1cc(CC(=O)Nc2cccc(C(=O)O)c2)ccc1O | COc1cc(CC(=O)Nc2cccc(C(=O)NC3CCCCC3)c2)ccc1O | null | null | C(Cl)Cl | Acylation | OtherReaction | 20ca78894bf7e264d3229302dbb353bb1bc57070fc6e4a53665cf48dfdaf6fdc | 1020db3dba86e4d14a590516e63a79d14860ee6fb77c36eacf741e79c98cfdd3 | O=C(Cc1ccccc1)Nc1cccc(C(=O)NC2CCCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-N(-[CH3;D1;+0:7])-C-C-[CH2;D2;+0:8]-[N;H0;D2;+0:9]=[C;H0;D2;+0:10]=N-[CH2;D2;+0:11]-[CH3;D1;+0:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[CH;D3;+0:10]1-[CH2;D2;+0:6]-[CH2;D2;+0:8]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[CH2;D2;+0:7]-1)-[c:3](:[c:4]):[c:5] | 94.7 | [{"value": 94.7, "product": "C1(CCCCC1)NC(=O)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 18 | HOUR | A mixture of N-(3-carboxyphenyl)-4-hydroxy-3-methoxyphenylacetamide (500 mg), pentafluorophenol (305 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (320 mg) and methylene chloride (10 ml) is stirred at 25° C. for 18 hours. The reaction solution is washed with water, and the solvent is evaporated under... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Secondary amide | null | C1CCCCC1 | c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | C(Cl)Cl | 25 | 18 | CCN=C=NCCCN(C)C.COc1cc(CC(=O)Nc2cccc(C(=O)O)c2)ccc1O>C(Cl)Cl>COc1cc(CC(=O)Nc2cccc(C(=O)NC3CCCCC3)c2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69c53f74268e4117b13f9b2679b14f4c | COc1cc(CC(=O)Oc2c(F)c(F)c(F)c(F)c2F)ccc1OCCN1C(=O)c2ccccc2C1=O.Nc1cccc(C2CCCCCC2)c1>>COc1cc(CC(=O)Nc2cccc(C3CCCCCC3)c2)ccc1OCCN1C(=O)c2ccccc2C1=O | FC1=C(C(=C(C(=C1OC(CC1=CC(=C(C=C1)OCCN1C(C=2C(C1=O)=CC=CC2)=O)OC)=O)F)F)F)F.C1(CCCCCC1)C=1C=C(N)C=CC1>>C1(CCCCCC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCCN1C(C=2C(C1=O)=CC=CC2)=O)OC)=O | Fc1c(F)c(F)c(O[C:7]([CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH2:27][CH2:28][N:29]3[C:30](=[O:31])[c:32]4[cH:33][cH:34][cH:35][cH:36][c:37]4[C:38]3=[O:39])[cH:24][cH:23]2)=[O:8])c(F)c1F.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[cH:22]1>>[CH3:1][O:2][... | COc1cc(CC(=O)Oc2c(F)c(F)c(F)c(F)c2F)ccc1OCCN1C(=O)c2ccccc2C1=O.Nc1cccc(C2CCCCCC2)c1 | COc1cc(CC(=O)Nc2cccc(C3CCCCCC3)c2)ccc1OCCN1C(=O)c2ccccc2C1=O | null | null | C(C)(=O)OCC | Acylation | Aminolysis of esters | bee80c17ba750e5b878660daaf03b34b83cc65c10d42a24fde7726a66e741f89 | f21fd5f8c88779686ca0dcd2a6ec464a4e9cd0b9a76d99bbd673ae535081dde3 | O=C(Cc1ccc(OCCN2C(=O)c3ccccc3C2=O)cc1)Nc1cccc(C2CCCCCC2)c1 | F-c1:c(-F):c(-F):c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):c(-F):c:1-F.[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 71.7 | [{"value": 71.7, "product": "C1(CCCCCC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCCN1C(C=2C(C1=O)=CC=CC2)=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 18 | HOUR | 3-Methoxy-4-(2-phthalimidoethoxy)phenylacetic acid pentafluorophenyl ester (690 mg) and 3-cycloheptylaniline (500 mg) are dissolved in ethyl acetate (10 ml), and the mixture is heated with stirring at 60° C. for 18 hours. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Ester.Primary amine | Secondary amide | c1ccccc1 | null | c1ccccc1.c1ccccc1.C1CCCCCC1.c1ccc2c(c1)C[NH]C2 | HF | C(C)(=O)OCC | 60 | 18 | COc1cc(CC(=O)Oc2c(F)c(F)c(F)c(F)c2F)ccc1OCCN1C(=O)c2ccccc2C1=O.Nc1cccc(C2CCCCCC2)c1>C(C)(=O)OCC>COc1cc(CC(=O)Nc2cccc(C3CCCCCC3)c2)ccc1OCCN1C(=O)c2ccccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8de8a8b5aa88425d8b13bde934774592 | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1OCCNC(=O)OC(C)(C)C.OB(O)c1ccccc1>>COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1OCCNC(=O)OC(C)(C)C | C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].O.C(C)(C)(C)OC(=O)NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)I)OC>>C(C)(C)(C)OC(=O)NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1=CC=CC=C1)OC | I[c:14]1[cH:13][cH:12][cH:11][c:10]([NH:9][C:7]([CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[cH:23][cH:22]2)=[O:8])[cH:21]1.OB(O)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:1... | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1OCCNC(=O)OC(C)(C)C.OB(O)c1ccccc1 | COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1OCCNC(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCCC1 | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(Cc1ccccc1)Nc1cccc(-c2ccccc2)c1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:2]:[c:3] | 77.3 | [{"value": 77.3, "product": "C(C)(C)(C)OC(=O)NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1=CC=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Intermediate 4 (500 mg) is dissolved in tetrahydrofuran (10 ml), and thereto are added tetrakis(triphenylphosphine)palladium (0) (110 mg), phenylboronic acid (230 mg), cesium carbonate (1.2 g) and water (2 ml), and the mixture is heated under reflux for 18 hours under argon atmosphere. The solvent is evaporated under r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCCC1 | null | null | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1OCCNC(=O)OC(C)(C)C.OB(O)c1ccccc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCCC1>COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1OCCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-475396a544d2493ca1fa498aca729fbe | CC(=O)Cl.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O>>COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OC(C)=O | C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O.C(C)N(CC)CC.C(C)(=O)Cl>>C(C)(=O)OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1CCC(CC1)C(C)(C)C)OC | Cl[C:30]([CH3:31])=[O:32].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([CH:15]3[CH2:16][CH2:17][CH:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]3)[cH:25]2)[cH:26][cH:27][c:28]1[OH:29]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c... | CC(=O)Cl.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OC(C)=O | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C(Cc1ccccc1)Nc1cccc(C2CCCCC2)c1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 81.4 | [{"value": 81.4, "product": "C(C)(=O)OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1CCC(CC1)C(C)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 18 | HOUR | N-[3-(4-tert-Butylcyclohexan-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide (100 mg) obtained in Example 20, triethylamine (94 mg) and 4-dimethylaminopyridine (5 mg) are dissolved in methylene chloride (5 ml), and thereto is added dropwise acetyl chloride (40 mg) under ice-cooling. The mixture is stirred at 25° C. for... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccccc1.c1ccccc1.C1CCCCC1 | HCl | CN(C1=CC=NC=C1)C.C(Cl)Cl | 25 | 18 | CC(=O)Cl.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O>CN(C1=CC=NC=C1)C.C(Cl)Cl>COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c144e12b7636471bb89c322c897a8c5d | CCOC(=O)CBr.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O>>CCOC(=O)COc1ccc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)cc1OC | C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCC(=O)OCC)OC)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][cH:10][c:11]([CH2:12][C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([CH:21]3[CH2:22][CH2:23][CH:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][CH2:30]3)[cH:31]2)[cH:32][c:33]1[O:34][CH3:35]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][... | CCOC(=O)CBr.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O | CCOC(=O)COc1ccc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)cc1OC | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | O=C(Cc1ccccc1)Nc1cccc(C2CCCCC2)c1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 75.8 | [{"value": 75.8, "product": "C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCC(=O)OCC)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide (130 mg) and ethyl bromoacetate (84 mg) are dissolved in acetone, and thereto is added potassium carbonate (180 mg), and the reaction solution is heated under reflux for 18 hours. The reaction solution is filtered, and the filtrate is concentr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | CC(=O)C | null | null | CCOC(=O)CBr.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O>CC(=O)C>CCOC(=O)COc1ccc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca4213a13adb45e8b1ae784052865be6 | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCBr.NCCO>>COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCNCCO | C(Cl)(Cl)Cl.BrCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1CCC(CC1)C(C)(C)C)OC.NCCO.C(C)N(CC)CC>>C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCCNCCO)OC)=O | Br[CH2:31][CH2:30][O:29][c:28]1[c:3]([O:2][CH3:1])[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([CH:15]3[CH2:16][CH2:17][CH:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]3)[cH:25]2)[cH:26][cH:27]1.[NH2:32][CH2:33][CH2:34][OH:35]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:... | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCBr.NCCO | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCNCCO | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C(Cc1ccccc1)Nc1cccc(C2CCCCC2)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4] | 88.5 | [{"value": 88.5, "product": "C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCCNCCO)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Intermediate 5 (200 mg), 2-aminoethanol (122 mg) and triethylamine (45 mg) are dissolved in acetonitrile (5 ml), and the mixture is heated under reflux for 18 hours. To the reaction solution is added chloroform, and the mixture is washed with water. The organic layer is dried over sodium sulfate, and the solvent is eva... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | C(C)#N | null | null | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCBr.NCCO>C(C)#N>COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCNCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a9766c478ba4aec9949a59023cce479 | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCN.O=CO>>COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCNC=O | NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1CCC(CC1)C(C)(C)C)OC.C(=O)O.C(C)(=O)OC(C)=O>>C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCCNC=O)OC)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([CH:15]3[CH2:16][CH2:17][CH:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]3)[cH:25]2)[cH:26][cH:27][c:28]1[O:29][CH2:30][CH2:31][NH2:32].O[CH:33]=[O:34]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH... | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCN.O=CO | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCNC=O | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccccc1)Nc1cccc(C2CCCCC2)c1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]-[C:4]-[NH;D2;+0:5]-[CH;D2;+0:1]=[O;D1;H0:2] | 75.2 | [{"value": 75.2, "product": "C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCCNC=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | Formic acid (30 mg) is slowly added to acetic anhydride (75 mg), and the mixture is heated with stirring at 60° C. for 2 hours. To the mixture is added dry tetrahydrofuran (0.2 ml), and further added 4-(2-aminoethoxy)-N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-3-methoxyphenylacetamide (100 mg) obtained in Example 62 at ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | O1CCCC1 | 60 | 2 | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCN.O=CO>O1CCCC1>COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCNC=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89b0d7fa5702421e85b242cc98976b63 | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.COc1cc(CC(=O)Nc2ccccc2I)ccc1O>>COc1cc(CC(=O)Nc2ccccc2C#Cc2ccccc2)ccc1O | OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)I)OC.OC1=C(C=C(C=C1)CC(=O)NC1=C(C=CC=C1)I)OC>>OC1=C(C=C(C=C1)CC(=O)NC1=C(C=CC=C1)C#CC1=CC=CC=C1)OC | COc1cc([CH2:17]C(=O)N[c:18]2[cH:19][cH:20][cH:21][c:16](I)[cH:23]2)c[cH:22]c1O.I[c:15]1[c:10]([NH:9][C:7]([CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:26]([OH:27])[cH:25][cH:24]2)=[O:8])[cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]#[C... | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.COc1cc(CC(=O)Nc2ccccc2I)ccc1O | COc1cc(CC(=O)Nc2ccccc2C#Cc2ccccc2)ccc1O | null | null | null | C-C Coupling | OtherReaction | f1cc0296bd9798f04e4f61cd804ae01007cdd4f297232864ecd543802f03e45a | 169ecbf7232d1ed0ade5b63e46d7de369830252e6d219f3a30bf728b864b0511 | O=C(Cc1ccccc1)Nc1ccccc1C#Cc1ccccc1 | C-O-c1:c:c(-[CH2;D2;+0:1]-C(=O)-N-[c;H0;D3;+0:2]2:[c:3]:[c:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-I):[cH;D2;+0:7]:2):c:[cH;D2;+0:8]:c:1-O.I-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[#7:13]-[C:14]=[O;D1;H0:15]):[c:16]>>[O;D1;H0:15]=[C:14]-[#7:13]-[c:12](:[c:16]):[c;H0;D3;+0:9](-[C;H0;D2;+0:6]#[C;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]... | null | [] | null | null | null | null | Instead of Intermediate 1 in Example 36, 4-hydroxy-N-(2-iodophenyl)-3-methoxyphenylacetamide is treated in a similar manner to Example 36 to give the desired compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Secondary amide.Aromatic alcohol | Alkyne | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HI | null | null | null | COc1cc(CC(=O)Nc2cccc(I)c2)ccc1O.COc1cc(CC(=O)Nc2ccccc2I)ccc1O>>COc1cc(CC(=O)Nc2ccccc2C#Cc2ccccc2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8b82934688844b438738b1ec34f7bba1 | COc1cc(CC(=O)Nc2ccccc2C#Cc2ccccc2)ccc1O>>COc1cc(CC(=O)Nc2ccccc2CCc2ccccc2)ccc1O | OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C#CC1=CC=CC=C1)OC.OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C#CC1=CC=CC=C1)OC.OC1=C(C=C(C=C1)CC(=O)NC1=C(C=CC=C1)C#CC1=CC=CC=C1)OC.OC1=C(C=C(C=C1)CC(=O)NC1=C(C=CC=C1)C#CC1=CC=CC=C1)OC>>OC1=C(C=C(C=C1)CC(=O)NC1=C(C=CC=C1)CCC1=CC=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]#[C:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25][c:26]1[OH:27]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[CH2:16][CH2:17][c:18]2[cH:19][cH:20]... | COc1cc(CC(=O)Nc2ccccc2C#Cc2ccccc2)ccc1O | COc1cc(CC(=O)Nc2ccccc2CCc2ccccc2)ccc1O | null | null | null | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | O=C(Cc1ccccc1)Nc1ccccc1CCc1ccccc1 | [c:1]:[c:2](-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]>>[c:1]:[c:2](-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8] | null | [] | null | null | null | null | Instead of 4-hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]-phenylacetamide (the compound of Example 36) in Example 54, 4-hydroxy-3-methoxy-N-[2-(2-phenylethynyl)phenyl]phenylacetamide (the compound of Example 107) is treated in a similar manner to Example 54 to give the desired compound.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | COc1cc(CC(=O)Nc2ccccc2C#Cc2ccccc2)ccc1O>>COc1cc(CC(=O)Nc2ccccc2CCc2ccccc2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87e6898308db4b26a4226ae53366324d | COc1cc(CC(=O)Nc2ccccc2C#Cc2ccccc2)ccc1O>>COc1cc(CC(=O)Nc2ccccc2/C=C\c2ccccc2)ccc1O | OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C#CC1=CC=CC=C1)OC.OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C#CC1=CC=CC=C1)OC.OC1=C(C=C(C=C1)CC(=O)NC1=C(C=CC=C1)C#CC1=CC=CC=C1)OC.OC1=C(C=C(C=C1)CC(=O)NC1=C(C=CC=C1)C#CC1=CC=CC=C1)OC>>OC1=C(C=C(C=C1)CC(=O)NC1=C(C=CC=C1)\C=C/C1=CC=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]#[C:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25][c:26]1[OH:27]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2/[CH:16]=[CH:17]\[c:18]2[cH:19][cH:20... | COc1cc(CC(=O)Nc2ccccc2C#Cc2ccccc2)ccc1O | COc1cc(CC(=O)Nc2ccccc2/C=C\c2ccccc2)ccc1O | null | null | null | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | O=C(Cc1ccccc1)Nc1ccccc1/C=C\c1ccccc1 | [c:1]:[c:2](-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]>>[c:1]:[c:2](/[CH;D2;+0:3]=[CH;D2;+0:4]\[c:5](:[c:6]):[c:7]):[c:8] | null | [] | null | null | null | null | Instead of 4-hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]-phenylacetamide (the compound of Example 36) in Example 56, 4-hydroxy-3-methoxy-N-[2-(2-phenylethynyl)phenyl]phenylacetamide (the compound of Example 107) is treated in a similar manner to Example 56 to give the desired compound.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | COc1cc(CC(=O)Nc2ccccc2C#Cc2ccccc2)ccc1O>>COc1cc(CC(=O)Nc2ccccc2/C=C\c2ccccc2)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f0de59c17766482bb51f793fa0da73f0 | COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1O.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O>>COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1OC(C)=O | C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)O)OC)=O.OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1=CC=CC=C1)OC>>C(C)(=O)OC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)C1=CC=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21]2)[cH:22][cH:23][c:24]1[OH:25].COc1cc([CH2:27][C:26](Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)=[O:28])ccc1O>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c... | COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1O.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O | COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1OC(C)=O | null | null | null | Acylation | OtherReaction | e0d56a47c67716640bd536846fe720d7b73adafd90b01e2646fbecfbfd3fc5ee | adafa9432fa22dd2f066ec6ca7535953d066e94d8294450448756f9ce83a498c | O=C(Cc1ccccc1)Nc1cccc(-c2ccccc2)c1 | C-O-c1:c:c(-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-N-c2:c:c:c:c(-C3-C-C-C(-C(-C)(-C)-C)-C-C-3):c:2):c:c:c:1-O.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[CH3;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Instead of N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide in Example 69, the compound of Example 35 is treated in a similar manner to Example 69 to give the desired compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amide.Aromatic alcohol.Aromatic alcohol | Ester | c1ccccc1.c1ccccc1.C1CCCCC1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1O.COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O>>COc1cc(CC(=O)Nc2cccc(-c3ccccc3)c2)ccc1OC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3bac02c0740548d09986b5f0c85dc5c5 | CCOC(=O)COc1ccc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)cc1OC>>COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCO | [Cl-].[NH4+].C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCC(=O)OCC)OC)=O.C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(C(C1=CC(=C(C=C1)C(=O)O)OC)OC)=O.[BH4-].[Na+]>>C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCCO)OC)=O | CCO[C:31]([CH2:30][O:29][c:28]1[c:3]([O:2][CH3:1])[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([CH:15]3[CH2:16][CH2:17][CH:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]3)[cH:25]2)[cH:26][cH:27]1)=[O:32]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][... | CCOC(=O)COc1ccc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)cc1OC | COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCO | null | null | C(C)O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C(Cc1ccccc1)Nc1cccc(C2CCCCC2)c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#8:4]>>[#8:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 50.2 | [{"value": 50.2, "product": "C(C)(C)(C)C1CCC(CC1)C=1C=C(C=CC1)NC(CC1=CC(=C(C=C1)OCCO)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | N-[3-(4-tert-Butylcyclohexan-1-yl)phenyl]-4-ethoxycarbonylmethyloxy-3-methoxyphenylacetamide (240 mg), which is an intermediate of Example 72, is dissolved in ethanol, and thereto is added sodium borohydride (35 mg), and the mixture is stirred at room temperature for 2 hours. A saturated aqueous ammonium chloride solut... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | C(C)O | null | 2 | CCOC(=O)COc1ccc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)cc1OC>C(C)O>COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-75cc4b5bd19f4a4696cb5248dd41f0c1 | CC=Cc1ccccc1.COc1cc(CC(=O)Nc2cccc(I)c2)ccc1OCCNC(=O)OC(C)(C)C.Cc1ccccc1P(c1ccccc1C)c1ccccc1C>>COc1cc(CC(=O)Nc2cccc(/C=C/c3cccc(C)c3)c2)ccc1OCCNC(=O)OC(C)(C)C | C(C)(=O)OCC.C(C)(C)(C)OC(=O)NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)I)OC.CC=CC=1C=CC=CC1.CC1=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C>>C(C)(C)(C)OC(=O)NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)\C=C\C1=CC(=CC=C1)C)OC | C[CH:15]=[CH:16][c:17]1cccc[cH:18]1.I[c:14]1[cH:13][cH:12][cH:11][c:10]([NH:9][C:7]([CH2:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH2:29][CH2:30][NH:31][C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[cH:26][cH:25]2)=[O:8])[cH:24]1.Cc1ccccc1P(c1ccccc1C)[c:23]1cc[cH:19][cH:20][c:21]1[CH3:22]>>[CH3:1][O:2][... | CC=Cc1ccccc1.COc1cc(CC(=O)Nc2cccc(I)c2)ccc1OCCNC(=O)OC(C)(C)C.Cc1ccccc1P(c1ccccc1C)c1ccccc1C | COc1cc(CC(=O)Nc2cccc(/C=C/c3cccc(C)c3)c2)ccc1OCCNC(=O)OC(C)(C)C | null | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C=O)C | C-C Coupling | OtherReaction | e4aaa8a6e12940b1dd3ecdf5c76a74167bfc49d654799b37ce3f63ab1bd61fc4 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | O=C(Cc1ccccc1)Nc1cccc(/C=C/c2ccccc2)c1 | C-[CH;D2;+0:1]=[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:c:c:c:c:1.C-c1:c:c:c:c:c:1-P(-[c;H0;D3;+0:5]1:c:c:[cH;D2;+0:6]:[c:7]:[c:8]:1-[C;D1;H3:9])-c1:c:c:c:c:c:1-C.I-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C;D1;H3:9]-[c:8]1:[c:7]:[cH;D2;+0:6]:[cH;D2;+0:4]:[c;H0;D3;+0:3](/[C:2]=[CH;D2;+0:1]/[c;H0;D3;+0:10](:[c:11]:[c:1... | 152.4 | [{"value": 152.4, "product": "C(C)(C)(C)OC(=O)NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)\\C=C\\C1=CC(=CC=C1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 97 | CELSIUS | 18 | HOUR | Intermediate 4 (1 g) is dissolved in dimethylformamide (10 ml), and thereto are added 3-methylvinylbenzene (826 mg), palladium (II) acetate (105 mg), tris(2-methylphenyl)phosphine (143 mg), tetra-n-butyl ammonium chloride (130 mg), and the mixture is heated with stirring at 97° C. for 18 hours under argon atmosphere. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HI | [Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C | 97 | 18 | CC=Cc1ccccc1.COc1cc(CC(=O)Nc2cccc(I)c2)ccc1OCCNC(=O)OC(C)(C)C.Cc1ccccc1P(c1ccccc1C)c1ccccc1C>[Cl-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C>COc1cc(CC(=O)Nc2cccc(/C=C/c3cccc(C)c3)c2)ccc1OCCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6faf8d70cb6a4ac0804d8ed31f4ed67f | COc1cc(CC(=O)Nc2cccc(/C=C/c3cccc(C)c3)c2)ccc1OCCNC(=O)OC(C)(C)C>>COc1cc(CC(=O)Nc2cccc(CCc3cccc(C)c3)c2)ccc1OCCNC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)\C=C\C1=CC(=CC=C1)C)OC>>C(C)(C)(C)OC(=O)NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)CCC1=CC(=CC=C1)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14](/[CH:15]=[CH:16]/[c:17]3[cH:18][cH:19][cH:20][c:21]([CH3:22])[cH:23]3)[cH:24]2)[cH:25][cH:26][c:27]1[O:28][CH2:29][CH2:30][NH:31][C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](... | COc1cc(CC(=O)Nc2cccc(/C=C/c3cccc(C)c3)c2)ccc1OCCNC(=O)OC(C)(C)C | COc1cc(CC(=O)Nc2cccc(CCc3cccc(C)c3)c2)ccc1OCCNC(=O)OC(C)(C)C | null | [Pd] | CO.C(C)(=O)O | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C(Cc1ccccc1)Nc1cccc(CCc2ccccc2)c1 | [c:1]:[c:2](/[CH;D2;+0:3]=[CH;D2;+0:4]/[c:5](:[c:6]):[c:7]):[c:8]>>[c:1]:[c:2](-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8] | 79.7 | [{"value": 79.7, "product": "C(C)(C)(C)OC(=O)NCCOC1=C(C=C(C=C1)CC(=O)NC1=CC(=CC=C1)CCC1=CC(=CC=C1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-[2-(tert-Butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide (100 mg) is dissolved in methanol (10 ml) and acetic acid (1 ml), and thereto is added 10% palladium on carbon (10 mg), and the mixture is subjected to catalytic hydrogenation at 50° C. The catalyst is removed by f... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | [Pd].CO.C(C)(=O)O | null | null | COc1cc(CC(=O)Nc2cccc(/C=C/c3cccc(C)c3)c2)ccc1OCCNC(=O)OC(C)(C)C>[Pd].CO.C(C)(=O)O>COc1cc(CC(=O)Nc2cccc(CCc3cccc(C)c3)c2)ccc1OCCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-18b1747dcc8a42479959da4aec8199c0 | COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)CCC3)ccc1O.O=Cc1ccccc1>>COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)C(=Cc2ccccc2)CC3)ccc1O | C1(=CCCCC1)C=1C=C(N)C=CC1.C1(=CCCCC1)C=1C=C(N)C=CC1.NC1=CC=C2CCCC(C2=C1)=O.OC1=C(C=C(C=C1)CC(=O)NC1=CC=C2CCCC(C2=C1)=O)OC.C(C1=CC=CC=C1)=O>>OC1=C(C=C(C=C1)CC(=O)NC1=CC=C2CCC(C(C2=C1)=O)=CC1=CC=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:15]2)[C:16](=[O:17])[CH2:18][CH2:26][CH2:27]3)[cH:28][cH:29][c:30]1[OH:31].O=[CH:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:1... | COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)CCC3)ccc1O.O=Cc1ccccc1 | COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)C(=Cc2ccccc2)CC3)ccc1O | null | null | Cl.C(C)O | C-C Coupling | Aldol condensation | cd07f60ebf87bf6a5ea60a0a56170ba2743f3105a037265dcd5d66e53d2a462f | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(Cc1ccccc1)Nc1ccc2c(c1)C(=O)C(=Cc1ccccc1)CC2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[C:5]-[C:6]-[C;H0;D3;+0:7](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8](=[O;D1;H0:9])-[c:10] | null | [] | 25 | CELSIUS | 18 | HOUR | Instead of 3-(cyclohexen-1-yl)aniline (Intermediate 2) in Example 9, 7-amino-1-tetralone is treated in a similar manner to Example 9. The resulting 4-hydroxy-3-methoxy-N-[1-oxo-1,2,3,4-tetrahydronaphthalen-7-yl]phenylacetamide (1 g) is dissolved in 30% hydrogen chloride-ethanol (5 ml), and thereto is added benzaldehyde... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccccc1 | HO- | Cl.C(C)O | 25 | 18 | COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)CCC3)ccc1O.O=Cc1ccccc1>Cl.C(C)O>COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)C(=Cc2ccccc2)CC3)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d8739e16661d40b6a3416da0f3f2f41c | COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)C(=Cc2ccccc2)CC3)ccc1O>>COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)C(Cc2ccccc2)CC3)ccc1O | OC1=C(C=C(C=C1)CC(=O)NC1=CC=C2CCC(C(C2=C1)=O)=CC1=CC=CC=C1)OC>>OC1=C(C=C(C=C1)CC(=O)NC1=CC=C2CCC(C(C2=C1)=O)CC1=CC=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:15]2)[C:16](=[O:17])[C:18](=[CH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]3)[cH:28][cH:29][c:30]1[OH:31]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:15]... | COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)C(=Cc2ccccc2)CC3)ccc1O | COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)C(Cc2ccccc2)CC3)ccc1O | null | [Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | ef5776194d0a56b0d0bcb4f3f44edabcb716b463d0f1a539f552dbead062784c | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | O=C(Cc1ccccc1)Nc1ccc2c(c1)C(=O)C(Cc1ccccc1)CC2 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[c:10]>>[C:1]-[C:2]-[CH;D3;+0:3](-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[c:10] | 69.7 | [{"value": 69.7, "product": "OC1=C(C=C(C=C1)CC(=O)NC1=CC=C2CCC(C(C2=C1)=O)CC1=CC=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound of Example 248 (500 mg) is dissolved in ethyl acetate (20 ml), and thereto is added 10% palladium on carbon (50 mg), and the mixture is subjected to catalytic hydrogenation at 25° C. The catalyst is removed by filtration, and the solvent is evaporated under reduced pressure. The residue is purified by sili... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccccc1 | null | [Pd].C(C)(=O)OCC | null | null | COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)C(=Cc2ccccc2)CC3)ccc1O>[Pd].C(C)(=O)OCC>COc1cc(CC(=O)Nc2ccc3c(c2)C(=O)C(Cc2ccccc2)CC3)ccc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b495aa703b04744bb5cf439eed00b5d | Nc1ccccc1S.O=C(O)CCl>>ClCc1nc2ccccc2o1.ClCc1nc2ccccc2s1 | C([O-])([O-])=O.[K+].[K+].NC1=C(C=CC=C1)S.ClCC(=O)O>>ClCC=1OC2=C(N1)C=CC=C2.ClCC=1SC2=C(N1)C=CC=C2 | [NH2:4][c:5]1[cH:6][cH:18][cH:19][cH:20][c:21]1[SH:22].O=[C:3]([CH2:2][Cl:1])[OH:11]>>[Cl:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[o:11]1.[Cl:12][CH2:13][c:14]1[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[s:22]1 | Nc1ccccc1S.O=C(O)CCl | ClCc1nc2ccccc2o1.ClCc1nc2ccccc2s1 | null | null | O | Aromatic Heterocycle Formation | Benzothiazole formation from ester/carboxylic acid | ee004ac6fd5efd4fbe3990632dbe3a69b3b2f5d6ea238a9ed644d344d491140a | ab7b409f4767e0df4e6ff7006d8fb0ad338bdadc0d4a7feb0fc305bbf86f77a6 | c1ccc2ocnc2c1.c1ccc2scnc2c1 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:1-[SH;D1;+0:12]>>[C:13]-[c:14]1:[#7;a:15]:[c:16]2:[c:17]:[cH;D2;+0:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:2:[s;H0;D2;+0:12]:1.[Cl;D1;H0:4]-[C:3]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:5]:[c;H0;D3;+0:6]2... | null | [] | 120 | CELSIUS | null | null | Using literature procedures (Addison, A. W.; Nageswara Rao, T.; Wahlgren, C. G. J. Heterocyclic Chem. 1983, 20, 1481–1484) a substituted 2-aminophenol (or a 2-aminothiophenol (5 mmol)) was mixed with chloroacetic acid (940 mg, 10 mmol) in polyphosphoric acid (5 mL), and the viscous mixture was then heated to 120° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Aromatic thiol | Primary halide | c1ccccc1 | c1ccc2ocnc2c1.c1ccc2scnc2c1 | c1ccc2ocnc2c1.c1ccc2scnc2c1 | null | O | 120 | null | Nc1ccccc1S.O=C(O)CCl>O>ClCc1nc2ccccc2o1.ClCc1nc2ccccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3e65d3523c4435f91103dac99cfb3aa | CC(C)(C)OC(=O)N(Cc1ccc(CNC2CCCc3cccnc32)cc1)Cc1ccccn1.O=C(c1ccccc1)c1ccc2nc(CCl)[nH]c2c1>>O=C(c1ccccc1)c1ccc2[nH]c(CN(Cc3ccc(CNCc4ccccn4)cc3)C3CCCc4cccnc43)nc2c1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N=C(N2)CCl)C=C1.C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)CNC1CCCC=2C=CC=NC12)CC1=NC=CC=C1.C(C)(C)N(C(C)C)CC>>N1=C(C=CC=C1)CNCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC(=C2)C(C2=CC=CC=C2)=O | CC(C)(C)OC(=O)[N:23]([CH2:22][c:21]1[cH:20][cH:19][c:18]([CH2:17][NH:16][CH:33]2[CH2:34][CH2:35][CH2:36][c:37]3[cH:38][cH:39][cH:40][n:41][c:42]32)[cH:32][cH:31]1)[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][n:30]1.Cl[CH2:15][c:14]1[n:13][c:12]2[cH:11][cH:10][c:9]([C:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][cH:7][cH:8]3)[cH:4... | CC(C)(C)OC(=O)N(Cc1ccc(CNC2CCCc3cccnc32)cc1)Cc1ccccn1.O=C(c1ccccc1)c1ccc2nc(CCl)[nH]c2c1 | O=C(c1ccccc1)c1ccc2[nH]c(CN(Cc3ccc(CNCc4ccccn4)cc3)C3CCCc4cccnc43)nc2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 12f2d9e088a426e3a12c1411954e2d6a6061a1a5ac7ba1b60dc56a7c356d917c | 0db62007b8285a919cd42ddbf58d70ae0f3c65f62f2ee3e518cb7dbb3101c3f4 | O=C(c1ccccc1)c1ccc2[nH]c(CN(Cc3ccc(CNCc4ccccn4)cc3)C3CCCc4cccnc43)nc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3])-[C:4]-[c:5]:[#7;a:6].[#7;a:7]:[c:8]-[C:9](-[NH;D2;+0:10]-[C:11]-[c:12])-[C:13].Cl-[CH2;D2;+0:14]-[c:15]1:[n;H0;D2;+0:16]:[c:17](:[c:18]):[c:19](:[c:20]):[nH;D2;+0:21]:1>>[#7;a:7]:[c:8]-[C:9](-[N;H0;D3;+0:10](-[C:11]-[c:12])-[CH2;D2;+0:14]-[c:15]1:[n;H0;D2;+0:21]:[c:19](:... | 75.9 | [{"value": 65.0, "product": "N1=C(C=CC=C1)CNCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC(=C2)C(C2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.9, "product": "N1=C(C=CC=C1)CNCC1=CC=C(C=C1)CN(C1CCCC=2C=CC=NC12)CC1=NC2=C(N1)C=CC(=C2)C(C2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIE... | null | null | null | null | A solution of 5-benzoyl-2-chloromethylbenzimidazole (284 mg, 1.05 mmol), N-(tert-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (476 mg, 1.04 mmol) and N,N-diisopropylethylamine (0.36 mL, 2.08 mmol) were stirred at 80□ C in DMF (4 mL) for 16 hours. The reaction was t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Secondary amine.Boc | Secondary amine.Tertiary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.c1ccccc1.c1ccncc1.c1cnc2c(c1)CCCC2 | HCl | CN(C)C=O | null | null | CC(C)(C)OC(=O)N(Cc1ccc(CNC2CCCc3cccnc32)cc1)Cc1ccccn1.O=C(c1ccccc1)c1ccc2nc(CCl)[nH]c2c1>CN(C)C=O>O=C(c1ccccc1)c1ccc2[nH]c(CN(Cc3ccc(CNCc4ccccn4)cc3)C3CCCc4cccnc43)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23441250a17843d69020cc61a28af1cf | CON.COc1cccc([N+](=O)[O-])c1>>COc1cccc([N+](=O)[O-])c1N | [N+](=O)([O-])C=1C=C(C=CC1)OC.Cl.CON.CC(C)([O-])C.[K+]>>NC1=C(C=CC=C1OC)[N+](=O)[O-] | CO[NH2:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]1[NH2:12] | CON.COc1cccc([N+](=O)[O-])c1 | COc1cccc([N+](=O)[O-])c1N | null | [Cu]Cl | CN(C)C=O | Functional Group Addition | OtherReaction | 52b564533ce6edc42710b51185c6a026108ffbc099c120ba8644d194d9341031 | 5d27deb117d58af1451678366bb9ef32f3c0470c7072ee34ccab01a4e73c86c7 | c1ccccc1 | C-O-[NH2;D1;+0:1].[#7;+:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[#8:7]):[c:8]>>[#7;+:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[NH2;D1;+0:1]):[c:6](-[#8:7]):[c:8] | 50.5 | [{"value": 50.0, "product": "NC1=C(C=CC=C1OC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.5, "product": "NC1=C(C=CC=C1OC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A suspension of 3-nitroanisole (1.550 g, 10.12 mmol) and O-methylhydroxylamine hydrochloride (1.078 g, 12.91 mmol) in DMF (15 mL) was added to a cold (0° C.) solution of potassium tert-butoxide (5.870 g, 52.30 mmol) and copper(I) chloride (0.200 g, 2.02 mmol) in DMF (35 mL). The cooling bath was removed and the resulta... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | [Cu]Cl.CN(C)C=O | null | 6 | CON.COc1cccc([N+](=O)[O-])c1>[Cu]Cl.CN(C)C=O>COc1cccc([N+](=O)[O-])c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24bc86431bd542409b1544b66fd7149e | COc1cccc([N+](=O)[O-])c1N.O=C(O)CCl>>COc1cccc2[nH]c(CCl)nc12 | Cl.NC1=C(C=CC=C1OC)[N+](=O)[O-].NC1=C(C=CC=C1OC)[N+](=O)[O-].ClCC(=O)O>>ClCC1=NC2=C(N1)C=CC=C2OC | O=[N+:8]([O-])[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:13]1[NH2:12].O=[C:9](O)[CH2:10][Cl:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[nH:8][c:9]([CH2:10][Cl:11])[n:12][c:13]12 | COc1cccc([N+](=O)[O-])c1N.O=C(O)CCl | COc1cccc2[nH]c(CCl)nc12 | null | [Pd] | CO | Aromatic Heterocycle Formation | OtherReaction | 8384218116d848b78bf34b4b754ff9fc4148ad62c3240f304bdba7d31edc77b2 | f52e6bb9bc8ea8fa01783041f5b57eb3dd246592c42af4381a04c54aeb42367e | c1ccc2[nH]cnc2c1 | O-[C;H0;D3;+0:1](=O)-[C:2]-[Cl;D1;H0:3].O=[N+;H0;D3:4](-[O-])-[c:5](:[c:6]):[c:7](-[NH2;D1;+0:8]):[c:9]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c:7](:[c:9]):[c:5](:[c:6]):[nH;D2;+0:4]:1 | 86.6 | [{"value": 86.6, "product": "ClCC1=NC2=C(N1)C=CC=C2OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-amino-3-methoxy-1-nitrobenzene (0.860 g, 5.11 mmol) in MeOH (50 mL) was hydrogenated (1 atm) over palladium, 10 wt. % on activated carbon (0.163 g). The resultant crude 3-methoxy-1,2-phenylenediamine was reacted with chloroacetic acid (0.953 g, 10.08 mmol) in refluxing 4 N HCl (10 mL) overnight. After a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HO- | [Pd].CO | null | null | COc1cccc([N+](=O)[O-])c1N.O=C(O)CCl>[Pd].CO>COc1cccc2[nH]c(CCl)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-754b34941ad244829017dcc78f4df6f3 | CON.O=[N+]([O-])c1ccccc1-c1ccccc1>>Nc1cccc(-c2ccccc2)c1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=CC=C1.Cl.CON.CC(C)([O-])C.[K+]>>NC1=C(C(=CC=C1)C1=CC=CC=C1)[N+](=O)[O-] | CO[NH2:1].[cH:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]1[N+:14](=[O:15])[O-:16]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13]1[N+:14](=[O:15])[O-:16] | CON.O=[N+]([O-])c1ccccc1-c1ccccc1 | Nc1cccc(-c2ccccc2)c1[N+](=O)[O-] | null | [Cu]Cl | CN(C)C=O | Functional Group Addition | OtherReaction | 52b564533ce6edc42710b51185c6a026108ffbc099c120ba8644d194d9341031 | 5d27deb117d58af1451678366bb9ef32f3c0470c7072ee34ccab01a4e73c86c7 | c1ccc(-c2ccccc2)cc1 | C-O-[NH2;D1;+0:1].[#7;+:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[#7;+:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[NH2;D1;+0:1]):[c:6]:[c:7] | 27.1 | [{"value": 27.0, "product": "NC1=C(C(=CC=C1)C1=CC=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.1, "product": "NC1=C(C(=CC=C1)C1=CC=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A suspension of 2-nitrobiphenyl (2.061 g, 10.34 mmol) and O-methylhydroxylamine hydrochloride (1.088 g, 13.02 mmol) in DMF (15 mL) was added to a cold (0° C.) solution of potassium tert-butoxide (5.993 g, 53.40 mmol) and copper(I) chloride (0.246 g, 2.48 mmol) in DMF (35 mL). The cooling bath was removed and the result... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | [Cu]Cl.CN(C)C=O | null | 20 | CON.O=[N+]([O-])c1ccccc1-c1ccccc1>[Cu]Cl.CN(C)C=O>Nc1cccc(-c2ccccc2)c1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba58e1f0c66642b68d676298060dbc50 | Nc1cccc(-c2ccccc2)c1[N+](=O)[O-].O=C(O)CCl>>ClCc1nc2c(-c3ccccc3)cccc2[nH]1 | NC1=C(C(=CC=C1)C1=CC=CC=C1)[N+](=O)[O-].NC1=C(C(=CC=C1)C1=CC=CC=C1)[N+](=O)[O-].ClCC(=O)O>>ClCC1=NC2=C(N1)C=CC=C2C2=CC=CC=C2 | O=[N+:4]([O-])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][cH:15][c:16]1[NH2:17].O=[C:3](O)[CH2:2][Cl:1]>>[Cl:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][cH:12]3)[cH:13][cH:14][cH:15][c:16]2[nH:17]1 | Nc1cccc(-c2ccccc2)c1[N+](=O)[O-].O=C(O)CCl | ClCc1nc2c(-c3ccccc3)cccc2[nH]1 | null | [Pd] | CO | Aromatic Heterocycle Formation | OtherReaction | 8384218116d848b78bf34b4b754ff9fc4148ad62c3240f304bdba7d31edc77b2 | f52e6bb9bc8ea8fa01783041f5b57eb3dd246592c42af4381a04c54aeb42367e | c1ccc(-c2cccc3[nH]cnc23)cc1 | O-[C;H0;D3;+0:1](=O)-[C:2]-[Cl;D1;H0:3].O=[N+;H0;D3:4](-[O-])-[c:5](:[c:6]):[c:7](-[NH2;D1;+0:8]):[c:9]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:9]):[nH;D2;+0:8]:1 | 92.7 | [{"value": 92.0, "product": "ClCC1=NC2=C(N1)C=CC=C2C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "ClCC1=NC2=C(N1)C=CC=C2C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-amino-6-phenyl-nitrobenzene (0.600 g, 2.80 mmol) in MeOH (28 mL) was hydrogenated (30 psi) over palladium, 10 wt. % on activated carbon (0.121 g). The resultant crude 3-phenyl-1,2-phenylenediamine was reacted with chloroacetic acid (0.537 g, 5.68 mmol) in refluxing 4 N Hl (6 mL) overnight. After normal ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | [Pd].CO | null | null | Nc1cccc(-c2ccccc2)c1[N+](=O)[O-].O=C(O)CCl>[Pd].CO>ClCc1nc2c(-c3ccccc3)cccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5da6dc30a40e4b98a9086a0a634513ee | CO[NH3+].O=[N+]([O-])c1cccc(Br)c1>>Nc1c(Br)cccc1[N+](=O)[O-] | CC(C)([O-])C.