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-6ecd98bd91e74b1eb0e6b30948b578ae | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc([N+](=O)[O-])cc3C2=O)ccc1OC>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(N)cc3C2=O)ccc1OC | C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=CC(=CC2)[N+](=O)[O-])=O)C2=CC(=C(C=C2)OC)OCC)=O.C(C)(=O)OCC>>NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC1 | O=[N+:20]([O-])[c:19]1[cH:18][cH:17][c:16]2[c:22]([cH:21]1)[C:23](=[O:24])[N:13]([CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][cH:25]1)[CH2:8][C:9](=[O:10])[NH:11][O:12]Cc1ccccc1)[C:14]2=[O:15]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[... | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc([N+](=O)[O-])cc3C2=O)ccc1OC | CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(N)cc3C2=O)ccc1OC | null | [OH-].[OH-].[Pd+2] | C(C)(=O)OCC.CO.O1CCCC1 | Reduction | OtherReaction | 9605e268a6d8edc603bdca29ba7634f60544d74f261e105d8148187748f92769 | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[O;H0;D2;+0:9]-C-c1:c:c:c:c:c:1>>[C:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[OH;D1;+0:9].[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 102 | [{"value": 100.0, "product": "NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 102.0, "product": "NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-Benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)-propionamide (2.3 g, 4.42 mmol) and Pd(OH)2/C (600 mg) in ethyl acetate/methanol/tetrahydrofuran (150 mL each) was shaken under hydrogen. After 24 hours the suspension was filtered through a pad of Celite, and then was washed with methanol (30... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | [OH-].[OH-].[Pd+2].C(C)(=O)OCC.CO.O1CCCC1 | null | null | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc([N+](=O)[O-])cc3C2=O)ccc1OC>[OH-].[OH-].[Pd+2].C(C)(=O)OCC.CO.O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(N)cc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-909a3d25a3a2447daf56d1285f6de8cb | COc1ccc(C(CC(=O)O)N2Cc3ccccc3C2=O)cc1OC.NO>>COc1ccc(C(CC(=O)NO)N2Cc3ccccc3C2=O)cc1OC | COC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C2=CC=CC=C2C1)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>ONC(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OC)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23]1)[N:13]1[CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22])=[O:10].[NH2:11][OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20... | COc1ccc(C(CC(=O)O)N2Cc3ccccc3C2=O)cc1OC.NO | COc1ccc(C(CC(=O)NO)N2Cc3ccccc3C2=O)cc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2CN1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 79 | [{"value": 79.0, "product": "ONC(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "ONC(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Hydroxy-3-(3,4-dimethoxyphenyl)-3-(1-oxoisoindolinyl)propionamide was prepared by the procedure of Example 1 from 3-(3,4-dimethoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid (5.00 g, 14.7 mmol), carbonyldiimidazole (2.49 g, 15.4 mmol) and hydroxylamine hydrochloride (1.30 g, 19.1 mmol) in tetrahydrofuran (15 mL) to a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | COc1ccc(C(CC(=O)O)N2Cc3ccccc3C2=O)cc1OC.NO>O1CCCC1>COc1ccc(C(CC(=O)NO)N2Cc3ccccc3C2=O)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a43f77e5fc949769fefe754c9431212 | COc1ccc(C(CC(=O)O)N2Cc3ccccc3C2=O)cc1OC1CCCC1.NO>>COc1ccc(C(CC(=O)NO)N2Cc3ccccc3C2=O)cc1OC1CCCC1 | C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C2=CC=CC=C2C1)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C2=CC=CC=C2C1)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)[cH:23]1)[N:13]1[CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22])=[O:10].[NH2:11][OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[CH2:14][c:15]3... | COc1ccc(C(CC(=O)O)N2Cc3ccccc3C2=O)cc1OC1CCCC1.NO | COc1ccc(C(CC(=O)NO)N2Cc3ccccc3C2=O)cc1OC1CCCC1 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2CN1Cc1cccc(OC2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 91.5 | [{"value": 91.0, "product": "C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C2=CC=CC=C2C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C2=CC=CC=C2C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Cyclopentyloxy-4-methoxyphenyl)-N-hydroxy-3-(1-oxoisoindolinyl)propionamide was prepared by the procedure of Example 1 from 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid (1.00 g, 2.53 mmol), carbonyldiimidazole (430 mg, 2.66 mmol) and hydroxylamine hydrochloride (230 mg, 3.29 mmol) in te... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCCC1 | HO- | O1CCCC1 | null | null | COc1ccc(C(CC(=O)O)N2Cc3ccccc3C2=O)cc1OC1CCCC1.NO>O1CCCC1>COc1ccc(C(CC(=O)NO)N2Cc3ccccc3C2=O)cc1OC1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-664c300c130748ff85e60a9debf7ae9f | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc([N+](=O)[O-])cc3C2=O)ccc1OC.NOCc1ccccc1>>CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc([N+](=O)[O-])cc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC(=CC2)[N+](=O)[O-])=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.C(C1=CC=CC=C1)ON>>C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=CC(=CC2)[N+](=O)[O-])=O)C2=CC(=C(C=C2)OC)OCC)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:36]([O:37][CH3:38])[cH:35][cH:34]1)[N:20]1[C:21](=[O:22])[c:23]2[cH:24][cH:25][c:26]([N+:27](=[O:28])[O-:29])[cH:30][c:31]2[C:32]1=[O:33])=[O:10].[NH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([... | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc([N+](=O)[O-])cc3C2=O)ccc1OC.NOCc1ccccc1 | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc([N+](=O)[O-])cc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CC(c1ccccc1)N1C(=O)c2ccccc2C1=O)NOCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#8:6]-[NH2;D1;+0:7]>>[C:5]-[#8:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 59 | [{"value": 59.0, "product": "C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=CC(=CC2)[N+](=O)[O-])=O)C2=CC(=C(C=C2)OC)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.0, "product": "C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=CC(=CC2)[N+](=O)[O-])=O)C2=CC(=C(C=C2)OC)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | null | null | N-Benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)propanoic acid (2.84 g, 6.85 mmol), carbonyldiimidazole (1.22 g, 7.52 mmol) and O-benzylhydroxylamine hydrochloride (1.32 g, 8.27 mmol) in tetrah... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc([N+](=O)[O-])cc3C2=O)ccc1OC.NOCc1ccccc1>O1CCCC1>CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc([N+](=O)[O-])cc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-76170310ada740d388a17b20754d0916 | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(N)c3C2=O)ccc1OC | C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=C(C=CC2)[N+](=O)[O-])=O)C2=CC(=C(C=C2)OC)OCC)=O.CCOCC>>NC1=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC=C1 | O=[N+:21]([O-])[c:20]1[cH:19][cH:18][cH:17][c:16]2[c:22]1[C:23](=[O:24])[N:13]([CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][cH:25]1)[CH2:8][C:9](=[O:10])[NH:11][O:12]Cc1ccccc1)[C:14]2=[O:15]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[O:... | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC | CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(N)c3C2=O)ccc1OC | null | [Pd] | C(C)(=O)OCC.CO | Reduction | OtherReaction | 9605e268a6d8edc603bdca29ba7634f60544d74f261e105d8148187748f92769 | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[#7:7].[C:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[O;H0;D2;+0:12]-C-c1:c:c:c:c:c:1>>[#7:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3].[C:8]-[C:9](=[O;D1;H0:10])-[#7:11]-[OH;D1;+0:12] | 64.1 | [{"value": 64.0, "product": "NC1=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.1, "product": "NC1=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A mixture of N-benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(3-nitrophthalimido)-propionamide (1.32 g, 2.54 mmol) and 10% Pd/C (230 mg) in ethyl acetate/methanol (150 mL each) was shaken under 50–60 psi of H2. After 3 days, the suspension was filtered through a pad of Celite, and the pad washed with methanol (75 mL) and me... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | [Pd].C(C)(=O)OCC.CO | null | 72 | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3cccc([N+](=O)[O-])c3C2=O)ccc1OC>[Pd].C(C)(=O)OCC.CO>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(N)c3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-77661165585244fc802bf825a6d261d5 | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.CNO.O=C(n1ccnc1)n1ccnc1>>CCOc1cc(C(CC(=O)N(C)O)N2Cc3ccccc3C2=O)ccc1OC.CCOc1cc(C(CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C2=CC=CC=C2C1)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.CNO>>ONC(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O.ON(C(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O)C | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[OH:13])[N:14]2[CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[C:22]2=[O:23])[cH:24][cH:25][c:26]1[O:27][CH3:28].[NH:39]([OH:40])[CH3:55].n1[cH:43][cH:42][n:41]([C:35](n2[cH:32][n:11][cH:12][cH:44]2)=[O:31])[cH:49]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6... | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.CNO.O=C(n1ccnc1)n1ccnc1 | CCOc1cc(C(CC(=O)N(C)O)N2Cc3ccccc3C2=O)ccc1OC.CCOc1cc(C(CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | f4592d64c00ed31ac9c18840ec71eb36951ee67e7bbf90b0864f860f09befbbb | c3de5cd3f492b712cc166a1880687e5d41a03f0c6ab91da832b6b1edc4ef3d58 | O=C1c2ccccc2CN1Cc1ccccc1.O=C1c2ccccc2CN1Cc1ccccc1 | [CH3;D1;+0:1]-[NH;D2;+0:2]-[O;D1;H1:3].[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[OH;D1;+0:8].[O;H0;D1;+0:9]=[C;H0;D3;+0:10](-[n;H0;D3;+0:11]1:[cH;D2;+0:12]:[cH;D2;+0:13]:n:[cH;D2;+0:14]:1)-n1:[cH;D2;+0:15]:[n;H0;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:1>>[C;D1;H3:19]-[C:20]-[O;H0;D2;+0:9]-[c;H0;D3;+0:15]1:[c:21]:[c:22](-... | 120.8 | [{"value": 61.0, "product": "ON(C(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 120.8, "product": "ON(C(CC(N1C(C2=CC=CC=C2C1)=O)C1=CC(=C(C=C1)OC)OCC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Hydroxy-3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid (1.0 g, 2.8 mmol), carbonyldiimidazole (500 mg, 3.1 mmol) and N-methyl-hydroxylamine hydrochloride (300 mg, 3.5 mmol) in tetrahydrofur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Ether.Ether.Secondary amide.Tertiary amide.Tertiary amide | c1c[nH]cn1.c1c[nH]cn1 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2.c1ccccc1.c1ccc2c(c1)C[NH]C2 | null | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.CNO.O=C(n1ccnc1)n1ccnc1>O1CCCC1>CCOc1cc(C(CC(=O)N(C)O)N2Cc3ccccc3C2=O)ccc1OC.CCOc1cc(C(CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-faaed52f1ef545619edc3cc0b4588d9b | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(O)c3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(O)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=C(C=CC2)O)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)O)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][cH:25]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([OH:21])[c:22]2[C:23]1=[O:24])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[O:15])[c:16]3[c... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(O)c3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(O)c3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 80.5 | [{"value": 80.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.5, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3-hydroxyphthalimido)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(3-hydroxyphthalimido)propanoic acid (0.70 g, 1.8 mmol), carbonyldiimidazole (690 mg, 4.25 mmol) and hydroxylamine hydrochloride (380 mg, 5.47 mmol) in tetrahydrofur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(O)c3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(O)c3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e6a4a7db9b74f96ab7573eca76e99a4 | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(O)cc3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(O)cc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=CC(=CC2)O)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC(=CC2)O)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][cH:25]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][c:22]2[C:23]1=[O:24])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[O:15])[c:16]3[c... | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(O)cc3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(O)cc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 44 | [{"value": 44.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC(=CC2)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.2, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=CC(=CC2)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(4-hydroxyphthalimido)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(4-hydroxyphthalimido)propanoic acid (4.0 g, 10.4 mmol), carbonyldiimidazole (2.02 g, 12.46 mmol) and hydroxylamine hydrochloride (1.13 g, 16.3 mmol) in tetrahydrofu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(O)cc3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(O)cc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c609a5f2321e426eb6400123fddcd3ac | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(C)c3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(C)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=C(C=CC2)C)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)C)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][cH:25]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([CH3:21])[c:22]2[C:23]1=[O:24])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[O:15])[c:16]3[... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(C)c3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(C)c3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 90 | [{"value": 90.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.9, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3-methylphthalimido)propionanide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(3-methylphthalimido)propanoic acid (1.50 g, 3.91 mmol), carbonyldiimidazole (698 mg, 4.30 mmol) and hydroxylamine hydrochloride (330 mg, 4.75 mmol) in tetrahydrofura... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(C)c3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(C)c3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a75726c51e0f48dfa51af8d442cbef32 | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC | C(C)(=O)NC1=C2C(C(=O)N(C2=O)C(CC(=O)O)C2=CC(=C(C=C2)OC)OCC)=CC=C1.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)(=O)NC1=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC=C1 | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:30]([O:31][CH3:32])[cH:29][cH:28]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][C:22]([CH3:23])=[O:24])[c:25]2[C:26]1=[O:27])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 48.2 | [{"value": 48.0, "product": "C(C)(=O)NC1=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.2, "product": "C(C)(=O)NC1=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Acetoamidophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamide was prepared by the procedure of Example 1 from 3-(3-acetoamidophthalimido)-3-(3-ethoxy-4-methoxyphenyl)propanoic acid (2.0 g, 4.7 mmol), carbonyldiimidazole (1.14 g, 7.03 mmol) and hydroxylamine hydrochloride (651 mg, 9.37 mmol) in tetrahyd... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b0758af3e654ab282fe636ca4a5ca33 | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)ccc1OC | C(C)(=O)NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)O)C2=CC(=C(C=C2)OC)OCC)=CC1.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)(=O)NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC1 | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:30]([O:31][CH3:32])[cH:29][cH:28]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24][c:25]2[C:26]1=[O:27])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[... | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 43.4 | [{"value": 43.0, "product": "C(C)(=O)NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.4, "product": "C(C)(=O)NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-Acetoamidophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamide was prepared by the procedure of Example 1 from 3-(4-acetoamidophthalimido)-3-(3-ethoxy-4-methoxyphenyl)propanoic acid (2.0 g, 4.7 mmol), carbonyldiimidazole (836 mg, 5.16 mmol) and hydroxylamine hydrochloride (391 mg, 5.63 mmol) in tetrahyd... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-10532929ea4b4862ae7fcf24e636a130 | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(C(C)(C)C)cc3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C(C)(C)C)cc3C2=O)ccc1OC | C(C)(C)(C)C=1C=C2C(C(=O)N(C2=O)C(CC(=O)O)C2=CC(=C(C=C2)OC)OCC)=CC1.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)(C)(C)C=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC1 | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:30]([O:31][CH3:32])[cH:29][cH:28]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24][c:25]2[C:26]1=[O:27])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:1... | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(C(C)(C)C)cc3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C(C)(C)C)cc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 85.5 | [{"value": 85.0, "product": "C(C)(C)(C)C=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.5, "product": "C(C)(C)(C)C=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OCC)=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-tert-Butylphthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamide was prepared by the procedure of Example 1 from 3-(4-tert-butylphthalimido)-3-(3-ethoxy-4-methoxyphenyl)propanoic acid (2.0 g, 4.7 mmol), carbonyldiimidazole (800 mg, 4.93 mmol) and hydroxylamine hydrochloride (377 mg, 5.43 mmol) in tetrahyd... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3ccc(C(C)(C)C)cc3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C(C)(C)C)cc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b24dedb7c5bf46e88937d1510d4fa0b3 | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=C(C=CC2)N(C)C)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)N(C)C)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][cH:27]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([N:21]([CH3:22])[CH3:23])[c:24]2[C:25]1=[O:26])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 87.3 | [{"value": 87.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)N(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)N(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3-dimethylaminophthalimido)-propion-amide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(3-dimethylaminophthalimido)propanoic acid (0.31 g, 0.75 mmol), carbonyldiimidazole (140 mg, 0.86 mmol) and hydroxylamine hydrochloride (66 mg, 0.95 mmol) in... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-902430e271cd4072b47e7f445e58b689 | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC | C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=C(C(=CC2)C)C)=O)C2=CC(=C(C=C2)OC)OCC)=O.[H][H]>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C(=CC2)C)C)=O | c1ccc(C[O:12][NH:11][C:9]([CH2:8][CH:7]([c:6]2[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27][cH:26]2)[N:13]2[C:14](=[O:15])[c:16]3[cH:17][cH:18][c:19]([CH3:20])[c:21]([CH3:22])[c:23]3[C:24]2=[O:25])=[O:10])cc1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](... | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC | CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC | null | [OH-].[OH-].