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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2530436b50534fbdbbf72c2ea6ad27e3 | Cc1cc([N+](=O)[O-])cnc1Cl.[F-]>>Cc1cc([N+](=O)[O-])cnc1F | ClC1=NC=C(C=C1C)[N+](=O)[O-].[F-].[K+]>>FC1=NC=C(C=C1C)[N+](=O)[O-] | Cl[c:10]1[c:2]([CH3:1])[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9]1.[F-:11]>>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9][c:10]1[F:11] | Cc1cc([N+](=O)[O-])cnc1Cl.[F-] | Cc1cc([N+](=O)[O-])cnc1F | null | [Br-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)#N.CCOCC | Functional Group Interconversion | OtherReaction | c5ee9801df82c43b4536f3b3bcf4d5fc4f4f88678c4231db54140fcd8ba626c5 | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[F-;H0;D0:7]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[F;H0;D1;+0:7]):[#7;a:2]:[c:3] | 61.9 | [{"value": 60.0, "product": "FC1=NC=C(C=C1C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.9, "product": "FC1=NC=C(C=C1C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Chloro-3-methyl-5-nitropyridine (15 g, 86.9 mmol; from Maybridge Chemical Co.), KF (12 g, 258 mmol) and tetraphenylphosphonium bromide (20 g, 47.7 mmol; Aldrich) were combined in 200 mL of acetonitrile and heated at reflux for 4 days. The mixture was diluted with Et2O (500 mL) and filtered, and the filtrate was conce... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | [Br-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)#N.CCOCC | null | null | Cc1cc([N+](=O)[O-])cnc1Cl.[F-]>[Br-].C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(C)#N.CCOCC>Cc1cc([N+](=O)[O-])cnc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8caea27682284e0fa725f4c5568af18a | Cc1cc([N+](=O)[O-])cnc1F>>Cc1cc(N)cnc1F | FC1=NC=C(C=C1C)[N+](=O)[O-]>>NC=1C=C(C(=NC1)F)C | O=[N+:5]([O-])[c:4]1[cH:3][c:2]([CH3:1])[c:8]([F:9])[n:7][cH:6]1>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:6][n:7][c:8]1[F:9] | Cc1cc([N+](=O)[O-])cnc1F | Cc1cc(N)cnc1F | null | [Pd] | CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccncc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 78.5 | [{"value": 78.0, "product": "NC=1C=C(C(=NC1)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "NC=1C=C(C(=NC1)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Fluoro-3-methyl-5-nitropyridine (8.2 g, mmol) was combined with 5% Pd/C (100 mg) in EtOH (100 mL) under a H2 atmosphere for 16 hours. The mixture was filtered and concentrated, and the crude product was chromatographed (silica gel; CHCl3 /MeOH 99:1 to 96:4) to afford a solid (5.2 g, 78% ): 1H NMR (DMSO-d6, 300 MHz) δ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1 | Other | [Pd].CCO | null | null | Cc1cc([N+](=O)[O-])cnc1F>[Pd].CCO>Cc1cc(N)cnc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b6a3efbece064552a88a0a3c4985d4a0 | C1CC2=[N+](C1)CCC2.Cc1cc(I)cnc1F>>Cc1cc(C23CCCN2CCC3)cnc1F | FC1=NC=C(C=C1C)I.[Li]C(C)(C)C.Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12>>FC1=C(C=C(C=N1)C12CCCN2CCC1)C | [C:5]12=[N+:9]([CH2:8][CH2:7][CH2:6]1)[CH2:10][CH2:11][CH2:12]2.I[c:4]1[cH:3][c:2]([CH3:1])[c:15]([F:16])[n:14][cH:13]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]23[CH2:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH2:12]3)[cH:13][n:14][c:15]1[F:16] | C1CC2=[N+](C1)CCC2.Cc1cc(I)cnc1F | Cc1cc(C23CCCN2CCC3)cnc1F | null | null | CCCCC.CCOCC | Functional Group Interconversion | OtherReaction | 6e757ff9396a07e923211312afac1c080dd23eff3444ff9c846ed5fe9d4243b6 | 773dbb8365a8bceadef31887b9f43d5f4f5443038ea5ede92ac6bcd66c5d17b4 | c1cncc(C23CCCN2CCC3)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[C;H0;D3;+0:10]2=[N+;H0;D3:11]-1-[C:12]-[C:13]-[C:14]-2>>[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:10]23-[C:9]-[C:8]-[C:7]-[N;H0;D3;+0:11]-2-[C:12]-[C:13]-[C:14]-3):[c:6]:[c:5]:[c:4]:1 | 67 | [{"value": 67.0, "product": "FC1=C(C=C(C=N1)C12CCCN2CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.5, "product": "FC1=C(C=C(C=N1)C12CCCN2CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -95 | CELSIUS | 2 | HOUR | 2-Fluoro-5-iodo-3-methylpyridine (200 mg, 0.84 mmol) was dissolved in Et2O and cooled to -95° C. A solution of 2.5M t-BuLi (1.7M in pentane, 1.1 mL, 1.80 mmol) in pentane was added dropwise. 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (265 mg, 1.26 mmol) was added, and the reaction mixture was allowed to warm to -10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Tertiary amine | C1CC2=[N+](C1)CCC2.c1ccncc1 | c1ccncc1.C1CC2CCCN2C1 | c1ccncc1.C1CC2CCCN2C1 | I- | CCCCC.CCOCC | -95 | 2 | C1CC2=[N+](C1)CCC2.Cc1cc(I)cnc1F>CCCCC.CCOCC>Cc1cc(C23CCCN2CCC3)cnc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-457e5f8be8b3495ea5aaa4132c8195ea | Cl>>Cl | Cl.FC1=C(C=C(C=N1)C12CCCN2CCC1)C>>Cl.FC1=C(C=C(C=N1)C12CCCN2CCC1)C | [ClH:17]>>[ClH:17] | Cl | Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 69 | [{"value": 69.0, "product": "Cl.FC1=C(C=C(C=N1)C12CCCN2CCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(6-Fluoro-5-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine (115 mg, 0.52 mmol, from step 18d) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was crystallized from MeOH/Et2O and dried to afford the title compound (white needles, 92 mg, 69%): mp 170-171° C.; 1H N... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCOCC | null | null | Cl>CCOCC>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fb181b43b2cf48a49bb845d00e4222a4 | Cc1cc([N+](=O)[O-])cnc1Cl>>Cc1cc(N)cnc1Cl | ClC1=NC=C(C=C1C)[N+](=O)[O-]>>NC=1C=C(C(=NC1)Cl)C | O=[N+:5]([O-])[c:4]1[cH:3][c:2]([CH3:1])[c:8]([Cl:9])[n:7][cH:6]1>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:6][n:7][c:8]1[Cl:9] | Cc1cc([N+](=O)[O-])cnc1Cl | Cc1cc(N)cnc1Cl | null | [Fe] | O.CC(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccncc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 89 | [{"value": 89.0, "product": "NC=1C=C(C(=NC1)Cl)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.6, "product": "NC=1C=C(C(=NC1)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 2-Chloro-3-methyl-5-nitropyridine (15 g, 86.9 mmol; from Maybridge Chemical Co.) was dissolved in a solution of H2O/AcOH (5:1, 60 mL). Iron powder was added to the reaction mixture while maintaining the temperature below 40° C., and the mixture was stirred for 5 hours. The mixture was filtered through celite and the aq... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1 | Other | [Fe].O.CC(=O)O | null | 5 | Cc1cc([N+](=O)[O-])cnc1Cl>[Fe].O.CC(=O)O>Cc1cc(N)cnc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b41b8bae64dd42eb82a4b840e4ce0359 | Cl>>Cl | Cl.ClC1=C(C=C(C=N1)C12CCCN2CCC1)C>>Cl.ClC1=C(C=C(C=N1)C12CCCN2CCC1)C | [ClH:17]>>[ClH:17] | Cl | Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 7a-(6-Chloro-5-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine (245 mg, 1.03 mmol) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was crystallized from MeOH/Et2O and dried to afford the title compound as white plates: mp 179°-180° C.; 1H NMR D2O, 300 MHz) δ2.14-2.4... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCOCC | null | null | Cl>CCOCC>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-25297c07e8f0461b9c58636fbdf6865e | C1CC2=[N+](C1)CCC2.Cc1ccc(I)cn1>>Cc1ccc(C23CCCN2CCC3)cn1 | IC=1C=CC(=NC1)C.[Li]C(C)(C)C.Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12>>CC1=CC=C(C=N1)C12CCCN2CCC1 | [C:6]12=[N+:10]([CH2:9][CH2:8][CH2:7]1)[CH2:11][CH2:12][CH2:13]2.I[c:5]1[cH:4][cH:3][c:2]([CH3:1])[n:15][cH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[cH:14][n:15]1 | C1CC2=[N+](C1)CCC2.Cc1ccc(I)cn1 | Cc1ccc(C23CCCN2CCC3)cn1 | null | null | CCCCC.CCOCC | Functional Group Interconversion | OtherReaction | 6e757ff9396a07e923211312afac1c080dd23eff3444ff9c846ed5fe9d4243b6 | 773dbb8365a8bceadef31887b9f43d5f4f5443038ea5ede92ac6bcd66c5d17b4 | c1cncc(C23CCCN2CCC3)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C:7]1-[C:8]-[C:9]-[C;H0;D3;+0:10]2=[N+;H0;D3:11]-1-[C:12]-[C:13]-[C:14]-2>>[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[C;H0;D4;+0:10]23-[C:9]-[C:8]-[C:7]-[N;H0;D3;+0:11]-2-[C:12]-[C:13]-[C:14]-3):[c:6]:[c:5]:[c:4]:1 | 45 | [{"value": 45.0, "product": "CC1=CC=C(C=N1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.8, "product": "CC1=CC=C(C=N1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -95 | CELSIUS | 2 | HOUR | 5-Iodo-2-methylpyridine (345 mg, 1.39 mmol) was dissolved in Et2O and cooled to -95° C. A solution of 2.5M t-BuLi (1.7M in pentane, 1.8 mL, 3.06 mmol) in pentane was added dropwise. 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (435 mg, 2.1 mmol) was added, and the reaction mixture was allowed to warm to -10° C. with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Tertiary amine | C1CC2=[N+](C1)CCC2.c1ccncc1 | c1ccncc1.C1CC2CCCN2C1 | c1ccncc1.C1CC2CCCN2C1 | I- | CCCCC.CCOCC | -95 | 2 | C1CC2=[N+](C1)CCC2.Cc1ccc(I)cn1>CCCCC.CCOCC>Cc1ccc(C23CCCN2CCC3)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ea2e0597cfc34b5fb0309e1466c6a737 | Cl>>Cl.Cl | Cl.CC1=CC=C(C=N1)C12CCCN2CCC1>>Cl.Cl.CC1=CC=C(C=N1)C12CCCN2CCC1 | [ClH:16]>>[ClH:16].[ClH:17] | Cl | Cl.Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 7a-(6-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine (115 mg, 0.57 mmol) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was crystallized from MeOH/Et2O and dried to afford the title compound as a free flowing white powder: mp 205°-208° C.; 1H NMR D2O, 300 MHz) δ2.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | CCOCC | null | null | Cl>CCOCC>Cl.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e9f462982753453bbfd8fa8e28ec7c0c | Cc1cc(C23CCCN2CCC3)cnc1Cl>>Cc1cncc(C23CCCN2CCC3)c1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].ClC1=C(C=C(C=N1)C12CCCN2CCC1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CC=1C=C(C=NC1)C12CCCN2CCC1 | Cl[c:3]1[c:2]([CH3:1])[cH:15][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:5][n:4]1>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15]1 | Cc1cc(C23CCCN2CCC3)cnc1Cl | Cc1cncc(C23CCCN2CCC3)c1 | null | null | C1CCOC1 | Functional Group Interconversion | Aromatic dehalogenation | ea85ec2fde5700c76b45764563e70d433b50e38e1af4209f646f155266c8ec96 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1cncc(C23CCCN2CCC3)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6]>>[C;D1;H3:5]-[c:4](:[c:6]):[cH;D2;+0:1]:[#7;a:2]:[c:3] | 49.4 | [{"value": 49.0, "product": "CC=1C=C(C=NC1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.4, "product": "CC=1C=C(C=NC1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 7a-(6-Chloro-5-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine (274 mg, 1.16 mmol, from Example 19c) and LAH (1.0M in THF, 1.2 mL, 1.16 mmol) were added to THF (4.5 mL), and the mixture was stirred at room temperature for 4 hours. An additional amount of LAH (1.0M in THF, 1.2 mL, 1.16 mmol) was added, and the reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC2CCCN2C1 | Other | C1CCOC1 | null | 4 | Cc1cc(C23CCCN2CCC3)cnc1Cl>C1CCOC1>Cc1cncc(C23CCCN2CCC3)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4307238908404aba91158ac3e78330d3 | Cl>>Cl | Cl.CC=1C=C(C=NC1)C12CCCN2CCC1>>Cl.CC=1C=C(C=NC1)C12CCCN2CCC1 | [ClH:16]>>[ClH:16] | Cl | Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 87 | [{"value": 87.0, "product": "Cl.CC=1C=C(C=NC1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(5-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine (109 mg, 0.54 mmol) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was triturated with Et2O and dried to afford the title compound as a white powder (112 mg, 87%); mp 153°-154° C.; 1H NMR D2O, 300 MHz) δ2.12-2.4... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CCOCC | null | null | Cl>CCOCC>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ac9c0ef6fceb47cd8829f6fc3aa7a252 | FC(F)(Br)C(F)(F)Br.Fc1ccc(C23CCCN2CCC3)cn1>>Fc1ncc(C23CCCN2CCC3)cc1Br | [Li]CCCC.C(C)(C)NC(C)C.FC1=CC=C(C=N1)C12CCCN2CCC1.BrC(C(F)(F)Br)(F)F>>BrC=1C=C(C=NC1F)C12CCCN2CCC1 | FC(F)(Br)C(F)(F)[Br:16].[F:1][c:2]1[n:3][cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[cH:14][cH:15]1>>[F:1][c:2]1[n:3][cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[cH:14][c:15]1[Br:16] | FC(F)(Br)C(F)(F)Br.Fc1ccc(C23CCCN2CCC3)cn1 | Fc1ncc(C23CCCN2CCC3)cc1Br | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | 3dc3f72be681445c7fd24ed7b03fe65530bdb1cf64ea351f6f33b0039b7c8253 | 019ad5fd0dfe62cfb4244afde83961e2345586820445df7561489ed4a5d090fa | c1cncc(C23CCCN2CCC3)c1 | Br-C(-F)(-F)-C(-F)(-F)-[Br;H0;D1;+0:1].[F;D1;H0:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[c:7]:[c:6]:[c:5]:[#7;a:4]:[c:3]:1-[F;D1;H0:2] | 37.4 | [{"value": 37.0, "product": "BrC=1C=C(C=NC1F)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.4, "product": "BrC=1C=C(C=NC1F)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | n-BuLi (2.5M in hexanes, 0.252 mL, 0.63 mmol) was added to di-isopropylamine (0.082 mL, 0.63 mmol) in THF and stirred at room temperature for 10 minutes, then cooled to -78° C. 7a-(6-Fluoro-3-pyridinyl)-hexahydro-1H-pyrrolizine (123 mg, 0.60 mmol, from Example 12d) and 1,2-dibromo-1,1,2,2-tetrafluoroethane (0.215 mL, 1... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC2CCCN2C1 | HF.Br- | C1CCOC1 | null | 0.166667 | FC(F)(Br)C(F)(F)Br.Fc1ccc(C23CCCN2CCC3)cn1>C1CCOC1>Fc1ncc(C23CCCN2CCC3)cc1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a8c5c25f4fb846a89628f7a3b1c115e3 | Fc1ncc(C23CCCN2CCC3)cc1Br>>Fc1ncc(C23CCCN2CCC3)cc1Br | Cl.BrC=1C=C(C=NC1F)C12CCCN2CCC1>>Cl.BrC=1C=C(C=NC1F)C12CCCN2CCC1 | [F:2][c:3]1[n:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15][c:16]1[Br:17]>>[F:2][c:3]1[n:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15][c:16]1[Br:17] | Fc1ncc(C23CCCN2CCC3)cc1Br | Fc1ncc(C23CCCN2CCC3)cc1Br | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | 87 | [{"value": 87.0, "product": "Cl.BrC=1C=C(C=NC1F)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(5-bromo-6-fluoro-3-pyridinyl)-hexahydro-1H-pyrrolizine was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was triturated with Et2O and dried to afford the title compound as a white powder (59 mg, 87%): mp 213°-215° C.; 1H NMR D2O, 300 MHz) δ2.15-2.49 (m, 6H), 2.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | CCOCC | null | null | Fc1ncc(C23CCCN2CCC3)cc1Br>CCOCC>Fc1ncc(C23CCCN2CCC3)cc1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-00bd9856a1bd4532834dd176039f25ee | ClC(Cl)(Cl)C(Cl)(Cl)Cl.Fc1ccc(C23CCCN2CCC3)cn1>>Fc1ncc(C23CCCN2CCC3)cc1Cl | [Li]CCCC.C(C)(C)NC(C)C.FC1=CC=C(C=N1)C12CCCN2CCC1.ClC(C(Cl)(Cl)Cl)(Cl)Cl>>ClC=1C=C(C=NC1F)C12CCCN2CCC1 | ClC(Cl)(Cl)C(Cl)(Cl)[Cl:16].[F:1][c:2]1[n:3][cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[cH:14][cH:15]1>>[F:1][c:2]1[n:3][cH:4][c:5]([C:6]23[CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13]3)[cH:14][c:15]1[Cl:16] | ClC(Cl)(Cl)C(Cl)(Cl)Cl.Fc1ccc(C23CCCN2CCC3)cn1 | Fc1ncc(C23CCCN2CCC3)cc1Cl | null | null | C1CCOC1 | Functional Group Interconversion | Chlorination | b6bfd9375f1a0668183fe0de435085183ec91305a2e1dcb5397f52bc008dc1b3 | 5299dd3c496bc7c94739e7d10382eb68ebc90d6d6c0c125f886657d3b41caf21 | c1cncc(C23CCCN2CCC3)c1 | Cl-C(-Cl)(-Cl)-C(-Cl)(-Cl)-[Cl;H0;D1;+0:1].[F;D1;H0:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[c:7]:[c:6]:[c:5]:[#7;a:4]:[c:3]:1-[F;D1;H0:2] | 34 | [{"value": 34.0, "product": "ClC=1C=C(C=NC1F)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.4, "product": "ClC=1C=C(C=NC1F)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | n-BuLi (2.5M in hexanes, 0.232 mL, 0.58 mmol) was added to di-isopropylamine (0.077 mL, 0.58 mmol) in THF and stirred at room temperature for 15 minutes, then cooled to -78° C. 7a-(6-Fluoro-3-pyridinyl)-hexahydro-1H-pyrrolizine (115 mg, 0.56 mmol, from Example 12d) and hexachloroethane (400 mg, 1.7 mmol) were added. Th... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC2CCCN2C1 | HCl | C1CCOC1 | null | 0.25 | ClC(Cl)(Cl)C(Cl)(Cl)Cl.Fc1ccc(C23CCCN2CCC3)cn1>C1CCOC1>Fc1ncc(C23CCCN2CCC3)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-de9abf64e74b42648268c346ed5db6f3 | Fc1ncc(C23CCCN2CCC3)cc1Cl>>Fc1ncc(C23CCCN2CCC3)cc1Cl | Cl.ClC=1C=C(C=NC1F)C12CCCN2CCC1>>Cl.ClC=1C=C(C=NC1F)C12CCCN2CCC1 | [F:2][c:3]1[n:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15][c:16]1[Cl:17]>>[F:2][c:3]1[n:4][cH:5][c:6]([C:7]23[CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14]3)[cH:15][c:16]1[Cl:17] | Fc1ncc(C23CCCN2CCC3)cc1Cl | Fc1ncc(C23CCCN2CCC3)cc1Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1cncc(C23CCCN2CCC3)c1 | null | 74 | [{"value": 74.0, "product": "Cl.ClC=1C=C(C=NC1F)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(5-chloro-6-fluoro-3-pyridinyl)-hexahydro-1H-pyrrolizine was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was triturated with Et2O and dried to afford the title compound as a white powder (35 mg, 74%): mp 181°-183° C.; 1H NMR (D2O, 300 MHz) δ2.15-2.50 (m, 6H), ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1.C1CC2CCCN2C1 | null | CCOCC | null | null | Fc1ncc(C23CCCN2CCC3)cc1Cl>CCOCC>Fc1ncc(C23CCCN2CCC3)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-25cc9381e06f48dab75a6ffa0b61c21d | C1CC2=[N+](C1)CCC2.Cc1ccncc1I>>Cc1ccncc1C12CCCN1CCC2 | IC=1C=NC=CC1C.[Li]C(C)(C)C.Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12>>CC1=C(C=NC=C1)C12CCCN2CCC1 | [C:8]12=[N+:12]([CH2:11][CH2:10][CH2:9]1)[CH2:13][CH2:14][CH2:15]2.I[c:7]1[c:2]([CH3:1])[cH:3][cH:4][n:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][cH:6][c:7]1[C:8]12[CH2:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH2:15]2 | C1CC2=[N+](C1)CCC2.Cc1ccncc1I | Cc1ccncc1C12CCCN1CCC2 | null | null | CCCCC.CCOCC | Functional Group Interconversion | OtherReaction | 6e757ff9396a07e923211312afac1c080dd23eff3444ff9c846ed5fe9d4243b6 | 773dbb8365a8bceadef31887b9f43d5f4f5443038ea5ede92ac6bcd66c5d17b4 | c1cncc(C23CCCN2CCC3)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7].[C:8]1-[C:9]-[N+;H0;D3:10]2=[C;H0;D3;+0:11](-[C:12]-[C:13]-[C:14]-2)-[C:15]-1>>[C;D1;H3:7]-[c:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[C;H0;D4;+0:11]12-[C:12]-[C:13]-[C:14]-[N;H0;D3;+0:10]-1-[C:9]-[C:8]-[C:15]-2 | 6.5 | [{"value": 6.0, "product": "CC1=C(C=NC=C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.5, "product": "CC1=C(C=NC=C1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -95 | CELSIUS | 2 | HOUR | 3-Iodo-4-methylpyridine (330 mg, 3.10 mmol) was dissolved in Et2O and cooled to -95° C. A solution of t-BuLi (1.7M in pentane, 4.0 ml, 6.80 mmol) in pentane was added dropwise. 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (960 mg, 4.60 mmol) was added, and the reaction mixture was allowed to warm to -10° C. with stir... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Tertiary amine | C1CC2=[N+](C1)CCC2.c1ccncc1 | c1ccncc1.C1CC2CCCN2C1 | c1ccncc1.C1CC2CCCN2C1 | I- | CCCCC.CCOCC | -95 | 2 | C1CC2=[N+](C1)CCC2.Cc1ccncc1I>CCCCC.CCOCC>Cc1ccncc1C12CCCN1CCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9f0d302e51834ee5ae59f2e30cfe7ffc | Cl>>Cl.Cl | Cl.CC1=C(C=NC=C1)C12CCCN2CCC1>>Cl.Cl.CC1=C(C=NC=C1)C12CCCN2CCC1 | [ClH:16]>>[ClH:16].[ClH:17] | Cl | Cl.Cl | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 61 | [{"value": 61.0, "product": "Cl.Cl.CC1=C(C=NC=C1)C12CCCN2CCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7a-(4-methyl-3-pyridinyl)-hexahydro-1H-pyrrolizine (37 mg, 0.18 mmol) was dissolved in Et2O, and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was triturated with Et2O and dried to afford the title compound as a white solid (26.2 mg, 61%): mp 244°-247° C.; 1H NMR D2O, 300 MHz) δ2.01-2.16... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | CCOCC | null | null | Cl>CCOCC>Cl.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f04c2e1d91b841f084faee8cc1432b9f | Brc1cncc(Br)c1.OB(O)c1ccccc1>>Brc1cncc(-c2ccccc2)c1 | BrC=1C=NC=C(C1)Br.C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>BrC=1C=NC=C(C1)C1=CC=CC=C1 | Br[c:6]1[cH:5][n:4][cH:3][c:2]([Br:1])[cH:13]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[Br:1][c:2]1[cH:3][n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13]1 | Brc1cncc(Br)c1.OB(O)c1ccccc1 | Brc1cncc(-c2ccccc2)c1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd] | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10]:[c:11] | null | [] | null | null | null | null | Portions of 3,5-dibromopyridine (1.0 g, 4.22 mmol), phenylboronic acid (570 mg, 4.6 mmol) and palladium tetra(triphenylphosphine) (60 mg) were combined in toluene (20 mL) with aqueous sodium carbonate solution (2M, 3.0 mL) and heated at reflux for 6 hours. The mixture was cooled to ambient temperature, and the solvent ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr.B | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].C1(=CC=CC=C1)C | null | null | Brc1cncc(Br)c1.OB(O)c1ccccc1>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].C1(=CC=CC=C1)C>Brc1cncc(-c2ccccc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5b22770333014a4da72ab520662759f7 | BrC1(c2ccccc2)C=CC=NC1.C1CC2=[N+](C1)CCC2>>c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1 | Cl.BrC1(CN=CC=C1)C1=CC=CC=C1.[Li]C(C)(C)C.Cl(=O)(=O)(=O)[O-].C1CC[N+]=2CCCC12>>C1(=CC=CC=C1)C=1C=C(C=NC1)C12CCCN2CCC1 | Br[C:5]1([c:4]2[cH:3][cH:2][cH:1][cH:20][cH:19]2)[CH2:6][N:7]=[CH:8][CH:9]=[CH:18]1.[C:10]12=[N+:14]([CH2:13][CH2:12][CH2:11]1)[CH2:15][CH2:16][CH2:17]2>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][n:7][cH:8][c:9]([C:10]34[CH2:11][CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH2:17]4)[cH:18]2)[cH:19][cH:20]1 | BrC1(c2ccccc2)C=CC=NC1.C1CC2=[N+](C1)CCC2 | c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1 | null | null | CCCCC.CCOCC | Aromatic Heterocycle Formation | OtherReaction | a2ceb260427fba4f3cceb32f0ad8f9216c0c2ec29532e72b1ad28507408fe0c8 | ec642e2a2ffda901ebc676763ee3ceea45718d26f8ee90442c60d1ad2244e11f | c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1 | Br-[C;H0;D4;+0:1]1(-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6])-[CH2;D2;+0:7]-[N;H0;D2;+0:8]=[CH;D2;+0:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-1.[C:12]1-[C:13]-[C:14]-[N+;H0;D3:15]2=[C;H0;D3;+0:16]-1-[C:17]-[C:18]-[C:19]-2>>[c:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[cH;D2;+0:11]:[c;H0;D3;+0:10](-[C;H0;D4;+0:16]23-[C:12]-[C:13]-... | 14.5 | [{"value": 14.5, "product": "C1(=CC=CC=C1)C=1C=C(C=NC1)C12CCCN2CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 10 | MINUTE | 3-Bromo-3-phenylpyridine (200 mg, 0.85 mmol) was dissolved in Et2O and cooled to -30° C. A solution of 2.5M t-BuLi (1.1 mL, 1.90 mmol) in pentane was added, and the reaction was stirred for 10 minutes. 1,2,3,5,6,7-Hexahydropyrrolizinium perchlorate (230 mg, 1.30 mmol) was added, and the reaction mixture was allowed to ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Substituted imine | Tertiary amine | C1=CCCN=C1.C1CC2=[N+](C1)CCC2 | c1ccncc1.C1CC2CCCN2C1 | c1ccccc1.c1ccncc1.C1CC2CCCN2C1 | HBr | CCCCC.CCOCC | -30 | 0.166667 | BrC1(c2ccccc2)C=CC=NC1.C1CC2=[N+](C1)CCC2>CCCCC.CCOCC>c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-67e631af3ef64f0490cab77fef17bd5e | c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1>>c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1 | Cl.C1(=CC=CC=C1)C=1C=C(C=NC1)C12CCCN2CCC1>>Cl.C1(=CC=CC=C1)C=1C=C(C=NC1)C12CCCN2CCC1 | [cH:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][cH:9][c:10]([C:11]34[CH2:12][CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][CH2:18]4)[cH:19]2)[cH:20][cH:21]1>>[cH:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][cH:9][c:10]([C:11]34[CH2:12][CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][CH2:18]4)[cH:19]2)[cH:20][cH:21]1 | c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1 | c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1 | null | null | CCOCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1 | null | null | [] | null | null | null | null | The 7a-(5-phenyl-3-pyridinyl)-hexahydro-1H-pyrrolizine compound from step 25b was dissolved in ether (5 mL) and Et2O saturated with HCl (g) was added. The solvent was removed, and the solid was dried to afford the title compound as yellow needles (13.5 mg): mp 217°-220° C. (dec.); 1H NMR D2O, 300 MHz) δ2.17-2.47 (m, 4H... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccncc1.C1CC2CCCN2C1 | null | CCOCC | null | null | c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1>CCOCC>c1ccc(-c2cncc(C34CCCN3CCC4)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-59a65a7056d742c49de82eb5c63762a4 | CC(C)(C)OC(=O)N=C(NCCCCCCNC(=O)CN)NC(=O)OC(C)(C)C.CC(C)(C)OC(=O)NCCCN(CCCCO)C(=O)OC(C)(C)C.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>>CC(C)(C)OC(=O)N=C(NCCCCCCNC(=O)CNC(=O)OCCCCN(CCCNC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)NC(=O)OC(C)(C)C | ClC(=O)OC1=CC=C(C=C1)[N+](=O)[O-].NCC(NCCCCCCNC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)=O.CC(C)(OC(=O)NCCCN(C(OC(C)(C)C)=O)CCCCO)C.C(C)N(CC)CC>>CC(C)(OC(=O)NC(=NC(=O)OC(C)(C)C)NCCCCCCNC(CNC(OCCCCN(CCCNC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O)=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]=[C:9]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:19])[CH2:20][NH2:21])[NH:48][C:49](=[O:50])[O:51][C:52]([CH3:53])([CH3:54])[CH3:55].[OH:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:35])[O:36][C:37... | CC(C)(C)OC(=O)N=C(NCCCCCCNC(=O)CN)NC(=O)OC(C)(C)C.CC(C)(C)OC(=O)NCCCN(CCCCO)C(=O)OC(C)(C)C.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1 | CC(C)(C)OC(=O)N=C(NCCCCCCNC(=O)CNC(=O)OCCCCN(CCCNC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)NC(=O)OC(C)(C)C | null | null | C(C)(=O)OCC.O1CCCC1 | Functional Group Interconversion | OtherReaction | efbcb474775e37b1c3f28b3cc99478861fbf52e5dd627e50d041f406eb58eb1c | f145f943676713212a06a6fc1485be73591da940d9f647b06c145d0e822eca44 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-c1:c:c:c(-[N+](=O)-[O-]):c:c:1.[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH2;D1;+0:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:11]-[C:10]-[C:9] | 44 | [{"value": 44.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | 1 g (2.89·10-3 mol) of [3-[[(1,1-dimethyl-ethoxy)carbonyl]amino]propyl](4-hydroxybutyl)carbamic acid, 1,1-dimethylethyl ester is dissolved in 20 ml of tetrahydrofuran (THF), and 0.45 g (4.5·10-3 mol) of triethylamine is added followed by a solution of 0.58 g (2.89·10-3 mol) of 4-nitrophenyl chloroformate in 5 ml of THF... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Nitro group.Primary alcohol.Primary amine | Carbamic ester | c1ccccc1 | null | null | HCl | C(C)(=O)OCC.O1CCCC1 | null | 15 | CC(C)(C)OC(=O)N=C(NCCCCCCNC(=O)CN)NC(=O)OC(C)(C)C.CC(C)(C)OC(=O)NCCCN(CCCCO)C(=O)OC(C)(C)C.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>C(C)(=O)OCC.O1CCCC1>CC(C)(C)OC(=O)N=C(NCCCCCCNC(=O)CNC(=O)OCCCCN(CCCNC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)NC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f0e0f1638dcd40c780aa7d8ec6375945 | CCOC(=O)CNC(=O)CCCCCBr.[C-]#N>>CCOC(=O)CNC(=O)CCCCCC#N | BrCCCCCC(=O)NCC(=O)OCC.[C-]#N.[K+].ClCCl>>C(#N)CCCCCC(=O)NCC(=O)OCC | Br[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:8]([NH:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:9].[C-:15]#[N:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][C:8](=[O:9])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16] | CCOC(=O)CNC(=O)CCCCCBr.[C-]#N | CCOC(=O)CNC(=O)CCCCCC#N | null | null | C(C)O | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C-;H0;D1:4]#[N;D1;H0:5]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D2;+0:4]#[N;D1;H0:5] | 99 | [{"value": 99.0, "product": "C(#N)CCCCCC(=O)NCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 23.73 g (84.7·10-3 mol) of N-(6-bromohexanoyl)-glycine, ethyl ester are dissolved in 200 ml of ethanol, and 6.5 g (0.1 mol) of powdered potassium cyanide are added. The reaction mixture is brought to the reflux point and stirred under reflux for 15 hours. After concentration of the mixture under reduced pressure, the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | null | Br- | C(C)O | null | null | CCOC(=O)CNC(=O)CCCCCBr.[C-]#N>C(C)O>CCOC(=O)CNC(=O)CCCCCC#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ae97e9d0be094c7d859d65239405a8ff | N#CCCCCCC(=O)NCC(=O)O>>NCCCCCCC(=O)NCC(=O)O | [OH-].[Na+].C(#N)CCCCCC(=O)NCC(=O)O.[Cl-].[Na+].Cl>>NCCCCCCC(=O)NCC(=O)O | [N:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[NH:10][CH2:11][C:12](=[O:13])[OH:14]>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[NH:10][CH2:11][C:12](=[O:13])[OH:14] | N#CCCCCCC(=O)NCC(=O)O | NCCCCCCC(=O)NCC(=O)O | null | [Ni] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | null | [] | null | null | 8 | HOUR | 8.2 g (41.4·10-3 mol) of N-(6-cyanohexanoyl)-glycine are dissolved in 100 ml of ethanol, and 60 ml of 1M sodium hydroxide solution and 800 mg of Raney nickel are added. The mixture is then stirred under a hydrogen atmosphere, at room temperature and under a pressure of 3.5·105Pa, for 8 hours. When the reaction has ende... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | null | null | [Ni].C(C)O | null | 8 | N#CCCCCCC(=O)NCC(=O)O>[Ni].C(C)O>NCCCCCCC(=O)NCC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8c72bfcb26eb4ce38bf4d9fcc1fda530 | BrCc1ccccc1.COc1cccc2[nH]c(C)cc12>>COc1cccc2c1cc(C)n2Cc1ccccc1 | C(C1=CC=CC=C1)Br.COC1=C2C=C(NC2=CC=C1)C.[H-].[Na+].CCCCCC>>COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[cH:9][c:10]([CH3:11])[nH:12]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[cH:9][c:10]([CH3:11])[n:12]2[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | BrCc1ccccc1.COc1cccc2[nH]c(C)cc12 | COc1cccc2c1cc(C)n2Cc1ccccc1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 16b46a8af20339f7ff0b611b4ac5dd01fe35ba577361e893c359dfa478dc1974 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 84 | [{"value": 84.0, "product": "COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.4, "product": "COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | 4-Methoxy-2-methyl-1H-indole (1 g, 6.2 mmol) was added to 248 mg (6.2 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 15 mL of DMF and after stirring for 0.5 hour, 0.74 mL (6.2 mmol) of benzyl bromide was added. The mixture was stirred at room temperature for 18 hours, diluted with wat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1.c1ccccc1 | HBr | CN(C)C=O.O | null | 0.5 | BrCc1ccccc1.COc1cccc2[nH]c(C)cc12>CN(C)C=O.O>COc1cccc2c1cc(C)n2Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b929091e25a74504966cd0bf54a67e49 | COc1cccc2c1cc(C)n2Cc1ccccc1>>Cc1cc2c(O)cccc2n1Cc1ccccc1 | COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C.B(Br)(Br)Br.C(Cl)Cl>>OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C | C[O:6][c:5]1[c:4]2[cH:3][c:2]([CH3:1])[n:11]([CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:10]2[cH:9][cH:8][cH:7]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([OH:6])[cH:7][cH:8][cH:9][c:10]2[n:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | COc1cccc2c1cc(C)n2Cc1ccccc1 | Cc1cc2c(O)cccc2n1Cc1ccccc1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 49 | [{"value": 49.0, "product": "OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.6, "product": "OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1.25 g (5 mmol) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole and 20 mL of 1M BBr3 /CH2Cl2 in 50 mL of methylene chloride was stirred at room temperature for 5 hours and concentrated at reduced pressure. The residue was dissolved in ethyl acetate, washed with brine and dried (MgSO4). After concentratin... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | Other | C(Cl)Cl | null | null | COc1cccc2c1cc(C)n2Cc1ccccc1>C(Cl)Cl>Cc1cc2c(O)cccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-19b0abee38be4025b9f496f094d7d0bd | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1ccccc1>>COC(=O)COc1cccc2c1cc(C)n2Cc1ccccc1 | OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C.[H-].[Na+].BrCC(=O)OC>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1ccccc1 | COC(=O)COc1cccc2c1cc(C)n2Cc1ccccc1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 88 | [{"value": 88.