[K+].BrC=1C=C(C=CC1)[N+](=O)[O-].CO[NH3+].[Cl-]>>NC1=C(C=CC=C1Br)[N+](=O)[O-] | CO[NH3+:1].[cH:2]1[c:3]([Br:4])[cH:5][cH:6][cH:7][c:8]1[N+:9](=[O:10])[O-:11]>>[NH2:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][cH:7][c:8]1[N+:9](=[O:10])[O-:11] | CO[NH3+].O=[N+]([O-])c1cccc(Br)c1 | Nc1c(Br)cccc1[N+](=O)[O-] | null | [Cu]Cl | CN(C)C=O | Functional Group Addition | OtherReaction | 60732f4102305dd78afd0dd3679bbaf7f92e00d937b526eb4d81318ee97c4790 | d69ce1fde4173969963123914389bef807fad83b73b8a587195a7122d5cdf1d2 | c1ccccc1 | C-O-[NH3+;D1:1].[#7;+:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[Br;D1;H0:7]):[c:8]>>[#7;+:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[NH2;D1;+0:1]):[c:6](-[Br;D1;H0:7]):[c:8] | 6 | [{"value": 6.0, "product": "NC1=C(C=CC=C1Br)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.5, "product": "NC1=C(C=CC=C1Br)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-bromonitrobenzene (6.06 g, 30 mmol) and o-methylhydroxylamine hydrochloride (3.13 g, 37.5 mmol) were reacted in the presence of copper (I) chloride (0.59 g, 6 mmol) and potassium t-butoxide (10.1 g, 90 mmol) in DMF (75 mL). Aqueous work-up and chromatography gave 2-amino-3-bromonitrobenzene (0.36 g, 6%) ... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | [Cu]Cl.CN(C)C=O | null | null | CO[NH3+].O=[N+]([O-])c1cccc(Br)c1>[Cu]Cl.CN(C)C=O>Nc1c(Br)cccc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-708aa2cb8cff44d5bab91807ea9877e3 | Nc1ccccc1N.O=C(O)CCCl>>ClCCc1nc2ccccc2[nH]1 | C1(=C(C=CC=C1)N)N.ClCCC(=O)O>>ClCCC1=NC2=C(N1)C=CC=C2 | [NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12].O=[C:4](O)[CH2:3][CH2:2][Cl:1]>>[Cl:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[nH:12]1 | Nc1ccccc1N.O=C(O)CCCl | ClCCc1nc2ccccc2[nH]1 | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | 8409c8c0d4e4ea3a5ac4d357a90931cd25bdeaf070f3095e8e16fa38a40808ca | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | c1ccc2[nH]cnc2c1 | O-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7](-[NH2;D1;+0:8]):[c:9]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c:7](:[c:9]):[c:5](:[c:6]):[nH;D2;+0:4]:1 | 32.3 | [{"value": 32.0, "product": "ClCCC1=NC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.3, "product": "ClCCC1=NC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,2-Phenylenediamine (1.3 g, 12.0 mmol) and 3-chloropropionic acid (2.0 g, 18.5 mmol) were refluxed in 4N HCl (13 mL) for 16 hours to give the title compound as white solid (700 mg, 32%). 1H NMR (CD3OD) □ 3.35 (t, 2H, J=6.8 Hz), 4.00 (t, 2H, J=6.8 Hz), 7.18–7.25 (m, 2H), 7.49–7.55 (m, 2H); ES-MS m/z 181.0 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HO- | Cl | null | null | Nc1ccccc1N.O=C(O)CCCl>Cl>ClCCc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9d7394b8fab4a7884fe9288c6c7895d | Nc1ccccc1N.O=C(O)CCCCl>>OCCCc1nc2ccccc2[nH]1 | C1(=C(C=CC=C1)N)N.ClCCCC(=O)O>>N1C(=NC2=C1C=CC=C2)CCCO | [NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[NH2:13].O=[C:5]([OH:1])[CH2:4][CH2:3][CH2:2]Cl>>[OH:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[nH:13]1 | Nc1ccccc1N.O=C(O)CCCCl | OCCCc1nc2ccccc2[nH]1 | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | 574739b6ccdd29924600663d81c3f40ba1dd84891b72844974ba42e0a5db564a | ffd3d519298b8aa87abb25559a5e3aaaf86fa8212a094f631d6c4830a48f681d | c1ccc2[nH]cnc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C;H0;D3;+0:4](=O)-[OH;D1;+0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[OH;D1;+0:5]-[CH2;D2;+0:1]-[C:2]-[C:3]-[c;H0;D3;+0:4]1:[n;H0;D2;+0:10]:[c:9](:[c:11]):[c:7](:[c:8]):[nH;D2;+0:6]:1 | 50 | [{"value": 50.0, "product": "N1C(=NC2=C1C=CC=C2)CCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.6, "product": "N1C(=NC2=C1C=CC=C2)CCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,2-Phenylenediamine (1.0 g, 12.0 mmol) and 4-chlorobutyric acid (1.5 mL, 15.17 mmol) were refluxed in 4N HCl (13 mL) for 16 hours under N2 to give the title compound as white solid (900 mg, 50%). 1H NMR (CD3OD) □ 2.04–2.08 (m, 2H), 2.97 (t, 2H, J=7.8 Hz), 5.64 (t, 2H, J=6.6 Hz), 7.15–7.21 (m, 2H), 7.47–7.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Primary amine.Primary amine | Primary alcohol | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HCl | Cl | null | null | Nc1ccccc1N.O=C(O)CCCCl>Cl>OCCCc1nc2ccccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32246227c8e542b2942983bba3e455fa | CC(C)(C)OC(=O)n1c(CCCO)nc2ccccc21>>CC(C)(C)OC(=O)n1c(CCC=O)nc2ccccc21 | C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CCCO.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CCC=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[c:9]([CH2:10][CH2:11][CH2:12][OH:13])[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[c:9]([CH2:10][CH2:11][CH:12]=[O:13])[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12 | CC(C)(C)OC(=O)n1c(CCCO)nc2ccccc21 | CC(C)(C)OC(=O)n1c(CCC=O)nc2ccccc21 | null | null | C(C)(=O)OCC.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2[nH]cnc2c1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 76.7 | [{"value": 76.0, "product": "C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CCC=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-(1-tert-butoxycarbonyl-Benzimidazol-2-yl)propan-1-ol (186 mg, 0.67 mmol) in CH2Cl2 (4 mL) was added Dess-Martin reagent (314 mg, 0.74 mmol) and the resulting mixture was allowed to stir at room temperature under N2 for 1 hour. The mixture was further diluted with 300-mL ethyl acetate, and washed with... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1nc2ccccc2[nH]1 | null | C(C)(=O)OCC.C(Cl)Cl | null | 1 | CC(C)(C)OC(=O)n1c(CCCO)nc2ccccc21>C(C)(=O)OCC.C(Cl)Cl>CC(C)(C)OC(=O)n1c(CCC=O)nc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9651c158160d4c42a424784a20c7783a | BrBr.CC(=O)c1ccccc1>>O=C(CBr)c1ccccc1 | C(C)(=O)C1=CC=CC=C1.C(C)(=O)O.BrBr>>BrCC(=O)C1=CC=CC=C1 | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | BrBr.CC(=O)c1ccccc1 | O=C(CBr)c1ccccc1 | null | null | null | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | 41 | [{"value": 41.0, "product": "BrCC(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "BrCC(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of acetophenone (5.0 g, 42.00 mmol), acetic acid (2.4 mL, 42.00 mmol), and bromine (2.5 mL, 48.00 mmol) followed by recrystallisation from cold EtOAc/Hexane gave the title compound (3.4 g, 41%) as a white crystal. 1H NMR (300 MHz, CDCl3) δ 4.47 (s, 2H), 7.51 (d, 2H, J=7.5 Hz), 7.63 (t, 1H, J=7.5 Hz), 8.00 (d, ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | null | null | null | BrBr.CC(=O)c1ccccc1>>O=C(CBr)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5367d4f1fa96453a9bf752f5ac239e8c | C[Si](C)(C)CCOCCl.c1ccc(-c2c[nH]cn2)cc1>>C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1 | C1(=CC=CC=C1)C=1N=CNC1.[H-].[Na+].C[Si](C)(C)CCOCCl>>C1(=CC=CC=C1)C=1N=CN(C1)COCC[Si](C)(C)C | Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[nH:9]1[cH:10][n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]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](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19]1 | C[Si](C)(C)CCOCCl.c1ccc(-c2c[nH]cn2)cc1 | C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(-c2c[nH]cn2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[c:4]-[c:5]1:[#7;a:6]:[c:7]:[nH;D2;+0:8]:[c:9]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:5](-[c:4]):[c:9]:1 | 67 | [{"value": 67.0, "product": "C1(=CC=CC=C1)C=1N=CN(C1)COCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.5, "product": "C1(=CC=CC=C1)C=1N=CN(C1)COCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-phenylimidazole (400 mg, 2.78 mmol), NaH (60%, 108 mg, 2.70 mmol), and SEMCl (520 uL/2.94 mmol) followed by column chromatography on silica gel (hexane/EtOAC 1:1) gave the title compound (500 mg, 67%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.92 (t, 2H, J=9.0 Hz), 3.54 (t, 2H, J=9.0 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | HCl | null | null | null | C[Si](C)(C)CCOCCl.c1ccc(-c2c[nH]cn2)cc1>>C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6edfac6400e2448493267b83d6e8ece7 | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1>>C[Si](C)(C)CCOCn1cc(-c2ccccc2)nc1C=O | C1(=CC=CC=C1)C=1N=CN(C1)COCC[Si](C)(C)C.[Li]CCCC.CN(C)C=O>>C1(=CC=CC=C1)C=1N=C(N(C1)COCC[Si](C)(C)C)C=O | CN(C)[CH:20]=[O:21].[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][cH:17]2)[n:18][cH:19]1>>[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][cH:17]2)[n:18][c:19]1[CH:20]=[O:21] | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1 | C[Si](C)(C)CCOCn1cc(-c2ccccc2)nc1C=O | null | null | null | C-C Coupling | OtherReaction | 497eb07a6b350068b10b6956179b63b10ae80db27b9b403f062644d98d07ac93 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(-c2c[nH]cn2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 98 | [{"value": 98.0, "product": "C1(=CC=CC=C1)C=1N=C(N(C1)COCC[Si](C)(C)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.8, "product": "C1(=CC=CC=C1)C=1N=C(N(C1)COCC[Si](C)(C)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (380 mg, 1.39 mmol), 2.5 M n-BuLi (720 uL, 1.80 mmol), and DMF (323 uL, 4.17 mmol) for 4 h at −40° C. gave the title compound (411 mg, 98%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.93 (t, 2H, J=9.0 Hz), 3.61 (t, 2H, J=9.0 Hz), 5.83 ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | Other | null | null | null | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1>>C[Si](C)(C)CCOCn1cc(-c2ccccc2)nc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9da17a98ecc54954bc7c708f1d2b6ac4 | COc1ccc(-c2c[nH]cn2)cc1.C[Si](C)(C)CCOCCl>>COc1ccc(-c2cn(COCC[Si](C)(C)C)cn2)cc1 | COC1=CC=C(C=C1)C=1N=CNC1.[H-].[Na+].C[Si](C)(C)CCOCCl>>COC1=CC=C(C=C1)C=1N=CN(C1)COCC[Si](C)(C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][nH:9][cH:18][n:19]2)[cH:20][cH:21]1.Cl[CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][n:19]2)[cH:20][cH:21]1 | COc1ccc(-c2c[nH]cn2)cc1.C[Si](C)(C)CCOCCl | COc1ccc(-c2cn(COCC[Si](C)(C)C)cn2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(-c2c[nH]cn2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[c:4]-[c:5]1:[#7;a:6]:[c:7]:[nH;D2;+0:8]:[c:9]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:5](-[c:4]):[c:9]:1 | 64 | [{"value": 64.0, "product": "COC1=CC=C(C=C1)C=1N=CN(C1)COCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.2, "product": "COC1=CC=C(C=C1)C=1N=CN(C1)COCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-(4-methoxyphenyl)-1H-imidazole (610 mg, 3.51 mmol), NaH (60%, 136 mg, 3.40 mmol), and SEMCl (656 uL, 3.71 mmol) followed by column chromatography on silica gel (hexane/EtOAC 1:1) gave the title compound (654 mg, 64%) as a yellow solid. 1H NMR (300 MHz, CDCl3) major isomer: δ 0.00 (s, 9H), 0.93 (t, 2H, J=7... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HCl | null | null | null | COc1ccc(-c2c[nH]cn2)cc1.C[Si](C)(C)CCOCCl>>COc1ccc(-c2cn(COCC[Si](C)(C)C)cn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f76d24e594c14444b92e85c37f612993 | C[Si](C)(C)CCOCCl.O=[N+]([O-])c1ccc(-c2c[nH]cn2)cc1>>C[Si](C)(C)CCOCn1cncc1-c1ccc([N+](=O)[O-])cc1 | [N+](=O)([O-])C1=CC=C(C=C1)C=1N=CNC1.[H-].