[Pd+2] | CO.C(C)(=O)OCC | Deprotection | OtherReaction | 94fa5e5ed4a5b32c4aba0dd3c8151bfdd08491d1bc6453e9fd01d7dc3e51cd0f | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[OH;D1;+0:5] | 84 | [{"value": 84.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C(=CC2)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.4, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C(=CC2)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3,4-dimethylphthalimido)propion-amide was prepared by the procedure of Example 16 N-benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(3,4-dimethylphthalimido)propanamide(0.63 g, 1.25 mmol), Pd(OH)2/C (100 mg) and hydrogen (50 psi) in ethyl acetate and methanol (30 mL each) to afford 3-... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | Other | [OH-].[OH-].[Pd+2].CO.C(C)(=O)OCC | null | null | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC>[OH-].[OH-].[Pd+2].CO.C(C)(=O)OCC>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df24891cbe8d43bea769f5fa06cf1cb6 | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC.NO>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C=2C(C1=O)=C(C=CC2)N(C)C)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)N(C)C)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][cH:27]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([N:21]([CH3:22])[CH3:23])[c:24]2[C:25]1=[O:26])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](... | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC.NO | CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 87.3 | [{"value": 87.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)N(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)N(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3-dimethylaminophthalimido)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(3-dimethylaminophthalimido)propanoic acid (0.31 g, 0.75 mmol), carbonyldiimidazole (140 mg, 0.86 mmol) and hydroxylamine hydrochloride (66 mg, 0.95 mmol) in t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc(C(CC(=O)O)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc(C(CC(=O)NO)N2C(=O)c3cccc(N(C)C)c3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-548f145afca445af86d4f509ed53fa20 | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC>>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC | C(C1=CC=CC=C1)ONC(CC(N1C(C=2C(C1=O)=C(C(=CC2)C)C)=O)C2=CC(=C(C=C2)OC)OCC)=O.[H][H]>>C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C(=CC2)C)C)=O | c1ccc(C[O:12][NH:11][C:9]([CH2:8][CH:7]([c:6]2[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27][cH:26]2)[N:13]2[C:14](=[O:15])[c:16]3[cH:17][cH:18][c:19]([CH3:20])[c:21]([CH3:22])[c:23]3[C:24]2=[O:25])=[O:10])cc1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](... | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC | CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC | null | [OH-].[OH-].[Pd+2] | CO.C(C)(=O)OCC | Deprotection | OtherReaction | 94fa5e5ed4a5b32c4aba0dd3c8151bfdd08491d1bc6453e9fd01d7dc3e51cd0f | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[OH;D1;+0:5] | 84 | [{"value": 84.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C(=CC2)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.4, "product": "C(C)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C(=CC2)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3,4-dimethylphthalimido)propionamide was prepared by the procedure of Example 16 from N-benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(3,4-dimethylphthalimido)propanamide (0.63 g, 1.25 mmol), Pd(OH)2/C (100 mg) and hydrogen (50 psi) in ethyl acetate and methanol (30 mL each) to affo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | Other | [OH-].[OH-].[Pd+2].CO.C(C)(=O)OCC | null | null | CCOc1cc(C(CC(=O)NOCc2ccccc2)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC>[OH-].[OH-].[Pd+2].CO.C(C)(=O)OCC>CCOc1cc(C(CC(=O)NO)N2C(=O)c3ccc(C)c(C)c3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8a336c5b273491683dad13c5371321d | COc1ccc(C(CC(=O)O)N2C(=O)c3cccc(C)c3C2=O)cc1OC1CCCC1.NO>>COc1ccc(C(CC(=O)NO)N2C(=O)c3cccc(C)c3C2=O)cc1OC1CCCC1 | C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)O)N1C(C2=CC=CC(=C2C1=O)C)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)C)=O | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[cH:25]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([CH3:21])[c:22]2[C:23]1=[O:24])=[O:10].[NH2:11][OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]... | COc1ccc(C(CC(=O)O)N2C(=O)c3cccc(C)c3C2=O)cc1OC1CCCC1.NO | COc1ccc(C(CC(=O)NO)N2C(=O)c3cccc(C)c3C2=O)cc1OC1CCCC1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1cccc(OC2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 94.6 | [{"value": 94.6, "product": "C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.2, "product": "C1(CCCC1)OC=1C=C(C=CC1OC)C(CC(=O)NO)N1C(C=2C(C1=O)=C(C=CC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Cyclopentyloxy-4-methoxyphenyl)-N-hydroxy-3-(3-methylphthalimido)propionamide was prepared by the procedure of Example 1 from 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(4-methyl-1,3-dioxoisoindolin-2-yl)propanoic acid (5.44 g, 12.9 mmol), carbonyldiimidazole (2.19 g, 13.5 mmol) and hydroxylamine hydrochloride (1.16 g... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCCC1 | HO- | C1CCOC1 | null | null | COc1ccc(C(CC(=O)O)N2C(=O)c3cccc(C)c3C2=O)cc1OC1CCCC1.NO>C1CCOC1>COc1ccc(C(CC(=O)NO)N2C(=O)c3cccc(C)c3C2=O)cc1OC1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03b4970485ca4da893f13eec5a26de19 | COc1ccc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)cc1OC1CCCC1.NO>>COc1ccc(C(CC(=O)NO)N2C(=O)c3cccc(NC(C)=O)c3C2=O)cc1OC1CCCC1 | C(C)(=O)NC1=C2C(C(=O)N(C2=O)C(CC(=O)O)C2=CC(=C(C=C2)OC)OC2CCCC2)=CC=C1.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)(=O)NC1=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OC2CCCC2)=CC=C1 | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35]2)[cH:28]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][C:22]([CH3:23])=[O:24])[c:25]2[C:26]1=[O:27])=[O:10].[NH2:11][OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10]... | COc1ccc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)cc1OC1CCCC1.NO | COc1ccc(C(CC(=O)NO)N2C(=O)c3cccc(NC(C)=O)c3C2=O)cc1OC1CCCC1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1cccc(OC2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 70 | [{"value": 70.0, "product": "C(C)(=O)NC1=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OC2CCCC2)=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.3, "product": "C(C)(=O)NC1=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OC2CCCC2)=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(3-Acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)-N-hydroxypropionamide was prepared by the procedure of Example 1 from 3-(3-acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid (3.0 g, 6.5 mmol), carbonyldiimidazole (1.16 g, 7.12 mmol) and hydroxylamine hydrochloride (0.56 g, 8.07 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCCC1 | HO- | C1CCOC1 | null | null | COc1ccc(C(CC(=O)O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)cc1OC1CCCC1.NO>C1CCOC1>COc1ccc(C(CC(=O)NO)N2C(=O)c3cccc(NC(C)=O)c3C2=O)cc1OC1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5cfb528261ed466e95bdfc3e1d9282d0 | COc1ccc(C(CC(=O)O)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)cc1OC1CCCC1.NO>>COc1ccc(C(CC(=O)NO)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)cc1OC1CCCC1 | C(C)(=O)NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)O)C2=CC(=C(C=C2)OC)OC2CCCC2)=CC1.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)(=O)NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OC2CCCC2)=CC1 | O[C:9]([CH2:8][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35]2)[cH:28]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24][c:25]2[C:26]1=[O:27])=[O:10].[NH2:11][OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10]... | COc1ccc(C(CC(=O)O)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)cc1OC1CCCC1.NO | COc1ccc(C(CC(=O)NO)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)cc1OC1CCCC1 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1cccc(OC2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 60 | [{"value": 60.0, "product": "C(C)(=O)NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OC2CCCC2)=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.8, "product": "C(C)(=O)NC=1C=C2C(C(=O)N(C2=O)C(CC(=O)NO)C2=CC(=C(C=C2)OC)OC2CCCC2)=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-Acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)-N-hydroxypropionamide was prepared by the procedure of Example 1 from 3-(4-acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid (1.78 g, 3.82 mmol), carbonyldiimidazole (0.74 g, 4.6 mmol) and hydroxylamine hydrochloride (0.38 g, 5.3 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCCC1 | HO- | O1CCCC1 | null | null | COc1ccc(C(CC(=O)O)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)cc1OC1CCCC1.NO>O1CCCC1>COc1ccc(C(CC(=O)NO)N2C(=O)c3ccc(NC(C)=O)cc3C2=O)cc1OC1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a37c9d35a6747b4bbf078b66156fb78 | CCOc1cc([C@@H](CC(=O)O)N2C(=O)c3ccccc3C2=O)ccc1OC.NO>>CCOc1cc([C@@H](CC(=O)NO)N2C(=O)c3ccccc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)[C@@H](CC(=O)O)N1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)OC=1C=C(C=CC1OC)[C@@H](CC(=O)NO)N1C(C=2C(C1=O)=CC=CC2)=O | O[C:9]([CH2:8][C@H:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][cH:24]1)[N:13]1[C:14](=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22]1=[O:23])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[C:14](=[O:15])[c:16]3[cH:17]... | CCOc1cc([C@@H](CC(=O)O)N2C(=O)c3ccccc3C2=O)ccc1OC.NO | CCOc1cc([C@@H](CC(=O)NO)N2C(=O)c3ccccc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 91.5 | [{"value": 91.0, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CC(=O)NO)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CC(=O)NO)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (3R)-3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide was prepared by the procedure of Example 1 from (3R)-3-(3-ethoxy-4-methoxyphenyl)-3-phthalimidopropanoic acid (14.6 g, 39.5 mmol), carbonyldiimidazole (7.1 g, 43.5 mmol) and hydroxylamine hydrochloride (3.3 g, 47.4 mmol) in tetrahydrofuran (50 mL) to... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc([C@@H](CC(=O)O)N2C(=O)c3ccccc3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc([C@@H](CC(=O)NO)N2C(=O)c3ccccc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5a12aad29b04ed695d6ae3b837538c8 | CCOc1cc([C@@H](CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.NO>>CCOc1cc([C@@H](CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)[C@@H](CC(=O)O)N1C(C2=CC=CC=C2C1)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.Cl.NO>>C(C)OC=1C=C(C=CC1OC)[C@@H](CC(=O)NO)N1C(C2=CC=CC=C2C1)=O | O[C:9]([CH2:8][C@H:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24][cH:23]1)[N:13]1[CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[C:21]1=[O:22])=[O:10].[NH2:11][OH:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:13]2[CH2:14][c:15]3[cH:16][cH:17][cH:18]... | CCOc1cc([C@@H](CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.NO | CCOc1cc([C@@H](CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2CN1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[O;D1;H1:6] | 69 | [{"value": 69.0, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CC(=O)NO)N1C(C2=CC=CC=C2C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.2, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CC(=O)NO)N1C(C2=CC=CC=C2C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (3R)-3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(1-oxoisoindolinyl)propionamide was prepared by the procedure of Example 1 from (3R)-3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid (3.48 g, 9.79 mmol), carbonyldiimidazole (1.91 g, 11.8 mmol) and hydroxylamine hydrochloride (0.95 g, 13.7 mmol) in tetrahyd... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | null | CCOc1cc([C@@H](CC(=O)O)N2Cc3ccccc3C2=O)ccc1OC.NO>O1CCCC1>CCOc1cc([C@@H](CC(=O)NO)N2Cc3ccccc3C2=O)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f8734ebc655840278913d393144d8314 | Cc1nc2cc(Cl)ccc2o1.O=[N+]([O-])O>>Cc1nc2cc(Cl)c([N+](=O)[O-])cc2o1 | [N+](=O)(O)[O-].ClC=1C=CC2=C(N=C(O2)C)C1.O1C=NC2=C1C=CC=C2>>ClC=1C(=CC2=C(N=C(O2)C)C1)[N+](=O)[O-] | [CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][cH:12][c:13]2[o:14]1.O[N+:9](=[O:10])[O-:11]>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]2[o:14]1 | Cc1nc2cc(Cl)ccc2o1.O=[N+]([O-])O | Cc1nc2cc(Cl)c([N+](=O)[O-])cc2o1 | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 0b7074aee7f439fceb55025132a5024a62a7b00095294aea643bedf877202bce | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2ocnc2c1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[Cl;D1;H0:4]-[c:5]1:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:2:[c:12]:[cH;D2;+0:13]:1>>[Cl;D1;H0:4]-[c:5]1:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:2:[c:12]:[c;H0;D3;+0:13]:1-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | null | [] | 20 | CELSIUS | 1 | HOUR | Concentrated sulfuric acid (150 mL) was stirred mechanically and cooled in an ice/water bath. To this was gradually added 5-chloro-2-methylbenzoxazole (1), (75 g, 0.45 Moles), at such a rate that the temperature stayed at 30° C., over a 15–20 minute period. A solution of concentrated sulfuric acid (40 mL), and concentr... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HO- | S(O)(O)(=O)=O | 20 | 1 | Cc1nc2cc(Cl)ccc2o1.O=[N+]([O-])O>S(O)(O)(=O)=O>Cc1nc2cc(Cl)c([N+](=O)[O-])cc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dfe50d41f12942da8b2bfc15e4f89f80 | Cc1nc2cc(Cl)c([N+](=O)[O-])cc2o1>>Cc1nc2cc(Cl)c(N)cc2o1 | ClC=1C(=CC2=C(N=C(O2)C)C1)[N+](=O)[O-]>>NC1=CC2=C(N=C(O2)C)C=C1Cl | O=[N+:9]([O-])[c:8]1[c:6]([Cl:7])[cH:5][c:4]2[n:3][c:2]([CH3:1])[o:12][c:11]2[cH:10]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([NH2:9])[cH:10][c:11]2[o:12]1 | Cc1nc2cc(Cl)c([N+](=O)[O-])cc2o1 | Cc1nc2cc(Cl)c(N)cc2o1 | null | null | O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ocnc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#8;a:6]>>[#8;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 1.5 | HOUR | 5-Chloro-2-methyl-6-nitrobenzoxazole (30 g), was dissolved in tetrahydrofuran (150 mL), and Raney-Nickel which had been pre-washed with water (×3) and tetrahydrofuran (×3), was added. The mixture was then hydrogenated at room temperature and 50 psi of hydrogen. The reaction is complete in approximately 1.5 hours. After... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ocnc2c1 | Other | O1CCCC1 | null | 1.5 | Cc1nc2cc(Cl)c([N+](=O)[O-])cc2o1>O1CCCC1>Cc1nc2cc(Cl)c(N)cc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e1a8a1d4fea343c68da40b757c689dec | Cc1nc2cc(Cl)c(N)cc2o1.O=S(=O)(Cl)Cl>>Cc1nc2cc(Cl)c(N)c(Cl)c2o1 | NC1=CC2=C(N=C(O2)C)C=C1Cl.S(=O)(=O)(Cl)Cl>>NC1=C(C2=C(N=C(O2)C)C=C1Cl)Cl | [CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([NH2:9])[cH:10][c:12]2[o:13]1.O=S(=O)(Cl)[Cl:11]>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([NH2:9])[c:10]([Cl:11])[c:12]2[o:13]1 | Cc1nc2cc(Cl)c(N)cc2o1.O=S(=O)(Cl)Cl | Cc1nc2cc(Cl)c(N)c(Cl)c2o1 | null | null | C(C)(=O)OCC | Functional Group Interconversion | Chlorination | c470576ff2f7b86aa529d1df087ace0fa7d38fd391894f28a43e2561d9d37acb | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ocnc2c1 | Cl-S(=O)(=O)-[Cl;H0;D1;+0:1].[N;D1;H2:2]-[c:3]1:[c:4]:[c:5]:[c:6]2:[#7;a:7]:[c:8]:[#8;a:9]:[c:10]:2:[cH;D2;+0:11]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:11]1:[c:10]2:[#8;a:9]:[c:8]:[#7;a:7]:[c:6]:2:[c:5]:[c:4]:[c:3]:1-[N;D1;H2:2] | null | [] | null | null | null | null | 6-Amino-5-chloro-2-methylbenzoxazole (10 g, 54.76 mMole) was dissolved in ethyl acetate (150 mL). At room temperature and with good stirring, sulfuryl chloride (8.8 mL, 109.52 mMole) was added drop by drop over a 20-minute period. As the addition proceeds, additional ethyl acetate (350 mL) was added to keep the mixture... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HCl | C(C)(=O)OCC | null | null | Cc1nc2cc(Cl)c(N)cc2o1.O=S(=O)(Cl)Cl>C(C)(=O)OCC>Cc1nc2cc(Cl)c(N)c(Cl)c2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd37e20faae04c81914e2285bd65c7dd | CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)O)cc1.O=S(Cl)Cl>>CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)Cl)cc1 | S(=O)(Cl)Cl.C(CCCCCCCCCCC)OC1=CC=C(C=C1)S(=O)(=O)C(C(=O)O)CC>>C(CCCCCCCCCCC)OC1=CC=C(C=C1)S(=O)(=O)C(C(=O)Cl)CC | O[C:24]([CH:21]([S:18]([c:17]1[cH:16][cH:15][c:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:28][cH:27]1)(=[O:19])=[O:20])[CH2:22][CH3:23])=[O:25].O=S(Cl)[Cl:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[... | CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)O)cc1.O=S(Cl)Cl | CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)Cl)cc1 | null | CN(C=O)C | C(C)(=O)OCC | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[#16:5])-[C:6]>>[#16:5]-[C:4](-[C:6])-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 70 | CELSIUS | null | null | 2-[(4-Dodecyloxyphenyl)sulfonyl]butanoic acid (19.5 g, 47.33 mMole) was suspended in ethyl acetate (150 mL) to which was added several drops of dimethylformamide and thionyl chloride (14.4 mL, 119 mMole). The mixture was heated at 70° C. for 1.5 hours, cooled, concentrated under reduced pressure, co-evaporated with eth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | CN(C=O)C.C(C)(=O)OCC | 70 | null | CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)O)cc1.O=S(Cl)Cl>CN(C=O)C.C(C)(=O)OCC>CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-883bf0378f38498bbd32d6b2b6251006 | Cc1nc2cc(F)ccc2o1.O=[N+]([O-])O>>Cc1nc2cc(F)c([N+](=O)[O-])cc2o1 | O1C=NC2=C1C=CC=C2.S(O)(O)(=O)=O.[N+](=O)(O)[O-].S(O)(O)(=O)=O.FC=1C=CC2=C(N=C(O2)C)C1>>FC=1C(=CC2=C(N=C(O2)C)C1)[N+](=O)[O-] | [CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([F:7])[cH:8][cH:12][c:13]2[o:14]1.O[N+:9](=[O:10])[O-:11]>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([F:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]2[o:14]1 | Cc1nc2cc(F)ccc2o1.O=[N+]([O-])O | Cc1nc2cc(F)c([N+](=O)[O-])cc2o1 | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 0b7074aee7f439fceb55025132a5024a62a7b00095294aea643bedf877202bce | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2ocnc2c1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[F;D1;H0:4]-[c:5]1:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:2:[c:12]:[cH;D2;+0:13]:1>>[F;D1;H0:4]-[c:5]1:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:2:[c:12]:[c;H0;D3;+0:13]:1-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | null | [] | 10 | CELSIUS | 1 | HOUR | Concentrated sulfuric acid (60 mL) was stirred mechanically and cooled in an ice/water bath. To this was gradually added 5-fluoro-2-methylbenzoxazole (9), (20 g, 0.132 Moles), at such a rate that the temperature stayed at 15–20° C., over a 15–20 minute period. A solution of concentrated sulfuric acid (11 mL), and conce... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HO- | null | 10 | 1 | Cc1nc2cc(F)ccc2o1.O=[N+]([O-])O>>Cc1nc2cc(F)c([N+](=O)[O-])cc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a44cb302d4a4d1a9a9ef3a7c37ee2cb | Cc1nc2cc(F)c([N+](=O)[O-])cc2o1>>Cc1nc2cc(F)c(N)cc2o1 | FC=1C(=CC2=C(N=C(O2)C)C1)[N+](=O)[O-].CO>>NC1=CC2=C(N=C(O2)C)C=C1F | O=[N+:9]([O-])[c:8]1[c:6]([F:7])[cH:5][c:4]2[n:3][c:2]([CH3:1])[o:12][c:11]2[cH:10]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([F:7])[c:8]([NH2:9])[cH:10][c:11]2[o:12]1 | Cc1nc2cc(F)c([N+](=O)[O-])cc2o1 | Cc1nc2cc(F)c(N)cc2o1 | null | null | O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ocnc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#8;a:6]>>[#8;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 1.5 | HOUR | 5-Fluoro-2-methyl-6-nitrobenzoxazole (16 g, 81.57 mMole), was dissolved in tetrahydrofuran (150 mL), and methanol (50 mL). Raney-Nickel which had been pre-washed with water (×3) and tetrahydrofuran (×3), was added and the mixture was then hydrogenated at room temperature and 50 psi of hydrogen. The reaction is complete... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ocnc2c1 | Other | O1CCCC1 | null | 1.5 | Cc1nc2cc(F)c([N+](=O)[O-])cc2o1>O1CCCC1>Cc1nc2cc(F)c(N)cc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a08b0ceaa33a43d2bb9dfbb41ffd28e1 | Cc1nc2cc(F)c(N)cc2o1.O=S(=O)(Cl)Cl>>Cc1nc2cc(F)c(N)c(Cl)c2o1 | NC1=CC2=C(N=C(O2)C)C=C1F.S(=O)(=O)(Cl)Cl>>NC1=C(C2=C(N=C(O2)C)C=C1F)Cl | [CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([F:7])[c:8]([NH2:9])[cH:10][c:12]2[o:13]1.O=S(=O)(Cl)[Cl:11]>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([F:7])[c:8]([NH2:9])[c:10]([Cl:11])[c:12]2[o:13]1 | Cc1nc2cc(F)c(N)cc2o1.O=S(=O)(Cl)Cl | Cc1nc2cc(F)c(N)c(Cl)c2o1 | null | null | C(C)(=O)OCC.C(Cl)Cl | Functional Group Interconversion | Chlorination | c470576ff2f7b86aa529d1df087ace0fa7d38fd391894f28a43e2561d9d37acb | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ocnc2c1 | Cl-S(=O)(=O)-[Cl;H0;D1;+0:1].[N;D1;H2:2]-[c:3]1:[c:4]:[c:5]:[c:6]2:[#7;a:7]:[c:8]:[#8;a:9]:[c:10]:2:[cH;D2;+0:11]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:11]1:[c:10]2:[#8;a:9]:[c:8]:[#7;a:7]:[c:6]:2:[c:5]:[c:4]:[c:3]:1-[N;D1;H2:2] | null | [] | null | null | 30 | MINUTE | 6-Amino-5-fluoro-2-methylbenzoxazole (12 g, 72.22 mMole) was dissolved in ethyl acetate (100 mL) containing dry pryidine (5.8 mL, 72.22 mMole). At room temperature and with good stirring, sulfuryl chloride (7.0 mL, 86.66 mMole) was added drop by drop over a 20-minute period. After stirring at room temperature for about... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HCl | C(C)(=O)OCC.C(Cl)Cl | null | 0.5 | Cc1nc2cc(F)c(N)cc2o1.O=S(=O)(Cl)Cl>C(C)(=O)OCC.C(Cl)Cl>Cc1nc2cc(F)c(N)c(Cl)c2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a5d47f9ffdd4f8e93a6b58ac33ac070 | CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)O)cc1.O=S(Cl)Cl>>CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)Cl)cc1 | S(=O)(Cl)Cl.C(CCCCCCCCCCC)OC1=CC=C(C=C1)S(=O)(=O)C(C(=O)O)CC>>C(CCCCCCCCCCC)OC1=CC=C(C=C1)S(=O)(=O)C(C(=O)Cl)CC | O[C:24]([CH:21]([S:18]([c:17]1[cH:16][cH:15][c:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:28][cH:27]1)(=[O:19])=[O:20])[CH2:22][CH3:23])=[O:25].O=S(Cl)[Cl:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][c:14]1[... | CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)O)cc1.O=S(Cl)Cl | CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)Cl)cc1 | null | CN(C=O)C | C(C)(=O)OCC | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[#16:5])-[C:6]>>[#16:5]-[C:4](-[C:6])-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 70 | CELSIUS | null | null | 2-[(4-Dodecyloxyphenyl)sulfonyl]butanoic acid (1.1 g, 26.92 mMole) was suspended in ethyl acetate (100 mL) to which was added several drops of dimethylformamide and thionyl chloride (10.0 mL, 134.6 mMole). The mixture was heated at 70° C. for 1.5 hours, cooled, concentrated under reduced pressure, co-evaporated with et... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | CN(C=O)C.C(C)(=O)OCC | 70 | null | CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)O)cc1.O=S(Cl)Cl>CN(C=O)C.C(C)(=O)OCC>CCCCCCCCCCCCOc1ccc(S(=O)(=O)C(CC)C(=O)Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4445a4fa7c3408b8f17654f35a6a381 | N.O=C1CCN2CCCC2C1>>NC1CCN2CCCC2C1 | C1CCN2CCC(CC12)=O.N.C(C)O.[H][H]>>NC1CCN2CCCC2C1 | [NH3:1].O=[C:2]1[CH2:3][CH2:4][N:5]2[CH2:6][CH2:7][CH2:8][CH:9]2[CH2:10]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]2[CH2:6][CH2:7][CH2:8][CH:9]2[CH2:10]1 | N.O=C1CCN2CCCC2C1 | NC1CCN2CCCC2C1 | null | [Pd] | null | Heteroatom Alkylation and Arylation | OtherReaction | f82040c6bc6f43a5cf2e1b65c4652300475b664edfaab30229e72dcf0fbc4065 | 57403092f2152b38361ff8e391b9a821f5623bf2a2bbf7514162beafc6524986 | C1CCN2CCCC2C1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | 98 | [{"value": 98.0, "product": "NC1CCN2CCCC2C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.5, "product": "NC1CCN2CCCC2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (±)-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one (5.0 g, 35.9 mmol) was dissolved in a solution of 2M ammonia/ethanol (54 ml, 108 mmol calculated in terms of ammonia). The resulting solution was stirred at room temperature in an atmosphere of hydrogen in the presence of 10% palladium on charcoal (500 mg) for 4 hours. At t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | C1CCN2CCCC2C1 | C1CCN2CCCC2C1 | C1CCN2CCCC2C1 | Other | [Pd] | null | null | N.O=C1CCN2CCCC2C1>[Pd]>NC1CCN2CCCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-48980c3bc29d442994e424cd77e71dc8 | NC1CCN2CCCC2C1.O=Cc1ccncc1>>C(=NC1CCN2CCCC2C1)c1ccncc1 | NC1CCN2CCCC2C1.C(=O)C1=CC=NC=C1.S(=O)(=O)([O-])[O-].[Mg+2]>>N1=CC=C(C=C1)C=NC1CCN2CCCC2C1 | [NH2:2][CH:3]1[CH2:4][CH2:5][N:6]2[CH2:7][CH2:8][CH2:9][CH:10]2[CH2:11]1.O=[CH:1][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1>>[CH:1](=[N:2][CH:3]1[CH2:4][CH2:5][N:6]2[CH2:7][CH2:8][CH2:9][CH:10]2[CH2:11]1)[c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1 | NC1CCN2CCCC2C1.O=Cc1ccncc1 | C(=NC1CCN2CCCC2C1)c1ccncc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | C(=NC1CCN2CCCC2C1)c1ccncc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]>>[C:8]-[C:9](-[N;H0;D2;+0:10]=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1)-[C:11] | 100.7 | [{"value": 100.7, "product": "N1=CC=C(C=C1)C=NC1CCN2CCCC2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 3 | HOUR | (±)-7-Amino-1,2,3,5,6,7,8,8a-octahydroindolizine (4.91 g (35.0 mmol), prepared as described in 1)) was dissolved in toluene (95 ml). To the solution were added 4-formylpyridine (3.34 ml, 35.0 mmol) and anhydrous magnesium sulfate (3.75 g, 31.2 mmol), and the resulting mixture was stirred at 70° C. for 3 hours. At the e... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | C1CCN2CCCC2C1.c1ccncc1 | HO- | C1(=CC=CC=C1)C | 70 | 3 | NC1CCN2CCCC2C1.O=Cc1ccncc1>C1(=CC=CC=C1)C>C(=NC1CCN2CCCC2C1)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8666654f56c240ce8062fe43832322e8 | C(=NC1CCN2CCCC2C1)c1ccncc1.[C-]#[N+]C(c1ccc(F)cc1)S(=O)(=O)c1ccc(C)cc1>>Fc1ccc(-c2ncn(C3CCN4CCCC4C3)c2-c2ccncc2)cc1 | C1(=CC=C(C=C1)S(=O)(=O)C(C1=CC=C(C=C1)F)[N+]#[C-])C.N1=CC=C(C=C1)C=NC1CCN2CCCC2C1.C1CCC2=NCCCN2CC1>>FC1=CC=C(C=C1)C=1N=CN(C1C1=CC=NC=C1)C1CCN2CCCC2C1 | [N:9]([CH:10]1[CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][CH:17]2[CH2:18]1)=[CH:19][c:20]1[cH:21][cH:22][n:23][cH:24][cH:25]1.Cc1ccc(S(=O)(=O)[CH:6]([c:5]2[cH:4][cH:3][c:2]([F:1])[cH:27][cH:26]2)[N+:7]#[C-:8])cc1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][cH:8][n:9]([CH:10]3[CH2:11][CH2:12][N:13]4[CH2:14][CH2:15][C... | C(=NC1CCN2CCCC2C1)c1ccncc1.[C-]#[N+]C(c1ccc(F)cc1)S(=O)(=O)c1ccc(C)cc1 | Fc1ccc(-c2ncn(C3CCN4CCCC4C3)c2-c2ccncc2)cc1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 785150d4047de8c81b3c4f522b9737b7ba9fd89990e4fa4dc7af651796978787 | 1662c8f3a063071c9e6188e3ec8abc9db4bb1d41627df7ac17392666c031f54d | c1ccc(-c2ncn(C3CCN4CCCC4C3)c2-c2ccncc2)cc1 | C-c1:c:c:c(-S(=O)(=O)-[CH;D3;+0:1](-[N+;H0;D2:2]#[C-;H0;D1:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):c:c:1.[C:9]-[C:10](-[N;H0;D2;+0:11]=[CH;D2;+0:12]-[c;H0;D3;+0:13]1:[c:14]:[c:15]:[#7;a:16]:[c:17]:[c:18]:1)-[C:19]>>[C:9]-[C:10](-[n;H0;D3;+0:11]1:[cH;D2;+0:3]:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:4](:[c:5]:[c... | 14.8 | [{"value": 14.0, "product": "FC1=CC=C(C=C1)C=1N=CN(C1C1=CC=NC=C1)C1CCN2CCCC2C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.8, "product": "FC1=CC=C(C=C1)C=1N=CN(C1C1=CC=NC=C1)C1CCN2CCCC2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | α-(p-Toluenesulfonyl)-4-fluorobenzylisocyanide (10.1 g, 34.9 mmol) and (±)-7-(4-pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizine (8.0 g (34.9 mmol), prepared as described in 2)) were dissolved in dichloromethane (150 ml). To the solution was added 1,8-diazabicyclo[5.4.0]-7-undecene (5.22 ml, 34.9 mmol), and ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Substituted imine.Isocyanide | null | c1ccccc1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.C1CCN2CCCC2C1.c1ccncc1 | TsOH.HO- | ClCCl | null | 2 | C(=NC1CCN2CCCC2C1)c1ccncc1.[C-]#[N+]C(c1ccc(F)cc1)S(=O)(=O)c1ccc(C)cc1>ClCCl>Fc1ccc(-c2ncn(C3CCN4CCCC4C3)c2-c2ccncc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-111964c177044a658f9701d6362bd642 | Fc1ccc(-c2[nH]ncc2-c2ccncc2)cc1.O=C1CCC(=O)N1Br>>Fc1ccc(-c2[nH]nc(Br)c2-c2ccncc2)cc1 | FC1=CC=C(C=C1)C1=C(C=NN1)C1=CC=NC=C1.BrN1C(CCC1=O)=O.O>>BrC1=NNC(=C1C1=CC=NC=C1)C1=CC=C(C=C1)F | [F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[nH:7][n:8][cH:9][c:11]2-[c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[cH:18][cH:19]1.O=C1CCC(=O)N1[Br:10]>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[nH:7][n:8][c:9]([Br:10])[c:11]2-[c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[cH:18][cH:19]1 | Fc1ccc(-c2[nH]ncc2-c2ccncc2)cc1.O=C1CCC(=O)N1Br | Fc1ccc(-c2[nH]nc(Br)c2-c2ccncc2)cc1 | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 2a2274254095ef22e1c9716ecd850d4c9963503313342c15a42bc51cf2e867f9 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(-c2[nH]ncc2-c2ccncc2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]-[c:3]1:[cH;D2;+0:4]:[#7;a:5]:[#7;a:6]:[c:7]:1-[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4]1:[#7;a:5]:[#7;a:6]:[c:7](-[c:8]):[c:3]:1-[c:2] | 72 | [{"value": 72.0, "product": "BrC1=NNC(=C1C1=CC=NC=C1)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.0, "product": "BrC1=NNC(=C1C1=CC=NC=C1)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 5-(4-Fluorophenyl)-4-(pyridin-4-yl)pyrazole (6.0 g (25 mmol), prepared as described in WO 00/31063) was dissolved in dimethylformamide (60 ml). To the solution was added N-bromosuccinimide (8.93 g, 50 mmol), and the resulting mixture was stirred at room temperature for 3 days. At the end of this time, water was added t... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cn[nH]c1.C1CCNC1 | c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1.c1ccncc1 | HO- | CN(C=O)C | null | 72 | Fc1ccc(-c2[nH]ncc2-c2ccncc2)cc1.O=C1CCC(=O)N1Br>CN(C=O)C>Fc1ccc(-c2[nH]nc(Br)c2-c2ccncc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f727051775ed4d1eac90c44fb5a04956 | Fc1ccc(-c2[nH]nc(Br)c2-c2ccncc2)cc1.O=C1CCN2CCCC2C1>>OC1(c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CCN2CCCC2C1 | C(O)([O-])=O.[Na+].C(CCC)[Li].CCCCCC.BrC1=NNC(=C1C1=CC=NC=C1)C1=CC=C(C=C1)F.C1CCN2CCC(CC12)=O>>FC1=CC=C(C=C1)C1=C(C(=NN1)C1(CCN2CCCC2C1)O)C1=CC=NC=C1 | Br[c:3]1[n:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[c:14]1-[c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1.[O:1]=[C:2]1[CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH:27]2[CH2:28]1>>[OH:1][C:2]1([c:3]2[n:4][nH:5][c:6](-[c:7]3[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]3)[c:14]2-[c:15]2[cH:16][cH:17][n:... | Fc1ccc(-c2[nH]nc(Br)c2-c2ccncc2)cc1.O=C1CCN2CCCC2C1 | OC1(c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CCN2CCCC2C1 | null | null | O1CCCC1 | C-C Coupling | Grignard_alcohol | 5d026ed7440eab4dd109a020579af686d44068d81a2535371b4438f680cabfab | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(-c2[nH]nc(C3CCN4CCCC4C3)c2-c2ccncc2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4](-[c:5]):[c:6]:1-[c:7].[O;H0;D1;+0:8]=[C;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:12]-[C:13]-[C:14]-1>>[OH;D1;+0:8]-[C;H0;D4;+0:9]1(-[c;H0;D3;+0:1]2:[#7;a:2]:[#7;a:3]:[c:4](-[c:5]):[c:6]:2-[c:7])-[C:10]-[C:11]-[#7:12]-[C:13]-[C:14]-1 | 22 | [{"value": 22.0, "product": "FC1=CC=C(C=C1)C1=C(C(=NN1)C1(CCN2CCCC2C1)O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.9, "product": "FC1=CC=C(C=C1)C1=C(C(=NN1)C1(CCN2CCCC2C1)O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 3-Bromo-5-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole (3.18 g (10 mmol), prepared as described in 1)) was dissolved in tetrahydrofuran (32 ml). To the solution was added a solution of 1.6 M butyl lithium/hexane (13.75 ml, 13.75 mmol) at −78° C., and the resulting mixture was stirred for 10 minutes. To the mixture was add... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1cn[nH]c1.C1CCN2CCCC2C1 | c1cn[nH]c1.C1CCN2CCCC2C1 | c1cn[nH]c1.c1ccccc1.c1ccncc1.C1CCN2CCCC2C1 | Br- | O1CCCC1 | null | 0.166667 | Fc1ccc(-c2[nH]nc(Br)c2-c2ccncc2)cc1.O=C1CCN2CCCC2C1>O1CCCC1>OC1(c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CCN2CCCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f2d7cc9ea376403b8f04a982db70e925 | OC1(c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CCN2CCCC2C1>>Fc1ccc(-c2[nH]nc(C3=CCN4CCCC4C3)c2-c2ccncc2)cc1 | FC1=CC=C(C=C1)C1=C(C(=NN1)C1(CCN2CCCC2C1)O)C1=CC=NC=C1.[OH-].[Na+]>>FC1=CC=C(C=C1)C1=C(C(=NN1)C1=CCN2CCCC2C1)C1=CC=NC=C1 | O[C:10]1([c:9]2[n:8][nH:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:27][cH:26]3)[c:19]2-[c:20]2[cH:21][cH:22][n:23][cH:24][cH:25]2)[CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][CH:17]2[CH2:18]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[nH:7][n:8][c:9]([C:10]3=[CH:11][CH2:12][N:13]4[CH2:14][CH2:15][CH2:16][CH:17]4[CH2:18]3... | OC1(c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CCN2CCCC2C1 | Fc1ccc(-c2[nH]nc(C3=CCN4CCCC4C3)c2-c2ccncc2)cc1 | null | null | Cl | Functional Group Interconversion | OtherReaction | 3e81cf4d1e7530ee5e63bf160da3b2040e2fa2906659636c4bcbacaa4a2c22b0 | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | C1=C(c2n[nH]c(-c3ccccc3)c2-c2ccncc2)CC2CCCN2C1 | O-[C;H0;D4;+0:1]1(-[c:2]2:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:2)-[C:7]-[C:8]-[#7:9](-[C:10])-[C:11]-[CH2;D2;+0:12]-1>>[C:10]-[#7:9]1-[C:11]-[CH;D2;+0:12]=[C;H0;D3;+0:1](-[c:2]2:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:2)-[C:7]-[C:8]-1 | 37.2 | [{"value": 37.0, "product": "FC1=CC=C(C=C1)C1=C(C(=NN1)C1=CCN2CCCC2C1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.2, "product": "FC1=CC=C(C=C1)C1=C(C(=NN1)C1=CCN2CCCC2C1)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound prepared as described in Example 2 (720 mg, 1.90 mmol) was dissolved in concentrated hydrochloric acid (14 ml). The resulting solution was heated under reflux for 8 hours. At the end of this time, the reaction mixture was neutralized with an aqueous solution of 1 N sodium hydroxide, and extracted with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | C1CCN2CCCC2C1 | C1=CCN2CCCC2C1 | c1ccccc1.c1cn[nH]c1.C1=CCN2CCCC2C1.c1ccncc1 | HO- | Cl | null | null | OC1(c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CCN2CCCC2C1>Cl>Fc1ccc(-c2[nH]nc(C3=CCN4CCCC4C3)c2-c2ccncc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23a18566ce224943aeb1c23107d57dc5 | CCOC(C)=S.O=C(Cc1ccncc1)c1ccc(F)cc1>>CCOC(=O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1 | CN(C=O)C.C(C)N(CC)CC.[OH-].[Na+].C(C)(=S)OCC.FC1=CC=C(C=C1)C(CC1=CC=NC=C1)=O.P(=O)(Cl)(Cl)Cl.CN(C=O)C>>C(C)OC(=O)C1=CC(=C(S1)C1=CC=C(C=C1)F)C1=CC=NC=C1 | [CH3:1][CH2:2][O:3][C:4]([CH3:6])=[S:23].[O:5]=[C:15]([CH2:8][c:9]1[cH:10][cH:11][n:12][cH:13][cH:14]1)[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]2)[s:23]1 | CCOC(C)=S.O=C(Cc1ccncc1)c1ccc(F)cc1 | CCOC(=O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1 | null | null | ClCCl.O | Aromatic Heterocycle Formation | OtherReaction | 96be3c6091e16cd775e6376ea24fc2b3e638f4f10cf1fecb48ea88c13fcbd965 | e0913a19ebac40ada1386bcf3e29aa5ddbe5b3c035b28c93234a66f291003ac6 | c1ccc(-c2sccc2-c2ccncc2)cc1 | [C:1]-[#8:2]-[C;H0;D3;+0:3](-[CH3;D1;+0:4])=[S;H0;D1;+0:5].[O;H0;D1;+0:6]=[C;H0;D3;+0:7](-[CH2;D2;+0:8]-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1)-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]>>[C:1]-[#8:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:6])-[c;H0;D3;+0:4]1:[c:20]:[c;H0;D3;+0:8](-[c;H0;D3;+0:9]2:[c:10]:[c:11... | 55 | [{"value": 55.0, "product": "C(C)OC(=O)C1=CC(=C(S1)C1=CC=C(C=C1)F)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Phosphorus oxychloride (7.9 ml, 85 mmol) was added to dimethylformamide (17.04 ml, 220 mmol) dropwise under ice cooling. The resulting mixture was stirred at room temperature for 1 hour. The mixture was then added dropwise under ice cooling to a solution of 1-(4-fluorophenyl)-2-(pyridin-4-yl)ethanone (21.5 g (100 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Thiocarbonyl | Ester | null | c1ccsc1 | c1ccsc1.c1ccncc1.c1ccccc1 | Other | ClCCl.O | null | 1 | CCOC(C)=S.O=C(Cc1ccncc1)c1ccc(F)cc1>ClCCl.O>CCOC(=O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d7ef2be036f64ada85c82b1e0ea6db93 | CCOC(=O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1>>O=C(O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1 | C(C)OC(=O)C1=CC(=C(S1)C1=CC=C(C=C1)F)C1=CC=NC=C1.[OH-].[Na+]>>C(=O)(O)C1=CC(=C(S1)C1=CC=C(C=C1)F)C1=CC=NC=C1 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[c:13](-[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[s:21]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[c:13](-[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[s:21]1 | CCOC(=O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1 | O=C(O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2sccc2-c2ccncc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#16;a:5]>>[#16;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 91.2 | [{"value": 91.0, "product": "C(=O)(O)C1=CC(=C(S1)C1=CC=C(C=C1)F)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "C(=O)(O)C1=CC(=C(S1)C1=CC=C(C=C1)F)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 30 | MINUTE | 5-Ethoxycarbonyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene (15.17 g (46.3 mmol), prepared as described in 1)) was dissolved in ethanol (150 ml). To the solution was added an aqueous solution of 1 N sodium hydroxide (93 ml, 93 mmol), and the resulting mixture was stirred at 100° C. for 30 minutes. At the end of this ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccsc1.c1ccncc1.c1ccccc1 | Other | C(C)O | 100 | 0.5 | CCOC(=O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1>C(C)O>O=C(O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6d16c84992d44c5ba2388e74f39994d | O=C(O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1>>Fc1ccc(-c2sccc2-c2ccncc2)cc1 | N1=CC=CC2=CC=CC=C12.C(=O)(O)C1=CC(=C(S1)C1=CC=C(C=C1)F)C1=CC=NC=C1>>FC1=CC=C(C=C1)C=1SC=CC1C1=CC=NC=C1 | O=C(O)[c:8]1[s:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([F:1])[cH:18][cH:17]2)[c:10](-[c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[cH:9]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[s:7][cH:8][cH:9][c:10]2-[c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[cH:17][cH:18]1 | O=C(O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1 | Fc1ccc(-c2sccc2-c2ccncc2)cc1 | null | [Cu] | null | Reduction | Decarboxylation | cd9bc0eb355fb706669604d9cf11a15fb575ac2d73c172624b43cd556e1867b3 | 292164ffdf89eeb341ee9424f24084b252a703a26bb77721b558b0f8a8528c45 | c1ccc(-c2sccc2-c2ccncc2)cc1 | O-C(=O)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1>>[#16;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:1]:1 | 109.6 | [{"value": 109.6, "product": "FC1=CC=C(C=C1)C=1SC=CC1C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 240 | CELSIUS | 2.5 | HOUR | Quinoline (42 ml) and copper powder (2.95 g, 46.4 mmol) were added to 5-carboxy-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene (12.64 g (42.2 mmol), prepared as described in 2))), and the resulting mixture was stirred at 240° C. for 2.5 hours. At the end of this time, the reaction mixture was cooled to room temperature a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1ccsc1 | c1ccsc1 | c1ccccc1.c1ccsc1.c1ccncc1 | Other | [Cu] | 240 | 2.5 | O=C(O)c1cc(-c2ccncc2)c(-c2ccc(F)cc2)s1>[Cu]>Fc1ccc(-c2sccc2-c2ccncc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b04067277869419fae990d7fe5bba5e8 | Fc1ccc(-c2sc(Br)c(Br)c2-c2ccncc2)cc1>>Fc1ccc(-c2scc(Br)c2-c2ccncc2)cc1 | BrC=1C(=C(SC1Br)C1=CC=C(C=C1)F)C1=CC=NC=C1.C(CCC)[Li].CCCCCC.O>>BrC=1C(=C(SC1)C1=CC=C(C=C1)F)C1=CC=NC=C1 | Br[c:8]1[s:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([F:1])[cH:19][cH:18]2)[c:11](-[c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[c:9]1[Br:10]>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[s:7][cH:8][c:9]([Br:10])[c:11]2-[c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[cH:18][cH:19]1 | Fc1ccc(-c2sc(Br)c(Br)c2-c2ccncc2)cc1 | Fc1ccc(-c2scc(Br)c2-c2ccncc2)cc1 | null | null | O1CCCC1 | Functional Group Interconversion | Aromatic dehalogenation | 305afd15d586f55c801d6d4acac09c00bdce7795c11721d329be09a54571e3e8 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2sccc2-c2ccncc2)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[Br;D1;H0:6]>>[Br;D1;H0:6]-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[cH;D2;+0:1]:1 | 99.7 | [{"value": 99.7, "product": "BrC=1C(=C(SC1)C1=CC=C(C=C1)F)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 15 | MINUTE | 4,5-Dibromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene (13.88 g (33.6 mmol), prepared as described in 4)) was dissolved in tetrahydrofuran (140 ml). To the solution was added dropwise at −78° C. a solution of 1.59 M butyl lithium/hexane (23.3 ml, 37 mmol). The resulting mixture was stirred at −78° C. for 15 minutes. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccsc1 | c1ccsc1 | c1ccccc1.c1ccsc1.c1ccncc1 | Br- | O1CCCC1 | -78 | 0.25 | Fc1ccc(-c2sc(Br)c(Br)c2-c2ccncc2)cc1>O1CCCC1>Fc1ccc(-c2scc(Br)c2-c2ccncc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b728612b8f384ff9a46a02296031b4b0 | Fc1ccc(-c2scc(Br)c2-c2ccncc2)cc1.O=C1CCN2CCC[C@H]2C1>>Fc1ccc(-c2scc(C3=CCN4CCC[C@H]4C3)c2-c2ccncc2)cc1 | BrC=1C(=C(SC1)C1=CC=C(C=C1)F)C1=CC=NC=C1.BrC1=NNC(=C1C1=CC=NC=C1)C1=CC=C(C=C1)F.C1CCN2CCC(C[C@H]12)=O>>FC1=CC=C(C=C1)C=1SC=C(C1C1=CC=NC=C1)C1=CCN2CCC[C@H]2C1 | Br[c:9]1[cH:8][s:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([F:1])[cH:27][cH:26]2)[c:19]1-[c:20]1[cH:21][cH:22][n:23][cH:24][cH:25]1.O=[C:10]1[CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][C@H:17]2[CH2:18]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[s:7][cH:8][c:9]([C:10]3=[CH:11][CH2:12][N:13]4[CH2:14][CH2:15][CH2:16][C@H:17]4[CH2:... | Fc1ccc(-c2scc(Br)c2-c2ccncc2)cc1.O=C1CCN2CCC[C@H]2C1 | Fc1ccc(-c2scc(C3=CCN4CCC[C@H]4C3)c2-c2ccncc2)cc1 | null | null | null | C-C Coupling | OtherReaction | 8cf6210c71de15f307bed050c46dd011446cc2faa42fa7c5edce250b051e5e8f | 554b1bee1ccf92984990164979ec7aaf354dc2a70796dc88c3036796633e99e1 | C1=C(c2csc(-c3ccccc3)c2-c2ccncc2)C[C@@H]2CCCN2C1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4](-[c:5]):[c:6]:1-[c:7].O=[C;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:11](-[C:12])-[C:13]-[CH2;D2;+0:14]-1>>[C:12]-[#7:11]1-[C:13]-[CH;D2;+0:14]=[C;H0;D3;+0:8](-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4](-[c:5]):[c:6]:2-[c:7])-[C:9]-[C:10]-1 | 23 | [{"value": 23.0, "product": "FC1=CC=C(C=C1)C=1SC=C(C1C1=CC=NC=C1)C1=CCN2CCC[C@H]2C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that described in Example 2-2), but using 4-bromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene prepared as described in 5) instead of 3-bromo-5-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole, and using (S)-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one instead of (±)-1,2,3,5,6,7,8,8a-octahydroind... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | null | c1ccsc1.C1CCN2CCC[C@H]2C1 | c1ccsc1.C1=CCN2CCC[C@H]2C1 | c1ccccc1.c1ccsc1.C1=CCN2CCC[C@H]2C1.c1ccncc1 | HBr | null | null | null | Fc1ccc(-c2scc(Br)c2-c2ccncc2)cc1.O=C1CCN2CCC[C@H]2C1>>Fc1ccc(-c2scc(C3=CCN4CCC[C@H]4C3)c2-c2ccncc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03390b047e824451a249e4a8748421c9 | C[Si](C)(C)CCOCCl.Clc1ccc(-c2[nH]ncc2-c2ccncc2)cc1>>C[Si](C)(C)CCOCn1ncc(-c2ccncc2)c1-c1ccc(Cl)cc1 | O.[H-].[Na+].ClC1=CC=C(C=C1)C1=C(C=NN1)C1=CC=NC=C1.C[Si](CCOCCl)(C)C>>ClC1=CC=C(C=C1)C1=C(C=NN1COCC[Si](C)(C)C)C1=CC=NC=C1 | Cl[CH2:8][O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[nH:9]1[n:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[c:19]1-[c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[n:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[... | C[Si](C)(C)CCOCCl.Clc1ccc(-c2[nH]ncc2-c2ccncc2)cc1 | C[Si](C)(C)CCOCn1ncc(-c2ccncc2)c1-c1ccc(Cl)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | dc4d908c674afe73241097d2ca3b36f91af0d5cbd08848ec67813e24a787e40f | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc(-c2[nH]ncc2-c2ccncc2)cc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[c:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1-[c:4] | 90 | [{"value": 90.0, "product": "ClC1=CC=C(C=C1)C1=C(C=NN1COCC[Si](C)(C)C)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "ClC1=CC=C(C=C1)C1=C(C=NN1COCC[Si](C)(C)C)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 55% Sodium hydride (1.41 g, 32.1 mmol) was suspended in tetrahydrofuran (300 ml). To the suspension was added 5-(4-chlorophenyl)-4-(pyridin-4-yl)pyrazole (8.21 g, 32.1 mmol), and the resulting mixture was stirred at room temperature for 1 hour. To the resulting mixture was added (2-trimethylsilylethoxy)methyl chloride ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1cn[nH]c1 | c1c[nH]nc1 | c1c[nH]nc1.c1ccncc1.c1ccccc1 | HCl | O1CCCC1 | null | 1 | C[Si](C)(C)CCOCCl.Clc1ccc(-c2[nH]ncc2-c2ccncc2)cc1>O1CCCC1>C[Si](C)(C)CCOCn1ncc(-c2ccncc2)c1-c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6937d3243994fd38024ea9b8260c2c5 | C[Si](C)(C)CCOCn1ncc(-c2ccncc2)c1-c1ccc(Cl)cc1.O=C1CCN2CCC[C@H]2C1>>Clc1ccc(-c2[nH]nc(C3=CCN4CCC[C@H]4C3)c2-c2ccncc2)cc1 | ClC1=CC=C(C=C1)C1=C(C=NN1COCC[Si](C)(C)C)C1=CC=NC=C1.BrC1=NNC(=C1C1=CC=NC=C1)C1=CC=C(C=C1)F.C1CCN2CCC(C[C@H]12)=O>>ClC1=CC=C(C=C1)C1=C(C(=NN1)C1=CCN2CCC[C@H]2C1)C1=CC=NC=C1 | C[Si](C)(C)CCOC[n:7]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:27][cH:26]2)[c:19](-[c:20]2[cH:21][cH:22][n:23][cH:24][cH:25]2)[cH:9][n:8]1.O=[C:10]1[CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][C@H:17]2[CH2:18]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[nH:7][n:8][c:9]([C:10]3=[CH:11][CH2:12][N:13]4[CH2:14][CH2:15][CH2:... | C[Si](C)(C)CCOCn1ncc(-c2ccncc2)c1-c1ccc(Cl)cc1.O=C1CCN2CCC[C@H]2C1 | Clc1ccc(-c2[nH]nc(C3=CCN4CCC[C@H]4C3)c2-c2ccncc2)cc1 | null | null | null | C-C Coupling | OtherReaction | 1d234ec63c3a78180cbb4977a0b8e74ba43a84bf90ccb884618ef49d808daebe | 1fc6550e09abd2d5b4591ecfaba7c8d4303bf771c68c437b2a3cfead146b42ed | C1=C(c2n[nH]c(-c3ccccc3)c2-c2ccncc2)C[C@@H]2CCCN2C1 | C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:1]1:[#7;a:2]:[cH;D2;+0:3]:[c:4](-[c:5]):[c:6]:1-[c:7].O=[C;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:11](-[C:12])-[C:13]-[CH2;D2;+0:14]-1>>[C:12]-[#7:11]1-[C:13]-[CH;D2;+0:14]=[C;H0;D3;+0:8](-[c;H0;D3;+0:3]2:[#7;a:2]:[nH;D2;+0:1]:[c:6](-[c:7]):[c:4]:2-[c:5])-[C:9]-[C:10]-1 | 4 | [{"value": 4.0, "product": "ClC1=CC=C(C=C1)C1=C(C(=NN1)C1=CCN2CCC[C@H]2C1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a procedure similar to that described in Example 2-2), but using 5-(4-chlorophenyl)-4-(pyridin-4-yl)-1-(2-trimethylsilylethoxy)methylpyrazole prepared as described in 1) instead of 3-bromo-5-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole, and using (S)-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one instead of (±)-1,2,3... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Silyl protective group | null | c1c[nH]nc1.C1CCN2CCC[C@H]2C1 | c1cn[nH]c1.C1=CCN2CCC[C@H]2C1 | c1ccccc1.c1cn[nH]c1.C1=CCN2CCC[C@H]2C1.c1ccncc1 | HO- | null | null | null | C[Si](C)(C)CCOCn1ncc(-c2ccncc2)c1-c1ccc(Cl)cc1.O=C1CCN2CCC[C@H]2C1>>Clc1ccc(-c2[nH]nc(C3=CCN4CCC[C@H]4C3)c2-c2ccncc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd1629c0454e45928b744802850b9f19 | C=CC(=O)CC1CCCN1C(=O)OC(C)(C)C>>O=C1CCN2CCCC2C1 | C(C)(C)(C)OC(=O)N1C(CCC1)CC(C=C)=O.Cl.C(O)([O-])=O.[Na+]>>C1CCN2CCC(CC12)=O | CC(C)(C)OC(=O)[N:5]1[CH2:6][CH2:7][CH2:8][CH:9]1[CH2:10][C:2](=[O:1])[CH:3]=[CH2:4]>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]2[CH2:6][CH2:7][CH2:8][CH:9]2[CH2:10]1 | C=CC(=O)CC1CCCN1C(=O)OC(C)(C)C | O=C1CCN2CCCC2C1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | af87826d2c9dca336b65a27b4938fb0696e341ad5014d8c39c8110ea888d9712 | de99f3f6451e88e5bcaf6a5933293c2ea547a9adc55ed546b9c80a7701d60f3a | O=C1CCN2CCCC2C1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6]-[C:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH2;D1;+0:10]>>[O;D1;H0:8]=[C:7]1-[C:6]-[C:5]2-[C:4]-[C:3]-[C:2]-[N;H0;D3;+0:1]-2-[CH2;D2;+0:10]-[CH2;D2;+0:9]-1 | 93 | [{"value": 93.0, "product": "C1CCN2CCC(CC12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.5, "product": "C1CCN2CCC(CC12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 4 | HOUR | (±)-1-(t-Butoxycarbonyl)-2-(2-oxo-3-butenyl)pyrrolidine (140 mg (0.59 mmol), prepared as described in 2)) was dissolved in tetrahydrofuran (2 ml). To the solution was added an aqueous solution of 1N hydrochloric acid (1.76 ml, 1.76 mmol), and the resulting mixture was stirred at 70° C. for 4 hours. At the end of this t... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Vinyl.Boc | Ketone.Tertiary amine | C1CC[NH]C1 | C1CCN2CCCC2C1 | C1CCN2CCCC2C1 | HO- | O1CCCC1 | 70 | 4 | C=CC(=O)CC1CCCN1C(=O)OC(C)(C)C>O1CCCC1>O=C1CCN2CCCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-82f6431d8ef44e6fb7bc43c55597e2a3 | C=CC(=O)CC1CCCN1C(=O)OC(C)(C)C.Cc1ccc(S)cc1.O=C(OO)c1cccc(Cl)c1>>Cc1ccc(S(=O)(=O)CCC(=O)CC2CCCN2C(=O)OC(C)(C)C)cc1 | S(=S)(=O)([O-])[O-].[Na+].[Na+].C(C)(C)(C)OC(=O)N1C(CCC1)CC(C=C)=O.CC1=CC=C(C=C1)S.C(O)([O-])=O.[Na+].ClC1=CC(=CC=C1)C(=O)OO>>C(C)(C)(C)OC(=O)N1C(CCC1)CC(CCS(=O)(=O)C1=CC=C(C=C1)C)=O | [CH2:9]=[CH:10][C:11](=[O:12])[CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][N:18]1[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25].[CH3:1][c:2]1[cH:3][cH:4][c:5]([SH:6])[cH:26][cH:27]1.Clc1cccc(C(O[OH:8])=[O:7])c1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[CH2:9][CH2:10][C:11](=[O:12])[CH2:13][CH:14]2[CH2:... | C=CC(=O)CC1CCCN1C(=O)OC(C)(C)C.Cc1ccc(S)cc1.O=C(OO)c1cccc(Cl)c1 | Cc1ccc(S(=O)(=O)CCC(=O)CC2CCCN2C(=O)OC(C)(C)C)cc1 | null | null | O1CCCC1 | Oxidation | OtherReaction | c946eb7c6f08b80e34a07d8cc1c01bd76d32978498d57ad819abd2cd9e9f1b61 | 4a6891bdb956d32b50f23ce01e54b081a33557b8476795f737b09669690f3cf7 | O=C(CCS(=O)(=O)c1ccccc1)CC1CCCN1 | Cl-c1:c:c:c:c(-C(=[O;H0;D1;+0:1])-O-[OH;D1;+0:2]):c:1.[C:3]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH2;D1;+0:7].[SH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[S;H0;D4;+0:8](=[O;H0;D1;+0:1])(=[O;H0;D1;+0:2])-[c:9](:[c:10]):[c:11] | 94 | [{"value": 94.0, "product": "C(C)(C)(C)OC(=O)N1C(CCC1)CC(CCS(=O)(=O)C1=CC=C(C=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (±)-1-(t-Butoxycarbonyl)-2-(2-oxo-3-butenyl)pyrrolidine (206 mg (10.86 mmol), prepared as described in Reference example 1–2)) was dissolved in tetrahydrofuran (2 ml). To the solution was added 4-methylthiophenol (107 mg, 0.86 mmol), and the resulting mixture was stirred at room temperature for 2 hours. At the end of t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Peroxide.Aromatic thiol.Vinyl | Tosylate.Ketone | c1ccccc1 | null | c1ccccc1.C1CC[NH]C1 | HCl | O1CCCC1 | null | 2 | C=CC(=O)CC1CCCN1C(=O)OC(C)(C)C.Cc1ccc(S)cc1.O=C(OO)c1cccc(Cl)c1>O1CCCC1>Cc1ccc(S(=O)(=O)CCC(=O)CC2CCCN2C(=O)OC(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-834874432cb64e90b07ca52638ef6387 | Cc1ccc(S(=O)(=O)CCC(=O)CC2CCCN2C(=O)OC(C)(C)C)cc1>>O=C1CCN2CCCC2C1 | C(C)(C)(C)OC(=O)N1C(CCC1)CC(CCS(=O)(=O)C1=CC=C(C=C1)C)=O.Cl.O1CCOCC1>>C1CCN2CCC(CC12)=O | Cc1ccc(S(=O)(=O)[CH2:4][CH2:3][C:2](=[O:1])[CH2:10][CH:9]2[N:5](C(=O)OC(C)(C)C)[CH2:6][CH2:7][CH2:8]2)cc1>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]2[CH2:6][CH2:7][CH2:8][CH:9]2[CH2:10]1 | Cc1ccc(S(=O)(=O)CCC(=O)CC2CCCN2C(=O)OC(C)(C)C)cc1 | O=C1CCN2CCCC2C1 | null | null | CO | Functional Group Interconversion | OtherReaction | 50b888dc6680519ac7650a44091f7748bcb6cdfc043884d9850c5b73b001fb25 | 08813e54791f0155668e7dc6e43143d673bbd8732ff68b4f4c042ab6fc742e4e | O=C1CCN2CCCC2C1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]2-[C:7]-[C:8]-[C:9]-[N;H0;D3;+0:10]-2-C(=O)-O-C(-C)(-C)-C):c:c:1>>[O;D1;H0:4]=[C:3]1-[C:5]-[C:6]2-[C:7]-[C:8]-[C:9]-[N;H0;D3;+0:10]-2-[CH2;D2;+0:1]-[C:2]-1 | 65.3 | [{"value": 65.0, "product": "C1CCN2CCC(CC12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.3, "product": "C1CCN2CCC(CC12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | (±)-1-(t-Butoxycarbonyl)-2-[4-(p-toluenesulfonyl)-2-oxobutyl]pyrrolidine (322 mg (0.814 mmol), prepared as described in 1)) was dissolved in methanol (3.2 ml). To the solution was added a solution of 4N hydrochloric acid/dioxane (0.61 ml, 2.44 mmol), and the resulting mixture was stirred at 50° C. for 30 minutes. At th... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Carbamic ester.Ether.Boc | Tertiary amine | c1ccccc1.C1CC[NH]C1 | C1CCN2CCCC2C1 | C1CCN2CCCC2C1 | TsOH.HO- | CO | 50 | 0.5 | Cc1ccc(S(=O)(=O)CCC(=O)CC2CCCN2C(=O)OC(C)(C)C)cc1>CO>O=C1CCN2CCCC2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a08229d4402d4ef2a70f15be053e3cac | COC(=O)C1C(=O)C[C@@H]2CCCN2C1=O>>O=C1CC(=O)N2CCC[C@H]2C1 | COC(=O)C1C(N2CCC[C@H]2CC1=O)=O.C(O)([O-])=O.[Na+]>>C1CCN2C(CC(C[C@H]12)=O)=O | COC(=O)[CH:3]1[C:2](=[O:1])[CH2:11][C@H:10]2[N:6]([C:4]1=[O:5])[CH2:7][CH2:8][CH2:9]2>>[O:1]=[C:2]1[CH2:3][C:4](=[O:5])[N:6]2[CH2:7][CH2:8][CH2:9][C@H:10]2[CH2:11]1 | COC(=O)C1C(=O)C[C@@H]2CCCN2C1=O | O=C1CC(=O)N2CCC[C@H]2C1 | null | null | C(C)(=O)O | Reduction | Decarboxylation | 6a7d1c4656edc48b2a8aa1db0bbc6b3602e9990cb9b1f55e23cd40a49ca70033 | f277909394d9f4e61cc2cdb65fef123102672ca91cfff7f8513cb0baf66138ac | O=C1CC(=O)N2CCC[C@H]2C1 | C-O-C(=O)-[CH;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[#7:6](-[C:7])-[C:8]-1=[O;D1;H0:9]>>[C:7]-[#7:6]1-[C:5]-[C:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[C:8]-1=[O;D1;H0:9] | 87.8 | [{"value": 87.0, "product": "C1CCN2C(CC(C[C@H]12)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "C1CCN2C(CC(C[C@H]12)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 30 | MINUTE | (8aS)-6-Methoxycarbonyl-1,2,3,5,6,7,8,8a-octahydroindolizin-5,7-dione (183 mg (0.87 mmol), prepared as described in 2)) was dissolved in an aqueous solution of 10% acetic acid (2 ml). The resulting mixture was stirred at 110° C. for 30 minutes, and then cooled to room temperature. To the reaction mixture was added a sa... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone | C1CCN2CCC[C@H]2C1 | C1CCN2CCC[C@H]2C1 | C1CCN2CCC[C@H]2C1 | HO- | C(C)(=O)O | 110 | 0.5 | COC(=O)C1C(=O)C[C@@H]2CCCN2C1=O>C(C)(=O)O>O=C1CC(=O)N2CCC[C@H]2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f9f9d01fa924902888dbe11994c4910 | O=C1CC(=O)N2CCC[C@H]2C1>>O=C1C=C(N2CCCC2)C[C@@H]2CCCN12 | C1CCN2C(CC(C[C@H]12)=O)=O.N1CCCC1>>N1CCCC1.N1(CCCC1)C1=CC(N2CCC[C@H]2C1)=O | O=[C:9]1[CH2:8][C:7](=[O:6])[N:20]2[C@H:16]([CH2:15]1)[CH2:17][CH2:18][CH2:19]2>>[O:6]=[C:7]1[CH:8]=[C:9]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:15][C@@H:16]2[CH2:17][CH2:18][CH2:19][N:20]12 | O=C1CC(=O)N2CCC[C@H]2C1 | O=C1C=C(N2CCCC2)C[C@@H]2CCCN12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 188c1bd05aab812050baa2efc05e135ebb2a7aef55d296ca4544915d4c5aa3db | c49e435c17a7f516f8c0ecdeb1ccc388912e78694cdb61580a824cab4048eae5 | O=C1C=C(N2CCCC2)C[C@@H]2CCCN12 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[C:5])-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-1>>[C:9]-[#7:10](-[C;H0;D3;+0:1]1=[CH;D2;+0:8]-[C:6](=[O;D1;H0:7])-[#7:4](-[C:5])-[C:3]-[C:2]-1)-[C:11] | 204.1 | [{"value": 204.1, "product": "N1(CCCC1)C1=CC(N2CCC[C@H]2C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | (S)-1,2,3,5,6,7,8,8a-octahydroindolizin-5,7-dione (117 mg (0.76 mmol), prepared as described in 3)) was dissolved in ethanol (1.2 ml). To the solution was added pyrrolidine (128 μl, 1.53 mmol), and the resulting mixture was allowed to stand at room temperature for 5 minutes. At the end of this time, the reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Enamine | C1CCN2CCC[C@H]2C1 | C1CC[NH]C1.C1=CCN2CCC[C@H]2C1 | C1CC[NH]C1.C1=CCN2CCC[C@H]2C1 | null | C(C)O | null | 0.083333 | O=C1CC(=O)N2CCC[C@H]2C1>C(C)O>O=C1C=C(N2CCCC2)C[C@@H]2CCCN12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d722b272eb34204b63355ecb07a090c | O=C1C=C(N2CCCC2)C[C@@H]2CCCN12>>O=C1CCN2CCC[C@H]2C1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].N1(CCCC1)C1=CC(N2CCC[C@H]2C1)=O.[OH-].[Na+].C(C)O>>C1CCN2CCC(C[C@H]12)=O | C1CCN([C:2]2=[CH:3][C:4](=[O:1])[N:5]3[CH2:6][CH2:7][CH2:8][C@H:9]3[CH2:10]2)C1>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]2[CH2:6][CH2:7][CH2:8][C@H:9]2[CH2:10]1 | O=C1C=C(N2CCCC2)C[C@@H]2CCCN12 | O=C1CCN2CCC[C@H]2C1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 45b7309ad9a4c7db7ea1541ac38ac35cfff92dc1cce2c7b10d3ed8421d07011f | e373248e3749116d6242b1a7fc884e893efad4360c09992b43d0736678d09309 | O=C1CCN2CCC[C@H]2C1 | [C:1]-[#7:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](-N2-C-C-C-C-2)=[CH;D2;+0:6]-[C;H0;D3;+0:7]-1=[O;H0;D1;+0:8]>>[C:1]-[#7:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:8])-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1 | 54 | [{"value": 54.0, "product": "C1CCN2CCC(C[C@H]12)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | (S)-7-(1-Pyrrolidinyl)-1,2,3,5,8,8a-hexahydroindolizin-5-one (645 mg (3.13 mmol), prepared as described in 4)) was dissolved in tetrahydrofuran (10 ml). To the solution was added lithium aluminum hydride (356 mg, 9.39 mmol) under ice cooling, and the resulting mixture was stirred at room temperature overnight. To the r... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Tertiary amide | Ketone | C1CCNC1.C1=CCN2CCC[C@H]2C1 | C1CCN2CCC[C@H]2C1 | C1CCN2CCC[C@H]2C1 | Other | O1CCCC1 | null | 8 | O=C1C=C(N2CCCC2)C[C@@H]2CCCN12>O1CCCC1>O=C1CCN2CCC[C@H]2C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b056c8ed15b41ed951feb84fb0fb850 | COC(=O)[C@@H]1CC(=O)CN1C(=O)OCc1ccccc1>>C=C1C[C@@H](C(=O)OC)N(C(=O)OCc2ccccc2)C1 | CC(C)([O-])C.[K+].COC([C@H]1N(CC(C1)=O)C(=O)OCC1=CC=CC=C1)=O.[Cl-].[NH4+]>>COC([C@H]1N(CC(C1)=C)C(=O)OCC1=CC=CC=C1)=O | O=[C:2]1[CH2:3][C@@H:4]([C:5](=[O:6])[O:7][CH3:8])[N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20]1>>[CH2:1]=[C:2]1[CH2:3][C@@H:4]([C:5](=[O:6])[O:7][CH3:8])[N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20]1 | COC(=O)[C@@H]1CC(=O)CN1C(=O)OCc1ccccc1 | C=C1C[C@@H](C(=O)OC)N(C(=O)OCc2ccccc2)C1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)OCC | Functional Group Interconversion | OtherReaction | 29122e0a9c25a037cfa43aa9953f5b17246a0411b55969835e7dbd90ad48801c | f395a9efbb80a99833acb686d4944d4880257993d074f4e04e21822999af09fe | C=C1CCN(C(=O)OCc2ccccc2)C1 | O=[C;H0;D3;+0:1]1-[C:2]-[#7:3](-[C:4](-[#8:5])=[O;D1;H0:6])-[C:7](-[C:8](-[#8:9])=[O;D1;H0:10])-[C:11]-1>>[#8:5]-[C:4](=[O;D1;H0:6])-[#7:3]1-[C:2]-[C;H0;D3;+0:1](=[C;D1;H2:12])-[C:11]-[C:7]-1-[C:8](-[#8:9])=[O;D1;H0:10] | 72.6 | [{"value": 72.0, "product": "COC([C@H]1N(CC(C1)=C)C(=O)OCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "COC([C@H]1N(CC(C1)=C)C(=O)OCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 15 | MINUTE | Potassium t-butoxide (1.41 g, 12.6 mmol) was suspended in diethyl ether (100 ml). To the suspension was added methyltriphenylphosphonium bromide (4.80 g, 13.4 mmol), and the resulting mixture was stirred at 5° C. for 15 minutes. To the mixture was added (S)-1-benzyloxycarbonyl-4-oxoproline methyl ester (2.50 g, 9.0 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Vinyl | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)OCC | 5 | 0.25 | COC(=O)[C@@H]1CC(=O)CN1C(=O)OCc1ccccc1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)OCC>C=C1C[C@@H](C(=O)OC)N(C(=O)OCc2ccccc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f51ae708c7b34b70880763ac6b68d07a | C=C1C[C@@H](C(=O)OC)N(C(=O)OCc2ccccc2)C1>>COC(=O)[C@@H]1CC(C)CN1 | COC([C@H]1N(CC(C1)=C)C(=O)OCC1=CC=CC=C1)=O.