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.67 | HOUR | 4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole (530 mg, 2.2 mmol) was added to 88 mg (2.2 mmol) of 60% NaH/mineral oil in 20 mL of DMF and the mixture stirred for 0.67 hours. Then, 0.21 mL (2.2 mmol) of methyl bromoacetate was added and stirring maintained for 17 hours. The mixture was diluted with water and extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | HBr | CN(C)C=O.O | null | 0.67 | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1ccccc1>CN(C)C=O.O>COC(=O)COc1cccc2c1cc(C)n2Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1c51dd5042944cafbcc75002bd31f9d1 | COC(=O)C(C)Br.Cc1cc2c(O)cccc2n1Cc1ccccc1>>CCCCCC.CCOC(C)=O.COC(=O)C(C)Oc1cccc2c1cc(C)n2Cc1ccccc1 | OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C.[H-].[Na+].BrC(C(=O)OC)C>>COC(C(C)OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C)=O.CCOC(=O)C.CCCCCC | Br[CH:17]([C:15](=[O:9])[O:14][CH3:13])[CH3:18].[cH:1]1[cH:32][c:31]([CH2:30][n:29]2[c:24]3[cH:23][cH:22][cH:21][c:20]([OH:19])[c:25]3[cH:26][c:27]2[CH3:28])[cH:36][cH:35][cH:34]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:7][CH2:8][O:9][C:10]([CH3:11])=[O:12].[CH3:13][O:14][C:15](=[O:16])[CH:17]([CH3:18])[O:19][... | COC(=O)C(C)Br.Cc1cc2c(O)cccc2n1Cc1ccccc1 | CCCCCC.CCOC(C)=O.COC(=O)C(C)Oc1cccc2c1cc(C)n2Cc1ccccc1 | null | null | CN(C)C=O | Acylation | Williamson Ether Synthesis | c05decc99b0034b12abc4520661d3e2054665934b67ff4efc33902f234192ca4 | 8e21a061e9e5b3d6a55f77e57128b08e82eb226539ffc927f65ff0ec9c28e997 | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[#8:5]-[C;D1;H3:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]:[c:11]:[#7;a:12]-[C:13]-[c:14]1:[c:15]:[c:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[cH;D2;+0:19]:1>>[C;D1;H3:6]-[#8:5]-[C;H0;D3;+0:3](=[O;D1;H0:20])-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]:[c... | 74 | [{"value": 74.0, "product": "CCOC(=O)C.CCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole (483 mg, 2.0 mmol) was reacted with 82 mg (2.0 mmol) of 60% NaH/mineral oil in 20 mL of DMF and then with 0.22 mL (2.0 mmol) of dl-methyl 2-bromopropionate as described in Example 1, Part E to give after chromatography on silica gel eluting with 20% EtOAc/hexane 480 mg (74%... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Aromatic alcohol | Ester.Ester.Ether | c1ccccc1 | c1ccccc1 | c1cc2ccccc2[nH]1.c1ccccc1 | Br- | CN(C)C=O | null | null | COC(=O)C(C)Br.Cc1cc2c(O)cccc2n1Cc1ccccc1>CN(C)C=O>CCCCCC.CCOC(C)=O.COC(=O)C(C)Oc1cccc2c1cc(C)n2Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9f95807db7ef46aaa34d1a46e928917e | COC(=O)C(C)Oc1cccc2c1cc(C)n2Cc1ccccc1.N.O=C(Cl)C(=O)Cl>>COC(=O)C(C)Oc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccccc1 | C(C(=O)Cl)(=O)Cl.COC(C(C)OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C)=O.N>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OC(C(=O)OC)C)CC1=CC=CC=C1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[cH:14][c:20]([CH3:21])[n:22]2[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.[NH3:18].Cl[C:15](=[O:16])[C:17](Cl)=[O:19]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]1[c:14]([C:15](=[O:16])[... | COC(=O)C(C)Oc1cccc2c1cc(C)n2Cc1ccccc1.N.O=C(Cl)C(=O)Cl | COC(=O)C(C)Oc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccccc1 | null | null | CCOC(=O)C | Acylation | OtherReaction | 2b4e5990a6b486febb67d1205a7fe80512d475c2d7f2428255890f94f2b89b0b | 1715a619707b7a78b1352b9fcc0d5da2f43c62973c7a9ceb4f5a9bcbea1c7854 | c1ccc(Cn2ccc3ccccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C:5]-[#7;a:6]1:[c:7](:[c:8]):[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:1-[C;D1;H3:13].[NH3;D0;+0:14]>>[C:5]-[#7;a:6]1:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-[NH2;D1;+0:14])=[O;D1;H0:4]):[c:12]:1-[C;D1;H3:13] | 90 | [{"value": 90.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OC(C(=O)OC)C)CC1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Oxalyl chloride (0.16 mL, 1.9 mmol) was reacted with 480 mg (1.5 mmol) of dl-2-[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester and then reacted with anhydrous ammonia as in Example 1, Part F and the reaction product was dissolved in EtOAc, washed with water, dried (MgSO4) and concentrated. The... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide | Ketone.Primary amide | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1.c1ccccc1 | HCl | CCOC(=O)C | null | null | COC(=O)C(C)Oc1cccc2c1cc(C)n2Cc1ccccc1.N.O=C(Cl)C(=O)Cl>CCOC(=O)C>COC(=O)C(C)Oc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-238c88d38f694e3fa5d1ff478152a137 | COC(=O)C(C)Oc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccccc1>>Cc1c(C(=O)C(N)=O)c2c(OC(C)C(=O)O)cccc2n1Cc1ccccc1 | COC(C(C)OC1=C2C(=C(N(C2=CC=C1)CC1=CC=CC=C1)C)C(C(=O)N)=O)=O.[OH-].[Na+]>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OC(C(=O)O)C)CC1=CC=CC=C1)C)=O | C[O:16][C:14]([CH:12]([O:11][c:10]1[c:9]2[c:3]([C:4](=[O:5])[C:6]([NH2:7])=[O:8])[c:2]([CH3:1])[n:21]([CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[c:20]2[cH:19][cH:18][cH:17]1)[CH3:13])=[O:15]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[C:6]([NH2:7])=[O:8])[c:9]2[c:10]([O:11][CH:12]([CH3:13])[C:14](=[O:15])[OH:16])[cH:17... | COC(=O)C(C)Oc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccccc1 | Cc1c(C(=O)C(N)=O)c2c(OC(C)C(=O)O)cccc2n1Cc1ccccc1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 50 | [{"value": 50.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OC(C(=O)O)C)CC1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A mixture of 521 mg (1.3 mmol) of dl-2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester and 10 mL of 1N NaOH in 30 mL of methanol was heated to maintain reflux for 0.17 hours, cooled to room temperature and stirred for 0.5 hour. The mixture was concentrated at reduced... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | Other | CO | null | 0.5 | COC(=O)C(C)Oc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccccc1>CO>Cc1c(C(=O)C(N)=O)c2c(OC(C)C(=O)O)cccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-12db1c229b3e4b39a2073d2783627aeb | COc1cccc2c1cc(C)n2Cc1ccccc1-c1ccccc1>>Cc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1 | C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)OC)C)C1=CC=CC=C1.ClCl>>C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1 | C[O:6][c:5]1[c:4]2[cH:3][c:2]([CH3:1])[n:11]([CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3-[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:10]2[cH:9][cH:8][cH:7]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([OH:6])[cH:7][cH:8][cH:9][c:10]2[n:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1-[c:19]1[cH:20][cH:21][cH:22][cH... | COc1cccc2c1cc(C)n2Cc1ccccc1-c1ccccc1 | Cc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1 | null | null | B(Br)(Br)Br | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2ccccc2Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 55 | [{"value": 55.0, "product": "C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 1.6 g (4.9 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-methyl-1H-indole was O-demethylated by treating it with 20 mL of 1M BBr3 /CH2 Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 841 mg (55% yield) of 1-([1,1'-biPhenyl]... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | Other | B(Br)(Br)Br | null | null | COc1cccc2c1cc(C)n2Cc1ccccc1-c1ccccc1>B(Br)(Br)Br>Cc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-574ffbc7e9b946328651db22944d9135 | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1>>COC(=O)COc1cccc2c1cc(C)n2Cc1ccccc1-c1ccccc1 | C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1.BrCC(=O)OC.[H-].[Na+]>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1-[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17]... | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1 | COC(=O)COc1cccc2c1cc(C)n2Cc1ccccc1-c1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(-c2ccccc2Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 77.3 | [{"value": 77.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-([1,1'-Biphenyl]-2-ylmethyl)-4-hydroxy-2-methyl-1H-indole (767 mg, 2.45 mmol) was alkylated by treating with 0.23 mL (2.45 mmol) of methyl bromoacetate and 98 mg (2.45 mmol) of 60% NaH/mineral oil in DMF as described in Example 1, Part E. The product was purified by chromatography over silica gel eluting with 20% EtO... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1>CN(C)C=O>COC(=O)COc1cccc2c1cc(C)n2Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-47a003f9624147efadac55f5c60b94a3 | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccccc1-c1ccccc1>>Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1-c1ccccc1 | COC(COC1=C2C(=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)C)C(C(=O)N)=O)=O.[Na]>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)C)=O | C[O:15][C:13]([CH2:12][O:11][c:10]1[c:9]2[c:3]([C:4](=[O:5])[C:6]([NH2:7])=[O:8])[c:2]([CH3:1])[n:20]([CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]3-[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[c:19]2[cH:18][cH:17][cH:16]1)=[O:14]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[C:6]([NH2:7])=[O:8])[c:9]2[c:10]([O:11][CH2:12][C:1... | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccccc1-c1ccccc1 | Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1-c1ccccc1 | null | null | [OH-].[Na+].CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccccc2Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 36.6 | [{"value": 35.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.6, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A mixture of 648 mg (1.4 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester in 10 mL of 1N NaOH and 20 mL of MeOH was heated to maintain reflux for 1 hour, cooled to room temperature and stirred 0.5 hour. The mixture was concentrated, the residue sti... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | Other | [OH-].[Na+].CO | null | 0.5 | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccccc1-c1ccccc1>[OH-].[Na+].CO>Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5df3c79084144f99bcdc789e25be2a1e | COc1cccc2c1cc(C)n2Cc1cccc(-c2ccccc2)c1>>Cc1cc2c(O)cccc2n1Cc1cccc(-c2ccccc2)c1 | C1(=CC(=CC=C1)CN1C(=CC2=C(C=CC=C12)OC)C)C1=CC=CC=C1.B(Br)(Br)Br.ClCl>>C1(=CC(=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1 | C[O:6][c:5]1[c:4]2[cH:3][c:2]([CH3:1])[n:11]([CH2:12][c:13]3[cH:14][cH:15][cH:16][c:17](-[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[cH:24]3)[c:10]2[cH:9][cH:8][cH:7]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([OH:6])[cH:7][cH:8][cH:9][c:10]2[n:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][... | COc1cccc2c1cc(C)n2Cc1cccc(-c2ccccc2)c1 | Cc1cc2c(O)cccc2n1Cc1cccc(-c2ccccc2)c1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2cccc(Cn3ccc4ccccc43)c2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 87 | [{"value": 87.0, "product": "C1(=CC(=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "C1(=CC(=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 1.25 g (3.8 mmol) of 1-([1,1'-biphenyl]-3-ylmethyl)-4-methoxy-2-methyl-1H-indole was O-demethylated by treating it with 15.2 mL of 1M BBr3 /CH2 Cl2 to give 1.03 g (87% yield) of crude 1-([1,1'-biphenyl]-3-ylmethyl)-4-hydroxy-2-methyl-1H-indole.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | Other | null | null | null | COc1cccc2c1cc(C)n2Cc1cccc(-c2ccccc2)c1>>Cc1cc2c(O)cccc2n1Cc1cccc(-c2ccccc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ddd7e0bd7cef44e8b59de3a93c55dc2b | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1cccc(-c2ccccc2)c1>>COC(=O)COc1cccc2c1cc(C)n2Cc1cccc(-c2ccccc2)c1 | C1(=CC(=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1.BrCC(=O)OC.[H-].[Na+]>>COC(COC1=C2C=C(N(C2=CC=C1)CC=1C=C(C=CC1)C1=CC=CC=C1)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[cH:19][cH:20][cH:21][c:22](-[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:1... | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1cccc(-c2ccccc2)c1 | COC(=O)COc1cccc2c1cc(C)n2Cc1cccc(-c2ccccc2)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(-c2cccc(Cn3ccc4ccccc43)c2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 79 | [{"value": 79.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC=1C=C(C=CC1)C1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.6, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC=1C=C(C=CC1)C1=CC=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-([1,1'-Biphenyl]-3-ylmethyl)-4-hydroxy-2-methyl-1H-indole (1.03 g, 3.3 mmol) was alkylated by treating with 0.31 mL (3.3 mmol) of methyl bromoacetate and 132 mg (3.3 mmol) of 60% NaH/mineral oil in DMF as described in Example 1, Part E. The product was purified by chromatography over silica gel eluting with 20% EtOAc... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1cccc(-c2ccccc2)c1>CN(C)C=O>COC(=O)COc1cccc2c1cc(C)n2Cc1cccc(-c2ccccc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a59e6c8dd5fb48dda0e37c75c7c2b042 | COc1cccc2c1cc(C)n2Cc1ccc(-c2ccccc2)cc1>>Cc1cc2c(O)cccc2n1Cc1ccc(-c2ccccc2)cc1 | C1(=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)OC)C)C1=CC=CC=C1.B(Br)(Br)Br.ClCl>>C1(=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1 | C[O:6][c:5]1[c:4]2[cH:3][c:2]([CH3:1])[n:11]([CH2:12][c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[cH:23][cH:24]3)[c:10]2[cH:9][cH:8][cH:7]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([OH:6])[cH:7][cH:8][cH:9][c:10]2[n:11]1[CH2:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2... | COc1cccc2c1cc(C)n2Cc1ccc(-c2ccccc2)cc1 | Cc1cc2c(O)cccc2n1Cc1ccc(-c2ccccc2)cc1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2ccc(Cn3ccc4ccccc43)cc2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 77.4 | [{"value": 77.0, "product": "C1(=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "C1(=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 1.3 g (4.0 mmol) of 1-([1,1'-biphenyl]-4-ylmethyl)-4-methoxy-2-methyl-1H-indole was O-demethylated by treating it with 16 mL of 1M BBr3 /CH2 Cl2 to give 970 mg (77% yield) of crude 1-([1,1'-biphenyl]-4-ylmethyl)-4-hydroxy-2-methyl-1H-indole.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | Other | null | null | null | COc1cccc2c1cc(C)n2Cc1ccc(-c2ccccc2)cc1>>Cc1cc2c(O)cccc2n1Cc1ccc(-c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6e4a7111550b4748814745d936cdc81f | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1cccc(-c2ccccc2)c1>>COC(=O)COc1cccc2c1cc(C)n2Cc1ccc(-c2ccccc2)cc1 | C1(=CC(=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C)C1=CC=CC=C1.[H-].[Na+].BrCC(=O)OC>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=C(C=C1)C1=CC=CC=C1)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[cH:19][cH:20][cH:28][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:29]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:1... | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1cccc(-c2ccccc2)c1 | COC(=O)COc1cccc2c1cc(C)n2Cc1ccc(-c2ccccc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7b00df63d7ae8680effc7ac2209a8a71eb4af9dc74b8220117411a77e22c75ef | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(-c2ccc(Cn3ccc4ccccc43)cc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]:[c:10]:[#7;a:11]-[C:12]-[c:13]1:[c:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[c;H0;D3;+0:17](-[c:18](:[c:19]):[c:20]):[cH;D2;+0:21]:1>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]:[c:10]:[#7;a:11]-[... | 125 | [{"value": 63.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=C(C=C1)C1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 125.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=C(C=C1)C1=CC=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure described in Example 1, Part E, 1-([1,1'-biphenyl]-3-ylmethyl)-4-hydroxy-2-methyl-1H-indole (970 mg, 3.1 mmol) was treated with 124 mg (3.1 mmol) of 60% NaH/mineral oil and then 0.29 mL (3.1 mmol) of methyl bromoacetate. The product was purified by chromatography over silica gel eluting with 20% EtO... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | c1ccccc1 | c1ccccc1 | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | HBr | null | null | null | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1cccc(-c2ccccc2)c1>>COC(=O)COc1cccc2c1cc(C)n2Cc1ccc(-c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2430659498234afdad6429ef09e67331 | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccc(-c2ccccc2)cc1>>Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccc(-c2ccccc2)cc1 | COC(COC1=C2C(=C(N(C2=CC=C1)CC1=CC=C(C=C1)C1=CC=CC=C1)C)C(C(=O)N)=O)=O.CO.[Na]>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC=C(C=C1)C1=CC=CC=C1)C)=O | C[O:15][C:13]([CH2:12][O:11][c:10]1[c:9]2[c:3]([C:4](=[O:5])[C:6]([NH2:7])=[O:8])[c:2]([CH3:1])[n:20]([CH2:21][c:22]3[cH:23][cH:24][c:25](-[c:26]4[cH:27][cH:28][cH:29][cH:30][cH:31]4)[cH:32][cH:33]3)[c:19]2[cH:18][cH:17][cH:16]1)=[O:14]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[C:6]([NH2:7])=[O:8])[c:9]2[c:10]([O:11][CH2:12][C... | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccc(-c2ccccc2)cc1 | Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccc(-c2ccccc2)cc1 | null | null | [OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(Cn3ccc4ccccc43)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 77.1 | [{"value": 74.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC=C(C=C1)C1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.1, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC=C(C=C1)C1=CC=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure described in Example 2, Part E, 803 mg (1.8 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-4-ylmethyl)-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester was hydrolyzed in 10 mL of 1N NaOH and 20 mL of MeOH to give 614 mg (74% yield) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-4-yl... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | Other | [OH-].[Na+] | null | null | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccc(-c2ccccc2)cc1>[OH-].[Na+]>Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccc(-c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-996f0a7d980d4f7db95b5a7e4dbfa2a5 | COc1cccc2c1cc(C)n2Cc1c(Cl)cccc1Cl>>Cc1cc2c(O)cccc2n1Cc1c(Cl)cccc1Cl | ClC1=C(C(=CC=C1)Cl)CN1C(=CC2=C(C=CC=C12)OC)C.B(Br)(Br)Br.C(Cl)Cl>>ClC1=C(C(=CC=C1)Cl)CN1C(=CC2=C(C=CC=C12)O)C | C[O:6][c:5]1[c:4]2[cH:3][c:2]([CH3:1])[n:11]([CH2:12][c:13]3[c:14]([Cl:15])[cH:16][cH:17][cH:18][c:19]3[Cl:20])[c:10]2[cH:9][cH:8][cH:7]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([OH:6])[cH:7][cH:8][cH:9][c:10]2[n:11]1[CH2:12][c:13]1[c:14]([Cl:15])[cH:16][cH:17][cH:18][c:19]1[Cl:20] | COc1cccc2c1cc(C)n2Cc1c(Cl)cccc1Cl | Cc1cc2c(O)cccc2n1Cc1c(Cl)cccc1Cl | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 83.3 | [{"value": 83.0, "product": "ClC1=C(C(=CC=C1)Cl)CN1C(=CC2=C(C=CC=C12)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.3, "product": "ClC1=C(C(=CC=C1)Cl)CN1C(=CC2=C(C=CC=C12)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 1.08 g (3.38 mmol) of 1-[(2,6 dichlorophenyl)methyl]-4-methoxy-2-methyl-1H-indole was O-demethylated by treating it with 13.5 mL of 1M BBr3 /CH2Cl2 to give 862 mg (83% yield) of 1-[(2,6-dichlorophenyl)methyl]-4-hydroxy-2-methyl-1H-indole, after chromatography on silica gel (elut... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | Other | null | null | null | COc1cccc2c1cc(C)n2Cc1c(Cl)cccc1Cl>>Cc1cc2c(O)cccc2n1Cc1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3d65a4f4324145edb476d47530c4a7b6 | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1c(Cl)cccc1Cl>>COC(=O)COc1cccc2c1cc(C)n2Cc1c(Cl)cccc1Cl | ClC1=C(C(=CC=C1)Cl)CN1C(=CC2=C(C=CC=C12)O)C.[H-].[Na+].BrCC(=O)OC>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1Cl)Cl)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[c:19]([Cl:20])[cH:21][cH:22][cH:23][c:24]1[Cl:25]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[c:19]([Cl:20])[cH:21]... | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1c(Cl)cccc1Cl | COC(=O)COc1cccc2c1cc(C)n2Cc1c(Cl)cccc1Cl | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 39 | [{"value": 39.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1Cl)Cl)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.8, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1Cl)Cl)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure described in Example 1, Part E, 1-[(2,6-dichlorophenyl)methyl]-4-hydroxy-2-methyl-1H-indole (862 mg, 2.8 mmol) was treated with 112 mg (2.8 mmol) of 60% NaH/mineral oil and then 0.27 mL (2.8 mmol) of methyl bromoacetate. The product was purified by chromatography over silica gel eluting with 20% EtO... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | HBr | null | null | null | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1c(Cl)cccc1Cl>>COC(=O)COc1cccc2c1cc(C)n2Cc1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-06734e09bf9f433d9b3795926278123c | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1c(Cl)cccc1Cl>>Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1c(Cl)cccc1Cl | COC(COC1=C2C(=C(N(C2=CC=C1)CC1=C(C=CC=C1Cl)Cl)C)C(C(=O)N)=O)=O.[OH-].[Na+].CO.C(C)(=O)OCC>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1Cl)Cl)C)=O | C[O:15][C:13]([CH2:12][O:11][c:10]1[c:9]2[c:3]([C:4](=[O:5])[C:6]([NH2:7])=[O:8])[c:2]([CH3:1])[n:20]([CH2:21][c:22]3[c:23]([Cl:24])[cH:25][cH:26][cH:27][c:28]3[Cl:29])[c:19]2[cH:18][cH:17][cH:16]1)=[O:14]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[C:6]([NH2:7])=[O:8])[c:9]2[c:10]([O:11][CH2:12][C:13](=[O:14])[OH:15])[cH:16][cH... | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1c(Cl)cccc1Cl | Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1c(Cl)cccc1Cl | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 86 | [{"value": 86.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1Cl)Cl)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1Cl)Cl)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A mixture of 420 mg (0.94 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-[(2,6-dichlorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester, 5 mL of 1N NaOH and 15 mL of MeOH was heated to maintain reflux for 0.17 hours, cooled to room temperature and stirred 0.5 hours. Ethyl acetate and water was added, the aqu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | Other | O | null | 0.5 | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1c(Cl)cccc1Cl>O>Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1c(Cl)cccc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-69862c99df73480e9bc323a291044204 | COc1cccc2[nH]c(C)cc12.Fc1ccc(CCl)cc1>>COc1cccc2c1cc(C)n2Cc1ccc(F)cc1 | FC1=CC=C(CCl)C=C1.COC1=C2C=C(NC2=CC=C1)C.[H-].[Na+].CCCCCC>>FC1=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)OC)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[cH:9][c:10]([CH3:11])[nH:12]2.Cl[CH2:13][c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[cH:9][c:10]([CH3:11])[n:12]2[CH2:13][c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1 | COc1cccc2[nH]c(C)cc12.Fc1ccc(CCl)cc1 | COc1cccc2c1cc(C)n2Cc1ccc(F)cc1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 16b46a8af20339f7ff0b611b4ac5dd01fe35ba577361e893c359dfa478dc1974 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 84 | [{"value": 84.0, "product": "FC1=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "FC1=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | 4-Methoxy-2-methyl-1H-indole (805 mg, 5 mmol) was added to a mixture of 200 mg (5 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 10 mL of DMF and after stirring for 0.5 hours, 0.6 mL (5 mmol) of 4-fluorobenzyl chloride was added. The mixture was stirred at room temperature for 18 hour... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1.c1ccccc1 | HCl | CN(C)C=O.O | null | 0.5 | COc1cccc2[nH]c(C)cc12.Fc1ccc(CCl)cc1>CN(C)C=O.O>COc1cccc2c1cc(C)n2Cc1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-858e366b919f470e923529fff24917ea | COc1cccc2c1cc(C)n2Cc1ccc(F)cc1>>Cc1cc2c(O)cccc2n1Cc1ccc(F)cc1 | FC1=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)OC)C.B(Br)(Br)Br.C(Cl)Cl>>FC1=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)O)C | C[O:6][c:5]1[c:4]2[cH:3][c:2]([CH3:1])[n:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]3)[c:10]2[cH:9][cH:8][cH:7]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([OH:6])[cH:7][cH:8][cH:9][c:10]2[n:11]1[CH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1 | COc1cccc2c1cc(C)n2Cc1ccc(F)cc1 | Cc1cc2c(O)cccc2n1Cc1ccc(F)cc1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 84.2 | [{"value": 84.0, "product": "FC1=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "FC1=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 1.1 g (4.1 mmol) of 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole was O-demethylated by treating it with 16.4 mL of 1M BBr3 /CH2Cl2 to give 881 mg (84% yield) of crude 1-[(4-fluorophenyl)methyl]-4-hydroxy-2-methyl-1H-indole.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | Other | null | null | null | COc1cccc2c1cc(C)n2Cc1ccc(F)cc1>>Cc1cc2c(O)cccc2n1Cc1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b5b468e495014e1391684d9a81922ee1 | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1ccc(F)cc1>>COC(=O)COc1cccc2c1cc(C)n2Cc1ccc(F)cc1 | FC1=CC=C(C=C1)CN1C(=CC2=C(C=CC=C12)O)C.[H-].[Na+].BrCC(=O)OC>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=C(C=C1)F)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[cH:19][cH:20][c:21]([F:22])[... | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1ccc(F)cc1 | COC(=O)COc1cccc2c1cc(C)n2Cc1ccc(F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 81 | [{"value": 81.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=C(C=C1)F)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=C(C=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure described in Example 1, Part E, 1-[(4-fluorophenyl)methyl]-4-hydroxy-2-methyl-1H-indole (881 mg, 3.45 mmol) was treated with 138 mg (3.45 mmol) of 60% NaH/mineral oil and then 0.33 mL (3.45 mmol) of methyl bromoacetate. The product was purified by chromatography over silica gel eluting with 20% EtOA... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | HBr | null | null | null | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1ccc(F)cc1>>COC(=O)COc1cccc2c1cc(C)n2Cc1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1f91a3ebc06246c6a616154657ef7250 | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccc(F)cc1>>Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccc(F)cc1 | COC(COC1=C2C(=C(N(C2=CC=C1)CC1=CC=C(C=C1)F)C)C(C(=O)N)=O)=O.[OH-].[Na+].CO.C(C)(=O)OCC>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC=C(C=C1)F)C)=O | C[O:15][C:13]([CH2:12][O:11][c:10]1[c:9]2[c:3]([C:4](=[O:5])[C:6]([NH2:7])=[O:8])[c:2]([CH3:1])[n:20]([CH2:21][c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]3)[c:19]2[cH:18][cH:17][cH:16]1)=[O:14]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[C:6]([NH2:7])=[O:8])[c:9]2[c:10]([O:11][CH2:12][C:13](=[O:14])[OH:15])[cH:16][cH:17][cH... | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccc(F)cc1 | Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccc(F)cc1 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 81.2 | [{"value": 81.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC=C(C=C1)F)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.2, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC=C(C=C1)F)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 767 mg (1.9 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-[(4-fluorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester, 10 mL of 1N NaOH and 30 mL of MeOH was heated to maintain reflux for 0.67 hours, cooled to room temperature and stirred 1 hour. Ethyl acetate and water were added and the aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | Other | O | null | 1 | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C)n2Cc1ccc(F)cc1>O>Cc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-80c7b751a3284a8b966f0ea7134ae600 | COc1cccc2[nH]c(C)cc12.ClCc1cccc2ccccc12>>COc1cccc2c1cc(C)n2Cc1cccc2ccccc12 | COC1=C2C=C(NC2=CC=C1)C.[H-].[Na+].ClCC1=CC=CC2=CC=CC=C12>>COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[cH:9][c:10]([CH3:11])[nH:12]2.Cl[CH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[cH:9][c:10]([CH3:11])[n:12]2[CH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12 | COc1cccc2[nH]c(C)cc12.ClCc1cccc2ccccc12 | COc1cccc2c1cc(C)n2Cc1cccc2ccccc12 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 16b46a8af20339f7ff0b611b4ac5dd01fe35ba577361e893c359dfa478dc1974 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(Cn3ccc4ccccc43)cccc2c1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 97.1 | [{"value": 97.0, "product": "COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.1, "product": "COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.67 | HOUR | 4-Methoxy-2-methyl-1H-indole (644 mg, 4 mmol) was dissolved in 10 mL of DMF and 160 mg (4 mmol) of 60% NaH/mineral oil was added. After 0.67 hours, 707 mg (4 mmol) of 1-(chloromethyl)naphthalene was added. After 5 hours, the mixture was diluted with water and extracted twice with ethyl acetate. The combined ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1.c1ccc2ccccc2c1 | HCl | CN(C)C=O.O | null | 0.67 | COc1cccc2[nH]c(C)cc12.ClCc1cccc2ccccc12>CN(C)C=O.O>COc1cccc2c1cc(C)n2Cc1cccc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ac45098226724296a2030ef33a83f824 | COc1cccc2c1cc(C)n2Cc1cccc2ccccc12>>Cc1cc2c(O)cccc2n1Cc1cccc2ccccc12 | COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C.B(Br)(Br)Br.C(Cl)Cl>>OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C | C[O:6][c:5]1[c:4]2[cH:3][c:2]([CH3:1])[n:11]([CH2:12][c:13]3[cH:14][cH:15][cH:16][c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]34)[c:10]2[cH:9][cH:8][cH:7]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([OH:6])[cH:7][cH:8][cH:9][c:10]2[n:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | COc1cccc2c1cc(C)n2Cc1cccc2ccccc12 | Cc1cc2c(O)cccc2n1Cc1cccc2ccccc12 | null | null | CCOC(=O)C.CCCCCC | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(Cn3ccc4ccccc43)cccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 71 | [{"value": 71.0, "product": "OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.0, "product": "OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 1.17 g (3.9 mmol) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole was O-demethylated by treating it with 15.6 mL of 1M BBr3 /CH2Cl2 to give a material that was chromatographed on silica gel (eluted with 20% EtOAc/hexane then 50% EtOAc/hexane) to give 796 mg (71% yield... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.c1ccc2ccccc2c1 | Other | CCOC(=O)C.CCCCCC | null | null | COc1cccc2c1cc(C)n2Cc1cccc2ccccc12>CCOC(=O)C.CCCCCC>Cc1cc2c(O)cccc2n1Cc1cccc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9be854f4426b4c0084e2dc374f4ca800 | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1cccc2ccccc12>>COC(=O)COc1cccc2c1cc(C)n2Cc1cccc2ccccc12 | OC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C.[H-].[Na+].BrCC(=O)OC>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[cH:19][cH:20][cH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH3:15])[n:16]2[CH2:17][c:18]1[cH:19][... | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1cccc2ccccc12 | COC(=O)COc1cccc2c1cc(C)n2Cc1cccc2ccccc12 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc2c(Cn3ccc4ccccc43)cccc2c1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 463.7 | [{"value": 45.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 463.7, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC2=CC=CC=C12)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure described in Example 1, Part E, 4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole (796 mg, 2.8 mmol) was treated with 112 mg (2.8 mmol) of 60% NaH/mineral oil and then 0.27 mL (0.27 mmol) of methyl bromoacetate. The product was purified by chromatography over silica gel eluting with 20% EtOAc/... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.c1ccc2ccccc2c1 | HBr | null | null | null | COC(=O)CBr.Cc1cc2c(O)cccc2n1Cc1cccc2ccccc12>>COC(=O)COc1cccc2c1cc(C)n2Cc1cccc2ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b617f8b18b4f46baa67bd4b913fc8d21 | CCC(=O)N(C)OC.COc1cccc(NC(=O)OC(C)(C)C)c1C>>CCC(=O)Cc1c(NC(=O)OC(C)(C)C)cccc1OC | C(C)(CC)[Li].C(C)(C)(C)OC(=O)NC1=C(C(=CC=C1)OC)C.CON(C(CC)=O)C>>C(C)(C)(C)OC(=O)NC1=C(C(=CC=C1)OC)CC(CC)=O | CON(C)[C:3]([CH2:2][CH3:1])=[O:4].[CH3:5][c:6]1[c:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17][cH:18][c:19]1[O:20][CH3:21]>>[CH3:1][CH2:2][C:3](=[O:4])[CH2:5][c:6]1[c:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17][cH:18][c:19]1[O:20][CH3:21] | CCC(=O)N(C)OC.COc1cccc(NC(=O)OC(C)(C)C)c1C | CCC(=O)Cc1c(NC(=O)OC(C)(C)C)cccc1OC | null | null | C1CCOC1.C1CCCCC1 | C-C Coupling | OtherReaction | e4f529a3ae374940e7335150c613235054eca93a08615af33523f392ef733189 | 4113f0e803c7e6f9f731016c87e547bd597c0045514b87ca0ff3566df8b4b2c4 | c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | -60 | CELSIUS | 5 | MINUTE | A solution of 140 mL (0.18 mol) of 1.3M sec-butyl lithium in cyclohexane was added slowly to N-tert-butoxycarbonyl-3-methoxy-2-methylaniline (21.3 g, 0.09 mol) in 250 mL of THF keeping the temperature below -40° C. with a dry ice-ethanol bath. The bath was removed and the temperature allowed to rise to 0° C. and then t... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | null | null | c1ccccc1 | HO- | C1CCOC1.C1CCCCC1 | -60 | 0.083333 | CCC(=O)N(C)OC.COc1cccc(NC(=O)OC(C)(C)C)c1C>C1CCOC1.C1CCCCC1>CCC(=O)Cc1c(NC(=O)OC(C)(C)C)cccc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e34bd1862e53447ea8a43dbc7cad8a0e | BrCc1ccccc1.CCc1cc2c(OC)cccc2[nH]1>>CCc1cc2c(OC)cccc2n1Cc1ccccc1 | C(C)C=1NC2=CC=CC(=C2C1)OC.[H-].[Na+].C(C1=CC=CC=C1)Br>>C(C)C=1N(C2=CC=CC(=C2C1)OC)CC1=CC=CC=C1 | Br[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([O:7][CH3:8])[cH:9][cH:10][cH:11][c:12]2[nH:13]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([O:7][CH3:8])[cH:9][cH:10][cH:11][c:12]2[n:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | BrCc1ccccc1.CCc1cc2c(OC)cccc2[nH]1 | CCc1cc2c(OC)cccc2n1Cc1ccccc1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 16b46a8af20339f7ff0b611b4ac5dd01fe35ba577361e893c359dfa478dc1974 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 49 | [{"value": 49.0, "product": "C(C)C=1N(C2=CC=CC(=C2C1)OC)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.7, "product": "C(C)C=1N(C2=CC=CC(=C2C1)OC)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 2-Ethyl-4-methoxy-1H-indole (4.2 g, 24 mmol) was dissolved in 30 mL of DMF and 960 mg (24 mmol) of 60% NaH/mineral oil was added. After 1.5 hours, 2.9 mL (24 mmol) of benzyl bromide was added. After 4 hours, the mixture was diluted with water and extracted twice with ethyl acetate. The combined ethyl acetate was washed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1.c1ccccc1 | HBr | CN(C)C=O.O | null | 1.5 | BrCc1ccccc1.CCc1cc2c(OC)cccc2[nH]1>CN(C)C=O.O>CCc1cc2c(OC)cccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a407b211fca84e1ca3a7311663e629e3 | CCc1cc2c(OC)cccc2n1Cc1ccccc1>>CCc1cc2c(O)cccc2n1Cc1ccccc1 | C(C)C=1N(C2=CC=CC(=C2C1)OC)CC1=CC=CC=C1.B(Br)(Br)Br.C(Cl)Cl>>C(C)C=1N(C2=CC=CC(=C2C1)O)CC1=CC=CC=C1 | C[O:7][c:6]1[c:5]2[cH:4][c:3]([CH2:2][CH3:1])[n:12]([CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:11]2[cH:10][cH:9][cH:8]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([OH:7])[cH:8][cH:9][cH:10][c:11]2[n:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CCc1cc2c(OC)cccc2n1Cc1ccccc1 | CCc1cc2c(O)cccc2n1Cc1ccccc1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 54 | [{"value": 54.0, "product": "C(C)C=1N(C2=CC=CC(=C2C1)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.7, "product": "C(C)C=1N(C2=CC=CC(=C2C1)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 3.1 g 11.7 mmol of 2ethyl-4-methoxy-1-(phenylmethyl)-1H-indole was O-demethylated by treating it with 48.6 mL of 1M BBr3 /CH2Cl2 to give a material that was chromatographed on silica gel (eluted with 20% EtOAc/hexane) to give 1.58 g (54% yield) of 2-ethyl-4-hydroxy-1-(phenylmeth... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | Other | null | null | null | CCc1cc2c(OC)cccc2n1Cc1ccccc1>>CCc1cc2c(O)cccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-093410cd99d04309ae041c581fea5247 | CCc1cc2c(O)cccc2n1Cc1ccccc1.COC(=O)CBr>>CCc1cc2c(OCC(=O)OC)cccc2n1Cc1ccccc1 | C(C)C=1N(C2=CC=CC(=C2C1)O)CC1=CC=CC=C1.[H-].[Na+].BrCC(=O)OC>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)=O | [CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([OH:7])[cH:13][cH:14][cH:15][c:16]2[n:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.Br[CH2:8][C:9](=[O:10])[O:11][CH3:12]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([O:7][CH2:8][C:9](=[O:10])[O:11][CH3:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22... | CCc1cc2c(O)cccc2n1Cc1ccccc1.COC(=O)CBr | CCc1cc2c(OCC(=O)OC)cccc2n1Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 69 | [{"value": 69.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.3, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure described in Example 1, Part E, 2-ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole (1.56 g, 6.2 mmol) was treated with 248 mg (6.2 mmol) of 60% NaH/mineral oil and then 0.6 mL (6.2 mmol) of methyl bromoacetate. The product was purified by chromatography over silica gel eluting with 20% EtOAc/hexane, to gi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | HBr | null | null | null | CCc1cc2c(O)cccc2n1Cc1ccccc1.COC(=O)CBr>>CCc1cc2c(OCC(=O)OC)cccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4103d8fa652146e388cdb839eb898e60 | CCc1cc2c(O)cccc2n1Cc1cccc(Cl)c1.COC(=O)CBr>>CCc1cc2c(OCC(=O)OC)cccc2n1Cc1cccc(Cl)c1 | ClC=1C=C(C=CC1)CN1C(=CC2=C(C=CC=C12)O)CC.[H-].[Na+].BrCC(=O)OC>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC(=CC=C1)Cl)CC)=O | [CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([OH:7])[cH:13][cH:14][cH:15][c:16]2[n:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]([Cl:24])[cH:25]1.Br[CH2:8][C:9](=[O:10])[O:11][CH3:12]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([O:7][CH2:8][C:9](=[O:10])[O:11][CH3:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1[CH2:18][c:19]1[cH:20][cH:2... | CCc1cc2c(O)cccc2n1Cc1cccc(Cl)c1.COC(=O)CBr | CCc1cc2c(OCC(=O)OC)cccc2n1Cc1cccc(Cl)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 65 | [{"value": 65.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC(=CC=C1)Cl)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.9, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC(=CC=C1)Cl)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure described in Example 1, Part E, 1-[(3-chlorophenyl)methyl]-2-ethyl-4-hydroxy-1H-indole (512 mg, 1.8 mmol) was treated with 72 mg (1.8 mmol) of 60% NaH/mineral oil and then 0.17 mL (1.8 mmol) of methyl bromoacetate. The product was purified by chromatography over silica gel eluting with 20% EtOAc/hex... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | HBr | null | null | null | CCc1cc2c(O)cccc2n1Cc1cccc(Cl)c1.COC(=O)CBr>>CCc1cc2c(OCC(=O)OC)cccc2n1Cc1cccc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0c7e8d43292048a8b5363fc3cec7be00 | CCc1c(C(=O)C(N)=O)c2c(OCC(=O)OC)cccc2n1Cc1cccc(Cl)c1>>CCc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1cccc(Cl)c1 | COC(COC1=C2C(=C(N(C2=CC=C1)CC1=CC(=CC=C1)Cl)CC)C(C(=O)N)=O)=O.CO.[Na]>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC(=CC=C1)Cl)CC)=O | C[O:16][C:14]([CH2:13][O:12][c:11]1[c:10]2[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:3]([CH2:2][CH3:1])[n:21]([CH2:22][c:23]3[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]3)[c:20]2[cH:19][cH:18][cH:17]1)=[O:15]>>[CH3:1][CH2:2][c:3]1[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:10]2[c:11]([O:12][CH2:13][C:14](=[O:15])[OH:16])... | CCc1c(C(=O)C(N)=O)c2c(OCC(=O)OC)cccc2n1Cc1cccc(Cl)c1 | CCc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1cccc(Cl)c1 | null | null | [OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 64.6 | [{"value": 61.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC(=CC=C1)Cl)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.6, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC(=CC=C1)Cl)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure described in Example 2, Part E, 418 mg (1 mmol) of [[3-(2-amino-1,2-dioxoethyl)1-[(3-chlorophenyl)methyl]-2-ethyl-1H-indol-4-yl]oxy]acetic acid methyl ester was hydrolyzed in 5 mL of 1N NaOH and 15 mL of MeOH to give 268 mg (61% yield) of [[3-(2-amino-1,2-dioxoethyl)1-[(3-chlorophenyl)methyl]-2-ethy... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | Other | [OH-].[Na+] | null | null | CCc1c(C(=O)C(N)=O)c2c(OCC(=O)OC)cccc2n1Cc1cccc(Cl)c1>[OH-].[Na+]>CCc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1cccc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1b52bb60c1944a8bb041ea0a07e47ab6 | CCc1cc2c(OC)cccc2n1Cc1ccccc1-c1ccccc1>>CCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1 | C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)OC)CC)C1=CC=CC=C1.ClCl>>C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)CC)C1=CC=CC=C1 | C[O:7][c:6]1[c:5]2[cH:4][c:3]([CH2:2][CH3:1])[n:12]([CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3-[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[c:11]2[cH:10][cH:9][cH:8]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([OH:7])[cH:8][cH:9][cH:10][c:11]2[n:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1-[c:20]1[cH:21][... | CCc1cc2c(OC)cccc2n1Cc1ccccc1-c1ccccc1 | CCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1 | null | null | B(Br)(Br)Br | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2ccccc2Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 69.3 | [{"value": 69.0, "product": "C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)CC)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.3, "product": "C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)CC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 911 mg (2.6 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-4-methoxy-1H-indole was O-demethylated by treating it with 10 mL of 1M BBr3 /CH2 Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 590 mg (69% yield) of 1-([1,1'-biphenyl]... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | Other | B(Br)(Br)Br | null | null | CCc1cc2c(OC)cccc2n1Cc1ccccc1-c1ccccc1>B(Br)(Br)Br>CCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a877d6e90efd4757a0744545d7206df9 | CCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1.COC(=O)CBr>>CCc1cc2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1 | C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)CC)C1=CC=CC=C1.BrCC(=O)OC.[H-].[Na+]>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)CC)=O | [CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([OH:7])[cH:13][cH:14][cH:15][c:16]2[n:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1-[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.Br[CH2:8][C:9](=[O:10])[O:11][CH3:12]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([O:7][CH2:8][C:9](=[O:10])[O:11][CH3:12])[cH:13][cH:14][cH:15][c:16]... | CCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1.COC(=O)CBr | CCc1cc2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(-c2ccccc2Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 59 | [{"value": 59.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.6, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-([1,1'-Biphenyl]-2-ylmethyl)-2-ethyl-4-hydroxy-1H-indole (911 mg, 2.8 mmol) was alkylated by treating with 0.26 mL (2.8 mmol) of methyl bromoacetate and 111 mg (2.8 mmol) of 60% NaH/mineral oil in DMF as described in Example 1, Part E. The product was purified by chromatography over silica gel eluting with 20% EtOAc/... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | CCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1.COC(=O)CBr>CN(C)C=O>CCc1cc2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-80e512c43b2e48fea09aa8564066a901 | CCc1c(C(=O)C(N)=O)c2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1>>CCc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1-c1ccccc1 | COC(COC1=C2C(=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)CC)C(C(=O)N)=O)=O>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)CC)=O | C[O:16][C:14]([CH2:13][O:12][c:11]1[c:10]2[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:3]([CH2:2][CH3:1])[n:21]([CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]3-[c:29]3[cH:30][cH:31][cH:32][cH:33][cH:34]3)[c:20]2[cH:19][cH:18][cH:17]1)=[O:15]>>[CH3:1][CH2:2][c:3]1[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:10]2[c:11]([O... | CCc1c(C(=O)C(N)=O)c2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1 | CCc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1-c1ccccc1 | null | null | [OH-].[Na+].CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccccc2Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 59.3 | [{"value": 59.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.3, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 600 mg (1.3 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-1H-indol-4-yl]oxy]acetic acid methyl ester in 8 mL of 1N NaOH and 20 mL of MeOH was heated to maintain reflux for 0.67 hours, concentrated at reduced pressure and the residue taken up in EtOAc/water. The aqueous layer ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | Other | [OH-].[Na+].CO | null | null | CCc1c(C(=O)C(N)=O)c2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1>[OH-].[Na+].CO>CCc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c14cbb85bdd54ffa9a54b464ff55f720 | CCCC(=O)N(C)OC.COc1cccc(NC(=O)OC(C)(C)C)c1C>>CCCC(=O)Cc1c(NC(=O)OC(C)(C)C)cccc1OC | C(C)(CC)[Li].C(C)(C)(C)OC(=O)NC1=C(C(=CC=C1)OC)C.CON(C(CCC)=O)C.C1CCOC1.C1CCOC1>>C(C)(C)(C)OC(=O)NC1=C(C(=CC=C1)OC)CC(CCC)=O | CON(C)[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[CH3:6][c:7]1[c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18][cH:19][c:20]1[O:21][CH3:22]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[CH2:6][c:7]1[c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18][cH:19][c:20]1[O:21][CH3:... | CCCC(=O)N(C)OC.COc1cccc(NC(=O)OC(C)(C)C)c1C | CCCC(=O)Cc1c(NC(=O)OC(C)(C)C)cccc1OC | null | null | C1CCCCC1 | C-C Coupling | OtherReaction | e4f529a3ae374940e7335150c613235054eca93a08615af33523f392ef733189 | 4113f0e803c7e6f9f731016c87e547bd597c0045514b87ca0ff3566df8b4b2c4 | c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | -60 | CELSIUS | 1 | HOUR | A solution of 50 mL (65 mmol) of 1.3M sec-butyl lithium in cyclohexane was added slowly to N-tert-butoxycarbonyl-3-methoxy-2-methylaniline (7.7 g, 32.5 mmol) in 100 mL. of THF keeping the temperature below -40° C. with a dry ice-ethanol bath. The bath was removed and the temperature allowed to rise to -10° C. and then ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | null | null | c1ccccc1 | HO- | C1CCCCC1 | -60 | 1 | CCCC(=O)N(C)OC.COc1cccc(NC(=O)OC(C)(C)C)c1C>C1CCCCC1>CCCC(=O)Cc1c(NC(=O)OC(C)(C)C)cccc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a277cd76b49147da9acb93045c400b7a | CCCc1cc2c(OC)cccc2n1Cc1ccccc1-c1ccccc1>>CCCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1 | C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)OC)CCC)C1=CC=CC=C1.B(Br)(Br)Br.ClCl>>C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)CCC)C1=CC=CC=C1 | C[O:8][c:7]1[c:6]2[cH:5][c:4]([CH2:3][CH2:2][CH3:1])[n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3-[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:12]2[cH:11][cH:10][cH:9]1>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]2[c:7]([OH:8])[cH:9][cH:10][cH:11][c:12]2[n:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1... | CCCc1cc2c(OC)cccc2n1Cc1ccccc1-c1ccccc1 | CCCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2ccccc2Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 71.1 | [{"value": 71.0, "product": "C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)CCC)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.1, "product": "C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)CCC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 1.16 g (3.27 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-propyl-1H-indole was O-demethylated by treating it with 13 mL of 1M BBr3 /CH2 Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 794 mg (71% yield) of 1-([1,1'-bipheny... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCCc1cc2c(OC)cccc2n1Cc1ccccc1-c1ccccc1>>CCCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-54c4d1b0dd394206b5c6af6828345e25 | CCCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1.COC(=O)CBr>>CCCc1cc2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1 | C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)CCC)C1=CC=CC=C1.BrCC(=O)OC.[H-].[Na+]>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)CCC)=O | [CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]2[c:7]([OH:8])[cH:14][cH:15][cH:16][c:17]2[n:18]1[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1-[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.Br[CH2:9][C:10](=[O:11])[O:12][CH3:13]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]2[c:7]([O:8][CH2:9][C:10](=[O:11])[O:12][CH3:13])[cH:14][cH:... | CCCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1.COC(=O)CBr | CCCc1cc2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(-c2ccccc2Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 56 | [{"value": 56.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)CCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-([1,1'-Biphenyl]-2-ylmethyl)-4-hydroxy-2-propyl-1H-indole (794 mg, 2.8 mmol) was alkylated by treating with 0.22 mL (2.3 mmol) of methyl bromoacetate and 93 mg (2.3 mmol) of 60% NaH/mineral oil in DMF as described in Example 1, Part E. The product was purified by chromatography over silica gel eluting with 20% EtOAc/... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | CCCc1cc2c(O)cccc2n1Cc1ccccc1-c1ccccc1.COC(=O)CBr>CN(C)C=O>CCCc1cc2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a09a8e58b974e14b921d02856d38d2a | CCCc1c(C(=O)C(N)=O)c2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1>>CCCc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1-c1ccccc1 | COC(COC1=C2C(=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)CCC)C(C(=O)N)=O)=O>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)CCC)=O | C[O:17][C:15]([CH2:14][O:13][c:12]1[c:11]2[c:5]([C:6](=[O:7])[C:8]([NH2:9])=[O:10])[c:4]([CH2:3][CH2:2][CH3:1])[n:22]([CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]3-[c:30]3[cH:31][cH:32][cH:33][cH:34][cH:35]3)[c:21]2[cH:20][cH:19][cH:18]1)=[O:16]>>[CH3:1][CH2:2][CH2:3][c:4]1[c:5]([C:6](=[O:7])[C:8]([NH2:9])=[O:10])... | CCCc1c(C(=O)C(N)=O)c2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1 | CCCc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1-c1ccccc1 | null | null | [OH-].[Na+].CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccccc2Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 88.3 | [{"value": 88.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)CCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.3, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.75 | HOUR | A mixture of 440 mg (0.9 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-propyl-1H-indol-4-yl]oxy]acetic acid methyl ester in 5 mL of 1N NaOH and 15 mL of MeOH was stirred for 0.75 hours, concentrated at reduced pressure and the residue taken up in EtOAc/water. The aqueous layer was separated, ma... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | Other | [OH-].[Na+].CO | null | 0.75 | CCCc1c(C(=O)C(N)=O)c2c(OCC(=O)OC)cccc2n1Cc1ccccc1-c1ccccc1>[OH-].[Na+].CO>CCCc1c(C(=O)C(N)=O)c2c(OCC(=O)O)cccc2n1Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-34fde6f5003d4e6dab0c33bf86ba9d7f | COc1cccc(NC(=O)OC(C)(C)C)c1CC(=O)C1CC1>>CON(C)C(=O)C1CC1 | C(C)(CC)[Li].C1(CC1)C(=O)CC1=C(C=CC=C1OC)NC(=O)OC(C)(C)C.C(C)(C)(C)OC(=O)NC1=C(C(=CC=C1)OC)C.C1CCOC1>>CON(C(=O)C1CC1)C | COc1cccc([NH:3]C(=O)OC(C)(C)C)c1C[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9]1>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9]1 | COc1cccc(NC(=O)OC(C)(C)C)c1CC(=O)C1CC1 | CON(C)C(=O)C1CC1 | null | null | C1CCCCC1 | Miscellaneous | OtherReaction | 61d785c76a3ba47dcf3109c06bbe63e6f2eb472c023dbdf1e08fee621d950a07 | 367ca7a9199e8fe44c8c84b98b000d76432684a8ad9412335aad1964c6e1b04d | C1CC1 | C-O-c1:c:c:c:c(-[NH;D2;+0:1]-C(=O)-O-C(-C)(-C)-C):c:1-C-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[C:6]-1>>[C;D1;H3:7]-[#8:8]-[N;H0;D3;+0:1](-[C;D1;H3:9])-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[C:6]-1 | null | [] | null | null | null | null | Using the procedure described in Example 9, Part A, 100 mL (130 mmol) of 1.3M sec-butyl lithium in cyclohexane was reacted with N-tert-butoxycarbonyl-3-methoxy-2-methylaniline (15.4 g, 65 mmol) in 100 mL of THF and then with 8.4 g (65 mmol) of N-methoxy-N-methylcyclopropylcarboxamide to give crude [2-(tert-butoxycarbon... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Ether.Boc | Tertiary amide | c1ccccc1 | null | C1CC1 | HO- | C1CCCCC1 | null | null | COc1cccc(NC(=O)OC(C)(C)C)c1CC(=O)C1CC1>C1CCCCC1>CON(C)C(=O)C1CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-90e6c368bccf4e26954b7d2f6022a3b3 | COc1cccc2c1cc(C1CC1)n2Cc1ccccc1>>Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1 | C1(CC1)C=1N(C2=CC=CC(=C2C1)OC)CC1=CC=CC=C1.B(Br)(Br)Br.C(Cl)Cl>>C1(CC1)C=1N(C2=CC=CC(=C2C1)O)CC1=CC=CC=C1 | C[O:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][c:9]([CH:10]1[CH2:11][CH2:12]1)[n:13]2[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][c:9]([CH:10]1[CH2:11][CH2:12]1)[n:13]2[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | COc1cccc2c1cc(C1CC1)n2Cc1ccccc1 | Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Cn2c(C3CC3)cc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 52.2 | [{"value": 52.0, "product": "C1(CC1)C=1N(C2=CC=CC(=C2C1)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.2, "product": "C1(CC1)C=1N(C2=CC=CC(=C2C1)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 630 g (2.3 mmol) of 2-cyclopropyl-4-methoxy-1-(phenylmethyl)-1H-indole was O-demethylated by treating it with 9 mL of 1M BBr3 /CH2Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 316 mg (52% yield) of 2-cyclopropyl-4-hydroxy-1-(ph... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.C1CC1.c1ccccc1 | Other | null | null | null | COc1cccc2c1cc(C1CC1)n2Cc1ccccc1>>Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-979ce933bd434af5ad518dda54297e9c | COC(=O)CBr.Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1>>COC(=O)COc1cccc2c1cc(C1CC1)n2Cc1ccccc1 | C1(CC1)C=1N(C2=CC=CC(=C2C1)O)CC1=CC=CC=C1.BrCC(=O)OC.[H-].[Na+]>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C1CC1)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH:15]1[CH2:16][CH2:17]1)[n:18]2[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH:15]1[CH2:16][CH2:17]1)[n:18]2[CH2:19][c:20]1[c... | COC(=O)CBr.Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1 | COC(=O)COc1cccc2c1cc(C1CC1)n2Cc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(Cn2c(C3CC3)cc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 63 | [{"value": 63.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.9, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=CC=CC=C1)C1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Cyclopropyl-4-hydroxy-1-(phenylmethyl)-1H-indole (316 mg, 1.2 mmol) was alkylated by treating with 0.11 mL (1.2 mmol) of methyl bromoacetate and 48 mg (1.2 mmol) of 60% NaH/mineral oil in DMF as described in Example 1, Part E. The product was purified by chromatography over silica gel eluting with 20% EtOAc/hexane, t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.C1CC1.c1ccccc1 | HBr | CN(C)C=O | null | null | COC(=O)CBr.Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1>CN(C)C=O>COC(=O)COc1cccc2c1cc(C1CC1)n2Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9ed6f8ff991a4fce822b81a34a0e86c5 | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C1CC1)n2Cc1ccccc1>>NC(=O)C(=O)c1c(C2CC2)n(Cc2ccccc2)c2cccc(OCC(=O)O)c12 | COC(COC1=C2C(=C(N(C2=CC=C1)CC1=CC=CC=C1)C1CC1)C(C(=O)N)=O)=O>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC=CC=C1)C1CC1)=O | C[O:28][C:26]([CH2:25][O:24][c:23]1[cH:22][cH:21][cH:20][c:19]2[n:11]([CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:7]([CH:8]3[CH2:9][CH2:10]3)[c:6]([C:4]([C:2]([NH2:1])=[O:3])=[O:5])[c:29]21)=[O:27]>>[NH2:1][C:2](=[O:3])[C:4](=[O:5])[c:6]1[c:7]([CH:8]2[CH2:9][CH2:10]2)[n:11]([CH2:12][c:13]2[cH:14][cH:15][cH:1... | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C1CC1)n2Cc1ccccc1 | NC(=O)C(=O)c1c(C2CC2)n(Cc2ccccc2)c2cccc(OCC(=O)O)c12 | null | null | [OH-].[Na+].CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2c(C3CC3)cc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 80 | [{"value": 80.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC=CC=C1)C1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=CC=CC=C1)C1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 220 mg (0.54 mmol) of [[3-(2-amino-1,2-dioxoethyl)-2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester in 5 mL of 1N NaOH and 15 mL of MeOH was heated to maintain reflux for 0.67 hours, concentrated at reduced pressure and the residue taken up in EtOAc/water. The aqueous layer was sep... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC1.c1ccccc1.c1cc2ccccc2[nH]1 | Other | [OH-].[Na+].CO | null | null | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C1CC1)n2Cc1ccccc1>[OH-].[Na+].CO>NC(=O)C(=O)c1c(C2CC2)n(Cc2ccccc2)c2cccc(OCC(=O)O)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4a94e879ce5b4777a46e8ccc576b08e1 | COc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1>>Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1 | C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)OC)C1CC1)C1=CC=CC=C1.B(Br)(Br)Br.ClCl>>C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C1CC1)C1=CC=CC=C1 | C[O:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][c:9]([CH:10]1[CH2:11][CH2:12]1)[n:13]2[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1-[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][c:9]([CH:10]1[CH2:11][CH2:12]1)[n:13]2[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1... | COc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1 | Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2ccccc2Cn2c(C3CC3)cc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 29.2 | [{"value": 29.0, "product": "C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C1CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.2, "product": "C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C1CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method used in Example 1, Part D, 1.25 g (3.7 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-methoxyl-1H-indole was O-demethylated by treating it with 15 mL of 1M BBr3 /CH2 Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 367 mg (29% yield) of 1-([1,1'-bi... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cc2ccccc2[nH]1.C1CC1.c1ccccc1.c1ccccc1 | Other | null | null | null | COc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1>>Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-541c15dabcdf432da126da56fb2ac26d | COC(=O)CBr.Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1>>COC(=O)COc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1 | C1(=C(C=CC=C1)CN1C(=CC2=C(C=CC=C12)O)C1CC1)C1=CC=CC=C1.BrCC(=O)OC.[H-].[Na+]>>COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)C1CC1)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH:15]1[CH2:16][CH2:17]1)[n:18]2[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1-[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][c:14]([CH:15]... | COC(=O)CBr.Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1 | COC(=O)COc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(-c2ccccc2Cn2c(C3CC3)cc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 59 | [{"value": 59.0, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)C1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.5, "product": "COC(COC1=C2C=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)C1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-([1,1'-Biphenyl]-2-ylmethyl)-2-cyclopropyl-4-hydroxy-1H-indole (367 mg, 1.1 mmol) was alkylated by treating with 0.1 mL (1.1 mmol) of methyl bromoacetate and 43 mg (1.1 mmol) of 60% NaH/mineral oil in DMF as described in Example 1, Part E. The product was purified by chromatography over silica gel eluting with 20% Et... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1cc2ccccc2[nH]1.C1CC1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | COC(=O)CBr.Oc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1>CN(C)C=O>COC(=O)COc1cccc2c1cc(C1CC1)n2Cc1ccccc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f3720dc9407a4917ba4d4d639555e0d7 | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C1CC1)n2Cc1ccccc1-c1ccccc1>>NC(=O)C(=O)c1c(C2CC2)n(Cc2ccccc2-c2ccccc2)c2cccc(OCC(=O)O)c12 | COC(COC1=C2C(=C(N(C2=CC=C1)CC1=C(C=CC=C1)C1=CC=CC=C1)C1CC1)C(C(=O)N)=O)=O>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)C1CC1)=O | C[O:34][C:32]([CH2:31][O:30][c:29]1[cH:28][cH:27][cH:26][c:25]2[n:11]([CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3-[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:7]([CH:8]3[CH2:9][CH2:10]3)[c:6]([C:4]([C:2]([NH2:1])=[O:3])=[O:5])[c:35]21)=[O:33]>>[NH2:1][C:2](=[O:3])[C:4](=[O:5])[c:6]1[c:7]([CH:8]2[CH2:9][CH2:10]... | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C1CC1)n2Cc1ccccc1-c1ccccc1 | NC(=O)C(=O)c1c(C2CC2)n(Cc2ccccc2-c2ccccc2)c2cccc(OCC(=O)O)c12 | null | null | [OH-].[Na+].CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccccc2Cn2c(C3CC3)cc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 62.3 | [{"value": 62.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)C1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.3, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)OCC(=O)O)CC1=C(C=CC=C1)C1=CC=CC=C1)C1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A mixture of 175 mg (0.36 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-1H-indol-4-yl]0xy]acetic acid methyl ester in 4 mL of 1N NaOH and 10 mL of MeOH was stirred for 0.5 hours, concentrated at reduced pressure and the residue taken up in EtOAc/water. The aqueous layer was separate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC1.c1ccccc1.c1ccccc1.c1cc2ccccc2[nH]1 | Other | [OH-].[Na+].CO | null | 0.5 | COC(=O)COc1cccc2c1c(C(=O)C(N)=O)c(C1CC1)n2Cc1ccccc1-c1ccccc1>[OH-].[Na+].CO>NC(=O)C(=O)c1c(C2CC2)n(Cc2ccccc2-c2ccccc2)c2cccc(OCC(=O)O)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e69aac2b440d40a899e0f8fb35b22bdc | CCC(=O)N(C)OC.COc1ccc(NC(=O)OC(C)(C)C)c(C)c1>>CCC(=O)Cc1cc(OC)ccc1NC(=O)OC(C)(C)C | CON(C(CC)=O)C.C(C)(CC)[Li].C1CCCCC1.C(C)(C)(C)OC(=O)NC1=C(C=C(C=C1)OC)C>>C(C)(C)(C)OC(=O)NC1=C(C=C(C=C1)OC)CC(CC)=O | CON(C)[C:3]([CH2:2][CH3:1])=[O:4].[CH3:5][c:6]1[cH:7][c:8]([O:9][CH3:10])[cH:11][cH:12][c:13]1[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21]>>[CH3:1][CH2:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([O:9][CH3:10])[cH:11][cH:12][c:13]1[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21] | CCC(=O)N(C)OC.COc1ccc(NC(=O)OC(C)(C)C)c(C)c1 | CCC(=O)Cc1cc(OC)ccc1NC(=O)OC(C)(C)C | null | null | C1CCOC1 | C-C Coupling | OtherReaction | e4f529a3ae374940e7335150c613235054eca93a08615af33523f392ef733189 | 4113f0e803c7e6f9f731016c87e547bd597c0045514b87ca0ff3566df8b4b2c4 | c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8] | 74.3 | [{"value": 74.0, "product": "C(C)(C)(C)OC(=O)NC1=C(C=C(C=C1)OC)CC(CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.3, "product": "C(C)(C)(C)OC(=O)NC1=C(C=C(C=C1)OC)CC(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -60 | CELSIUS | 1 | HOUR | A solution of 1.3M sec-butyl lithium/cyclohexane (81 mL, 0.105 mol) was added slowly to 11.85 g (0.05 mol) of N-tert-butoxycarbonyl-4-methoxy-2-methylaniline in 80 mL of THF while keeping the temperature below -40° C. with a dry ice-ethanol bath. The bath was removed and the temperature allowed to rise to -20° C. and t... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | null | null | c1ccccc1 | HO- | C1CCOC1 | -60 | 1 | CCC(=O)N(C)OC.COc1ccc(NC(=O)OC(C)(C)C)c(C)c1>C1CCOC1>CCC(=O)Cc1cc(OC)ccc1NC(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a1ba7dd968ef42de8f7d8852721b5d4d | CCC(=O)Cc1cc(OC)ccc1NC(=O)OC(C)(C)C>>CCc1cc2cc(OC)ccc2[nH]1 | C(C)(C)(C)OC(=O)NC1=C(C=C(C=C1)OC)CC(CC)=O>>C(C)C=1NC2=CC=C(C=C2C1)OC | CC(C)(C)OC(=O)[NH:13][c:12]1[c:5]([CH2:4][C:3](=O)[CH2:2][CH3:1])[cH:6][c:7]([O:8][CH3:9])[cH:10][cH:11]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([O:8][CH3:9])[cH:10][cH:11][c:12]2[nH:13]1 | CCC(=O)Cc1cc(OC)ccc1NC(=O)OC(C)(C)C | CCc1cc2cc(OC)ccc2[nH]1 | null | null | C(Cl)Cl.FC(C(=O)O)(F)F | Aromatic Heterocycle Formation | OtherReaction | 4256a7d4346290a91222b072361f174c5a38107f7ea1eee59c70bf31e7b48d79 | 77f05d7356e9f98235278e7a1d7d92c710704d628109c2563233a98cb56f0099 | c1ccc2[nH]ccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4](-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=O)-[C:7]-[C;D1;H3:8]):[c:9]>>[C;D1;H3:8]-[C:7]-[c;H0;D3;+0:6]1:[cH;D2;+0:5]:[c:4](:[c:9]):[c:2](:[c:3]):[nH;D2;+0:1]:1 | 58 | [{"value": 58.0, "product": "C(C)C=1NC2=CC=C(C=C2C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.0, "product": "C(C)C=1NC2=CC=C(C=C2C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[2-(tert-Butoxycarbonylamino)-5-methoxyphenyl]-2-butanone (7.33 g, 0.025 mol) in 120 mL of CH2Cl2 and 20 mL of trifluoroacetic acid was stirred for 20 hours, washed with water, NaHCO3 solution and the product chromatographed on silica (eluted with 20% EtOAc/hexane) to give 2.54 g (58% yield) of 2-ethyl-5-methoxy-1H-i... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ketone.Ether.Boc | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | C(Cl)Cl.FC(C(=O)O)(F)F | null | null | CCC(=O)Cc1cc(OC)ccc1NC(=O)OC(C)(C)C>C(Cl)Cl.FC(C(=O)O)(F)F>CCc1cc2cc(OC)ccc2[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-58e3159b6ca6432dae5a788f94e6f3a6 | BrCc1ccccc1.CCc1cc2cc(OC)ccc2[nH]1>>CCc1cc2cc(OC)ccc2n1Cc1ccccc1 | C(C1=CC=CC=C1)Br.C1CCOC1.[H-].[Na+].C(C)C=1NC2=CC=C(C=C2C1)OC>>C(C)C=1N(C2=CC=C(C=C2C1)OC)CC1=CC=CC=C1 | Br[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([O:8][CH3:9])[cH:10][cH:11][c:12]2[nH:13]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([O:8][CH3:9])[cH:10][cH:11][c:12]2[n:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | BrCc1ccccc1.CCc1cc2cc(OC)ccc2[nH]1 | CCc1cc2cc(OC)ccc2n1Cc1ccccc1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 82 | [{"value": 82.0, "product": "C(C)C=1N(C2=CC=C(C=C2C1)OC)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.6, "product": "C(C)C=1N(C2=CC=C(C=C2C1)OC)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.17 | HOUR | 2-Ethyl-5-methoxy-1H-indole (5.6 g, 21.5 mmol) was dissolved in 150 mL of DMF and 20 mL of THF and 1.0 g (25 mmol) of 60% sodium hydride was added. After stirring for 0.17 hours, 3.0 mL (25 mmol) of benzyl bromide was added. The mixture was stirred at room temperature for 10 hours, diluted with water and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr | CN(C)C=O.O | null | 0.17 | BrCc1ccccc1.CCc1cc2cc(OC)ccc2[nH]1>CN(C)C=O.O>CCc1cc2cc(OC)ccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-799c09d15d7344de8182a414b9bb0211 | CCc1c(C(=O)C(N)=O)c2cc(OCCCC(=O)OC(C)(C)C)ccc2n1Cc1ccccc1>>CCc1c(C(=O)C(N)=O)c2cc(OCCCC(=O)O)ccc2n1Cc1ccccc1 | C(C)(C)(C)OC(CCCOC=1C=C2C(=C(N(C2=CC1)CC1=CC=CC=C1)CC)C(C(=O)N)=O)=O>>NC(C(=O)C1=C(N(C2=CC=C(C=C12)OCCCC(=O)O)CC1=CC=CC=C1)CC)=O | CC(C)(C)[O:19][C:17]([CH2:16][CH2:15][CH2:14][O:13][c:12]1[cH:11][c:10]2[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:3]([CH2:2][CH3:1])[n:23]([CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[c:22]2[cH:21][cH:20]1)=[O:18]>>[CH3:1][CH2:2][c:3]1[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:10]2[cH:11][c:12]([O:13][CH2:14][... | CCc1c(C(=O)C(N)=O)c2cc(OCCCC(=O)OC(C)(C)C)ccc2n1Cc1ccccc1 | CCc1c(C(=O)C(N)=O)c2cc(OCCCC(=O)O)ccc2n1Cc1ccccc1 | null | null | C(Cl)Cl.FC(C(=O)O)(F)F | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | c1ccc(Cn2ccc3ccccc32)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 63.1 | [{"value": 63.0, "product": "NC(C(=O)C1=C(N(C2=CC=C(C=C12)OCCCC(=O)O)CC1=CC=CC=C1)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.1, "product": "NC(C(=O)C1=C(N(C2=CC=C(C=C12)OCCCC(=O)O)CC1=CC=CC=C1)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 450 mg (0.97 mmol) of 4-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid tert-butyl ester in 75 mL of methylene chloride and 1 mL of trifluoroacetic acid was stirred-at room temperature for 2.25 hours and concentrated at reduced pressure. The residue was chromatographe... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | Other | C(Cl)Cl.FC(C(=O)O)(F)F | null | null | CCc1c(C(=O)C(N)=O)c2cc(OCCCC(=O)OC(C)(C)C)ccc2n1Cc1ccccc1>C(Cl)Cl.FC(C(=O)O)(F)F>CCc1c(C(=O)C(N)=O)c2cc(OCCCC(=O)O)ccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-39e0ce5ac6fe453c825a8e16562f634e | BrCc1ccccc1.COc1ccc2[nH]ccc2c1>>Oc1ccc2c(ccn2Cc2ccccc2)c1 | B(Br)(Br)Br.C(Cl)Cl.COC=1C=C2C=CNC2=CC1.[H-].[Na+].C(C1=CC=CC=C1)Br>>OC=1C=C2C=CN(C2=CC1)CC1=CC=CC=C1 | Br[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.C[O:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][cH:8][nH:9]2)[cH:17]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][cH:8][n:9]2[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1 | BrCc1ccccc1.COc1ccc2[nH]ccc2c1 | Oc1ccc2c(ccn2Cc2ccccc2)c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | b8b8c936f1222ba4dcc39cac77417eb1c24a0b1a19b1a7aa4ee3960753f3d06a | cf1086715641611cede41736f13bebea69e2422e9980e019e3ae4f0472190f48 | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6]1:[c:7]:[c:8]2:[c:9]:[c:10]:[nH;D2;+0:11]:[c:12]:2:[c:13]:[c:14]:1>>[OH;D1;+0:5]-[c:6]1:[c:7]:[c:8]2:[c:9]:[c:10]:[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:12]:2:[c:13]:[c:14]:1 | 19 | [{"value": 19.0, "product": "OC=1C=C2C=CN(C2=CC1)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.1, "product": "OC=1C=C2C=CN(C2=CC1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | 1.75 | HOUR | 5-Methoxy-1H-indole (5.6 g, 21.5 mmol) was reacted with 1.0 g (25 mmol) of 60% sodium hydride and then 3.0 mL (25 mmol) of benzyl bromide by the method described in Example 12, Part D to give crude 5-methoxy-1-(phenylmethyl)-1H-indole. This material was dissolved in 250 mL of methylene chloride, cooled to -5° C., 50 mL... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Aromatic alcohol | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr | C(Cl)Cl | -5 | 1.75 | BrCc1ccccc1.COc1ccc2[nH]ccc2c1>C(Cl)Cl>Oc1ccc2c(ccn2Cc2ccccc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bbf8230acb4c4efbbe2e5b95721c489b | BrCc1ccccc1.CCc1cc2c([N+](=O)[O-])cccc2[nH]1>>CCc1cc2c([N+](=O)[O-])cccc2n1Cc1ccccc1 | C(C1=CC=CC=C1)Br.C(C)C=1NC2=CC=CC(=C2C1)[N+](=O)[O-].[H-].[Na+].CCCCCC>>C1(=CC=CC=C1)CN1C(=CC2=C(C=CC=C12)[N+](=O)[O-])CC | Br[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][cH:12][c:13]2[nH:14]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][cH:12][c:13]2[n:14]1[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | BrCc1ccccc1.CCc1cc2c([N+](=O)[O-])cccc2[nH]1 | CCc1cc2c([N+](=O)[O-])cccc2n1Cc1ccccc1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 16b46a8af20339f7ff0b611b4ac5dd01fe35ba577361e893c359dfa478dc1974 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C:5]-[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 91 | [{"value": 91.0, "product": "C1(=CC=CC=C1)CN1C(=CC2=C(C=CC=C12)[N+](=O)[O-])CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.8, "product": "C1(=CC=CC=C1)CN1C(=CC2=C(C=CC=C12)[N+](=O)[O-])CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | 2-Ethyl-4-nitro-1H-indole (4.75 g, 25 mmol) was added to a mixture of 1.0 g (25 mmol) of 60% NaH/mineral oil (washed with hexane before adding DMF) in 40 ml DMF. After 45 minutes, 3.0 ml (25 mmol) of benzyl bromide was added. The mixture was stirred at room temperature for four hours, diluted with water, and extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1.c1ccccc1 | HBr | CN(C)C=O.O | null | 0.75 | BrCc1ccccc1.CCc1cc2c([N+](=O)[O-])cccc2[nH]1>CN(C)C=O.O>CCc1cc2c([N+](=O)[O-])cccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-530aa127a76e4169b9ca650bd1dc8905 | CCc1c(C(=O)C(N)=O)c2c([N+](=O)[O-])cccc2n1Cc1ccccc1>>CCc1c(C(=O)C(N)=O)c2c(N)cccc2n1Cc1ccccc1 | C(C)C=1N(C2=CC=CC(=C2C1C(C(=O)N)=O)[N+](=O)[O-])CC1=CC=CC=C1.CCO>>NC1=C2C(=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)C(C(=O)N)=O | O=[N+:12]([O-])[c:11]1[c:10]2[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:3]([CH2:2][CH3:1])[n:17]([CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:16]2[cH:15][cH:14][cH:13]1>>[CH3:1][CH2:2][c:3]1[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:10]2[c:11]([NH2:12])[cH:13][cH:14][cH:15][c:16]2[n:17]1[CH2:18][c:19]1[cH:20]... | CCc1c(C(=O)C(N)=O)c2c([N+](=O)[O-])cccc2n1Cc1ccccc1 | CCc1c(C(=O)C(N)=O)c2c(N)cccc2n1Cc1ccccc1 | null | null | C1CCOC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Cn2ccc3ccccc32)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 30.2 | [{"value": 30.0, "product": "NC1=C2C(=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)C(C(=O)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.2, "product": "NC1=C2C(=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)C(C(=O)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of 6.0 g (17.1 mmol) of 2-Ethyl-4-Nitro-α-oxo-1-(phenylmethyl)-1H-indole-3-acetamide in 140 ml of 1:1 THF:EtOH containing 1,0 g of 5% Pt/BaSO4 was hydrogenated at room temperature and 60 psi (4.22 Kg/cm2) for four hours. The catalyst was filtered and the filtrate evaporated in vacuo. The residue was chromato... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | Other | C1CCOC1 | null | 4 | CCc1c(C(=O)C(N)=O)c2c([N+](=O)[O-])cccc2n1Cc1ccccc1>C1CCOC1>CCc1c(C(=O)C(N)=O)c2c(N)cccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e62040325e0347dba1d20052ff7e6f97 | CCc1c(C(=O)C(N)=O)c2c(N)cccc2n1Cc1ccccc1.COC(=O)CBr>>CCc1c(C(=O)C(N)=O)c2c(NCC(=O)OC)cccc2n1Cc1ccccc1 | BrCC(=O)OC.NC1=C2C(=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)C(C(=O)N)=O>>COC(CNC1=C2C(=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)C(C(=O)N)=O)=O | [CH3:1][CH2:2][c:3]1[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:10]2[c:11]([NH2:12])[cH:18][cH:19][cH:20][c:21]2[n:22]1[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.Br[CH2:13][C:14](=[O:15])[O:16][CH3:17]>>[CH3:1][CH2:2][c:3]1[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:10]2[c:11]([NH:12][CH2:13][C:14](=[O:15])[O:16... | CCc1c(C(=O)C(N)=O)c2c(N)cccc2n1Cc1ccccc1.COC(=O)CBr | CCc1c(C(=O)C(N)=O)c2c(NCC(=O)OC)cccc2n1Cc1ccccc1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 308780347cfd56717124ea78bf2bc5de380db774d7ce948246e279dfd7d8998b | d2327a8d30a39f085182e5e2f77f5b022ac99c077866b86103acfec639a8f73d | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH;D2;+0:10]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5]):[c:11] | 64 | [{"value": 64.0, "product": "COC(CNC1=C2C(=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)C(C(=O)N)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.9, "product": "COC(CNC1=C2C(=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)C(C(=O)N)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 0.5 | HOUR | Methyl bromoacetate (0.07 ml, 0.78 mmol) was added to 250 mg (0.78 mmol) of 4-Amino-2-Ethyl-α-oxo-1-(phenylmethyl)-1H-indole-3-Acetamide in 4 ml of DMF, stirred at 60° C. for 0.5 hour, and then at room temperature for 20 hours. The mixture was diluted with water and extracted with EtOAc. The EtOAC solution was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Ester.Secondary amine | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | HBr | CN(C)C=O.O | 60 | 0.5 | CCc1c(C(=O)C(N)=O)c2c(N)cccc2n1Cc1ccccc1.COC(=O)CBr>CN(C)C=O.O>CCc1c(C(=O)C(N)=O)c2c(NCC(=O)OC)cccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4cedd0f2818c450b8027d96b9714b239 | CCc1c(C(=O)C(N)=O)c2c(NCC(=O)OC)cccc2n1Cc1ccccc1>>CCc1c(C(=O)C(N)=O)c2c(NCC(=O)O)cccc2n1Cc1ccccc1 | COC(CNC1=C2C(=C(N(C2=CC=C1)CC1=CC=CC=C1)CC)C(C(=O)N)=O)=O.[OH-].[Na+].CO.Cl>>NC(C(=O)C1=C(N(C2=CC=CC(=C12)NCC(=O)O)CC1=CC=CC=C1)CC)=O | C[O:16][C:14]([CH2:13][NH:12][c:11]1[c:10]2[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:3]([CH2:2][CH3:1])[n:21]([CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[c:20]2[cH:19][cH:18][cH:17]1)=[O:15]>>[CH3:1][CH2:2][c:3]1[c:4]([C:5](=[O:6])[C:7]([NH2:8])=[O:9])[c:10]2[c:11]([NH:12][CH2:13][C:14](=[O:15])[OH:16])[cH:17... | CCc1c(C(=O)C(N)=O)c2c(NCC(=O)OC)cccc2n1Cc1ccccc1 | CCc1c(C(=O)C(N)=O)c2c(NCC(=O)O)cccc2n1Cc1ccccc1 | null | null | CCOC(=O)C | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 53 | [{"value": 53.0, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)NCC(=O)O)CC1=CC=CC=C1)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.7, "product": "NC(C(=O)C1=C(N(C2=CC=CC(=C12)NCC(=O)O)CC1=CC=CC=C1)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 190 mg (0.48 mmol) of [[3-(Aminooxoacetyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]amino]acetic acid methyl ester, 5 ml of 1N NaOH, and 15 ml of MeOH was refluxed 0.33 hour, cooled, and stirred at room temperature for 1 hour. EtOAc and aqueous HCl were added and the EtOAc layer was washed with brine, dried ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ccccc2[nH]1.c1ccccc1 | Other | CCOC(=O)C | null | 1 | CCc1c(C(=O)C(N)=O)c2c(NCC(=O)OC)cccc2n1Cc1ccccc1>CCOC(=O)C>CCc1c(C(=O)C(N)=O)c2c(NCC(=O)O)cccc2n1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d7fa7aa712274215b5d8790b097c1874 | CC(=O)c1cc(Nc2cc(C)nc(N)n2)cc(C(C)=O)c1.CI>>CC(=O)c1cc(Nc2cc(C)[n+](C)c(N)n2)cc(C(C)=O)c1.[I-] | NC1=NC(=CC(=N1)NC1=CC(=CC(=C1)C(C)=O)C(C)=O)C.CI>>[I-].NC1=[N+](C(=CC(=N1)NC1=CC(=CC(=C1)C(C)=O)C(C)=O)C)C | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH:7][c:8]2[cH:9][c:10]([CH3:11])[n:12][c:14]([NH2:15])[n:16]2)[cH:17][c:18]([C:19]([CH3:20])=[O:21])[cH:22]1.[CH3:13][I:23]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH:7][c:8]2[cH:9][c:10]([CH3:11])[n+:12]([CH3:13])[c:14]([NH2:15])[n:16]2)[cH:17][c:18]([C:19]([CH3:20])=[O:21])[cH:... | CC(=O)c1cc(Nc2cc(C)nc(N)n2)cc(C(C)=O)c1.CI | CC(=O)c1cc(Nc2cc(C)[n+](C)c(N)n2)cc(C(C)=O)c1.[I-] | null | null | C(C)#N.O1CCCC1 | Functional Group Interconversion | OtherReaction | f6f373ff15af259a6a955d28c8e1504795e14c395f484b607df25a875abe05b3 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(Nc2cc[nH+]cn2)cc1 | [C;D1;H3:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6](-[N;D1;H2:7]):[n;H0;D2;+0:8]:1.[CH3;D1;+0:9]-[I;H0;D1;+0:10]>>[C;D1;H3:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6](-[N;D1;H2:7]):[n+;H0;D3:8]:1-[CH3;D1;+0:9].[I-;H0;D0:10] | null | [] | null | null | null | null | Compound No. 2, FIG. 1A: A suspension of Compound No. 11 (2-amino-4-(3,5-diacetylphenyl)amino-6-methylpyrimidine) (0.284 g), was suspended in 1:1 acetonitrile-tetrahydrofuran was treated with methyl iodide (2 mL) and heated at 40°-45° C. under a reflux condenser for 18 hr. Cooling and filtration gave 0.35 g of 2-amino-... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cncnc1 | C1=CN=C[NH+]=C1 | c1ccccc1.C1=CN=C[NH+]=C1 | null | C(C)#N.O1CCCC1 | null | null | CC(=O)c1cc(Nc2cc(C)nc(N)n2)cc(C(C)=O)c1.CI>C(C)#N.O1CCCC1>CC(=O)c1cc(Nc2cc(C)[n+](C)c(N)n2)cc(C(C)=O)c1.[I-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-705eb0cf3a5441248217ccc079f91152 | CC(=O)c1cc(N)cc(C(C)=O)c1.N#CNC(=N)N>>CC(=O)c1cc(NC(=N)NC(=N)N)cc(C(C)=O)c1 | C(C)(=O)C=1C=C(N)C=C(C1)C(C)=O.C(#N)NC(=N)N.Cl>>Cl.C(C)(=O)C=1C=C(C=C(C1)C(C)=O)NC(=N)NC(=N)N | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:14][c:15]([C:16]([CH3:17])=[O:18])[cH:19]1.