[Na+].C[Si](C)(C)CCOCCl>>[N+](=O)([O-])C1=CC=C(C=C1)C1=CN=CN1COCC[Si](C)(C)C | Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[n:9]1[cH:10][nH:11][cH:12][c:13]1-[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[cH:10][n:11][cH:12][c:13]1-[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[cH:21][cH:22... | C[Si](C)(C)CCOCCl.O=[N+]([O-])c1ccc(-c2c[nH]cn2)cc1 | C[Si](C)(C)CCOCn1cncc1-c1ccc([N+](=O)[O-])cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 59f9db71a8587a55a59c0444ab4770f67569a3a2152b8595d595420e66dd1732 | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(-c2cnc[nH]2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[c:4]-[c:5]1:[c:6]:[nH;D2;+0:7]:[c:8]:[n;H0;D2;+0:9]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[n;H0;D2;+0:7]:[c:6]:[c:5]:1-[c:4] | 65 | [{"value": 65.0, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C1=CN=CN1COCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C1=CN=CN1COCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-(4-nitrophenyl)-1H-imidazole (160 mg, 0.85 mmol), NaH (60%, 33 mg, 0.82 mmol), and SEMCl (158 uL, 0.89 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (170 mg, 65%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.94 (t, 2H, J=7.5 Hz), 3.55 (t, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccccc1 | HCl | null | null | null | C[Si](C)(C)CCOCCl.O=[N+]([O-])c1ccc(-c2c[nH]cn2)cc1>>C[Si](C)(C)CCOCn1cncc1-c1ccc([N+](=O)[O-])cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f51e7c3bacdb4dd4962c9369beed6438 | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccc([N+](=O)[O-])cc2)c1>>C[Si](C)(C)CCOCn1cc(-c2ccc([N+](=O)[O-])cc2)nc1C=O | [N+](=O)([O-])C1=CC=C(C=C1)C=1N=CN(C1)COCC[Si](C)(C)C.[Li+].CC(C)[N-]C(C)C.CN(C)C=O>>[N+](=O)([O-])C1=CC=C(C=C1)C=1N=C(N(C1)COCC[Si](C)(C)C)C=O | CN(C)[CH:23]=[O:24].[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][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]2)[n:21][cH:22]1>>[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][c:15]([N+:16](=[O:17])[O-:18])[cH:19][... | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccc([N+](=O)[O-])cc2)c1 | C[Si](C)(C)CCOCn1cc(-c2ccc([N+](=O)[O-])cc2)nc1C=O | null | null | null | C-C Coupling | OtherReaction | 497eb07a6b350068b10b6956179b63b10ae80db27b9b403f062644d98d07ac93 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(-c2c[nH]cn2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 30 | [{"value": 30.0, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C=1N=C(N(C1)COCC[Si](C)(C)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.9, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C=1N=C(N(C1)COCC[Si](C)(C)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-(4-nitro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (170 mg, 0.53 mmol), 0.53 M LDA (1 mL, 0.53 mmol), and DMF (232 uL, 1.60 mmol) for 4 h at −40° C. followed by column chromatography on silica gel (EtOAc/hexane 9:1) gave the title compound (55 mg, 30%) as a yellow oil. 1H NMR (300 MHz, CDCl... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | Other | null | null | null | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccc([N+](=O)[O-])cc2)c1>>C[Si](C)(C)CCOCn1cc(-c2ccc([N+](=O)[O-])cc2)nc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ec767f45f16403d89c56740c4d47ee5 | C[Si](C)(C)CCOCCl.Cc1nc[nH]c1-c1ccccc1>>Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1 | CC=1N=CNC1C1=CC=CC=C1.[H-].[Na+].C[Si](C)(C)CCOCCl>>CC=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C | Cl[CH2:6][O:7][CH2:8][CH2:9][Si:10]([CH3:11])([CH3:12])[CH3:13].[CH3:1][c:2]1[n:3][cH:4][nH:5][c:14]1-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][c:2]1[n:3][cH:4][n:5]([CH2:6][O:7][CH2:8][CH2:9][Si:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C[Si](C)(C)CCOCCl.Cc1nc[nH]c1-c1ccccc1 | Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(-c2cnc[nH]2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7]:[nH;D2;+0:8]:[c:9]:1-[c:10]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:5](-[C;D1;H3:4]):[c:9]:1-[c:10] | 46 | [{"value": 46.0, "product": "CC=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.3, "product": "CC=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-methyl-5-phenyl-1H-imidazole (400 mg, 2.53 mmol), NaH (60%, 98 mg, 2.46 mmol), and SEMCl (474 uL, 2.68 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (323 mg, 46%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.92 (t, 2H, J=7.5 Hz), 2.47 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | HCl | null | null | null | C[Si](C)(C)CCOCCl.Cc1nc[nH]c1-c1ccccc1>>Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4a3f90489d343c5b7d420cdfafaff11 | CN(C)C=O.Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1>>Cc1nc(C=O)n(COCC[Si](C)(C)C)c1-c1ccccc1 | CC=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C.[Li]CCCC.CN(C)C=O>>CC=1N=C(N(C1C1=CC=CC=C1)COCC[Si](C)(C)C)C=O | CN(C)[CH:5]=[O:6].[CH3:1][c:2]1[n:3][cH:4][n:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1-[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][c:2]1[n:3][c:4]([CH:5]=[O:6])[n:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1-[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:2... | CN(C)C=O.Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1 | Cc1nc(C=O)n(COCC[Si](C)(C)C)c1-c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 497eb07a6b350068b10b6956179b63b10ae80db27b9b403f062644d98d07ac93 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(-c2cnc[nH]2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 99 | [{"value": 99.0, "product": "CC=1N=C(N(C1C1=CC=CC=C1)COCC[Si](C)(C)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "CC=1N=C(N(C1C1=CC=CC=C1)COCC[Si](C)(C)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-methyl-5-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (187 mg, 0.65 mmol), 2.5 M n-BuLi (338 uL, 0.84 mmol), and DMF (151 uL, 1.95 mmol) for 2 h at −40° C. gave the title compound (199 mg, 99%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.94 (t, 2H, J=7.5 Hz), 2.54 (s, 3H), 3.61 (... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | Other | null | null | null | CN(C)C=O.Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1>>Cc1nc(C=O)n(COCC[Si](C)(C)C)c1-c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e0545001fcd4dd3860975accf109709 | C[Si](C)(C)CCOCCl.Cc1nc[nH]c1-c1ccccc1>>Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1 | CC=1N=CNC1C1=CC=CC=C1.[H-].[Na+].C[Si](C)(C)CCOCCl>>CC=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C | Cl[CH2:6][O:7][CH2:8][CH2:9][Si:10]([CH3:11])([CH3:12])[CH3:13].[CH3:1][c:2]1[n:3][cH:4][nH:5][c:14]1-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][c:2]1[n:3][cH:4][n:5]([CH2:6][O:7][CH2:8][CH2:9][Si:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C[Si](C)(C)CCOCCl.Cc1nc[nH]c1-c1ccccc1 | Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(-c2cnc[nH]2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7]:[nH;D2;+0:8]:[c:9]:1-[c:10]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:5](-[C;D1;H3:4]):[c:9]:1-[c:10] | 46 | [{"value": 46.0, "product": "CC=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.3, "product": "CC=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-methyl-5-phenyl-1H-imidazole (400 mg, 2.53 mmol), NaH (60%, 98 mg, 2.46 mmol), and SEMCl (474 uL, 2.68 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (323 mg, 46%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.92 (t, 2H, J=7.5 Hz), 2.47 (s, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | HCl | null | null | null | C[Si](C)(C)CCOCCl.Cc1nc[nH]c1-c1ccccc1>>Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4d6fe304fc04465fb9fead7a864ca008 | CN(C)C=O.Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1>>Cc1nc(C=O)n(COCC[Si](C)(C)C)c1-c1ccccc1 | CC=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C.[Li]CCCC.CN(C)C=O>>CC=1N=C(N(C1C1=CC=CC=C1)COCC[Si](C)(C)C)C=O | CN(C)[CH:5]=[O:6].[CH3:1][c:2]1[n:3][cH:4][n:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1-[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][c:2]1[n:3][c:4]([CH:5]=[O:6])[n:7]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1-[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:2... | CN(C)C=O.Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1 | Cc1nc(C=O)n(COCC[Si](C)(C)C)c1-c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 497eb07a6b350068b10b6956179b63b10ae80db27b9b403f062644d98d07ac93 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(-c2cnc[nH]2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 99 | [{"value": 99.0, "product": "CC=1N=C(N(C1C1=CC=CC=C1)COCC[Si](C)(C)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "CC=1N=C(N(C1C1=CC=CC=C1)COCC[Si](C)(C)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-methyl-5-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (187 mg, 0.65 mmol), 2.5 M n-BuLi (338 uL, 0.84 mmol), and DMF (151 uL, 1.95 mmol) for 2 h at −40° C. gave the title compound (199 mg, 99%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.94 (t, 2H, J=7.5 Hz), 2.54 (s, 3H), 3.61 (... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | Other | null | null | null | CN(C)C=O.Cc1ncn(COCC[Si](C)(C)C)c1-c1ccccc1>>Cc1nc(C=O)n(COCC[Si](C)(C)C)c1-c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-387a8ed2067c4b49ae065cb773dcae43 | CC(C)(C)C(=O)CBr.NC=O.[NH4+]>>CC(C)(C)c1cnc[nH]1 | BrCC(C(C)(C)C)=O.C(=O)N.C(Cl)Cl.CO.[NH4+].[OH-]>>C(C)(C)(C)C1=CN=CN1 | O=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:6]Br.O=[CH:8][NH2:7].[NH4+:9]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][cH:8][nH:9]1 | CC(C)(C)C(=O)CBr.NC=O.[NH4+] | CC(C)(C)c1cnc[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6907b212f6ed2ef44167a5311fd5c85d16f34e450b84662aef7944ef5cc1727b | 5a724a9223d53cbf2bb1ed354a2db350dd6d10aa40058c7a1ca373081e191f17 | c1c[nH]cn1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].O=[CH;D2;+0:7]-[NH2;D1;+0:8].[NH4+;D0:9]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D2;+0:8]:[cH;D2;+0:7]:[nH;D2;+0:9]:1 | 21 | [{"value": 21.0, "product": "C(C)(C)(C)C1=CN=CN1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 1-bromo-3,3-dimethyl-butan-2-one (3.0 g, 16.80 mmol), and formamide (4.7 mL, 117.20 mmol), followed by chromatography (CH2Cl2/MeOH/NH4OH 94:3:3) gave the title compound (450 mg, 21%) as a yellow foam. 1H NMR (300 MHz, CDCl3) δ 1.29 (s, 9H), 6.77 (s, 1H), 7.57, (s, 1H). ES-MS m/z 125 (M+H).
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amide | null | null | c1c[nH]cn1 | c1c[nH]cn1 | HBr | null | null | null | CC(C)(C)C(=O)CBr.NC=O.[NH4+]>>CC(C)(C)c1cnc[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80ab18e9c9bf4fefb0d2677227570bf5 | CC(C)(C)c1cnc[nH]1.C[Si](C)(C)CCOCCl>>CC(C)(C)c1cncn1COCC[Si](C)(C)C | C(C)(C)(C)C1=CN=CN1.[H-].[Na+].C[Si](C)(C)CCOCCl>>C(C)(C)(C)C1=CN=CN1COCC[Si](C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][cH:8][nH:9]1.Cl[CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][cH:8][n:9]1[CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17] | CC(C)(C)c1cnc[nH]1.C[Si](C)(C)CCOCCl | CC(C)(C)c1cncn1COCC[Si](C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1c[nH]cn1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[C:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[nH;D2;+0:9]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[#7;a:7]:[c:6]:[c:5]:1-[C:4] | 57.6 | [{"value": 57.0, "product": "C(C)(C)(C)C1=CN=CN1COCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "C(C)(C)(C)C1=CN=CN1COCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 5-tert-butyl-1H-imidazole (423 mg, 3.41 mmol), NaH (60%, 132 mg, 3.31 mmol), and SEMCl (639 uL, 3.61 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (500 mg, 57%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ major isomer: 0.00 (s, 9H), 0.89 (t, 2H, J=7.5 Hz), 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HCl | null | null | null | CC(C)(C)c1cnc[nH]1.C[Si](C)(C)CCOCCl>>CC(C)(C)c1cncn1COCC[Si](C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d74faec5e83541cbbd0bd727ffa8fc30 | CC(C)(C)c1cncn1COCC[Si](C)(C)C.CN(C)C=O>>CC(C)(C)c1cnc(C=O)n1COCC[Si](C)(C)C | C(C)(C)(C)C1=CN=CN1COCC[Si](C)(C)C.