[H][H]>>COC([C@H]1NCC(C1)C)=O | O=C(OCc1ccccc1)[N:10]1[C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][C:7](=[CH2:8])[CH2:9]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH:7]([CH3:8])[CH2:9][NH:10]1 | C=C1C[C@@H](C(=O)OC)N(C(=O)OCc2ccccc2)C1 | COC(=O)[C@@H]1CC(C)CN1 | null | [Pd] | CO | Reduction | OtherReaction | 7ce259223c0040a2183927aade18d71c862a63f780848739ac2dc935af64b1d9 | 4693d071c7195c4d1d1e30a5794ffc365d4c1fab9edd2d709ddf2a18cef75754 | C1CCNC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1]1-[C:2]-[C;H0;D3;+0:3](=[CH2;D1;+0:4])-[C:5]-[C:6]-1-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]>>[C;D1;H3:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C:6]1-[C:5]-[CH;D3;+0:3](-[CH3;D1;+0:4])-[C:2]-[NH;D2;+0:1]-1 | 99.9 | [{"value": 99.9, "product": "COC([C@H]1NCC(C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-1-Benzyloxycarbonyl-4-methylideneproline methyl ester (1.80 g (6.5 mmol), prepared as described in 1)) was dissolved in methanol (50 ml). The resulting solution was stirred at room temperature in an atmosphere of hydrogen in the presence of 10% palladium on charcoal (180 mg) for 2 hours. At the end of this time, th... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Vinyl | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | C1CCNC1 | HO- | [Pd].CO | null | null | C=C1C[C@@H](C(=O)OC)N(C(=O)OCc2ccccc2)C1>[Pd].CO>COC(=O)[C@@H]1CC(C)CN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c44e3068064646e1832ac5b3443cc9f4 | COC(=O)[C@@H]1CC(C)CN1.O=C(Cl)OCc1ccccc1>>COC(=O)[C@@H]1CC(C)CN1C(=O)OCc1ccccc1 | COC([C@H]1NCC(C1)C)=O.C(O)([O-])=O.[Na+].ClC(=O)OCC1=CC=CC=C1>>COC([C@H]1N(CC(C1)C)C(=O)OCC1=CC=CC=C1)=O | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH:7]([CH3:8])[CH2:9][NH:10]1.Cl[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH:7]([CH3:8])[CH2:9][N:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | COC(=O)[C@@H]1CC(C)CN1.O=C(Cl)OCc1ccccc1 | COC(=O)[C@@H]1CC(C)CN1C(=O)OCc1ccccc1 | null | null | C1(=CC=CC=C1)C | Protection | N-alkylation of secondary amines with alkyl halides | 9dfceb007b1ffbcf1807491089b61fcc6b42027629f9ce16a6b45690ed8aec78 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(OCc1ccccc1)N1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[C:10]-[C:9]-1-[C:7](=[O;D1;H0:8])-[#8:6]-[C;D1;H3:5] | 99 | [{"value": 99.0, "product": "COC([C@H]1N(CC(C1)C)C(=O)OCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.7, "product": "COC([C@H]1N(CC(C1)C)C(=O)OCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | (2S)-4-Methylproline methyl ester (0.93 g (6.5 mmol), prepared as described in 2)) was dissolved in toluene (20 ml). To the solution were added an aqueous solution (20 ml) of sodium hydrogencarbonate (1.89 g, 22.5 mmol) and benzyl chloroformate (1.54 ml, 10.8 mmol), and the resulting mixture was stirred at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | 8 | COC(=O)[C@@H]1CC(C)CN1.O=C(Cl)OCc1ccccc1>C1(=CC=CC=C1)C>COC(=O)[C@@H]1CC(C)CN1C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e289eb070e44fd5bd336895d77677ad | CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NCCN>>CCn1cnc2c(Nc3cccc(Cl)c3)nc(NCCN)nc21 | ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl.C(CN)N>>NCCNC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl | Cl[c:17]1[n:16][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]2)[c:6]2[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:23]2[n:22]1.[NH2:18][CH2:19][CH2:20][NH2:21]>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]3)[n:16][c:17]([NH:18][CH2:19][CH2:20][NH2:21])[n:22][c:2... | CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NCCN | CCn1cnc2c(Nc3cccc(Cl)c3)nc(NCCN)nc21 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d29b1bab4afefe0db66c5d87d4d37a8be0c49cfdb04c6c8844dee54b4b5d425a | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1 | null | [] | 150 | CELSIUS | null | null | 250 mg (0.81 mmol) of 2-chloro-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine are dissolved in 5.8 ml (97 mmol) of ethylenediamine and the solution is heated under reflux for 3 hours (oil bath temperature of 150° C.). After cooling to room temperature, the reaction mixture is taken up in ethyl acetate (250 ml) and extract... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | C(C)(=O)OCC | 150 | null | CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NCCN>C(C)(=O)OCC>CCn1cnc2c(Nc3cccc(Cl)c3)nc(NCCN)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf753584cff448f29f411f9c50bea731 | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(Cl)c1>>Clc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | ClC=1C=C(N)C=CC1.ClC1=NC(=C2NC=NC2=N1)Cl>>ClC1=NC(=C2NC=NC2=N1)NC1=CC(=CC=C1)Cl | Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][c:13]2[n:14][cH:15][nH:16][c:17]12.[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:18]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([Cl:11])[n:12][c:13]3[n:14][cH:15][nH:16][c:17]23)[cH:18]1 | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(Cl)c1 | Clc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | null | null | C(CCCC)O.C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | cc3f24fffcaf974b16f52ce977955348405e93cb36102dc19c5151f40ad54b4f | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3nc[nH]c23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | null | [] | 100 | CELSIUS | 3 | HOUR | 1.4 ml (13 mmol) of 3-chloro-aniline are added to a suspension of 650 mg (3.44 mmol) of 2,6-dichloro-purine in 5 ml of 1-pentanol. The reaction mixture is stirred at 100° C. (oil bath temperature) for 3 hours. After cooling to room temperature, the mixture is diluted with isopropanol and stirred at 10° C. for 90 minute... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | C(CCCC)O.C(C)(C)O | 100 | 3 | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(Cl)c1>C(CCCC)O.C(C)(C)O>Clc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d405be57821f4dbb93ac2b274583a947 | CCI.Clc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1>>CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21 | ClC1=NC(=C2NC=NC2=N1)NC1=CC(=CC=C1)Cl.C([O-])([O-])=O.[K+].[K+].C(C)I>>ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl | I[CH2:2][CH3:1].[n:3]1[cH:4][nH:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]3)[n:16][c:17]([Cl:18])[n:19][c:20]12>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]3)[n:16][c:17]([Cl:18])[n:19][c:20]12 | CCI.Clc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[#7:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[n;H0;D2;+0:9]:[c:10]:[nH;D2;+0:11]:[c:12]:2:1>>[#7:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[c:12]:1:[n;H0;D2;+0:11]:[c:10]:[n;H0;D3;+0:9]:2-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 2 | HOUR | 676 mg (2.413 mmol) of 2-chloro-6-(3-chloro-phenyl-amino)-purine are dissolved in 10 ml of abs. DMF by means of gentle heating. 375 mg (2.713 mmol) of potassium carbonate, followed by 0.97 ml (12.01 mmol) of ethyl iodide are added at room temperature. The reaction mixture is stirred at room temperature for 2 hours. Whe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HI | CN(C)C=O | null | 2 | CCI.Clc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1>CN(C)C=O>CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-10cbb19efc2447da90278f6f11f5b438 | CC(C)n1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NCCN>>CC(C)n1cnc2c(Nc3cccc(Cl)c3)nc(NCCN)nc21 | ClC1=NC(=C2N=CN(C2=N1)C(C)C)NC1=CC(=CC=C1)Cl.C(CN)N>>NCCNC1=NC(=C2N=CN(C2=N1)C(C)C)NC1=CC(=CC=C1)Cl | Cl[c:18]1[n:17][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([Cl:15])[cH:16]2)[c:7]2[n:6][cH:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:24]2[n:23]1.[NH2:19][CH2:20][CH2:21][NH2:22]>>[CH3:1][CH:2]([CH3:3])[n:4]1[cH:5][n:6][c:7]2[c:8]([NH:9][c:10]3[cH:11][cH:12][cH:13][c:14]([Cl:15])[cH:16]3)[n:17][c:18]([NH:19][CH2:20][CH2:21][... | CC(C)n1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NCCN | CC(C)n1cnc2c(Nc3cccc(Cl)c3)nc(NCCN)nc21 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d29b1bab4afefe0db66c5d87d4d37a8be0c49cfdb04c6c8844dee54b4b5d425a | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1 | null | [] | 150 | CELSIUS | null | null | 200 mg (0.58 mmol) of 2-chloro-6-(3-chloro-phenyl-amino)-9-isopropyl-9H-purine are dissolved in 6 ml (90 mmol) of ethylenediamine and the mixture is heated under reflux for 3 hours (oil bath temperature of 150° C.). After cooling to room temperature, the reaction mixture is taken up in 250 ml of ethyl acetate and extra... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | C(C)(=O)OCC | 150 | null | CC(C)n1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NCCN>C(C)(=O)OCC>CC(C)n1cnc2c(Nc3cccc(Cl)c3)nc(NCCN)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-74fde67f2a9f47cb945db7fa6bea0160 | CC(C)I.Clc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1>>CC(C)n1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21 | ClC1=NC(=C2NC=NC2=N1)NC1=CC(=CC=C1)Cl.C([O-])([O-])=O.[Cs+].[Cs+].C(C)(C)I>>ClC1=NC(=C2N=CN(C2=N1)C(C)C)NC1=CC(=CC=C1)Cl | I[CH:2]([CH3:1])[CH3:3].[n:4]1[cH:5][nH:6][c:7]2[c:8]([NH:9][c:10]3[cH:11][cH:12][cH:13][c:14]([Cl:15])[cH:16]3)[n:17][c:18]([Cl:19])[n:20][c:21]12>>[CH3:1][CH:2]([CH3:3])[n:4]1[cH:5][n:6][c:7]2[c:8]([NH:9][c:10]3[cH:11][cH:12][cH:13][c:14]([Cl:15])[cH:16]3)[n:17][c:18]([Cl:19])[n:20][c:21]12 | CC(C)I.Clc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | CC(C)n1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21 | null | null | CN(C)C=O.O.C(C)(=O)OCC.O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 945badfe62d08793a7a77e1f7911213401b8f39f60cb6469278838440322098e | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[#7:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[n;H0;D2;+0:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:1>>[#7:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:13]:1:[n;H0;D2;+0:12]:[c:11]:[n;H0;D3;+0:10]:2-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | null | [] | null | null | 18 | HOUR | 500 mg (1.78 mmol) of 2-chloro-6-(3-chloro-phenyl-amino)-purine are dissolved in a mixture of 29.5 ml of DMF/water (85/15) and 5 ml of dioxane by means of gentle heating. 870 mg (2.67 mmol) of caesium carbonate, followed by 1.78 ml (17.8 mmol) of isopropyl iodide are added at room temperature. The reaction mixture is s... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HI | CN(C)C=O.O.C(C)(=O)OCC.O1CCOCC1 | null | 18 | CC(C)I.Clc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1>CN(C)C=O.O.C(C)(=O)OCC.O1CCOCC1>CC(C)n1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66d3e0ffc92349d497cdf78b8c94e762 | CCI.Clc1nc(Cl)c2[nH]cnc2n1>>CCn1cnc2c(Cl)nc(Cl)nc21.CCn1cnc2nc(Cl)nc(Cl)c21 | C(C)I.ClC1=NC(=C2NC=NC2=N1)Cl.[H-].[Na+]>>ClC1=NC(=C2N(C=NC2=N1)CC)Cl.ClC1=NC(=C2N=CN(C2=N1)CC)Cl | I[CH2:2][CH3:1].[n:3]1[c:21]([Cl:22])[n:20][c:19]2[n:18][cH:17][nH:16][c:26]2[c:24]1[Cl:8]>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([Cl:8])[n:9][c:10]([Cl:11])[n:12][c:13]12.[CH3:14][CH2:15][n:16]1[cH:17][n:18][c:19]2[n:20][c:21]([Cl:22])[n:23][c:24]([Cl:25])[c:26]12 | CCI.Clc1nc(Cl)c2[nH]cnc2n1 | CCn1cnc2c(Cl)nc(Cl)nc21.CCn1cnc2nc(Cl)nc(Cl)c21 | null | null | C(C)(=O)OCC.CN(C)C=O | Aromatic Heterocycle Formation | N-alkylation of secondary amines with alkyl halides | d52b00c6149363487fdc0ae67a5060cbc4e8e1a4aeca6262806992e2ff9a0532 | 00e6d21d25322b85c8780acf512cbf2329f7d5b4053a40c50dee16614a7b8e59 | c1ncc2[nH]cnc2n1.c1ncc2nc[nH]c2n1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[Cl;D1;H0:3]-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6]2:[#7;a:7]:[c:8]:[nH;D2;+0:9]:[c:10]:2:[c;H0;D3;+0:11](-[Cl;H0;D1;+0:12]):[n;H0;D2;+0:13]:1>>[#7;a:14]:[c:15]1:[c:16](:[#7;a:17]:[c:18]:[n;H0;D3;+0:13]:1-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:19](-[Cl;H0;D1;+0:12]):[#7;a:20].[C;D1;H3:21]-[C:22]-[n;H0;D3;+0:... | null | [] | null | null | 0.5 | HOUR | 1.0 g (5.29 mmol) of 2,6-dichloro-purine is dissolved in DMF (20 ml) and treated with 152 mg (80%, 5.3 mmol) of sodium hydride and the mixture is stirred at RT for 0.5 hours. After addition of 0.42 ml (5.3 mmol) of ethyl iodide, the mixture is stirred at 70° C. for 3 hours, diluted with ethyl acetate (100 ml) and extra... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary halide | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1.c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1.c1ncc2[nH]cnc2n1 | I- | C(C)(=O)OCC.CN(C)C=O | null | 0.5 | CCI.Clc1nc(Cl)c2[nH]cnc2n1>C(C)(=O)OCC.CN(C)C=O>CCn1cnc2c(Cl)nc(Cl)nc21.CCn1cnc2nc(Cl)nc(Cl)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a5c495ce8bd459ab04cfd5ab755e0c5 | CCn1cnc2c(Nc3cccc(C(F)(F)F)c3)nc(Cl)nc21.NCCCO>>CCn1cnc2c(Nc3cccc(C(F)(F)F)c3)nc(NCCCO)nc21 | ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)C(F)(F)F.NCCCO>>C(C)N1C2=NC(=NC(=C2N=C1)NC1=CC(=CC=C1)C(F)(F)F)NCCCO | Cl[c:20]1[n:19][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]2)[c:6]2[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:27]2[n:26]1.[NH2:21][CH2:22][CH2:23][CH2:24][OH:25]>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]3)[n:19]... | CCn1cnc2c(Nc3cccc(C(F)(F)F)c3)nc(Cl)nc21.NCCCO | CCn1cnc2c(Nc3cccc(C(F)(F)F)c3)nc(NCCCO)nc21 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d29b1bab4afefe0db66c5d87d4d37a8be0c49cfdb04c6c8844dee54b4b5d425a | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1 | null | [] | null | null | null | null | 200 mg (0.58 mmol) of 2-chloro-9-ethyl-6-(3-trifluoromethyl-phenyl-amino)-9H-purine and 2 ml of 3-amino-1-propanol are stirred at 140° C. for 2 h and the mixture is allowed to cool and is diluted with 60 ml of ethyl acetate. The organic phase is washed with water and dried over sodium sulfate. After removal of the solv... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | C(C)(=O)OCC | null | null | CCn1cnc2c(Nc3cccc(C(F)(F)F)c3)nc(Cl)nc21.NCCCO>C(C)(=O)OCC>CCn1cnc2c(Nc3cccc(C(F)(F)F)c3)nc(NCCCO)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2af4c11d8f47436cb6ca27b9d322a6e7 | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(C(F)(F)F)c1>>FC(F)(F)c1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | ClC1=NC(=C2NC=NC2=N1)Cl.FC(C=1C=C(N)C=CC1)(F)F.C(C)(=O)OCC>>ClC1=NC(=C2NC=NC2=N1)NC1=CC(=CC=C1)C(F)(F)F | Cl[c:11]1[n:12][c:13]([Cl:14])[n:15][c:16]2[n:17][cH:18][nH:19][c:20]12.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:21]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][c:13]([Cl:14])[n:15][c:16]3[n:17][cH:18][nH:19][c:20]23)[cH:21]1 | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(C(F)(F)F)c1 | FC(F)(F)c1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | null | null | C(CCC)O.CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | cc3f24fffcaf974b16f52ce977955348405e93cb36102dc19c5151f40ad54b4f | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3nc[nH]c23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | null | [] | 40 | CELSIUS | 60 | MINUTE | 1.9 g (10 mmol) of 2,6-dichloro-purine and 8.05 g (50 mmol) of 3-trifluoromethyl-aniline (Fluka, Buchs, Switzerland) in 60 ml of n-butanol and 3 ml of DMF are stirred at 60° C. for 6 h. 50 ml of ethyl acetate are added to the cooled reaction solution and the precipitate is filtered off and further stirred in 40 ml of i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | C(CCC)O.CN(C)C=O | 40 | 1 | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(C(F)(F)F)c1>C(CCC)O.CN(C)C=O>FC(F)(F)c1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf83831a158f40d799e226584860bcea | CCI.FC(F)(F)c1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1>>CCn1cnc2c(Nc3cccc(C(F)(F)F)c3)nc(Cl)nc21 | ClC1=NC(=C2NC=NC2=N1)NC1=CC(=CC=C1)C(F)(F)F.C([O-])([O-])=O.[Cs+].[Cs+].C(C)I>>ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)C(F)(F)F | I[CH2:2][CH3:1].[n:3]1[cH:4][nH:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]3)[n:19][c:20]([Cl:21])[n:22][c:23]12>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]3)[n:19][c:20]([Cl:21])[n:22][c:23]12 | CCI.FC(F)(F)c1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | CCn1cnc2c(Nc3cccc(C(F)(F)F)c3)nc(Cl)nc21 | null | null | O1CCOCC1.O.CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[#7:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[n;H0;D2;+0:9]:[c:10]:[nH;D2;+0:11]:[c:12]:2:1>>[#7:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[c:12]:1:[n;H0;D2;+0:11]:[c:10]:[n;H0;D3;+0:9]:2-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | null | null | A mixture comprising 1 g (3.2 mmol) of 2-chloro-6-(3-trifluoromethyl-phenyl-amino)-purine, 1.7 g (5.1 mmol) of caesium carbonate and 2.1 ml (25.6 mmol) of ethyl iodide in 7 ml of dioxane/water/DMF (8:2:2) is stirred at RT for 18 h. It is then diluted with ethyl acetate and the organic phase is washed with water. This p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HI | O1CCOCC1.O.CN(C)C=O.C(C)(=O)OCC | null | null | CCI.FC(F)(F)c1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1>O1CCOCC1.O.CN(C)C=O.C(C)(=O)OCC>CCn1cnc2c(Nc3cccc(C(F)(F)F)c3)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4bf9e65b4ca4dc8a7893f11d1c680e7 | CI.COc1cc(Nc2nc(Cl)nc3nc[nH]c23)cc(OC)c1OC>>COc1cc(Nc2nc(Cl)nc3c2ncn3C)cc(OC)c1OC | C(C)(=O)OCC.ClC1=NC(=C2NC=NC2=N1)NC1=CC(=C(C(=C1)OC)OC)OC.C([O-])([O-])=O.[K+].[K+].CI>>ClC1=NC(=C2N=CN(C2=N1)C)NC1=CC(=C(C(=C1)OC)OC)OC | I[CH3:17].[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]([Cl:10])[n:11][c:12]3[c:13]2[nH:14][cH:15][n:16]3)[cH:18][c:19]([O:20][CH3:21])[c:22]1[O:23][CH3:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]([Cl:10])[n:11][c:12]3[c:13]2[n:14][cH:15][n:16]3[CH3:17])[cH:18][c:19]([O:20][CH3:21])[c:22]1[O:23][CH... | CI.COc1cc(Nc2nc(Cl)nc3nc[nH]c23)cc(OC)c1OC | COc1cc(Nc2nc(Cl)nc3c2ncn3C)cc(OC)c1OC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 011a6d20d1a2cde13aab96bd8efb9a0393d2f8a89a318e20bc7624b0300657a4 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | I-[CH3;D1;+0:1].[#7:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]2:[n;H0;D2;+0:8]:[c:9]:[nH;D2;+0:10]:[c:11]:2:1>>[#7:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]2:[c:11]:1:[n;H0;D2;+0:10]:[c:9]:[n;H0;D3;+0:8]:2-[CH3;D1;+0:1] | null | [] | null | null | null | null | 168 mg (0.5 mmol) of 2-chloro-6-(3,4,5-trimethoxy-phenyl-amino)-purine, 103 mg (0.75 mmol) of potassium carbonate and 0.156 ml (2.5 mmol) of methyl iodide are stirred in 3 ml of dimethylformamide at room temperature for 5 h. 30 ml of ethyl acetate are added to the slightly cloudy reaction solution and the mixture is ex... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.c1ncc2[nH]cnc2n1 | HI | CN(C=O)C | null | null | CI.COc1cc(Nc2nc(Cl)nc3nc[nH]c23)cc(OC)c1OC>CN(C=O)C>COc1cc(Nc2nc(Cl)nc3c2ncn3C)cc(OC)c1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fd3d040b94b4e42bff04a40542aedcf | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@@H]3CC[C@H](N)CC3)nc21.CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@H]3CC[C@H](N)CC3)nc21>>CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NC1CCC(N)CC1 | N[C@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl.N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl>>ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl.NC1CCC(CC1)N | CCn1cnc2c(Nc3cccc([Cl:18])c3)nc([NH:21][C@H:22]3[CH2:23][CH2:24][C@@H:25]([NH2:26])[CH2:27][CH2:28]3)nc21.N[C@H]1CC[C@H](N[c:17]2[n:16][c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]3)[c:6]3[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:20]3[n:19]2)CC1>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][c... | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@@H]3CC[C@H](N)CC3)nc21.CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@H]3CC[C@H](N)CC3)nc21 | CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NC1CCC(N)CC1 | null | null | null | Functional Group Interconversion | OtherReaction | 7cbabe8ae84b99d74089667d6d4a86bd888f023989e112149bed53cda2a027d3 | 9a171446d6c20a9eda6f7d859c1ae6eaec2eeca5274d08c68c59b33d6947d52b | C1CCCCC1.c1ccc(Nc2ncnc3[nH]cnc23)cc1 | C-C-n1:c:n:c2:c(-N-c3:c:c:c:c(-[Cl;H0;D1;+0:1]):c:3):n:c(-[NH;D2;+0:2]-[C@@H;D3;+0:3](-[C:4]-[C:5])-[C:6]-[C:7]):n:c:2:1.N-[C@@H]1-C-C-[C@H](-N-[c;H0;D3;+0:8]2:[#7;a:9]:[c:10]:[c:11]3:[#7;a:12]:[c:13]:[#7;a:14](-[C:15]):[c:16]:3:[#7;a:17]:2)-C-C-1>>[C:15]-[#7;a:14]1:[c:13]:[#7;a:12]:[c:11]2:[c:10]:[#7;a:9]:[c;H0;D3;+0:... | null | [] | null | null | null | null | Analogously to Example 1, 2-(trans-4-amino-cyclohexyl-amino)-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine; FAB-MS: (M+H)+=386; HPLC: tret (grad20/2)=8.47 minutes, and 2-(cis-4-amino-cyclohexyl-amino)-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine; FAB-MS: (M+H)+=386; HPLC: tret (grad20/2)=9.37 minutes are obtained from 308... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Secondary amine.Secondary amine.Secondary amine | Aromatic halide.Primary amine | c1ccccc1.c1ncc2nc[nH]c2n1.C1CCCCC1.c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1.C1CCCCC1 | Other | null | null | null | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@@H]3CC[C@H](N)CC3)nc21.CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@H]3CC[C@H](N)CC3)nc21>>CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NC1CCC(N)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05c776ffbc4f41dcb9d445d2286fbd63 | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@H]3CCC[C@@H](N)C3)nc21.CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@H]3CCC[C@H](N)C3)nc21>>CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NC1CCCC(N)C1 | N[C@H]1C[C@H](CCC1)NC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl.N[C@@H]1C[C@H](CCC1)NC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl>>ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl.NC1CC(CCC1)N | CCn1cnc2c(Nc3cccc([Cl:18])c3)nc([NH:21][C@H:22]3[CH2:23][CH2:24][CH2:25][C@@H:26]([NH2:27])[CH2:28]3)nc21.N[C@H]1CCC[C@H](N[c:17]2[n:16][c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]3)[c:6]3[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:20]3[n:19]2)C1>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][c... | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@H]3CCC[C@@H](N)C3)nc21.CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@H]3CCC[C@H](N)C3)nc21 | CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NC1CCCC(N)C1 | null | null | null | Functional Group Interconversion | OtherReaction | 7cbabe8ae84b99d74089667d6d4a86bd888f023989e112149bed53cda2a027d3 | 9a171446d6c20a9eda6f7d859c1ae6eaec2eeca5274d08c68c59b33d6947d52b | C1CCCCC1.c1ccc(Nc2ncnc3[nH]cnc23)cc1 | C-C-n1:c:n:c2:c(-N-c3:c:c:c:c(-[Cl;H0;D1;+0:1]):c:3):n:c(-[NH;D2;+0:2]-[C@@H;D3;+0:3](-[C:4]-[C:5])-[C:6]-[C:7]):n:c:2:1.N-[C@@H]1-C-C-C-[C@H](-N-[c;H0;D3;+0:8]2:[#7;a:9]:[c:10]:[c:11]3:[#7;a:12]:[c:13]:[#7;a:14](-[C:15]):[c:16]:3:[#7;a:17]:2)-C-1>>[C:15]-[#7;a:14]1:[c:13]:[#7;a:12]:[c:11]2:[c:10]:[#7;a:9]:[c;H0;D3;+0:... | null | [] | null | null | null | null | Analogously to Example 1, 2-(trans-3-amino-cyclohexyl-amino)-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine; FAB-MS: (M+H)+=386; HPLC: tret (grad20/2)=9.32 minutes, and 2-(cis-3-amino-cyclohexyl-amino)-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine; FAB-MS: (M+H)+=386; HPLC: tret (grad20/2)=9.19 minutes, are obtained from 30... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Secondary amine.Secondary amine.Secondary amine | Aromatic halide.Primary amine | c1ccccc1.c1ncc2nc[nH]c2n1.C1CCCCC1.c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1.C1CCCCC1 | Other | null | null | null | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@H]3CCC[C@@H](N)C3)nc21.CCn1cnc2c(Nc3cccc(Cl)c3)nc(N[C@H]3CCC[C@H](N)C3)nc21>>CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.NC1CCCC(N)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ef4aabf87cb4b2fa299fa5c108e3467 | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@@H]3C(N)=O)nc21>>CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@@H]3CN)nc21 | C1CCOC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1CCOC1.C(N)(=O)[C@@H]1N(CCC1)C1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>NC[C@@H]1N(CCC1)C1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl | O=[C:23]([C@@H:22]1[N:18]([c:17]2[n:16][c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]3)[c:6]3[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:26]3[n:25]2)[CH2:19][CH2:20][CH2:21]1)[NH2:24]>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]3)[n:16][c:17]([N:18]3[CH2:19][... | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@@H]3C(N)=O)nc21 | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@@H]3CN)nc21 | null | null | O | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | c1ccc(Nc2nc(N3CCCC3)nc3[nH]cnc23)cc1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[C:3](-[C:4])-[#7:5](-[c:6](:[#7;a:7]):[#7;a:8])-[C:9]>>[#7;a:7]:[c:6](-[#7:5](-[C:9])-[C:3](-[CH2;D2;+0:1]-[N;D1;H2:2])-[C:4]):[#7;a:8] | null | [] | null | null | null | null | A suspension of 56 mg (1.47 mmol) of LiAlH4 in 2 ml of abs. THF is added to a suspension of 150 mg of 2-[(R)-(−)-2-carbamoyl-pyrrolidin-1-yl]-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine (cf. Example 45) in 10 ml of abs. THF and the mixture is stirred at 80° C. for 22 h. After further addition of 56 mg of LiAlH4, the mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | c1ccccc1.c1ncc2nc[nH]c2n1.C1CC[NH]C1 | Other | O | null | null | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@@H]3C(N)=O)nc21>O>CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@@H]3CN)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb7bddbd8fa94af28adb4dd86f8741bb | CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.Nc1ccccc1N>>CCn1cnc2c(Nc3cccc(Cl)c3)nc(Nc3ccccc3N)nc21 | ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl.C1(=C(C=CC=C1)N)N.C1(=C(C=CC=C1)N)N>>NC1=C(C=CC=C1)NC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl | Cl[c:17]1[n:16][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]2)[c:6]2[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:27]2[n:26]1.[NH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[NH2:25]>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]3)[n:16][c:17]([NH:18][c:19]3[c... | CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.Nc1ccccc1N | CCn1cnc2c(Nc3cccc(Cl)c3)nc(Nc3ccccc3N)nc21 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | d29b1bab4afefe0db66c5d87d4d37a8be0c49cfdb04c6c8844dee54b4b5d425a | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc(Nc3ccccc3)c3nc[nH]c3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:8]-[#7;a:7]1:[c:6]:[#7;a:5]:[c:4]2:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]):[#7;a:10]:[c:9]:1:2 | null | [] | null | null | null | null | Analogously to Example 1, 308 mg (1.0 mmol) of 2-chloro-6-(3-chloro-phenyl-amino)-9-ethyl-9H-purine [described in Stage 1.2] and 324 mg (3 mmol) of 1,2-phenylenediamine are reacted in 10 ml of n-butanol in a glass pressure reactor for 19 h at 140° C., followed by addition of 486 mg (4.5 mmol) of 1,2-phenylenediamine an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1.c1ccccc1 | HCl | C(CCC)O | null | null | CCn1cnc2c(Nc3cccc(Cl)c3)nc(Cl)nc21.Nc1ccccc1N>C(CCC)O>CCn1cnc2c(Nc3cccc(Cl)c3)nc(Nc3ccccc3N)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-badd9b1876bd40f3979aa10f70c6a780 | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@H]3C(N)=O)nc21>>CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@H]3CN)nc21 | ClC=1C=C(C=CC1)NC1=C2N=CN(C2=NC(=N1)N1[C@@H](CCC1)C(N)=O)CC.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>NC[C@H]1N(CCC1)C1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)Cl | O=[C:23]([C@H:22]1[N:18]([c:17]2[n:16][c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]3)[c:6]3[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:26]3[n:25]2)[CH2:19][CH2:20][CH2:21]1)[NH2:24]>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]3)[n:16][c:17]([N:18]3[CH2:19][C... | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@H]3C(N)=O)nc21 | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@H]3CN)nc21 | null | null | C1CCOC1 | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | c1ccc(Nc2nc(N3CCCC3)nc3[nH]cnc23)cc1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[C:3](-[C:4])-[#7:5](-[c:6](:[#7;a:7]):[#7;a:8])-[C:9]>>[#7;a:7]:[c:6](-[#7:5](-[C:9])-[C:3](-[CH2;D2;+0:1]-[N;D1;H2:2])-[C:4]):[#7;a:8] | null | [] | null | null | null | null | A suspension of 230 mg (6.07 mmol) of LiAlH4 in 5 ml of abs. THF is added dropwise to a suspension of 600 mg (1.6 mmol) of 6-(3-chloro-phenyl-amino)-9-ethyl-[(S)-2-carbamoyl-pyrrolidin-1-yl]-9H-purine (cf. Example 64) in 15 ml of abs. THF, and the mixture is stirred at 80° C. for 24 h. Thereafter, 10 ml of ice/water ar... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | c1ccccc1.c1ncc2nc[nH]c2n1.C1CC[NH]C1 | Other | C1CCOC1 | null | null | CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@H]3C(N)=O)nc21>C1CCOC1>CCn1cnc2c(Nc3cccc(Cl)c3)nc(N3CCC[C@H]3CN)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91c9829968e24bb3a557a7a85a8195ae | CCn1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21>>CCn1cnc2c(Nc3cccc(F)c3)nc(NCCN)nc21.Cl | ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)F>>Cl.NCCNC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)F | [CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]3)[n:16][c:17]([Cl:24])[n:18][c:23]12>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]3)[n:16][c:17]([NH:18][CH2:19][CH2:20][NH2:21])[n:22][c:23]12.[ClH:24] | CCn1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21 | CCn1cnc2c(Nc3cccc(F)c3)nc(NCCN)nc21.Cl | null | null | C(C)(=O)OCC.C(CN)N | Miscellaneous | OtherReaction | 1043a04994a654b1a506ef92e49aca79e9522ad88263e474d87180fb68088057 | cadfe368d317d1eccff1660dc26b2c6a5933ff2f7361568a6180cb3824bc4f92 | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | [#7:1]-[c:2]1:[#7;a:3]:[c;H0;D3;+0:4](-[Cl;H0;D1;+0:5]):[n;H0;D2;+0:6]:[c;H0;D3;+0:7]2:[#7;a:8](-[C:9]):[c:10]:[#7;a:11]:[c:12]:1:2>>[#7:1]-[c:2]1:[#7;a:3]:[c;H0;D3;+0:4](-[NH;D2;+0:6]-[C:13]-[C:14]):[#7;a:15]:[c;H0;D3;+0:7]2:[#7;a:8](-[C:9]):[c:10]:[#7;a:11]:[c:12]:1:2.[ClH;D0;+0:5] | null | [] | null | null | null | null | 0.2 g (0.62 mmol) of 2-chloro-9-ethyl-6-(3-fluoro-phenyl-amino)-9H-purine is stirred in 2.5 ml of ethylenediamine at 75° C. for 3 h, and the mixture is allowed to cool and is diluted with ethyl acetate. The organic phase is washed with water, separated off and dried over sodium sulfate. After removal of the solvent, th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine.Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | Other | C(C)(=O)OCC.C(CN)N | null | null | CCn1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21>C(C)(=O)OCC.C(CN)N>CCn1cnc2c(Nc3cccc(F)c3)nc(NCCN)nc21.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b882d8a91c4f492da930efef14481420 | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(F)c1>>Fc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | C(C)(C)O.ClC1=NC(=C2NC=NC2=N1)Cl.FC=1C=C(N)C=CC1.CN(C)C=O>>ClC1=NC(=C2NC=NC2=N1)NC1=CC(=CC=C1)F | Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][c:13]2[n:14][cH:15][nH:16][c:17]12.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:18]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([Cl:11])[n:12][c:13]3[n:14][cH:15][nH:16][c:17]23)[cH:18]1 | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(F)c1 | Fc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | cc3f24fffcaf974b16f52ce977955348405e93cb36102dc19c5151f40ad54b4f | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3nc[nH]c23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | null | [] | null | null | null | null | 2 g (10.58 mmol) of 2,6-dichloro-purine and 5.9 g (52.9 mmol) of 3-fluoro-aniline (Fluka, Buchs, Switzerland) are stirred in 60 ml of n-butanol and 3 ml of DMF at 80° C. for 5 h. The cooled reaction mixture is treated with isopropanol and the crystal mass which has precipitated out is filtered off and dried. 2-Chloro-6... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | C(CCC)O | null | null | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(F)c1>C(CCC)O>Fc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-598185acff304cc3a86a995c03c157bb | CCI.Fc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1>>CCn1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21 | CN(C)C=O.ClC1=NC(=C2NC=NC2=N1)NC1=CC(=CC=C1)F.C([O-])([O-])=O.[Cs+].[Cs+].ICC>>ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)F | I[CH2:2][CH3:1].[n:3]1[cH:4][nH:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]3)[n:16][c:17]([Cl:18])[n:19][c:20]12>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]3)[n:16][c:17]([Cl:18])[n:19][c:20]12 | CCI.Fc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | CCn1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21 | null | null | O1CCOCC1.O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[#7:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[n;H0;D2;+0:9]:[c:10]:[nH;D2;+0:11]:[c:12]:2:1>>[#7:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[c:12]:1:[n;H0;D2;+0:11]:[c:10]:[n;H0;D3;+0:9]:2-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | null | null | 1 g (3.47 mmol) of 2-chloro-6-(3-fluoro-phenyl-amino)-purine, 1.8 g (5.5 mmol) of caesium carbonate and 2.3 ml (27.8 mmol) of iodoethane are stirred in 14 ml of a dioxane/water mixture (4:3) and 12 ml of DMF at RT for 16 h. Thereafter, the reaction mixture is diluted with ethyl acetate and the organic phase is washed w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HI | O1CCOCC1.O.C(C)(=O)OCC | null | null | CCI.Fc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1>O1CCOCC1.O.C(C)(=O)OCC>CCn1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-65634670e10c47c68865d9e95be13558 | CCn1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21.NCCO>>CCn1cnc2c(Nc3cccc(F)c3)nc(NCCO)nc21 | ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)F.C(O)CN>>OCCNC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)F | Cl[c:17]1[n:16][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]2)[c:6]2[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:23]2[n:22]1.[NH2:18][CH2:19][CH2:20][OH:21]>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]3)[n:16][c:17]([NH:18][CH2:19][CH2:20][OH:21])[n:22][c:23]12 | CCn1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21.NCCO | CCn1cnc2c(Nc3cccc(F)c3)nc(NCCO)nc21 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d29b1bab4afefe0db66c5d87d4d37a8be0c49cfdb04c6c8844dee54b4b5d425a | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1 | null | [] | null | null | null | null | 0.2 g (0.62 mmol) of 2-chloro-9-ethyl-6-(3-fluoro-phenyl-amino)-9H-purine (prepared according to Stage 90.2) is stirred in 1 ml of ethanolamine at 150° C. for 3 h, and the mixture is allowed to cool and is diluted with ethyl acetate. The organic phase is washed with water, separated off and dried over sodium sulfate. O... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | C(C)(=O)OCC | null | null | CCn1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21.NCCO>C(C)(=O)OCC>CCn1cnc2c(Nc3cccc(F)c3)nc(NCCO)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc726c1fc81845349676ec0b25429a73 | CC(C)n1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21.NCCO>>CC(C)n1cnc2c(Nc3cccc(F)c3)nc(NCCO)nc21 | ClC1=NC(=C2N=CN(C2=N1)C(C)C)NC1=CC(=CC=C1)F.C(O)CN>>FC=1C=C(C=CC1)NC1=C2N=CN(C2=NC(=N1)NCCO)C(C)C | Cl[c:18]1[n:17][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]2)[c:7]2[n:6][cH:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:24]2[n:23]1.[NH2:19][CH2:20][CH2:21][OH:22]>>[CH3:1][CH:2]([CH3:3])[n:4]1[cH:5][n:6][c:7]2[c:8]([NH:9][c:10]3[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]3)[n:17][c:18]([NH:19][CH2:20][CH2:21][OH:... | CC(C)n1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21.NCCO | CC(C)n1cnc2c(Nc3cccc(F)c3)nc(NCCO)nc21 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d29b1bab4afefe0db66c5d87d4d37a8be0c49cfdb04c6c8844dee54b4b5d425a | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7](-[C:8]):[c:9]:2:[#7;a:10]:1 | null | [] | null | null | null | null | 0.2 g (0.63 mmol) of 2-chloro-9-isopropyl-6-(3-fluoro-phenyl-amino)-9H-purine (prepared according to Stage 91.1) is stirred in 1 ml of ethanolamine at 150° C. for 5 h, and the mixture is then allowed to cool and is diluted with ethyl acetate. The organic phase is washed with water and dried over sodium sulfate. On conc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | C(C)(=O)OCC | null | null | CC(C)n1cnc2c(Nc3cccc(F)c3)nc(Cl)nc21.NCCO>C(C)(=O)OCC>CC(C)n1cnc2c(Nc3cccc(F)c3)nc(NCCO)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a04becea6d8048c8891d2c8f7011ff40 | CCn1cnc2c(Nc3cccc(C#N)c3)nc(Cl)nc21>>CCn1cnc2c(Nc3cccc(C#N)c3)nc(NCCN)nc21.Cl | ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)C#N>>Cl.NCCNC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)C#N | [CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16]3)[n:17][c:18]([Cl:25])[n:19][c:24]12>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16]3)[n:17][c:18]([NH:19][CH2:20][CH2:21][NH2:22])[n:23][c:24]12.[ClH:25] | CCn1cnc2c(Nc3cccc(C#N)c3)nc(Cl)nc21 | CCn1cnc2c(Nc3cccc(C#N)c3)nc(NCCN)nc21.Cl | null | null | C(C)(=O)OCC.C(CN)N | Miscellaneous | OtherReaction | 1043a04994a654b1a506ef92e49aca79e9522ad88263e474d87180fb68088057 | cadfe368d317d1eccff1660dc26b2c6a5933ff2f7361568a6180cb3824bc4f92 | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | [#7:1]-[c:2]1:[#7;a:3]:[c;H0;D3;+0:4](-[Cl;H0;D1;+0:5]):[n;H0;D2;+0:6]:[c;H0;D3;+0:7]2:[#7;a:8](-[C:9]):[c:10]:[#7;a:11]:[c:12]:1:2>>[#7:1]-[c:2]1:[#7;a:3]:[c;H0;D3;+0:4](-[NH;D2;+0:6]-[C:13]-[C:14]):[#7;a:15]:[c;H0;D3;+0:7]2:[#7;a:8](-[C:9]):[c:10]:[#7;a:11]:[c:12]:1:2.[ClH;D0;+0:5] | null | [] | null | null | null | null | 0.2 g (0.6 mmol) of 2-chloro-9-ethyl-6-(3-cyano-phenyl-amino)-9H-purine is stirred in 2.5 ml of ethylenediamine at 75° C. for 3.5 h, and the mixture is allowed to cool and is diluted with ethyl acetate. The organic phase is washed with water, separated off and dried over sodium sulfate. After removal of the solvent, th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine.Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | Other | C(C)(=O)OCC.C(CN)N | null | null | CCn1cnc2c(Nc3cccc(C#N)c3)nc(Cl)nc21>C(C)(=O)OCC.C(CN)N>CCn1cnc2c(Nc3cccc(C#N)c3)nc(NCCN)nc21.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b125fb03c3bd4ad09878ca15f280ae05 | CCI.N#Cc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1>>CCn1cnc2c(Nc3cccc(C#N)c3)nc(Cl)nc21 | ClC1=NC(=C2NC=NC2=N1)NC1=CC(=CC=C1)C#N.C([O-])([O-])=O.[Cs+].[Cs+].ICC.O1CCOCC1>>ClC1=NC(=C2N=CN(C2=N1)CC)NC1=CC(=CC=C1)C#N | I[CH2:2][CH3:1].[n:3]1[cH:4][nH:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16]3)[n:17][c:18]([Cl:19])[n:20][c:21]12>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]#[N:15])[cH:16]3)[n:17][c:18]([Cl:19])[n:20][c:21]12 | CCI.N#Cc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | CCn1cnc2c(Nc3cccc(C#N)c3)nc(Cl)nc21 | null | null | O.C(C)(=O)OCC.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 453c185c7ca08f316f04eb7765c2f018ec3b56836368f5fa1ad0e7a49cf724d8 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[#7:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[n;H0;D2;+0:9]:[c:10]:[nH;D2;+0:11]:[c:12]:2:1>>[#7:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]2:[c:12]:1:[n;H0;D2;+0:11]:[c:10]:[n;H0;D3;+0:9]:2-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | null | null | 1.5 g (3.95 mmol) of 2-chloro-6-(3-cyano-phenyl-amino)-purine, 2.1 g (6.3 mmol) of caesium carbonate and 2.6 ml (31.6 mmol) of iodoethane are stirred in 66 ml of a mixture comprising dioxane:water:DMF in a ratio of 1:2:3 at RT for 19 h. Thereafter, the reaction mixture is diluted with ethyl acetate and the organic phas... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HI | O.C(C)(=O)OCC.CN(C)C=O | null | null | CCI.N#Cc1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1>O.C(C)(=O)OCC.CN(C)C=O>CCn1cnc2c(Nc3cccc(C#N)c3)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c8bd4d0a66984a0e969d11562e64778e | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(C(F)(F)F)c1>>FC(F)(F)c1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | ClC1=NC(=C2NC=NC2=N1)Cl.CN(C)C=O.NC=1C=C(C=CC1)C(F)(F)F>>ClC1=NC(=C2NC=NC2=N1)NC1=CC(=CC=C1)C(F)(F)F | Cl[c:11]1[n:12][c:13]([Cl:14])[n:15][c:16]2[n:17][cH:18][nH:19][c:20]12.