[Li]CCCC.CN(C)C=O>>C(C)(C)(C)C1=CN=C(N1COCC[Si](C)(C)C)C=O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][cH:8][n:11]1[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19].CN(C)[CH:9]=[O:10]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][c:8]([CH:9]=[O:10])[n:11]1[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19] | CC(C)(C)c1cncn1COCC[Si](C)(C)C.CN(C)C=O | CC(C)(C)c1cnc(C=O)n1COCC[Si](C)(C)C | null | null | null | C-C Coupling | OtherReaction | 497eb07a6b350068b10b6956179b63b10ae80db27b9b403f062644d98d07ac93 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1c[nH]cn1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 99 | [{"value": 99.0, "product": "C(C)(C)(C)C1=CN=C(N1COCC[Si](C)(C)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.7, "product": "C(C)(C)(C)C1=CN=C(N1COCC[Si](C)(C)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction 5-tert-butyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (276 mg, 1.09 mmol), 2.5 M n-BuLi (567 uL, 1.42 mmol), and DMF (253 uL, 3.27 mmol) for 2 h at −40° C. gave the title compound (304 mg, 99%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.91 (t, 2H, J=9.0 Hz), 1.33 (s, 9H), 3.57 (t, 2H,... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | Other | null | null | null | CC(C)(C)c1cncn1COCC[Si](C)(C)C.CN(C)C=O>>CC(C)(C)c1cnc(C=O)n1COCC[Si](C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b62c3f96ba814eb4be149d7636ad3228 | BrBr.COc1cccc(C(C)=O)c1>>COc1cccc(C(=O)CBr)c1 | COC=1C=C(C=CC1)C(C)=O.C(C)(=O)O.BrBr>>BrCC(=O)C1=CC(=CC=C1)OC | Br[Br:11].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[CH3:10])[cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][Br:11])[cH:12]1 | BrBr.COc1cccc(C(C)=O)c1 | COc1cccc(C(=O)CBr)c1 | null | null | null | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | 33 | [{"value": 33.0, "product": "BrCC(=O)C1=CC(=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.8, "product": "BrCC(=O)C1=CC(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 1-(3-methoxy-phenyl)-ethanone (5.0 g, 33.30 mmol), acetic acid (1.9 mL, 33.30 mmol), and bromine (1.9 mL, 38.30 mmol) followed by recrystallisation from cold EtOAc/Hexane gave the title compound (2.5 g, 33%) as a yellow powder. 1H NMR (300 MHz, CDCl3) δ 3.87 (s, 3H), 4.46 (s, 2H), 7.16 (d, 1H, J=8.4 Hz), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | null | null | null | BrBr.COc1cccc(C(C)=O)c1>>COc1cccc(C(=O)CBr)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30260ab47f414dc78970ad3e75435932 | COc1cccc(C(=O)CBr)c1.NC=O.[NH4+]>>COc1cccc(-c2cnc[nH]2)c1 | BrCC(=O)C1=CC(=CC=C1)OC.C(=O)N.C(Cl)Cl.CO.[NH4+].[OH-]>>COC=1C=C(C=CC1)C1=CN=CN1 | O=[C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:13]1)[CH2:9]Br.O=[CH:11][NH2:10].[NH4+:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10][cH:11][nH:12]2)[cH:13]1 | COc1cccc(C(=O)CBr)c1.NC=O.[NH4+] | COc1cccc(-c2cnc[nH]2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6907b212f6ed2ef44167a5311fd5c85d16f34e450b84662aef7944ef5cc1727b | 5a724a9223d53cbf2bb1ed354a2db350dd6d10aa40058c7a1ca373081e191f17 | c1ccc(-c2cnc[nH]2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].O=[CH;D2;+0:8]-[NH2;D1;+0:9].[NH4+;D0:10]>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D2;+0:9]:[cH;D2;+0:8]:[nH;D2;+0:10]:1):[c:6]:[c:7] | 43 | [{"value": 43.0, "product": "COC=1C=C(C=CC1)C1=CN=CN1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 2-bromo-1-(3-methoxy-phenyl)-ethanone (2.5 g, 10.90 mmol), and formamide (3.1 mL, 76.40 mmol), followed by chromatography (CH2Cl2/MeOH/NH4OH 48:1:1) gave the title compound (820 mg, 43%) as a white solid. 1H NMR (300 MHz, CD3OD) δ 3.83 (s, 3H), 6.78–6.82 (m, 1H), 7.26–7.28 (m, 3H), 7.42 (s, 1H), 7.72 (s, 1H... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amide | null | null | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HBr | null | null | null | COc1cccc(C(=O)CBr)c1.NC=O.[NH4+]>>COc1cccc(-c2cnc[nH]2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dffa0c7add784dc6a1254a1423326e8a | COc1cccc(-c2cnc[nH]2)c1.C[Si](C)(C)CCOCCl>>COc1cccc(-c2cncn2COCC[Si](C)(C)C)c1 | COC=1C=C(C=CC1)C1=CN=CN1.[H-].[Na+].C[Si](C)(C)CCOCCl>>COC=1C=C(C=CC1)C1=CN=CN1COCC[Si](C)(C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10][cH:11][nH:12]2)[cH:21]1.Cl[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10][cH:11][n:12]2[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[cH:21]1 | COc1cccc(-c2cnc[nH]2)c1.C[Si](C)(C)CCOCCl | COc1cccc(-c2cncn2COCC[Si](C)(C)C)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(-c2cnc[nH]2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[c:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[nH;D2;+0:9]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[#7;a:7]:[c:6]:[c:5]:1-[c:4] | 60 | [{"value": 60.0, "product": "COC=1C=C(C=CC1)C1=CN=CN1COCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.8, "product": "COC=1C=C(C=CC1)C1=CN=CN1COCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 5-(3-methoxy-phenyl)-1H-imidazole (500 mg, 2.87 mmol), NaH (60%, 112 mg, 2.79 mmol), and SEMCl (598 uL, 3.35 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (505 mg, 60%) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.93 (t, 2H, J=7.5 Hz), 3.52 (t,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HCl | null | null | null | COc1cccc(-c2cnc[nH]2)c1.C[Si](C)(C)CCOCCl>>COc1cccc(-c2cncn2COCC[Si](C)(C)C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22ca2d6219a14374a7496dc13cfb2647 | CN(C)C=O.COc1cccc(-c2cncn2COCC[Si](C)(C)C)c1>>COc1cccc(-c2cnc(C=O)n2COCC[Si](C)(C)C)c1 | COC=1C=C(C=CC1)C1=CN=CN1COCC[Si](C)(C)C.[Li]CCCC.CN(C)C=O>>COC=1C=C(C=CC1)C1=CN=C(N1COCC[Si](C)(C)C)C=O | CN(C)[CH:12]=[O:13].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10][cH:11][n:14]2[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10][c:11]([CH:12]=[O:13])[n:14]2[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[C... | CN(C)C=O.COc1cccc(-c2cncn2COCC[Si](C)(C)C)c1 | COc1cccc(-c2cnc(C=O)n2COCC[Si](C)(C)C)c1 | null | null | null | C-C Coupling | OtherReaction | 497eb07a6b350068b10b6956179b63b10ae80db27b9b403f062644d98d07ac93 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(-c2cnc[nH]2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 22 | [{"value": 22.0, "product": "COC=1C=C(C=CC1)C1=CN=C(N1COCC[Si](C)(C)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.5, "product": "COC=1C=C(C=CC1)C1=CN=C(N1COCC[Si](C)(C)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 5-(3-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (470 mg, 1.55 mmol), 2.5 M n-BuLi (800 uL, 2.00 mmol), and DMF (479 uL, 6.18 mmol) for 2 h at −40° C. followed by column chromatography on silica gel (EtOAc/hexane 9:1) gave the title compound (111 mg, 22%) as a yellow oil. 1H NMR (300 MH... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | Other | null | null | null | CN(C)C=O.COc1cccc(-c2cncn2COCC[Si](C)(C)C)c1>>COc1cccc(-c2cnc(C=O)n2COCC[Si](C)(C)C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8c37062441fa4ea7bc4e4f6680d6e890 | BrBr.CC(=O)O.CC(=O)c1ccc2c(c1)CCCC2>>COc1cccc(C(=O)CBr)c1 | C1=C(C=CC=2CCCCC12)C(C)=O.C(C)(=O)O.BrBr>>BrCC(=O)C1=CC(=CC=C1)OC | Br[Br:11].C[C:1](=O)[OH:2].C1CC[c:4]2[c:3]([cH:12][c:7]([C:8](=[O:9])[CH3:10])[cH:6][cH:5]2)C1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][Br:11])[cH:12]1 | BrBr.CC(=O)O.CC(=O)c1ccc2c(c1)CCCC2 | COc1cccc(C(=O)CBr)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3073327730c9a299671d905fe3e836e5dd7494729ddaaec4ba68b30d5e4b4751 | c56662ab01b086365e2d1f1bf6a362d8a15a518b2d0e46000dfbd1a74832ea66 | c1ccccc1 | Br-[Br;H0;D1;+0:1].C-[C;H0;D3;+0:2](=O)-[OH;D1;+0:3].[CH3;D1;+0:4]-[C:5](=[O;D1;H0:6])-[c:7]1:[c:8]:[c;H0;D3;+0:9]2:[c;H0;D3;+0:10](:[c:11]:[c:12]:1)-C-C-C-C-2>>[Br;H0;D1;+0:1]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7]1:[c:8]:[c;H0;D3;+0:9](-[O;H0;D2;+0:3]-[CH3;D1;+0:2]):[cH;D2;+0:10]:[c:11]:[c:12]:1 | 28.9 | [{"value": 26.0, "product": "BrCC(=O)C1=CC(=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.9, "product": "BrCC(=O)C1=CC(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (5 g, 28.70 mmol), acetic acid (1.6 mL, 28.70 mmol), and bromine (1.7 mL, 33.00 mmol) followed by recrystallisation from cold EtOAc/Hexane gave the title compound (1.9 g, 26%) as a yellow powder. 1H NMR (300 MHz, CD3OD) δ 1.84 (t, 4H, J=6.6 Hz), 2.80–2.85 (m, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Primary halide.Ketone.Ether | c1ccc2c(c1)CCCC2 | c1ccccc1 | c1ccccc1 | HBr | null | null | null | BrBr.CC(=O)O.CC(=O)c1ccc2c(c1)CCCC2>>COc1cccc(C(=O)CBr)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7285f921cb546fbaf1c59e4fdf52952 | C[Si](C)(C)CCOCCl.c1ncc(-c2ccc3c(c2)CCCC3)[nH]1>>C[Si](C)(C)CCOCn1cncc1-c1ccc2c(c1)CCCC2 | C1=C(C=CC=2CCCCC12)C1=CN=CN1.[H-].[Na+].C[Si](C)(C)CCOCCl>>C1=C(C=CC=2CCCCC12)C1=CN=CN1COCC[Si](C)(C)C | Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[nH:9]1[cH:10][n:11][cH:12][c:13]1-[c:14]1[cH:15][cH:16][c:17]2[c:18]([cH:19]1)[CH2:20][CH2:21][CH2:22][CH2:23]2>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[cH:10][n:11][cH:12][c:13]1-[c:14]1[cH:15][cH:16][c:17]2[c:18]([cH:19]1)[CH2:20][CH... | C[Si](C)(C)CCOCCl.c1ncc(-c2ccc3c(c2)CCCC3)[nH]1 | C[Si](C)(C)CCOCn1cncc1-c1ccc2c(c1)CCCC2 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 59f9db71a8587a55a59c0444ab4770f67569a3a2152b8595d595420e66dd1732 | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ncc(-c2ccc3c(c2)CCCC3)[nH]1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[c:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[nH;D2;+0:9]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[#7;a:7]:[c:6]:[c:5]:1-[c:4] | 52 | [{"value": 52.0, "product": "C1=C(C=CC=2CCCCC12)C1=CN=CN1COCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.1, "product": "C1=C(C=CC=2CCCCC12)C1=CN=CN1COCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 5-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1H-imidazole (387 mg, 1.95 mmol), NaH (60%, 76 mg, 1.89 mmol), and SEMCl (474 uL, 2.28 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (321 mg, 52%) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.92 (t, 2H, J=... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccc2c(c1)CCCC2 | HCl | null | null | null | C[Si](C)(C)CCOCCl.c1ncc(-c2ccc3c(c2)CCCC3)[nH]1>>C[Si](C)(C)CCOCn1cncc1-c1ccc2c(c1)CCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8cca7825779048e586da57d8d41dcd5a | CN(C)C=O.C[Si](C)(C)CCOCn1cncc1-c1ccc2c(c1)CCCC2>>C[Si](C)(C)CCOCn1c(-c2ccc3c(c2)CCCC3)cnc1C=O | C1=C(C=CC=2CCCCC12)C1=CN=CN1COCC[Si](C)(C)C.[Li]CCCC.CN(C)C=O>>C1=C(C=CC=2CCCCC12)C1=CN=C(N1COCC[Si](C)(C)C)C=O | CN(C)[CH:24]=[O:25].[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[c:10](-[c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[CH2:17][CH2:18][CH2:19][CH2:20]3)[cH:21][n:22][cH:23]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[c:10](-[c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[CH2:17][CH2:... | CN(C)C=O.C[Si](C)(C)CCOCn1cncc1-c1ccc2c(c1)CCCC2 | C[Si](C)(C)CCOCn1c(-c2ccc3c(c2)CCCC3)cnc1C=O | null | null | null | C-C Coupling | OtherReaction | 814f426ff2a9ad749905a41d96765a13d0866a98ecc2ead85c1dcdd2dd1d65fd | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ncc(-c2ccc3c(c2)CCCC3)[nH]1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 57 | [{"value": 57.0, "product": "C1=C(C=CC=2CCCCC12)C1=CN=C(N1COCC[Si](C)(C)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "C1=C(C=CC=2CCCCC12)C1=CN=C(N1COCC[Si](C)(C)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 5-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1-(2-trimethylsilanyl ethoxymethyl)-1H-imidazole (268 mg, 0.82 mmol), 2.5 M n-BuLi (424 uL, 1.06 mmol), and DMF (253 uL, 3.27 mmol) for 2 h at −40° C. followed by column chromatography on silica gel (EtOAc/hexane 9:1) gave the title compound (166 mg, 57%) as a yellow o... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1cnc[nH]1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CN(C)C=O.C[Si](C)(C)CCOCn1cncc1-c1ccc2c(c1)CCCC2>>C[Si](C)(C)CCOCn1c(-c2ccc3c(c2)CCCC3)cnc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a2d8e6ec5404012af9ef0d00a03d67b | COc1c(Br)cccc1-c1cnc[nH]1.C[Si](C)(C)CCOCCl>>COc1c(Br)cccc1-c1cncn1COCC[Si](C)(C)C | BrC=1C(=C(C=CC1)C1=CN=CN1)OC.[H-].[Na+].C[Si](C)(C)CCOCCl>>BrC=1C(=C(C=CC1)C1=CN=CN1COCC[Si](C)(C)C)OC | [CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][n:12][cH:13][nH:14]1.Cl[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][n:12][cH:13][n:14]1[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:21])[CH3:22] | COc1c(Br)cccc1-c1cnc[nH]1.C[Si](C)(C)CCOCCl | COc1c(Br)cccc1-c1cncn1COCC[Si](C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(-c2cnc[nH]2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[c:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[nH;D2;+0:9]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[#7;a:7]:[c:6]:[c:5]:1-[c:4] | 60 | [{"value": 60.0, "product": "BrC=1C(=C(C=CC1)C1=CN=CN1COCC[Si](C)(C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.8, "product": "BrC=1C(=C(C=CC1)C1=CN=CN1COCC[Si](C)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 5-(3-bromo-2-methoxy-phenyl)-1H-imidazole (539 mg, 3.10 mmol), NaH (60%, 120 mg, 3.00 mmol), and SEMCl (751 uL, 3.61 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (485 mg, 60%) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.93 (t, 2H, J=7.5 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HCl | null | null | null | COc1c(Br)cccc1-c1cnc[nH]1.C[Si](C)(C)CCOCCl>>COc1c(Br)cccc1-c1cncn1COCC[Si](C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-190fd705a6c045a0847e973b190773f6 | CN(C)C=O.COc1c(Br)cccc1-c1cncn1COCC[Si](C)(C)C>>COc1c(Br)cccc1-c1cnc(C=O)n1COCC[Si](C)(C)C | BrC=1C(=C(C=CC1)C1=CN=CN1COCC[Si](C)(C)C)OC.[Li]CCCC.CN(C)C=O>>BrC=1C(=C(C=CC1)C1=CN=C(N1COCC[Si](C)(C)C)C=O)OC | CN(C)[CH:14]=[O:15].[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][n:12][cH:13][n:16]1[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24]>>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][n:12][c:13]([CH:14]=[O:15])[n:16]1[CH2:17][O:18][CH2:19][CH2:20][Si:21](... | CN(C)C=O.COc1c(Br)cccc1-c1cncn1COCC[Si](C)(C)C | COc1c(Br)cccc1-c1cnc(C=O)n1COCC[Si](C)(C)C | null | null | null | C-C Coupling | OtherReaction | 497eb07a6b350068b10b6956179b63b10ae80db27b9b403f062644d98d07ac93 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(-c2cnc[nH]2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 47 | [{"value": 47.0, "product": "BrC=1C(=C(C=CC1)C1=CN=C(N1COCC[Si](C)(C)C)C=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.3, "product": "BrC=1C(=C(C=CC1)C1=CN=C(N1COCC[Si](C)(C)C)C=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction 5-(3-bromo-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (485 mg, 1.26 mmol), 2.5 M n-BuLi (828 uL, 2.07 mmol), and DMF (494 uL, 6.38 mmol) for 2 h at −40° C. followed by column chromatography on silica gel (EtOAc/hexane 9:1) gave the title compound (240 mg, 47%) as a yellow oil. 1H NMR (3... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | Other | null | null | null | CN(C)C=O.COc1c(Br)cccc1-c1cncn1COCC[Si](C)(C)C>>COc1c(Br)cccc1-c1cnc(C=O)n1COCC[Si](C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-578a18139f5d4addb9915a533ffb08bb | C[Si](C)(C)CCOCCl.c1ccc(-c2nc[nH]c2-c2ccccc2)cc1>>C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1-c1ccccc1 | C1(=CC=CC=C1)C=1N=CNC1C1=CC=CC=C1.[H-].[Na+].C[Si](C)(C)CCOCCl>>C1(=CC=CC=C1)C=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C | Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[nH:9]1[cH:10][n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]1-[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]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](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]1... | C[Si](C)(C)CCOCCl.c1ccc(-c2nc[nH]c2-c2ccccc2)cc1 | C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1-c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(-c2nc[nH]c2-c2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[c:4]-[c:5]1:[#7;a:6]:[c:7]:[nH;D2;+0:8]:[c:9]:1-[c:10]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:5](-[c:4]):[c:9]:1-[c:10] | 64 | [{"value": 64.0, "product": "C1(=CC=CC=C1)C=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.8, "product": "C1(=CC=CC=C1)C=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4,5-diphenyl-1H-imidazole (300 mg, 1.36 mmol), NaH (60%, 55 mg, 1.36 mmol), and SEMCl (289 uL, 1.63 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (304 mg, 64%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.88 (t, 2H, J=7.5 Hz), 3.46 (t, 2H, J=... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1.c1ccccc1 | HCl | null | null | null | C[Si](C)(C)CCOCCl.c1ccc(-c2nc[nH]c2-c2ccccc2)cc1>>C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1-c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9859a6948503434bb774da6cf0b533f3 | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1-c1ccccc1>>C[Si](C)(C)CCOCn1c(C=O)nc(-c2ccccc2)c1-c1ccccc1 | C1(=CC=CC=C1)C=1N=CN(C1C1=CC=CC=C1)COCC[Si](C)(C)C.[Li]CCCC.CN(C)C=O>>C1(=CC=CC=C1)C=1N=C(N(C1C1=CC=CC=C1)COCC[Si](C)(C)C)C=O | CN(C)[CH:11]=[O:12].[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[cH:10][n:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]1-[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[c:10]([CH:11]=[O:12])[n:13][c:14](-[c:15]2[cH:16][cH:17... | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1-c1ccccc1 | C[Si](C)(C)CCOCn1c(C=O)nc(-c2ccccc2)c1-c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 497eb07a6b350068b10b6956179b63b10ae80db27b9b403f062644d98d07ac93 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(-c2nc[nH]c2-c2ccccc2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 78 | [{"value": 78.0, "product": "C1(=CC=CC=C1)C=1N=C(N(C1C1=CC=CC=C1)COCC[Si](C)(C)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "C1(=CC=CC=C1)C=1N=C(N(C1C1=CC=CC=C1)COCC[Si](C)(C)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (304 mg, 0.87 mmol), 2.5 M n-BuLi (452 uL, 1.13 mmol), and DMF (269 uL, 3.48 mmol) for 1 h at −40° C. gave the title compound (257 mg, 78%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.89 (t, 2H, J=9.0 Hz), 3.58 (t, 2H, J=7.5 Hz),... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1.c1ccccc1 | Other | null | null | null | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccccc2)c1-c1ccccc1>>C[Si](C)(C)CCOCn1c(C=O)nc(-c2ccccc2)c1-c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47026e1cef3744f1990fdb7e58671a9d | C[Si](C)(C)CCOCCl.FC(F)(F)c1c[nH]cn1>>C[Si](C)(C)CCOCn1cnc(C(F)(F)F)c1 | FC(C=1N=CNC1)(F)F.[H-].[Na+].C[Si](C)(C)CCOCCl>>FC(C=1N=CN(C1)COCC[Si](C)(C)C)(F)F | Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[nH:9]1[cH:10][n:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]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]([C:13]([F:14])([F:15])[F:16])[cH:17]1 | C[Si](C)(C)CCOCCl.FC(F)(F)c1c[nH]cn1 | C[Si](C)(C)CCOCn1cnc(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1c[nH]cn1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[F;D1;H0:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[c:8]1:[#7;a:9]:[c:10]:[nH;D2;+0:11]:[c:12]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:10]:[#7;a:9]:[c:8](-[C:5](-[F;D1;H0:4])(-[F;D1;H0:6])-[F;D1;H0:7]):[c:12]:1 | null | [] | null | null | null | null | Reaction of 4-trifluoromethyl-1H-imidazole (301 mg, 2.21 mmol), 95% NaH (61 mg, 2.4 mmol), and SEMCl (406 mg, 2.44 mmol) gave the title compound as a brown oil that was used without further purification. 1H NMR (CDCl3) □ 0.00 (s, 9H), 0.93 (m, 2H), 3.51 (m, 2H), 5.30 (s, 2H), 7.39 (s, 1H), 7.64 (s, 1H).
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HCl | null | null | null | C[Si](C)(C)CCOCCl.FC(F)(F)c1c[nH]cn1>>C[Si](C)(C)CCOCn1cnc(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-913b3d980e304cedbb460f4705c41b8f | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(C(F)(F)F)c1>>C[Si](C)(C)CCOCn1cc(C(F)(F)F)nc1C=O | FC(C=1N=CN(C1)COCC[Si](C)(C)C)(F)F.[Li]CCCC.CN(C)C=O>>FC(C=1N=C(N(C1)COCC[Si](C)(C)C)C=O)(F)F | CN(C)[CH:18]=[O:19].[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]([F:13])([F:14])[F:15])[n:16][cH:17]1>>[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]([F:13])([F:14])[F:15])[n:16][c:17]1[CH:18]=[O:19] | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(C(F)(F)F)c1 | C[Si](C)(C)CCOCn1cc(C(F)(F)F)nc1C=O | null | null | null | C-C Coupling | OtherReaction | 497eb07a6b350068b10b6956179b63b10ae80db27b9b403f062644d98d07ac93 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1c[nH]cn1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 14.2 | [{"value": 14.0, "product": "FC(C=1N=C(N(C1)COCC[Si](C)(C)C)C=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.2, "product": "FC(C=1N=C(N(C1)COCC[Si](C)(C)C)C=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (590 mg, 2.2 mmol), 2.3 M n-BuLi (1.3 mL, 3.0 mmol), and DMF (0.51 mL, 6.6 mmol) followed by purification of the crude material on silica gel (10% EtOAc/hexanes) gave the title compound as a yellow oil (92 mg, 14% over two steps). 1H NMR (CD... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | Other | null | null | null | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(C(F)(F)F)c1>>C[Si](C)(C)CCOCn1cc(C(F)(F)F)nc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ce8c33449d24c529eb9f14ef794ff3b | C[Si](C)(C)CCOCCl.Fc1ccc(-c2c[nH]cn2)cc1>>C[Si](C)(C)CCOCn1cnc(-c2ccc(F)cc2)c1 | FC1=CC=C(C=C1)C=1N=CNC1.[H-].[Na+].C[Si](C)(C)CCOCCl>>FC1=CC=C(C=C1)C=1N=CN(C1)COCC[Si](C)(C)C | Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[nH:9]1[cH:10][n:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[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](-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[cH:20]1 | C[Si](C)(C)CCOCCl.Fc1ccc(-c2c[nH]cn2)cc1 | C[Si](C)(C)CCOCn1cnc(-c2ccc(F)cc2)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1620ec2a36b8ae1ddec6099aa0e6468b196c3616868eb853045474c752cdeeee | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(-c2c[nH]cn2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[c:4]-[c:5]1:[#7;a:6]:[c:7]:[nH;D2;+0:8]:[c:9]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:5](-[c:4]):[c:9]:1 | 67.3 | [{"value": 67.0, "product": "FC1=CC=C(C=C1)C=1N=CN(C1)COCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "FC1=CC=C(C=C1)C=1N=CN(C1)COCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-(4-fluoro-phenyl)-1H-imidazole (573 mg, 3.53 mmol), 95% NaH (100 mg, 4.0 mmol), and SEMCl (650 mg, 3.90 mmol) followed by purification of the crude material on silica gel (50% EtOAc/hexanes) gave the title compound as yellow crystals (695 mg, 67%). 1H NMR (CDCl3) □−0.01 (s, 9H), 0.93 (m, 2H), 3.52 (m, 2H)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | HCl | null | null | null | C[Si](C)(C)CCOCCl.Fc1ccc(-c2c[nH]cn2)cc1>>C[Si](C)(C)CCOCn1cnc(-c2ccc(F)cc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-13b6571ec35743d3b589ceff38dab232 | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccc(F)cc2)c1>>C[Si](C)(C)CCOCn1cc(-c2ccc(F)cc2)nc1C=O | FC1=CC=C(C=C1)C=1N=CN(C1)COCC[Si](C)(C)C.[Li]CCCC.CN(C)C=O>>FC1=CC=C(C=C1)C=1N=C(N(C1)COCC[Si](C)(C)C)C=O | CN(C)[CH:21]=[O:22].[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][c:15]([F:16])[cH:17][cH:18]2)[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][c:11](-[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[n:19][c:20]1[CH:21]=[O:22... | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccc(F)cc2)c1 | C[Si](C)(C)CCOCn1cc(-c2ccc(F)cc2)nc1C=O | null | null | null | C-C Coupling | OtherReaction | 497eb07a6b350068b10b6956179b63b10ae80db27b9b403f062644d98d07ac93 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(-c2c[nH]cn2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | null | null | null | null | Reaction of 4-(4-fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (688 mg, 2.35 mmol), 1.5 M n-BuLi (2.0 mL, 3.0 mmol), and DMF (0.55 mL, 7.1 mmol) gave the title compound as a brown oil that was used without further purification in the next step. 1H NMR (CDCl3) 0.00 (s, 9H), 0.95 (m, 2H), 3.61 (m, 2H), ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | Other | null | null | null | CN(C)C=O.C[Si](C)(C)CCOCn1cnc(-c2ccc(F)cc2)c1>>C[Si](C)(C)CCOCn1cc(-c2ccc(F)cc2)nc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-655576af4ad44e24a96242ee25b4c37c | OCC(O)CBr.c1ccc2[nH]cnc2c1>>CC(O)C(O)n1cnc2ccccc21 | N1=CNC2=C1C=CC=C2.BrCC(CO)O.C([O-])([O-])=O.[K+].[K+]>>N1(C=NC2=C1C=CC=C2)C(C(C)O)O | Br[CH2:1][CH:2]([OH:3])[CH2:4][OH:5].[nH:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[CH3:1][CH:2]([OH:3])[CH:4]([OH:5])[n:6]1[cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | OCC(O)CBr.c1ccc2[nH]cnc2c1 | CC(O)C(O)n1cnc2ccccc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 3f242480e395d5b73818145a91825d244c51478e75133109a4b1072d80a1050f | fb3625d7b91e39fdf32ac78352ada1c99e471c10a71f1343eae51a765874cf2f | c1ccc2[nH]cnc2c1 | Br-[CH2;D2;+0:1]-[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[O;D1;H1:5].