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:21]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][c:13]([Cl:14])[n:15][c:16]3[n:17][cH:18][nH:19][c:20]23)[cH:21]1 | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(C(F)(F)F)c1 | FC(F)(F)c1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | cc3f24fffcaf974b16f52ce977955348405e93cb36102dc19c5151f40ad54b4f | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3nc[nH]c23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | null | [] | null | null | null | null | 1.9 g (10 mmol) of 2,6-dichloro-purine are stirred in 60 ml of butanol and 3 ml of DMF with 8.05 g (50 mmol) of 3-amino-benzotrifluoride at 60° C. for 3 h. On cooling, 2-chloro-6-(3-trifluoromethyl-phenyl-amino)-purine is obtained as a crystalline mass. This is filtered off and dried in vacuo; m.p. 248° C.; FAB-MS: (M+... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | C(CCC)O | null | null | Clc1nc(Cl)c2[nH]cnc2n1.Nc1cccc(C(F)(F)F)c1>C(CCC)O>FC(F)(F)c1cccc(Nc2nc(Cl)nc3nc[nH]c23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aafe9cd2ac154742ae3af14c87c79dc2 | CC(C)I.Fc1ccc(Nc2nc(Cl)nc3nc[nH]c23)cc1>>CC(C)n1cnc2c(Nc3ccc(F)cc3)nc(Cl)nc21 | ClC1=NC(=C2NC=NC2=N1)NC1=CC=C(C=C1)F.C([O-])([O-])=O.[Cs+].[Cs+].C(C)(C)I.O1CCOCC1>>ClC1=NC(=C2N=CN(C2=N1)C(C)C)NC1=CC=C(C=C1)F | I[CH:2]([CH3:1])[CH3:3].[n:4]1[cH:5][nH:6][c:7]2[c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]3)[n:17][c:18]([Cl:19])[n:20][c:21]12>>[CH3:1][CH:2]([CH3:3])[n:4]1[cH:5][n:6][c:7]2[c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]3)[n:17][c:18]([Cl:19])[n:20][c:21]12 | CC(C)I.Fc1ccc(Nc2nc(Cl)nc3nc[nH]c23)cc1 | CC(C)n1cnc2c(Nc3ccc(F)cc3)nc(Cl)nc21 | null | null | O.C(C)(=O)OCC.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 945badfe62d08793a7a77e1f7911213401b8f39f60cb6469278838440322098e | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[#7:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[n;H0;D2;+0:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:1>>[#7:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:13]:1:[n;H0;D2;+0:12]:[c:11]:[n;H0;D3;+0:10]:2-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | null | [] | null | null | null | null | A mixture comprising 1 g (3.3 mmol) of 2-chloro-6-(4-fluoro-phenyl-amino)-purine, 2.1 g (6.6 mmol) of caesium carbonate and 2 ml of isopropyl iodide is stirred in 32 ml of a mixture comprising dioxane, water and DMF in a ratio of 2:3:7 at 100° C. for 20 h. Thereafter, the reaction mixture is diluted with ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HI | O.C(C)(=O)OCC.CN(C)C=O | null | null | CC(C)I.Fc1ccc(Nc2nc(Cl)nc3nc[nH]c23)cc1>O.C(C)(=O)OCC.CN(C)C=O>CC(C)n1cnc2c(Nc3ccc(F)cc3)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d522069b2134617b6bccb18014497dc | Clc1nc(Cl)c2[nH]cnc2n1.Nc1ccc([N+](=O)[O-])cc1>>O=[N+]([O-])c1ccc(Nc2nc(Cl)nc3nc[nH]c23)cc1 | ClC1=NC(=C2NC=NC2=N1)Cl.[N+](=O)([O-])C1=CC=C(N)C=C1>>ClC1=NC(=C2NC=NC2=N1)NC1=CC=C(C=C1)[N+](=O)[O-] | Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][c:14]2[n:15][cH:16][nH:17][c:18]12.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:19][cH:20]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([Cl:12])[n:13][c:14]3[n:15][cH:16][nH:17][c:18]23)[cH:19][cH:20]1 | Clc1nc(Cl)c2[nH]cnc2n1.Nc1ccc([N+](=O)[O-])cc1 | O=[N+]([O-])c1ccc(Nc2nc(Cl)nc3nc[nH]c23)cc1 | null | null | CN(C)C=O.C(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | cc3f24fffcaf974b16f52ce977955348405e93cb36102dc19c5151f40ad54b4f | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncnc3nc[nH]c23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | null | [] | null | null | null | null | 1.9 g (10 mmol) of 2,6-dichloro-purine are stirred in 40 ml of DMF/n-butanol (1:3) with 4.1 g (30 mmol) of 4-nitro-aniline at 130° C. for 24 h and the crystal mass which precipitates out on cooling is filtered off and dried in vacuo. 2-Chloro-6-(4-nitro-phenyl-amino)-purine is obtained; m.p.>270° C.; FAB-MS: (M+H)+=291... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | CN(C)C=O.C(CCC)O | null | null | Clc1nc(Cl)c2[nH]cnc2n1.Nc1ccc([N+](=O)[O-])cc1>CN(C)C=O.C(CCC)O>O=[N+]([O-])c1ccc(Nc2nc(Cl)nc3nc[nH]c23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-11beb6d00d1b42dca5407a695e214e9e | CC(C)I.O=[N+]([O-])c1ccc(Nc2nc(Cl)nc3nc[nH]c23)cc1>>CC(C)n1cnc2c(Nc3ccc([N+](=O)[O-])cc3)nc(Cl)nc21 | ClC1=NC(=C2NC=NC2=N1)NC1=CC=C(C=C1)[N+](=O)[O-].C([O-])([O-])=O.[Cs+].[Cs+].C(C)(C)I.O1CCOCC1>>ClC1=NC(=C2N=CN(C2=N1)C(C)C)NC1=CC=C(C=C1)[N+](=O)[O-] | I[CH:2]([CH3:1])[CH3:3].[n:4]1[cH:5][nH:6][c:7]2[c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]3)[n:19][c:20]([Cl:21])[n:22][c:23]12>>[CH3:1][CH:2]([CH3:3])[n:4]1[cH:5][n:6][c:7]2[c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]3)[n:19][c:20]([Cl:21])[n:22][c:... | CC(C)I.O=[N+]([O-])c1ccc(Nc2nc(Cl)nc3nc[nH]c23)cc1 | CC(C)n1cnc2c(Nc3ccc([N+](=O)[O-])cc3)nc(Cl)nc21 | null | null | O.C(C)(=O)OCC.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 945badfe62d08793a7a77e1f7911213401b8f39f60cb6469278838440322098e | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[#7:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[n;H0;D2;+0:10]:[c:11]:[nH;D2;+0:12]:[c:13]:2:1>>[#7:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]2:[c:13]:1:[n;H0;D2;+0:12]:[c:11]:[n;H0;D3;+0:10]:2-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | null | [] | null | null | null | null | A mixture comprising 0.87 g (3 mmol) of 2-chloro-6-(4-nitro-phenyl-amino)-purine, 0.15 g (4.5 mmol) of caesium carbonate and 1.8 ml (18 mmol) of isopropyl iodide is stirred in 22 ml of a mixture comprising dioxane:water:DMF in a ratio of 2:1:4 at 100° C. for 48 h. Thereafter, the reaction mixture is diluted with ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HI | O.C(C)(=O)OCC.CN(C)C=O | null | null | CC(C)I.O=[N+]([O-])c1ccc(Nc2nc(Cl)nc3nc[nH]c23)cc1>O.C(C)(=O)OCC.CN(C)C=O>CC(C)n1cnc2c(Nc3ccc([N+](=O)[O-])cc3)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-070bedf9f90b4842b0782e22b1a25f04 | CCn1cnc2c(Nc3ccc(NC(=O)OCc4ccccc4)cc3)nc(NCCO)nc21>>CCn1cnc2c(Nc3ccc(N)cc3)nc(NCCO)nc21 | OCCNC1=NC(=C2N=CN(C2=N1)CC)NC1=CC=C(C=C1)NC(=O)OCC1=CC=CC=C1>>NC1=CC=C(C=C1)NC1=C2N=CN(C2=NC(=N1)NCCO)CC | O=C(OCc1ccccc1)[NH:13][c:12]1[cH:11][cH:10][c:9]([NH:8][c:7]2[c:6]3[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:23]3[n:22][c:17]([NH:18][CH2:19][CH2:20][OH:21])[n:16]2)[cH:15][cH:14]1>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]3)[n:16][c:17]([NH:18][CH2:19][CH2:20][OH:21])... | CCn1cnc2c(Nc3ccc(NC(=O)OCc4ccccc4)cc3)nc(NCCO)nc21 | CCn1cnc2c(Nc3ccc(N)cc3)nc(NCCO)nc21 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccc(Nc2ncnc3[nH]cnc23)cc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 0.45 g (1 mmol) of 2-(2-hydroxy-ethyl-amino)-6-(4-benzyloxycarbonylamino-phenyl-amino)-9-ethyl-9H-purine (prepared according to Example 107) are hydrogenated with 0.1 g of 10% Pd/C in 8 ml of methanol at RT for 5 h. The catalyst is filtered off, the residue on the filter is rinsed with dioxane/water (95:5) and the solv... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | [Pd].CO | null | null | CCn1cnc2c(Nc3ccc(NC(=O)OCc4ccccc4)cc3)nc(NCCO)nc21>[Pd].CO>CCn1cnc2c(Nc3ccc(N)cc3)nc(NCCO)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-070783df20e7489689e0498417256699 | CCn1cnc2c(Nc3ccc(N)cc3)nc(NCCO)nc21.O=C(O)c1cccc(Cl)c1>>CCn1cnc2c(Nc3ccc(NC(=O)c4cccc(Cl)c4)cc3)nc(NCCO)nc21 | NC1=CC=C(C=C1)NC1=C2N=CN(C2=NC(=N1)NCCO)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.ON1N=NC2=C1C=CC=C2.C(C)(C)NC(C)C.ClC=1C=C(C(=O)O)C=CC1>>ClC=1C=C(C(=O)NC2=CC=C(C=C2)NC2=C3N=CN(C3=NC(=N2)NCCO)CC)C=CC1 | [CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][c:12]([NH2:13])[cH:23][cH:24]3)[n:25][c:26]([NH:27][CH2:28][CH2:29][OH:30])[n:31][c:32]12.O[C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1>>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]([NH:8][c:9]3[cH:10][cH:11][c:12]([NH:13][C:14](=... | CCn1cnc2c(Nc3ccc(N)cc3)nc(NCCO)nc21.O=C(O)c1cccc(Cl)c1 | CCn1cnc2c(Nc3ccc(NC(=O)c4cccc(Cl)c4)cc3)nc(NCCO)nc21 | null | null | CC(=O)N(C)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccc(Nc2ncnc3[nH]cnc23)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 30 | MINUTE | 62 mg (0.2 mmol) of 6-(4-amino-phenyl-amino)-9-ethyl-2-(2-hydroxy-ethyl-amino)-9H-purine (prepared according to Example 108), 0.18 g (0.4 mmol) of (benzotriazol-1-yloxy)-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP), 54 mg (0.4 mmol) of 1-hydroxybenzotriazole (HOBT) and 68 μl of diisopropylamine are stirre... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | CC(=O)N(C)C.C(C)(=O)OCC | null | 0.5 | CCn1cnc2c(Nc3ccc(N)cc3)nc(NCCO)nc21.O=C(O)c1cccc(Cl)c1>CC(=O)N(C)C.C(C)(=O)OCC>CCn1cnc2c(Nc3ccc(NC(=O)c4cccc(Cl)c4)cc3)nc(NCCO)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9a8619cf766f4e9b8699861270e51844 | O=[N+]([O-])c1ccc(Cl)cc1.[F-]>>O=[N+]([O-])c1ccc(F)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)Cl.[F-].[K+]>>[N+](=O)([O-])C1=CC=C(C=C1)F | Cl[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:10][cH:9]1.[F-:8]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1 | O=[N+]([O-])c1ccc(Cl)cc1.[F-] | O=[N+]([O-])c1ccc(F)cc1 | null | null | CS(=O)C | Functional Group Interconversion | OtherReaction | b78ae091f9ea90a571f2e011b77da2eac9952c7b340e2e0185fb0decffadd167 | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[F-;H0;D0:6]>>[F;H0;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 96 | [{"value": 96.0, "product": "[N+](=O)([O-])C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | 170 | CELSIUS | 5 | HOUR | 157 g of 4-nitrochlorobenzene, 200 g of dimethylsulfoxide, 62.7 g of potassium fluoride, and 2.49 g of (N,N-dimethylimidazolidino)tetramethyl-guanidinium chloride were placed in a 1 liter four-neck flask equipped with thermometer, anchor stirrer, and reflux condenser with bubble counter. The mixture was heated with sti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CS(=O)C | 170 | 5 | O=[N+]([O-])c1ccc(Cl)cc1.[F-]>CS(=O)C>O=[N+]([O-])c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f9b2d5d03764f1a87b8b010a3ba32b6 | N#Cc1ccc(Cl)c(Cl)c1.[F-]>>N#Cc1ccc(F)c(Cl)c1 | ClC=1C=C(C#N)C=CC1Cl.[F-].[K+]>>ClC=1C=C(C#N)C=CC1F | Cl[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:10][c:8]1[Cl:9].[F-:7]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([Cl:9])[cH:10]1 | N#Cc1ccc(Cl)c(Cl)c1.[F-] | N#Cc1ccc(F)c(Cl)c1 | null | null | CS(=O)C | Functional Group Interconversion | OtherReaction | b78ae091f9ea90a571f2e011b77da2eac9952c7b340e2e0185fb0decffadd167 | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[F-;H0;D0:7]>>[Cl;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[F;H0;D1;+0:7]):[c:2]:[c:3] | 92 | [{"value": 92.0, "product": "ClC=1C=C(C#N)C=CC1F", "details": "PERCENTYIELD", "is_desired": false}] | 170 | CELSIUS | null | null | 172 g of 3,4-dichlorobenzonitrile, 200 g of dimethylsulfoxide, 69.6 g of potassium fluoride, and 3.95 g of (N,N-dimethylimidazolidino)tris-(diethylamino)phosphazenium chloride were placed in a 1 liter four-neck flask equipped with anchor stirrer, thermometer, and reflux condenser with bubble counter. The mixture was th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CS(=O)C | 170 | null | N#Cc1ccc(Cl)c(Cl)c1.[F-]>CS(=O)C>N#Cc1ccc(F)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86800bf9397e44b882523bdaca98c2ce | N#Cc1ccc(Cl)cc1.[F-]>>N#Cc1ccc(F)cc1 | ClC1=CC=C(C#N)C=C1.[F-].[K+]>>FC1=CC=C(C#N)C=C1 | Cl[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:9][cH:8]1.[F-:7]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1 | N#Cc1ccc(Cl)cc1.[F-] | N#Cc1ccc(F)cc1 | null | null | CS(=O)C | Functional Group Interconversion | OtherReaction | b78ae091f9ea90a571f2e011b77da2eac9952c7b340e2e0185fb0decffadd167 | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[F-;H0;D0:6]>>[F;H0;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 75 | [{"value": 75.0, "product": "FC1=CC=C(C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | 200 g of 4-chlorobenzonitrile, 101.4 g of potassium fluoride, 25 g of dimethyl sulfoxide, and 5.60 g of (N,N-dimethylimidazolidino)tetramethyl-guanidinium chloride were placed in a 1 liter 4-neck flask equipped with anchor stirrer, thermometer, and reflux condenser with bubble counter. The mixture was then heated with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CS(=O)C | 180 | null | N#Cc1ccc(Cl)cc1.[F-]>CS(=O)C>N#Cc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3478ddd948db4d8dac58867c45716e85 | CCC(C(=O)OC(C)(C)C)[C@@H](N)O>>CC[C@](N)(C=O)C(=O)OC(C)(C)C | C(O)([O-])=O.[Na+].C(=O)(OC(C)(C)C)C([C@H](O)N)CC.CC1(CCCC(N1[O])(C)C)C.[Br-].[Na+]>>C(C)(C)(C)OC(=O)[C@@](C=O)(CC)N | [CH3:1][CH2:2][CH:3]([C@@H:5]([NH2:4])[OH:6])[C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13]>>[CH3:1][CH2:2][C@:3]([NH2:4])([CH:5]=[O:6])[C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13] | CCC(C(=O)OC(C)(C)C)[C@@H](N)O | CC[C@](N)(C=O)C(=O)OC(C)(C)C | null | null | ClCCl.O | Miscellaneous | OtherReaction | 845859823695c11e5aa1307611e5bf17f477ba7c61d37586ec99baeb79e1cae8 | 9681f627bb213daf9f596ff92114fc91a27e1754b2a691cb1a22b5ad6374db6b | null | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[C:9]-[C;D1;H3:10])-[C@@H;D3;+0:11](-[NH2;D1;+0:12])-[OH;D1;+0:13]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[C@;H0;D4;+0:8](-[NH2;D1;+0:12])(-[C:9]-[C;D1;H3:10])-[CH;D2;+0:11]=[O;H0;D1;+0:13] | 77 | [{"value": 77.0, "product": "C(C)(C)(C)OC(=O)[C@@](C=O)(CC)N", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a solution of (S)-2-Boc-aminobutanol (50 g; 264 mmol) in dichloromethane (500 mL) and water (350 mL) were added at 20° C. TEMPO (0.01 eq), sodium bromide (1 eq) and sodium hydrogencarbonate (3 eq). The reaction mixture was stirred at 0° C. and diluted bleach (1.3 eq, 450 mL) was added over 40 min. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Primary amine | Aldehyde.Ester.Primary amine | null | null | null | null | ClCCl.O | 0 | null | CCC(C(=O)OC(C)(C)C)[C@@H](N)O>ClCCl.O>CC[C@](N)(C=O)C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f7f3745dfef454bbb9619689f26fde3 | CC[C@@H](C=O)NC(=O)OC(C)(C)C.c1cnc2ncoc2c1>>CC(NC(=O)OC(C)(C)C)[C@H](O)c1nc2ncccc2o1 | C(C)(C)(C)OC(=O)N[C@H](C=O)CC.O1C=NC2=NC=CC=C21.C(C)(C)[Mg]Cl>>C(C)(C)(C)OC(=O)NC([C@H](O)C=1OC=2C(=NC=CC2)N1)C | C[CH2:1][C@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH:11]=[O:12].[cH:13]1[n:14][c:15]2[n:16][cH:17][cH:18][cH:19][c:20]2[o:21]1>>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[C@H:11]([OH:12])[c:13]1[n:14][c:15]2[n:16][cH:17][cH:18][cH:19][c:20]2[o:21]1 | CC[C@@H](C=O)NC(=O)OC(C)(C)C.c1cnc2ncoc2c1 | CC(NC(=O)OC(C)(C)C)[C@H](O)c1nc2ncccc2o1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 07d54923a95553fd36ec9c72f903520c8bd61bc55106b3c0341331dea8813dd7 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1cnc2ncoc2c1 | C-[CH2;D2;+0:1]-[C@H;D3;+0:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[CH;D2;+0:11]=[O;H0;D1;+0:12].[#7;a:13]:[c:14]1:[#7;a:15]:[cH;D2;+0:16]:[#8;a:17]:[c:18]:1>>[#7;a:13]:[c:14]1:[#7;a:15]:[c;H0;D3;+0:16](-[C@@H;D3;+0:11](-[OH;D1;+0:12])-[CH;D3;+0:2](-[CH3;D1;+0:1])-[#7:3]-[C... | 43.5 | [{"value": 43.5, "product": "C(C)(C)(C)OC(=O)NC([C@H](O)C=1OC=2C(=NC=CC2)N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | In a clean roundbottom flask equipped with stir bar was placed oxazolo[4,5-b]pyridine (600 mg, 5 mmol) in 30 mL THF and the reaction mixture was cooled to 0° C. under N2 atmosphere. Isopropylmagnesium chloride (2M in THF, 2.5 ml, 5 mmol ) was added. After stirring for 1 h at 0° C., (S)-2-(tert-butoxycarbonyl)aminobutyr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1cnc2ncoc2c1 | c1cnc2ncoc2c1 | c1cnc2ncoc2c1 | Other | C1CCOC1 | 0 | 2 | CC[C@@H](C=O)NC(=O)OC(C)(C)C.c1cnc2ncoc2c1>C1CCOC1>CC(NC(=O)OC(C)(C)C)[C@H](O)c1nc2ncccc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b59c10a751ce41438cf1eb1cd9957f87 | CON(C)C(=O)C=Cc1ccccc1C(F)(F)F>>CC(=O)C=Cc1ccccc1C(F)(F)F | O.C[Li].CON(C(C=CC1=C(C=CC=C1)C(F)(F)F)=O)C.C(C)(=O)OCC>>FC(C1=C(C=CC=C1)C=CC(C)=O)(F)F | CON(C)[C:2](=[O:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[C:12]([F:13])([F:14])[F:15]>>[CH3:1][C:2](=[O:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[C:12]([F:13])([F:14])[F:15] | CON(C)C(=O)C=Cc1ccccc1C(F)(F)F | CC(=O)C=Cc1ccccc1C(F)(F)F | null | null | O1CCCC1.C(C)OCC | Functional Group Interconversion | OtherReaction | 0e1b501f4aadb0e84ffc93b33216cc37dfe617cb6c3e325779c58539a7f5c4e4 | af85307a4412ed48cedcfde84079732215472ffbe274bdc1dc12e9979d5c5e06 | c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5]>>[C;D1;H3:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5] | null | [] | -78 | CELSIUS | 2 | HOUR | 11 g of N-methoxy-N-methyl-3-(2-trifluoromethylphenyl)acrylamide are dissolved in 150 ml of dry tetrahydrofuran under a nitrogen atmosphere, cooled to −78° C. and treated dropwise with 36 ml of a 1.4N solution of methyllithium in diethyl ether in 10 minutes. The solution is subsequently furthermore stirred at −78° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | null | null | c1ccccc1 | HO- | O1CCCC1.C(C)OCC | -78 | 2 | CON(C)C(=O)C=Cc1ccccc1C(F)(F)F>O1CCCC1.C(C)OCC>CC(=O)C=Cc1ccccc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-456684d1f9d94974b8fd4c859ea625b7 | CC(=O)C=Cc1ccccc1C(F)(F)F>>CC(=O)CCc1ccccc1C(F)(F)F | FC(C1=C(C=CC=C1)C=CC(C)=O)(F)F>>FC(C1=C(C=CC=C1)CCC(C)=O)(F)F | [CH3:1][C:2](=[O:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[C:12]([F:13])([F:14])[F:15]>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[C:12]([F:13])([F:14])[F:15] | CC(=O)C=Cc1ccccc1C(F)(F)F | CC(=O)CCc1ccccc1C(F)(F)F | null | [Ni] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | 6556ac5f7a00160b061cac263043ece7ea2394a4006031c4a0b899c0ea4ccfef | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | c1ccccc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 7 | HOUR | 200 mg of Raney nickel are added to a solution of 2.05 g of 4-(2-trifluoromethylphenyl)-3-buten-2-one in 100 ml of ethyl acetate and the mixture is stirred under a hydrogen atmosphere and at standard pressure for 7 h. The mixture is subsequently filtered and the filtrate is evaporated under reduced pressure, whereby th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | null | null | c1ccccc1 | null | [Ni].C(C)(=O)OCC | null | 7 | CC(=O)C=Cc1ccccc1C(F)(F)F>[Ni].C(C)(=O)OCC>CC(=O)CCc1ccccc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f7bffe1edf2743528fa2a6dad5094133 | CC(=O)CCc1ccccc1C(F)(F)F.[C-]#N.[NH4+]>>CC(N)(C#N)CCc1ccccc1C(F)(F)F | FC(C1=C(C=CC=C1)CCC(C)=O)(F)F.[C-]#N.[Na+].[Cl-].[NH4+].C(C)O>>NC(C#N)(CCC1=C(C=CC=C1)C(F)(F)F)C | O=[C:2]([CH3:1])[CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[C:14]([F:15])([F:16])[F:17].[C-:4]#[N:5].[NH4+:3]>>[CH3:1][C:2]([NH2:3])([C:4]#[N:5])[CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[C:14]([F:15])([F:16])[F:17] | CC(=O)CCc1ccccc1C(F)(F)F.[C-]#N.[NH4+] | CC(N)(C#N)CCc1ccccc1C(F)(F)F | null | null | N | Functional Group Interconversion | OtherReaction | bf6fa2c5d28d887cff72f321ae6c28dd716e15f777677717232b44f5fabc2c13 | ff0d0afb9b8e2a9484b4ef42a76d567293aefe55b04928483f9f6aa47c49d0fc | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].[C-;H0;D1:5]#[N;D1;H0:6].[NH4+;D0:7]>>[C:4]-[C:3]-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[NH2;D1;+0:7])-[C;H0;D2;+0:5]#[N;D1;H0:6] | null | [] | null | null | 7 | HOUR | 1.5 g of 4-(2-trifluoromethylphenyl)butan-2-one, 0.41 g of sodium cyanide and 0.56 g of ammonium chloride are dissolved in 77 ml of a 2M solution of ammonia in ethanol and the mixture is stirred at ambient temperature for 7 h. The mixture is subsequently concentrated under reduced pressure and the residue is redissolve... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Nitrile.Primary amine | null | null | c1ccccc1 | HO- | N | null | 7 | CC(=O)CCc1ccccc1C(F)(F)F.