[c:6]:[c:7]1:[#7;a:8]:[c:9]:[nH;D2;+0:10]:[c:11]:1:[c:12]>>[CH3;D1;+0:1]-[C:2](-[O;D1;H1:3])-[CH;D3;+0:4](-[O;D1;H1:5])-[n;H0;D3;+0:10]1:[c:9]:[#7;a:8]:[c:7](:[c:6]):[c:11]:1:[c:12] | 69 | [{"value": 69.0, "product": "N1(C=NC2=C1C=CC=C2)C(C(C)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.7, "product": "N1(C=NC2=C1C=CC=C2)C(C(C)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Benzimidazole (590 mg, 5.0 mmol) and 3-bromo-1,2-propanediol (0.52 mL, 6.0 mmol) were dissolved in anhydrous acetonitrile (50 mL) and dry potassium carbonate (2.07 g, 15 mmol) was added. The solution was then heated to reflux for 3 days. Upon cooling the mixture was filtered and the filtrates were concentrated, giving ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Secondary alcohol | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HBr | C(C)#N | null | null | OCC(O)CBr.c1ccc2[nH]cnc2c1>C(C)#N>CC(O)C(O)n1cnc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50f12f9a7e5d407b848aeee13aedd1a7 | CC(O)C(O)n1cnc2ccccc21>>O=CCn1cnc2ccccc21 | N1(C=NC2=C1C=CC=C2)C(C(C)O)O.I(=O)(=O)(=O)[O-].[Na+]>>N1(C=NC2=C1C=CC=C2)CC=O | C[CH:2]([OH:1])[CH:3](O)[n:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12>>[O:1]=[CH:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12 | CC(O)C(O)n1cnc2ccccc21 | O=CCn1cnc2ccccc21 | null | null | O | Miscellaneous | OtherReaction | 2a1c618d233ea288cefda40fc735a34dc6ca88b6d9db7a646e57af41ca9dfcb9 | d011355d7866084135779ab6a9a0c9a792c05e7f59c9d732d5cd5c44c4fc6498 | c1ccc2[nH]cnc2c1 | C-[CH;D3;+0:1](-[OH;D1;+0:2])-[CH;D3;+0:3](-O)-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:1>>[O;H0;D1;+0:2]=[CH;D2;+0:1]-[CH2;D2;+0:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:1 | 41.2 | [{"value": 41.2, "product": "N1(C=NC2=C1C=CC=C2)CC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | The intermediate, N-benzimidazolyl-1,2-propanediol (0.66 g, 3.4 mmol) from above was dissolved in water (25 mL) and treated with sodium periodate (0.88 g, 4.1 mmol) with stirring for 1.5 hours. The solution was then extracted with dichloromethane, dried (MgSO4), filtered and concentrated to yield 2-(benzimidazol-1-yl)-... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Aldehyde | null | null | c1ccc2[nH]cnc2c1 | HO- | O | null | 1.5 | CC(O)C(O)n1cnc2ccccc21>O>O=CCn1cnc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2168bdfd01ef43e599b82ce28d951c97 | CCOC(=O)CCBr.c1ccc2[nH]cnc2c1>>CCOC(=O)CCn1cnc2ccccc21 | C(C)OC(CCBr)=O.N1=CNC2=C1C=CC=C2.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(CCN1C=NC2=C1C=CC=C2)=O | Br[CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[nH:8]1[cH:9][n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][n:8]1[cH:9][n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12 | CCOC(=O)CCBr.c1ccc2[nH]cnc2c1 | CCOC(=O)CCn1cnc2ccccc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6a48d391cdf145ccb5ef1a354bce7505b4cdb90ce38c614e9a7da9db53649cbd | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]cnc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[c:7]:[c:8]1:[#7;a:9]:[c:10]:[nH;D2;+0:11]:[c:12]:1:[c:13]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:10]:[#7;a:9]:[c:8](:[c:7]):[c:12]:1:[c:13] | 91 | [{"value": 91.0, "product": "C(C)OC(CCN1C=NC2=C1C=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "C(C)OC(CCN1C=NC2=C1C=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl-3-bromopropanoate (1.29 g, 7.1 mmol), benzimidazole (0.70 g, 5.9 mmol), and potassium carbonate (2.44 g, 17.7 mmol) were combined in anhydrous acetonitrile (60 mL) and heated to reflux for 3 days. Aqueous work-up gave ethyl-3-(benzimidazol-1-yl)propanoate (1.17 g, 91%). 1H NMR (CDCl3) δ 2.02 (s, 3H), 2.26 (m, 2H)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HBr | C(C)#N | null | null | CCOC(=O)CCBr.c1ccc2[nH]cnc2c1>C(C)#N>CCOC(=O)CCn1cnc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bc92aaa2a180438db02ee28088d457c3 | OCCCn1cnc2ccccc21>>O=CCCn1cnc2ccccc21 | C([O-])(O)=O.[Na+].S(=S)(=O)([O-])[O-].[Na+].[Na+].[Na].N1(C=NC2=C1C=CC=C2)CCCO>>N1(C=NC2=C1C=CC=C2)CCC=O | [OH:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[O:1]=[CH:2][CH2:3][CH2:4][n:5]1[cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | OCCCn1cnc2ccccc21 | O=CCCn1cnc2ccccc21 | null | null | ClCCl.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2[nH]cnc2c1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 81.6 | [{"value": 80.0, "product": "N1(C=NC2=C1C=CC=C2)CCC=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.6, "product": "N1(C=NC2=C1C=CC=C2)CCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 3-(benzimidazol-1-yl)propan-1-ol (100 mg, 0.57 mmol) was dissolved in dichloromethane (6 mL), and treated with sodium periodinane (290 mg, 0.68 mmol). After stirring 5 hours, the mixture was treated with sodium bicarbonate (10 mL), ethyl acetate (10 mL), sodium thiosulfate (2 g) and extracted with ethyl acetate (2×10 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2[nH]cnc2c1 | null | ClCCl.C(C)(=O)OCC | null | 5 | OCCCn1cnc2ccccc21>ClCCl.C(C)(=O)OCC>O=CCCn1cnc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fb8e651edbfe42a48a8f431330505aa7 | C=CCCOc1cccnc1Br>>C=C1CCOc2cccnc21 | BrC1=NC=CC=C1OCCC=C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)[O-].[K+]>>C=C1CCOC=2C1=NC=CC2 | Br[c:11]1[c:6]([O:5][CH2:4][CH2:3][CH:2]=[CH2:1])[cH:7][cH:8][cH:9][n:10]1>>[CH2:1]=[C:2]1[CH2:3][CH2:4][O:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]21 | C=CCCOc1cccnc1Br | C=C1CCOc2cccnc21 | null | O.[Cl-].C(C)[N+](CC)(CC)CC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | null | Functional Group Interconversion | OtherReaction | cd829a3f5ed08026fc8b59bf42ee14ab7d58b04e6bfc80aeec2f2d45825404bd | ecb364866943409dcd47801bce479b63d5745111cbd7d97be831f522bd48d935 | C=C1CCOc2cccnc21 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#8:5]-[C:6]-[C:7]-[CH;D2;+0:8]=[C;D1;H2:9]):[c:10]>>[C;D1;H2:9]=[C;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[c:4](:[c:10]):[c;H0;D3;+0:1]-1:[#7;a:2]:[c:3] | 52.8 | [{"value": 52.0, "product": "C=C1CCOC=2C1=NC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.8, "product": "C=C1CCOC=2C1=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | A reaction tube was charged with 2-Bromo-3-but-3-enyloxy-pyridine (106 mg, 0.45 mmol), triphenylphosphine (35 mg, 0.133 mmol), palladium acetate (10 mg, 0.044 mmol), potassium acetate (223 mg, 2.27 mmol), tetraethylammonium chloride hydrate (151 mg, 0.91 mmol) and degassed DMF (2 mL). A rubber septum was used to seal t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Allyl | Vinyl | c1ccncc1 | c1cnc2c(c1)OCCC2 | c1cnc2c(c1)OCCC2 | HBr | O.[Cl-].C(C)[N+](CC)(CC)CC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | 110 | null | C=CCCOc1cccnc1Br>O.[Cl-].C(C)[N+](CC)(CC)CC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-]>C=C1CCOc2cccnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a5aedd732142427e9c1f6c658953ff73 | OC1CCCc2cccnc21>>O=C1CCCc2cccnc21.OC1CCCc2cccnc21 | OC1CCCC=2C=CC=NC12>>OC1CCCC=2C=CC=NC12.N1=CC=CC=2CCCC(C12)=O | [OH:1][CH:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]21>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][n:10][c:11]21.[OH:12][CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][n:21][c:22]21 | OC1CCCc2cccnc21 | O=C1CCCc2cccnc21.OC1CCCc2cccnc21 | null | [O-2].[O-2].[Mn+4] | C(Cl)Cl | Aromatic Heterocycle Formation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 6b5b23e3148046eeed7756722000f56208fcf5ae56f52cfd85bfc1c2dcb9d14b | d0d79dd69d2558c00a590859cbd596e894d9fc69928b02ff3453d5a679e727d0 | O=C1CCCc2cccnc21.c1cnc2c(c1)CCCC2 | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[#7;a:7]:[c:8] | 170.2 | [{"value": 85.0, "product": "N1=CC=CC=2CCCC(C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 170.2, "product": "N1=CC=CC=2CCCC(C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | 8-hydroxy-5,6,7,8-tetrahydroquinoline was prepared as described in Bridger et al. PCT International Application PCT/CA00/00321. To a stirred solution of 8-hydroxy-5,6,7,8-tetrahydroquinoline (1.37 g, 9.18 mmol) in dry CH2Cl2 (50 mL) was added activated manganese dioxide (85% purity, 7.51 g, 73.5 mmol) in one portion. T... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone.Secondary alcohol | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2.c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2.c1cnc2c(c1)CCCC2 | Other | [O-2].[O-2].[Mn+4].C(Cl)Cl | null | 96 | OC1CCCc2cccnc21>[O-2].[O-2].[Mn+4].C(Cl)Cl>O=C1CCCc2cccnc21.OC1CCCc2cccnc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-da10064715ba4368ab44a1416b1d9cee | C[Si](C)(C)CCOCCl.ClCc1nc2ccccc2[nH]1>>C[Si](C)(C)CCOCn1c(CCl)nc2ccccc21 | ClCC=1NC2=C(N1)C=CC=C2.C(C)(C)N(C(C)C)CC.C[Si](CCOCCl)(C)C>>ClCC1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2 | Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[nH:9]1[c:10]([CH2:11][Cl:12])[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[c:10]([CH2:11][Cl:12])[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | C[Si](C)(C)CCOCCl.ClCc1nc2ccccc2[nH]1 | C[Si](C)(C)CCOCn1c(CCl)nc2ccccc21 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9c85dcc828756c0974009bcfb80913201b76af77200773bdad77209726d6e70a | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc2[nH]cnc2c1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[C:4]-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C:4]-[c:5]1:[#7;a:6]:[c:7](:[c:8]):[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[#8:2]-[C:3] | 67.7 | [{"value": 65.0, "product": "ClCC1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.7, "product": "ClCC1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a stirred solution of 2-chloromethylbenzimidazole (1.89 g, 11.4 mmol) in dry THF (57 mL) was added N,N-diisopropylethylamine (3.00 mL, 17.2 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (1.90 mL, 10.8 mmol) both via syringe under nitrogen at room temperature. The mixture was stirred for 3 days at which time the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1ccc2[nH]cnc2c1 | c1nc2ccccc2[nH]1 | c1nc2ccccc2[nH]1 | HCl | C1CCOC1 | null | 72 | C[Si](C)(C)CCOCCl.ClCc1nc2ccccc2[nH]1>C1CCOC1>C[Si](C)(C)CCOCn1c(CCl)nc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59b8031d09e547afbae5a50f1d8b8662 | CC(C)(C)OC(=O)N(Cc1ccc(CNC2(C)CCCc3cccnc32)cc1)Cc1ccccn1.C[Si](C)(C)CCOCn1c(CCl)nc2ccccc21>>CC(C)(C)OC(=O)N(Cc1ccc(CN(Cc2nc3ccccc3n2COCC[Si](C)(C)C)C2(C)CCCc3cccnc32)cc1)Cc1ccccn1 | C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)CNC1(CCCC=2C=CC=NC12)C)CC1=NC=CC=C1.ClCC1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2.C(C)(C)N(CC)C(C)C>>C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)CN(C1(CCCC=2C=CC=NC12)C)CC1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2)CC2=NC=CC=C2 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][NH:15][C:34]2([CH3:35])[CH2:36][CH2:37][CH2:38][c:39]3[cH:40][cH:41][cH:42][n:43][c:44]32)[cH:45][cH:46]1)[CH2:47][c:48]1[cH:49][cH:50][cH:51][cH:52][n:53]1.Cl[CH2:16][c:17]1[n:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2... | CC(C)(C)OC(=O)N(Cc1ccc(CNC2(C)CCCc3cccnc32)cc1)Cc1ccccn1.C[Si](C)(C)CCOCn1c(CCl)nc2ccccc21 | CC(C)(C)OC(=O)N(Cc1ccc(CN(Cc2nc3ccccc3n2COCC[Si](C)(C)C)C2(C)CCCc3cccnc32)cc1)Cc1ccccn1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CNCc2ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc2)nc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[C:7].[#7;a:8]:[c:9]-[C:10](-[C;D1;H3:11])(-[NH;D2;+0:12]-[C:13]-[c:14])-[C:15]>>[#7;a:8]:[c:9]-[C:10](-[C;D1;H3:11])(-[N;H0;D3;+0:12](-[C:13]-[c:14])-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:1-[C:7])-[C:15] | 48 | [{"value": 48.0, "product": "C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)CN(C1(CCCC=2C=CC=NC12)C)CC1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2)CC2=NC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.2, "product": "C(C)(C)(C)OC(=O)N(CC1=CC=C(C=C1)CN(C1(CCCC=2C=CC=NC12)C)CC1=NC2=C(N1COCC[Si](C)(C)C)C=CC=C2)CC2=NC=CC=C2", ... | null | null | null | null | Reaction of N-tert-Butoxycarbonyl-N-(2-pyridinylmethyl)-N′-(8-methyl-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (120 mg, 0.26 mmol), 2-chloromethyl-1-(2-trimethylsilylethoxymethyl)-1H-benzimidazole (234 mg, 0.79 mmol) and diisopropylethylamine (229 uL, 1.31 mmol) in DMF (2.6 mL) for 18 h at 90° C. follow... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1nc2ccccc2[nH]1.c1cnc2c(c1)CCCC2.c1ccncc1 | HCl | CN(C)C=O | null | null | CC(C)(C)OC(=O)N(Cc1ccc(CNC2(C)CCCc3cccnc32)cc1)Cc1ccccn1.C[Si](C)(C)CCOCn1c(CCl)nc2ccccc21>CN(C)C=O>CC(C)(C)OC(=O)N(Cc1ccc(CN(Cc2nc3ccccc3n2COCC[Si](C)(C)C)C2(C)CCCc3cccnc32)cc1)Cc1ccccn1 |
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