[C-]#N.[NH4+]>N>CC(N)(C#N)CCc1ccccc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-645a5165719843d689ffc71ed8b89810 | COC(=O)Cc1ccccc1.NO>>O=C(Cc1ccccc1)NO | C1(=CC=CC=C1)CC(=O)OC.NO.[C-]#N.[K+].C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>ONC(CC1=CC=CC=C1)=O | CO[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[NH2:10][OH:11]>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[NH:10][OH:11] | COC(=O)Cc1ccccc1.NO | O=C(Cc1ccccc1)NO | null | null | CO.C1CCOC1 | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[O;D1;H1:6] | 77 | [{"value": 77.0, "product": "ONC(CC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To methyl phenylacetate (0.288 mL, 2.0 mmol) in THF:MeOH: 50% aqueous NH2OH (1:1:0.5, 2.5 mL) was added KCN (5 mg, 0.08 mmol, 4 mol %) and the mixture was stirred at ambient temperature. After 2 h the reaction was complete by HPLC. To the mixture was added saturated aqueous citric acid (25 mL) followed by extraction wi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CO.C1CCOC1 | null | 2 | COC(=O)Cc1ccccc1.NO>CO.C1CCOC1>O=C(Cc1ccccc1)NO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5b76ebe2f85c4797a129d4a766435beb | C1CCOC1.CO.NO.O=C(O)CC(O)(CC(=O)O)C(=O)O.[C-]#N>>O=C(CCc1ccccc1)NO | CO.NO.[C-]#N.[K+].C1CCOC1.C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>ONC(CCC1=CC=CC=C1)=O | O1[CH2:7][CH2:6][CH2:5][CH2:10]1.O[CH3:9].[NH2:11][OH:12].O=C(O)C[C:4](O)(C(=O)O)[CH2:3][C:8](O)=[O:1].N#[C-:2]>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][OH:12] | C1CCOC1.CO.NO.O=C(O)CC(O)(CC(=O)O)C(=O)O.[C-]#N | O=C(CCc1ccccc1)NO | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 0d5dd69e6d81e873abb2fccd603943032da24a916bed6f004bb3bea58713659d | b51f423e0e51af972c814ad1ed4e6678d885ef8cd82ab6ddb186ac8115ae9982 | c1ccccc1 | N#[C-;H0;D1:1].O-C(=O)-C-[C;H0;D4;+0:2](-O)(-[CH2;D2;+0:3]-[C;H0;D3;+0:4](-O)=[O;H0;D1;+0:5])-C(-O)=O.O-[CH3;D1;+0:6].O1-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-1.[NH2;D1;+0:11]-[O;D1;H1:12]>>[O;D1;H1:12]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;H0;D1;+0:5])-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[c;H0;D3;+0:8]1:[cH;D2;+... | 67 | [{"value": 67.0, "product": "ONC(CCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To methyl 3-phenyl propionate (0.328 g, 2.0 mmol) in THF:MeOH:50% aqueous NH2OH (1:1:0.5, 2.5 mL) was added KCN (5 mg, 0.08 mmol, 4 mol %)) and the mixture was stirred at ambient temperature. After 3 h the reaction was complete by HPLC and saturated aqueous citric acid was added (25 mL) followed by extraction with EtOA... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Carboxylic acid.Ether.Tertiary alcohol.Primary amine.Methanol | Secondary amide | C1CCOC1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | C1CCOC1.CO.NO.O=C(O)CC(O)(CC(=O)O)C(=O)O.[C-]#N>>O=C(CCc1ccccc1)NO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8694885db9e4896bdea2997d3fc339d | CC(=O)NCCCCCCNC(C)=O.NC(=O)c1ccccc1CO.NO>>NC(Cc1ccccc1)C(=O)O | COC1=CC=C(C=C1)S(=O)(=O)Cl.CC(=O)NCCCCCCNC(=O)C.N1CCCCC1.CN(C)C=O.NO.OCC1=C(C(=O)N)C=CC=C1.C1CCC(CC1)N=C=NC2CCCCC2.[C-]#N>>NC(CC1=CC=CC=C1)C(=O)O | CC(=O)NCCCCCCN[C:10]([CH3:2])=[O:11].NC(=O)[c:9]1[c:4]([CH2:3][OH:12])[cH:5][cH:6][cH:7][cH:8]1.O[NH2:1]>>[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12] | CC(=O)NCCCCCCNC(C)=O.NC(=O)c1ccccc1CO.NO | NC(Cc1ccccc1)C(=O)O | null | null | null | Acylation | OtherReaction | b944122eb7b859b899f4e6d0dce9dc4c10a4cf2041d2360b5d7b238a8f1fb742 | d4d0136d421c9e21f21f8069ce6ff0772a66a9aa273dcad32253cde33b66421a | c1ccccc1 | C-C(=O)-N-C-C-C-C-C-C-N-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].N-C(=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[CH2;D2;+0:8]-[OH;D1;+0:9]):[c:10].O-[NH2;D1;+0:11]>>[NH2;D1;+0:11]-[CH;D3;+0:2](-[CH2;D2;+0:8]-[c:7](:[c:10]):[cH;D2;+0:4]:[c:5]:[c:6])-[C;H0;D3;+0:1](=[O;D1;H0:3])-[OH;D1;+0:9] | null | [] | null | null | null | null | To explore the effectiveness of cyanide in the assistance of hydroxylamine mediated cleavage for solid phase library synthesis, hydroxymethylbenzamide (HMBA-AM) resin was chosen for the well-established compatibility between the ester linkage and Fmoc- and Boc-chemistry, and its stability towards Mitsunobu and reductiv... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide.Secondary amide.Primary alcohol.Primary amine | Carboxylic acid.Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | CC(=O)NCCCCCCNC(C)=O.NC(=O)c1ccccc1CO.NO>>NC(Cc1ccccc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-96aef0fe07034eea9b0b57368813915a | C=COCCCC.CN(C=O)c1ccccc1>>C=CC(=O)N(C)c1ccccc1 | ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O.CN(C1=CC=CC=C1)C=O.C(=C)OCCCC>>CN(C1=CC=CC=C1)C(=O)C=C | CCCCO[CH:2]=[CH2:1].[CH:3](=[O:4])[N:5]([CH3:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]([CH3:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | C=COCCCC.CN(C=O)c1ccccc1 | C=CC(=O)N(C)c1ccccc1 | null | null | O1CCOCC1 | C-C Coupling | OtherReaction | 7c917fcb5b08b86ef51e37de36b72c38b4ea882bb4f46412ef21c5ed69710c88 | 0b28fcc99a5cd09661fff597667bbe8dec1342c125d1e7dfc8a3617c7c6677ba | c1ccccc1 | C-C-C-C-O-[CH;D2;+0:1]=[C;D1;H2:2].[C;D1;H3:3]-[#7:4](-[c:5])-[CH;D2;+0:6]=[O;D1;H0:7]>>[C;D1;H2:2]=[CH;D2;+0:1]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#7:4](-[C;D1;H3:3])-[c:5] | 70.6 | [{"value": 70.6, "product": "CN(C1=CC=CC=C1)C(=O)C=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of N-methylformanilide (30 g), butyl vinyl ether (22.2 g) in 25 ml of 1,4-dioxane under stirring at 10–15° C., a solution of bis-trichloromethylcarbonate (28.3 g) in 50 ml of 1,4-dioxane is added dropwise in 90 min. The reaction mixture is kept under stirring at room temperature overnight, then the solven... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Vinyl | Tertiary amide.Vinyl | null | null | c1ccccc1 | HO- | O1CCOCC1 | null | 8 | C=COCCCC.CN(C=O)c1ccccc1>O1CCOCC1>C=CC(=O)N(C)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2c6fe20e4d64de2bcd48d7fe2059e60 | C=COCCCC.CN(C=O)c1ccccc1>>C=CC(=O)N(C)c1ccccc1 | CN(C1=CC=CC=C1)C=O.C(=C)OCCCC.ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O.[OH-].[Na+]>>CN(C1=CC=CC=C1)C(=O)C=C | CCCCO[CH:2]=[CH2:1].[CH:3](=[O:4])[N:5]([CH3:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]([CH3:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | C=COCCCC.CN(C=O)c1ccccc1 | C=CC(=O)N(C)c1ccccc1 | null | null | ClC1=CC=CC=C1.O | C-C Coupling | OtherReaction | 7c917fcb5b08b86ef51e37de36b72c38b4ea882bb4f46412ef21c5ed69710c88 | 0b28fcc99a5cd09661fff597667bbe8dec1342c125d1e7dfc8a3617c7c6677ba | c1ccccc1 | C-C-C-C-O-[CH;D2;+0:1]=[C;D1;H2:2].[C;D1;H3:3]-[#7:4](-[c:5])-[CH;D2;+0:6]=[O;D1;H0:7]>>[C;D1;H2:2]=[CH;D2;+0:1]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#7:4](-[C;D1;H3:3])-[c:5] | 69 | [{"value": 69.0, "product": "CN(C1=CC=CC=C1)C(=O)C=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of N-methylformanilide (30 g), butyl vinyl ether (22.2 g) in 25 ml of clorobenzene under stirring at 10° C., a solution of bis-trichloromethylcarbonate (24.3 g) in 50 ml of clorobenzene is added dropwise in 2 hours. The reaction mixture is kept under stirring at room temperature overnight. Water (50 ml) i... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Vinyl | Tertiary amide.Vinyl | null | null | c1ccccc1 | HO- | ClC1=CC=CC=C1.O | null | 8 | C=COCCCC.CN(C=O)c1ccccc1>ClC1=CC=CC=C1.O>C=CC(=O)N(C)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de574b356eba403c974162d6944dc7cc | C=COCCCC.CN(C=O)c1ccccc1>>C=CC(=O)N(C)c1ccccc1 | ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O.CN(C1=CC=CC=C1)C=O.C(=C)OCCCC>>CN(C1=CC=CC=C1)C(=O)C=C | CCCCO[CH:2]=[CH2:1].[CH:3](=[O:4])[N:5]([CH3:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]([CH3:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | C=COCCCC.CN(C=O)c1ccccc1 | C=CC(=O)N(C)c1ccccc1 | null | null | O1CCOCC1 | C-C Coupling | OtherReaction | 7c917fcb5b08b86ef51e37de36b72c38b4ea882bb4f46412ef21c5ed69710c88 | 0b28fcc99a5cd09661fff597667bbe8dec1342c125d1e7dfc8a3617c7c6677ba | c1ccccc1 | C-C-C-C-O-[CH;D2;+0:1]=[C;D1;H2:2].[C;D1;H3:3]-[#7:4](-[c:5])-[CH;D2;+0:6]=[O;D1;H0:7]>>[C;D1;H2:2]=[CH;D2;+0:1]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#7:4](-[C;D1;H3:3])-[c:5] | null | [] | null | null | 8 | HOUR | To a solution of N-methylformanilide (30 g), butyl vinyl ether (22.2 g) in 25 ml of 1,4-dioxane under stirring at 10–15° C., a solution of bis-trichloromethylcarbonate (28.3 g) in 50 ml of 1,4-dioxane is added dropwise in 90 min. The reaction mixture is kept under stirring at room temperature overnight, then the solven... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Vinyl | Tertiary amide.Vinyl | null | null | c1ccccc1 | HO- | O1CCOCC1 | null | 8 | C=COCCCC.CN(C=O)c1ccccc1>O1CCOCC1>C=CC(=O)N(C)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3433aa238654c3094a8e2f17d344453 | C=CC=O.CC(C)n1cc(-c2ccc(F)cc2)c2ccccc21>>CC(C)n1c(C=CC=O)c(-c2ccc(F)cc2)c2ccccc21 | O.C(=O)C=C.C(=O)C=C.FC1=CC=C(C=C1)C1=CN(C2=CC=CC=C12)C(C)C>>FC1=CC=C(C=C1)C1=C(N(C2=CC=CC=C12)C(C)C)C=CC=O | [CH2:6]=[CH:7][CH:8]=[O:9].[CH3:1][CH:2]([CH3:3])[n:4]1[cH:5][c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5]([CH:6]=[CH:7][CH:8]=[O:9])[c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][... | C=CC=O.CC(C)n1cc(-c2ccc(F)cc2)c2ccccc21 | CC(C)n1c(C=CC=O)c(-c2ccc(F)cc2)c2ccccc21 | null | null | C(C)#N | C-C Coupling | OtherReaction | d3d5312ddbc6c140e36e567a08135a66ca72d3675bfc436a188f49ab92c0b927 | 48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2 | c1ccc(-c2c[nH]c3ccccc23)cc1 | [CH2;D1;+0:1]=[C:2]-[C:3]=[O;D1;H0:4].[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9](-[c:10]):[cH;D2;+0:11]:1>>[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9](-[c:10]):[c;H0;D3;+0:11]:1-[CH;D2;+0:1]=[C:2]-[C:3]=[O;D1;H0:4] | null | [] | 60 | CELSIUS | 4 | HOUR | Use of the crude acrolein coming from Example 3a. To a suspension of 3-[3-(4-Fluorophenyl)-1-(1-Methylethyl)-1H-Indole (35.8 g) phosphorus oxychloride (31.4 g) in acetonitrile (35 ml) cooled at 5° C. a solution of crude acrolein (32.3 g from Example 3a) in acetonitrile (40 ml) is added dropwise in 30 minutes. The react... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1c[nH]c2ccccc12 | c1cc2ccccc2[nH]1 | c1ccccc1.c1cc2ccccc2[nH]1 | null | C(C)#N | 60 | 4 | C=CC=O.CC(C)n1cc(-c2ccc(F)cc2)c2ccccc21>C(C)#N>CC(C)n1c(C=CC=O)c(-c2ccc(F)cc2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38c716d7c7e943708a6e3647fcb2217f | C=COCCCC.CN(C=O)c1ccccc1>>C=CC(=O)N(C)c1ccccc1 | CN(C1=CC=CC=C1)C=O.C(=C)OCCCC.ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O.[OH-].[Na+]>>CN(C1=CC=CC=C1)C(=O)C=C | CCCCO[CH:2]=[CH2:1].[CH:3](=[O:4])[N:5]([CH3:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]([CH3:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | C=COCCCC.CN(C=O)c1ccccc1 | C=CC(=O)N(C)c1ccccc1 | null | null | ClC1=CC=CC=C1 | C-C Coupling | OtherReaction | 7c917fcb5b08b86ef51e37de36b72c38b4ea882bb4f46412ef21c5ed69710c88 | 0b28fcc99a5cd09661fff597667bbe8dec1342c125d1e7dfc8a3617c7c6677ba | c1ccccc1 | C-C-C-C-O-[CH;D2;+0:1]=[C;D1;H2:2].[C;D1;H3:3]-[#7:4](-[c:5])-[CH;D2;+0:6]=[O;D1;H0:7]>>[C;D1;H2:2]=[CH;D2;+0:1]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#7:4](-[C;D1;H3:3])-[c:5] | null | [] | null | null | 8 | HOUR | To a solution of N-methylformanilide (100 g), butyl vinyl ether (74.12 g) in 85 ml of clorobenzene under stirring at 5° C., a solution of bis-trichloromethylcarbonate (87.84 g) in 170 ml of clorobenzene is added dropwise in 2 hours. The reaction mixture is kept under stirring at room temperature overnight. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Vinyl | Tertiary amide.Vinyl | null | null | c1ccccc1 | HO- | ClC1=CC=CC=C1 | null | 8 | C=COCCCC.CN(C=O)c1ccccc1>ClC1=CC=CC=C1>C=CC(=O)N(C)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f435dfa66004070964eaa59ec28607f | C=CC=O.CC(C)n1cc(-c2ccc(F)cc2)c2ccccc21>>CC(C)n1c(C=CC=O)c(-c2ccc(F)cc2)c2ccccc21 | C(=O)C=C.FC1=CC=C(C=C1)C1=CN(C2=CC=CC=C12)C(C)C.P(=O)(Cl)(Cl)Cl.C(=O)C=C.O>>FC1=CC=C(C=C1)C1=C(N(C2=CC=CC=C12)C(C)C)C=CC=O | [CH2:6]=[CH:7][CH:8]=[O:9].[CH3:1][CH:2]([CH3:3])[n:4]1[cH:5][c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5]([CH:6]=[CH:7][CH:8]=[O:9])[c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][... | C=CC=O.CC(C)n1cc(-c2ccc(F)cc2)c2ccccc21 | CC(C)n1c(C=CC=O)c(-c2ccc(F)cc2)c2ccccc21 | null | null | C(C)#N | C-C Coupling | OtherReaction | d3d5312ddbc6c140e36e567a08135a66ca72d3675bfc436a188f49ab92c0b927 | 48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2 | c1ccc(-c2c[nH]c3ccccc23)cc1 | [CH2;D1;+0:1]=[C:2]-[C:3]=[O;D1;H0:4].[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9](-[c:10]):[cH;D2;+0:11]:1>>[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9](-[c:10]):[c;H0;D3;+0:11]:1-[CH;D2;+0:1]=[C:2]-[C:3]=[O;D1;H0:4] | null | [] | 60 | CELSIUS | 6 | HOUR | Use of the crude acrolein coming from Example 4a. To a suspension of 3-[3-(4-Fluorophenyl)-1-(1-Methylethyl)-1H-Indole (130.7 g), phosphorus oxychloride (114.6 g) in acetonitrile (128 ml) cooled at 5° C. a solution of crude acrolein (116.9 g from Example 4a) in acetonitrile (145 ml) is added dropwise in 60 minutes. The... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1c[nH]c2ccccc12 | c1cc2ccccc2[nH]1 | c1ccccc1.c1cc2ccccc2[nH]1 | null | C(C)#N | 60 | 6 | C=CC=O.CC(C)n1cc(-c2ccc(F)cc2)c2ccccc21>C(C)#N>CC(C)n1c(C=CC=O)c(-c2ccc(F)cc2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3d53efdb7a5449338c2b2634ab6dd476 | C=COCCCC.CC(C)n1cc(-c2ccc(F)cc2)c2ccccc21.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>CC(C)n1c(C=CC=O)c(-c2ccc(F)cc2)c2ccccc21 | P(=O)(Cl)(Cl)Cl.FC1=CC=C(C=C1)C1=CN(C2=CC=CC=C12)C(C)C.CN(C1=CC=CC=C1)C=O.C(=C)OCCCC.ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O>>FC1=CC=C(C=C1)C1=C(N(C2=CC=CC=C12)C(C)C)C=CC=O | CCCC[O:9][CH:8]=[CH2:7].[CH3:1][CH:2]([CH3:3])[n:4]1[cH:5][c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12.O=[C:6](OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5]([CH:6]=[CH:7][CH:8]=[O:9])[c:10](-[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[c:18... | C=COCCCC.CC(C)n1cc(-c2ccc(F)cc2)c2ccccc21.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | CC(C)n1c(C=CC=O)c(-c2ccc(F)cc2)c2ccccc21 | null | null | C(C)#N | Acylation | OtherReaction | 960b8c75dc54f4607fc8d9341538a0c97384d5111dff5305190a515654a910e4 | 8eb804ae7377aea0659b4594df9c1eb464b5394d29a8104bab494097bef1cf4c | c1ccc(-c2c[nH]c3ccccc23)cc1 | C-C-C-C-[O;H0;D2;+0:1]-[CH;D2;+0:2]=[CH2;D1;+0:3].Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:4](=O)-O-C(-Cl)(-Cl)-Cl.[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9](-[c:10]):[cH;D2;+0:11]:1>>[C:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9](-[c:10]):[c;H0;D3;+0:11]:1-[CH;D2;+0:4]=[CH;D2;+0:3]-[CH;D2;+0:2]=[O;H0;D1;+0:1] | 69 | [{"value": 69.0, "product": "FC1=CC=C(C=C1)C1=C(N(C2=CC=CC=C12)C(C)C)C=CC=O", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 8 | HOUR | To a solution of N-methylformanilide (30 g), butyl vinyl ether (22.2 g) in 15 ml of acetonitrile under stirring at 5° C., a solution of bis-trichloromethylcarbonate (26.1 g) in 70 ml of acetonitrile is added dropwise in 80 min. The reaction mixture is kept under stirring at 5° C. overnight, then phosphorus oxychloride ... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Ether.Vinyl | Aldehyde | c1c[nH]c2ccccc12 | c1cc2ccccc2[nH]1 | c1ccccc1.c1cc2ccccc2[nH]1 | HCl | C(C)#N | 5 | 8 | C=COCCCC.CC(C)n1cc(-c2ccc(F)cc2)c2ccccc21.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>C(C)#N>CC(C)n1c(C=CC=O)c(-c2ccc(F)cc2)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c8bc77dc55d4a88890aa30b737c9dda | O=C(O)[C@@H]1C[C@@H](O)CN1>>CN1C[C@H](O)C[C@H]1C(=O)O | C1[C@H](CN[C@@H]1C(=O)O)O.C(=O)N.[H][H]>>O[C@@H]1C[C@H](N(C1)C)C(=O)O | [NH:2]1[CH2:3][C@H:4]([OH:5])[CH2:6][C@H:7]1[C:8](=[O:9])[OH:10]>>[CH3:1][N:2]1[CH2:3][C@H:4]([OH:5])[CH2:6][C@H:7]1[C:8](=[O:9])[OH:10] | O=C(O)[C@@H]1C[C@@H](O)CN1 | CN1C[C@H](O)C[C@H]1C(=O)O | null | [Pd] | O.C(C)O | Miscellaneous | OtherReaction | 8e80b4f4b7042b748282a2f4c695bd44912d6f8b26c2523ed95efd55cabd75a9 | 06e4cfdff0e70e885199cc5de7382cc871277954ed1dd9750edc3ce3b12c44bd | C1CCNC1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[C;D1;H3:9]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[C:5]-[C:4]-1-[C:2](=[O;D1;H0:1])-[O;D1;H1:3] | 92.1 | [{"value": 92.0, "product": "O[C@@H]1C[C@H](N(C1)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "O[C@@H]1C[C@H](N(C1)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of (2S,4R)-trans-4-hydroxyproline (5 g), 37% aqueous formamide solution (4.6 g) and 7.5% palladium on charcoal (53% water content, 3.2 g) in water (15 mL) was stirred at room temperature in an atmosphere of high-pressure hydrogen for 10 hours. After removing the palladium on charcoal by filtration, the wat... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | Other | [Pd].O.C(C)O | null | null | O=C(O)[C@@H]1C[C@@H](O)CN1>[Pd].O.C(C)O>CN1C[C@H](O)C[C@H]1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55d72b300a22485dbbea2a791668145a | CN1C[C@H](O)C[C@H]1C(=O)O.CO>>COC(=O)[C@@H]1C[C@@H](O)CN1C | Cl.O[C@@H]1C[C@H](N(C1)C)C(=O)O.CO>>Cl.O[C@@H]1C[C@H](N(C1)C)C(=O)OC | O[C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([OH:8])[CH2:9][N:10]1[CH3:11].[CH3:1][OH:2]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([OH:8])[CH2:9][N:10]1[CH3:11] | CN1C[C@H](O)C[C@H]1C(=O)O.CO | COC(=O)[C@@H]1C[C@@H](O)CN1C | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | C1CCNC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C;D1;H3:6])-[C:7].[C;D1;H3:8]-[OH;D1;+0:9]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C;D1;H3:8])-[#7:5](-[C;D1;H3:6])-[C:7] | 100 | [{"value": 100.0, "product": "Cl.O[C@@H]1C[C@H](N(C1)C)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Concentrated hydrochloric acid (3 mL) was added to a suspension of (2S, 4R)-4-hydroxy-1-methyl-2-pyrrolidinecarboxylic acid (3 g) in methanol (15 mL), and the mixture was refluxed for 4 hours. The solvent of the reaction mixture was removed by distillation under reduced pressure to give the title compound (4.0 g, yield... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | C1CC[NH]C1 | HO- | null | null | null | CN1C[C@H](O)C[C@H]1C(=O)O.CO>>COC(=O)[C@@H]1C[C@@H](O)CN1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1588a0231fd14c6f8e892efabb879249 | COC(=O)[C@@H]1C[C@@H](O)CN1C.CS(=O)(=O)Cl>>COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C | C(O)([O-])=O.[Na+].C(C)N(CC)CC.Cl.O[C@@H]1C[C@H](N(C1)C)C(=O)OC.S(=O)(=O)(C)Cl>>CS(=O)(=O)O[C@@H]1C[C@H](N(C1)C)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([OH:8])[CH2:13][N:14]1[CH3:15].Cl[S:9]([CH3:10])(=[O:11])=[O:12]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]([O:8][S:9]([CH3:10])(=[O:11])=[O:12])[CH2:13][N:14]1[CH3:15] | COC(=O)[C@@H]1C[C@@H](O)CN1C.CS(=O)(=O)Cl | COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C | null | null | C(C)(=O)OCC.O1CCCC1 | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCNC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]-[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[#7:5]-[C:6]-[C:7](-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:9] | 83 | [{"value": 83.0, "product": "CS(=O)(=O)O[C@@H]1C[C@H](N(C1)C)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 3 | HOUR | Triethylamine (1.53 mL) was added to a suspension of methyl (2S, 4R)-4-hydroxy-1-methyl-2-pyrrolidinecarboxylate hydrochloride (1 g) obtained from Reference example 1 or 3 in tetrahydrofuran (10 mL) and the mixture was stirred at 40° C. for 3 hours. Mesyl chloride was added to the mixture under ice cooling and the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1 | HCl | C(C)(=O)OCC.O1CCCC1 | 40 | 3 | COC(=O)[C@@H]1C[C@@H](O)CN1C.CS(=O)(=O)Cl>C(C)(=O)OCC.O1CCCC1>COC(=O)[C@@H]1C[C@@H](OS(C)(=O)=O)CN1C |
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