[C:8](=[NH:9])([NH:10][C:11]#[N:12])[NH2:13]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH:7][C:8](=[NH:9])[NH:10][C:11](=[NH:12])[NH2:13])[cH:14][c:15]([C:16]([CH3:17])=[O:18])[cH:19]1 | CC(=O)c1cc(N)cc(C(C)=O)c1.N#CNC(=N)N | CC(=O)c1cc(NC(=N)NC(=N)N)cc(C(C)=O)c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 4fa302539962125b5afbc3b7c652c5f6ac0c848b65cc6ee9a8cc31fc37dac702 | 69bab17abd42218af70031a95089cb8497f520bead244a193d73e0f37115ac3b | c1ccccc1 | [N;D1;H1:1]=[C;H0;D3;+0:2](-[NH2;D1;+0:3])-[#7:4]-[C;H0;D2;+0:5]#[N;H0;D1;+0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[N;D1;H1:1]=[C;H0;D3;+0:2](-[#7:4]-[C;H0;D3;+0:5](-[NH2;D1;+0:3])=[NH;D1;+0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | Compound No. 12. A suspension of 3,5-diacetylaniline (0.531 g) in water (8 mL) was treated with cyanoguanidine (0.285 g) and conc. HCl (0.25 mL) and heated at reflux. After 6 hr the mixture was cooled and concentrated and 0.248 g of off-white solid was filtered out and dried to give N-(3,5-diacetylphenyl)biguanide hydr... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine.Primary amine | Primary amine.Secondary amine | null | null | c1ccccc1 | null | O | null | null | CC(=O)c1cc(N)cc(C(C)=O)c1.N#CNC(=N)N>O>CC(=O)c1cc(NC(=N)NC(=N)N)cc(C(C)=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f5ab73fd88e543f2b4cd602c407b93f7 | CC(=O)c1cc(N)cc(C(C)=O)c1.Nc1nc(N)nc(Cl)n1>>CC(=O)c1cc(Nc2nc(N)nc(N)n2)cc(C(C)=O)c1 | Cl.ClC1=NC(=NC(=N1)N)N.Cl.C(C)(=O)C=1C=C(N)C=C(C1)C(C)=O>>C(C)(=O)C=1C=C(C=C(C1)C(C)=O)NC1=NC(=NC(=N1)N)N | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:16][c:17]([C:18]([CH3:19])=[O:20])[cH:21]1.Cl[c:8]1[n:9][c:10]([NH2:11])[n:12][c:13]([NH2:14])[n:15]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([NH2:11])[n:12][c:13]([NH2:14])[n:15]2)[cH:16][c:17]([C:18]([CH3:19])=[O:20])[cH:21]1 | CC(=O)c1cc(N)cc(C(C)=O)c1.Nc1nc(N)nc(Cl)n1 | CC(=O)c1cc(Nc2nc(N)nc(N)n2)cc(C(C)=O)c1 | null | null | O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 565b1b62b297a3b1aad544a4f6d7760fc3910e7d367c9719d0e48a6d3fe6c36e | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6]:[#7;a:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[N;D1;H2:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:2]:1 | 62.5 | [{"value": 62.5, "product": "C(C)(=O)C=1C=C(C=C(C1)C(C)=O)NC1=NC(=NC(=N1)N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound No. 13: A suspension of 3,5-diacetylaniline (1.95 g) in water (10 mL) was treated with 2-chloro-4,6-diamino-1,3,5-triazine (1.455 g) and concentrated HCl (0.1 mL) and heated at reflux for 20 min. After cooling the hydrochloride of Compound No. 13 separated as a white powder. This was filtered out, dissolved in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncncn1 | c1ncncn1 | c1ccccc1.c1ncncn1 | HCl | O | null | null | CC(=O)c1cc(N)cc(C(C)=O)c1.Nc1nc(N)nc(Cl)n1>O>CC(=O)c1cc(Nc2nc(N)nc(N)n2)cc(C(C)=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-74a2ccfcddee49eb8680c2a9e7272626 | CC(=O)c1cccc(Nc2cc(C)nc(N)n2)c1.CI>>CC(=O)c1cccc(Nc2cc(C)[n+](C)c(N)n2)c1.[I-] | C(C)(=O)C=1C=C(C=CC1)NC1=NC(=NC(=C1)C)N.CI>>[I-].C(C)(=O)C=1C=C(C=CC1)NC1=NC(=[N+](C(=C1)C)C)N | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][c:12]([CH3:13])[n:14][c:16]([NH2:17])[n:18]2)[cH:19]1.[CH3:15][I:20]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][c:12]([CH3:13])[n+:14]([CH3:15])[c:16]([NH2:17])[n:18]2)[cH:19]1.[I-:20] | CC(=O)c1cccc(Nc2cc(C)nc(N)n2)c1.CI | CC(=O)c1cccc(Nc2cc(C)[n+](C)c(N)n2)c1.[I-] | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | f6f373ff15af259a6a955d28c8e1504795e14c395f484b607df25a875abe05b3 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc(Nc2cc[nH+]cn2)cc1 | [C;D1;H3:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6](-[N;D1;H2:7]):[n;H0;D2;+0:8]:1.[CH3;D1;+0:9]-[I;H0;D1;+0:10]>>[C;D1;H3:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6](-[N;D1;H2:7]):[n+;H0;D3:8]:1-[CH3;D1;+0:9].[I-;H0;D0:10] | null | [] | null | null | null | null | Compound No. 14: 4-(3-acetylphenyl)amino-2-amino-6methylpyrimidine, Compound No. 15, (0.968 g) was suspended in acetone (5 mL) containing methyl iodide (2 mL) was heated at reflux for 48 hr. Filtration after cooling gave 0.657 g of 4-(3-acetylphenyl)amino-2-amino-1,6-dimethylpyrimidinium iodide as a white powder, mp 23... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cncnc1 | C1=CN=C[NH+]=C1 | c1ccccc1.C1=CN=C[NH+]=C1 | null | CC(=O)C | null | null | CC(=O)c1cccc(Nc2cc(C)nc(N)n2)c1.CI>CC(=O)C>CC(=O)c1cccc(Nc2cc(C)[n+](C)c(N)n2)c1.[I-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b3ee4c95f2d64d7599ce13045545da3c | CC(=O)c1cccc(N)c1.Cc1cc(Cl)nc(N)n1>>CC(=O)c1cccc(Nc2cc(C)nc(N)n2)c1 | [OH-].[K+].NC=1C=C(C=CC1)C(C)=O.NC1=NC(=CC(=N1)Cl)C.Cl>>C(C)(=O)C=1C=C(C=CC1)NC1=NC(=NC(=C1)C)N | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH2:9])[cH:18]1.Cl[c:10]1[cH:11][c:12]([CH3:13])[n:14][c:15]([NH2:16])[n:17]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[cH:11][c:12]([CH3:13])[n:14][c:15]([NH2:16])[n:17]2)[cH:18]1 | CC(=O)c1cccc(N)c1.Cc1cc(Cl)nc(N)n1 | CC(=O)c1cccc(Nc2cc(C)nc(N)n2)c1 | null | null | O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[N;D1;H2:4]):[#7;a:5]:[c:6](-[C;D1;H3:7]):[c:8]:1.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:3](-[N;D1;H2:4]):[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:8]:1 | 78.5 | [{"value": 78.5, "product": "C(C)(=O)C=1C=C(C=CC1)NC1=NC(=NC(=C1)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound No. 15: A suspension of m-aminoacetophenone (2.7 g) and 2-amino-4-chloro-6-methylpyrimidine (2.87 g) in 40 mL water was treated with 1.7 mL concentrated HCl and heated at reflux for 1 hour. Addition of 40 mL 1N KOH gave a light buff solid, which was filtered out and dried to give 3.8 g 4-(3-acetylphenyl)amino-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | O | null | null | CC(=O)c1cccc(N)c1.Cc1cc(Cl)nc(N)n1>O>CC(=O)c1cccc(Nc2cc(C)nc(N)n2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0b3c68dde58a4f4fbcd3c8750233eef7 | CC(=O)c1cc(N)cc(C(C)=O)c1.Clc1ncnc2nc[nH]c12>>CC(=O)c1cc(Nc2ncnc3nc[nH]c23)cc(C(C)=O)c1 | [OH-].[K+].ClC1=C2NC=NC2=NC=N1.Cl.C(C)(=O)C=1C=C(N)C=C(C1)C(C)=O>>C(C)(=O)C=1C=C(C=C(C1)C(C)=O)NC1=C2NC=NC2=NC=N1 | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:17][c:18]([C:19]([CH3:20])=[O:21])[cH:22]1.Cl[c:8]1[n:9][cH:10][n:11][c:12]2[n:13][cH:14][nH:15][c:16]12>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][n:11][c:12]3[n:13][cH:14][nH:15][c:16]23)[cH:17][c:18]([C:19]([CH3:20])=[O:21])[cH:22]1 | CC(=O)c1cc(N)cc(C(C)=O)c1.Clc1ncnc2nc[nH]c12 | CC(=O)c1cc(Nc2ncnc3nc[nH]c23)cc(C(C)=O)c1 | null | null | 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] | 90.4 | [{"value": 90.4, "product": "C(C)(=O)C=1C=C(C=C(C1)C(C)=O)NC1=C2NC=NC2=NC=N1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Compound No. 16: A suspension of 3,5-diacetylaniline (0.531 g) in water (10 mL) was treated with 6-chloropurine (0.464 g) and concentrated HCl (0.25 mL) and heated at reflux for 30 min. After cooling the mixture was treated with 6 mL of aqueous 1N KOH. The mixture was stirred for 10 min and the solid was filtered out, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | O | null | 0.166667 | CC(=O)c1cc(N)cc(C(C)=O)c1.Clc1ncnc2nc[nH]c12>O>CC(=O)c1cc(Nc2ncnc3nc[nH]c23)cc(C(C)=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-123a12fd08654e45b37f1f604736d38c | BrCc1ccccc1.CCOC(=O)CC(C)=O>>CCOC(=O)CC(=O)CCc1ccccc1 | C(C1=CC=CC=C1)Br.[H-].[Na+].C(CC(=O)C)(=O)OCC>>C(C)OC(CC(=O)CCC1=CC=CC=C1)=O | Br[CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH3:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | BrCc1ccccc1.CCOC(=O)CC(C)=O | CCOC(=O)CC(=O)CCc1ccccc1 | null | null | C1CCOC1.CCCCCC | C-C Coupling | OtherReaction | e8b75e5efb691ecf3c9116420e15918cdd0fda7b899536fb179ed39cbdad1bc2 | 836e0f77354d9f44b98dde88e343d5cebbf81f14d452aa51d1e50ec699999492 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9](-[CH3;D1;+0:10])=[O;D1;H0:11]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9](=[O;D1;H0:11])-[CH2;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | -10 | CELSIUS | 30 | MINUTE | NaH (13.8 g, 0.6 mole) was washed twice with hexane (2×50 ml) and suspended in 250 ml of freshly distilled THF. Next ethyl acetoacetate (75 ml, excess) was added dropwise carefully while the receiving flask was cooled at -10° C. After the addition was complete, it was stirred at -10° C. for 2 hours and at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | null | null | c1ccccc1 | HBr | C1CCOC1.CCCCCC | -10 | 0.5 | BrCc1ccccc1.CCOC(=O)CC(C)=O>C1CCOC1.CCCCCC>CCOC(=O)CC(=O)CCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-97c55ca915ef4418862fcb86ab30f5ed | CC1=C(C(=O)O)Cc2ccccc21.O=S(Cl)Cl>>CC1=C(C(=O)Cl)Cc2ccccc21 | CC1=C(CC2=CC=CC=C12)C(=O)O.S(=O)(Cl)Cl>>CC1=C(CC2=CC=CC=C12)C(=O)Cl | O[C:4]([C:3]1=[C:2]([CH3:1])[c:13]2[c:8]([cH:9][cH:10][cH:11][cH:12]2)[CH2:7]1)=[O:5].O=S(Cl)[Cl:6]>>[CH3:1][C:2]1=[C:3]([C:4](=[O:5])[Cl:6])[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21 | CC1=C(C(=O)O)Cc2ccccc21.O=S(Cl)Cl | CC1=C(C(=O)Cl)Cc2ccccc21 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | C1=Cc2ccccc2C1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](=[C:5](-[C;D1;H3:6])-[c:7])-[C:8]>>[C:8]-[C:4](-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3])=[C:5](-[C;D1;H3:6])-[c:7] | null | [] | null | null | null | null | 1.0 g of 3-methylindene-2-carboxylic acid and 5 ml thionyl chloride were refluxed for 4 hours. Careful removal of the solvent by distillation under reduced pressure gave 3-methylindene-2-oyl chloride. The acid chloride dissolved in THF was dropped into a mixture of guanidine and sodium hydroxide at room temperature ove... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | C1=Cc2ccccc2C1 | HCl | null | null | null | CC1=C(C(=O)O)Cc2ccccc21.O=S(Cl)Cl>>CC1=C(C(=O)Cl)Cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-234d9f67d5bc456d83ed16d8d4de410c | CCOC(=O)Cl.O=C1CCc2ccccc21>>CCOC(=O)C1Cc2ccccc2C1=O | C1(CCC2=CC=CC=C12)=O.C(CCC)[Li].ClC(=O)OCC>>C(=O)(OCC)C1C(C2=CC=CC=C2C1)=O | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[CH2:6]1[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15] | CCOC(=O)Cl.O=C1CCc2ccccc21 | CCOC(=O)C1Cc2ccccc2C1=O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | b0a5f5f290e5c12fb11be71000c002bcdea12c9d72177ea1938da57ba51b3784 | f78bb7d35ddd1449899d9ed779d19c78d02ee4567d7058af2b421741fd5818d2 | O=C1CCc2ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7]1-[C:8]-[c:9]:[c:10]-[C:6]-1=[O;D1;H0:5] | null | [] | -20 | CELSIUS | 45 | MINUTE | 1-Indanone (1.5 g, 11.36 mmols) was dissolved in dry THF in a three neck flask equipped with nitrogen inlet, septum and a guard tube. The flask was cooled to -20° C. for 10 minutes. Then butyl lithium (11.37 ml, 12.48 mmols) was added dropwise through the septum using the syringe. The reaction mixture was allowed to st... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone | Ketone.Ester | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HCl | C1CCOC1 | -20 | 0.75 | CCOC(=O)Cl.O=C1CCc2ccccc21>C1CCOC1>CCOC(=O)C1Cc2ccccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b6a54649e164413f940a06f93c2f9e8d | CCOC(=O)C1Cc2ccccc2C1=O>>CCOC(=O)C1=Cc2ccccc2C1 | C(=O)(OCC)C1C(C2=CC=CC=C2C1)=O>>C1C(=CC2=CC=CC=C12)C(=O)OCC | O=[C:7]1[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:14][c:13]2[c:8]1[cH:9][cH:10][cH:11][cH:12]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[CH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14]1 | CCOC(=O)C1Cc2ccccc2C1=O | CCOC(=O)C1=Cc2ccccc2C1 | null | null | CO.[BH4-].[Na+] | Miscellaneous | OtherReaction | e414f0ca5ed080038ee89dbe3cd83303296907ec5c3e5aff0278dc8f995f117a | d0cb29f74e619dcc00fec504ad2e56043281b867cf4b0a815622ce66567392f1 | C1=Cc2ccccc2C1 | O=[C;H0;D3;+0:1]1-[CH;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7]-[c:8]:[c:9]-1:[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:2]1=[CH;D2;+0:1]-[c:9](:[c:10]):[c:8]-[C:7]-1 | null | [] | null | null | null | null | 2-Carbethoxy-1-indanone was dissolved in dry methanol at room temperature, to which sodium borohydride was added in three lots while the reaction mixture was kept stirring. The reaction mixture was further stirred for 30 minutes, after which the solid was filtered and the filtrate was evaporated to dryness. The residue... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ester | c1ccc2c(c1)CCC2 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | Other | CO.[BH4-].[Na+] | null | null | CCOC(=O)C1Cc2ccccc2C1=O>CO.[BH4-].[Na+]>CCOC(=O)C1=Cc2ccccc2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-490d143774ec4390a10e9b0953bb6484 | CCCCCNC[C@@H]1CC[C@@H](CNCCCCC)CC1.CN(C)c1ccc(N=C=O)cc1>>CCCCCN(C[C@@H]1CC[C@@H](CN(CCCCC)C(=O)Nc2ccc(N(C)C)cc2)CC1)C(=O)Nc1ccc(N(C)C)cc1 | C(CCCC)NC[C@@H]1CC[C@H](CC1)CNCCCCC.CN(C1=CC=C(C=C1)N=C=O)C>>CN(C1=CC=C(C=C1)NC(N(CCCCC)C[C@@H]1CC[C@H](CC1)CN(C(=O)NC1=CC=C(C=C1)N(C)C)CCCCC)=O)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:31][CH2:32]1.[C:19](=[O:20])=[N:21][c:22]1[cH:23][cH:24][c:25]([N:26]([CH3:28])[CH3:33])[cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][C@H:8]1[CH2:9][CH2:10][C@... | CCCCCNC[C@@H]1CC[C@@H](CNCCCCC)CC1.CN(C)c1ccc(N=C=O)cc1 | CCCCCN(C[C@@H]1CC[C@@H](CN(CCCCC)C(=O)Nc2ccc(N(C)C)cc2)CC1)C(=O)Nc1ccc(N(C)C)cc1 | null | null | C(C)#N.CCOCC | Aromatic Heterocycle Formation | OtherReaction | 5ebc203e1c64fa87330062f7941396943f49aa4192cca3ea1ed2a05e2647f68c | bb423a2f04d7886357135cd179d5334129f095917bd9e365b4b0b3498b284c57 | O=C(NC[C@H]1CC[C@H](CNC(=O)Nc2ccccc2)CC1)Nc1ccccc1 | [C;D1;H3:1]-[N;H0;D3;+0:2](-[CH3;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[O;D1;H0:10]):[c:11]:[c:12]:1.[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17].[C:18]-[C:19]-[NH;D2;+0:20]-[C:21]-[C:22]>>[C:18]-[C:19]-[N;H0;D3;+0:20](-[C:21]-[C:22])-[C;H0;D3;+0:3](=[O;D1;H0:23])-[#7:24]-[c:25].[C:13]-[C:14]-[... | 89 | [{"value": 89.0, "product": "CN(C1=CC=C(C=C1)NC(N(CCCCC)C[C@@H]1CC[C@H](CC1)CN(C(=O)NC1=CC=C(C=C1)N(C)C)CCCCC)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | Trans-1,4-bis[(normalpentylamino)methyl]cyclohexane, 0.56 g, was dissolved in 10 ml of ether. A solution of 0.81 g of 4-dimethylaminophenyl isocyanate in 20 ml of acetonitrile was added. The reaction mixture was stirred at room temperature for 10 hours. The solvent of the reaction mixture was distilled off under reduce... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine.Secondary amine.Tertiary amine | Urea.Urea.Tertiary amine.Tertiary amine | null | c1ccccc1 | C1CCCCC1.c1ccccc1.c1ccccc1 | Other | C(C)#N.CCOCC | null | 10 | CCCCCNC[C@@H]1CC[C@@H](CNCCCCC)CC1.CN(C)c1ccc(N=C=O)cc1>C(C)#N.CCOCC>CCCCCN(C[C@@H]1CC[C@@H](CN(CCCCC)C(=O)Nc2ccc(N(C)C)cc2)CC1)C(=O)Nc1ccc(N(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a24726e74e5d4a6ca7abb5ec691259ae | O=C(Nc1ccc([N+](=O)[O-])cc1)N(C[C@@H]1CC[C@@H](CN(C(=O)Nc2ccc([N+](=O)[O-])cc2)C2CCCCC2)CC1)C1CCCCC1>>Nc1ccc(NC(=O)N(C[C@@H]2CC[C@@H](CN(C(=O)Nc3ccc(N)cc3)C3CCCCC3)CC2)C2CCCCC2)cc1 | C1(CCCCC1)N(C(=O)NC1=CC=C(C=C1)[N+](=O)[O-])C[C@@H]1CC[C@H](CC1)CN(C(=O)NC1=CC=C(C=C1)[N+](=O)[O-])C1CCCCC1.[H][H]>>C1(CCCCC1)N(C(=O)NC1=CC=C(C=C1)N)C[C@@H]1CC[C@H](CC1)CN(C(=O)NC1=CC=C(C=C1)N)C1CCCCC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[N:9]([CH2:10][C@H:11]2[CH2:12][CH2:13][C@H:14]([CH2:15][N:16]([C:17](=[O:18])[NH:19][c:20]3[cH:21][cH:22][c:23]([N+:24](=O)[O-])[cH:25][cH:26]3)[CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)[CH2:33][CH2:34]2)[CH:35]2[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]2)... | O=C(Nc1ccc([N+](=O)[O-])cc1)N(C[C@@H]1CC[C@@H](CN(C(=O)Nc2ccc([N+](=O)[O-])cc2)C2CCCCC2)CC1)C1CCCCC1 | Nc1ccc(NC(=O)N(C[C@@H]2CC[C@@H](CN(C(=O)Nc3ccc(N)cc3)C3CCCCC3)CC2)C2CCCCC2)cc1 | null | [Pd].[C].[Pd] | CN(C)C=O | Reduction | OtherReaction | 6748a51a25102225412593c5a930e43f5a8904a80803177de025a6f83c59d65e | a303b0dfb15cc6bade463acf71681cf3ba7580b599dfa4d28d8caac83d08cd17 | O=C(Nc1ccccc1)N(C[C@H]1CC[C@H](CN(C(=O)Nc2ccccc2)C2CCCCC2)CC1)C1CCCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4].O=[N+;H0;D3:5](-[O-])-[c:6](:[c:7]):[c:8]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8] | 106.6 | [{"value": 95.0, "product": "C1(CCCCC1)N(C(=O)NC1=CC=C(C=C1)N)C[C@@H]1CC[C@H](CC1)CN(C(=O)NC1=CC=C(C=C1)N)C1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.6, "product": "C1(CCCCC1)N(C(=O)NC1=CC=C(C=C1)N)C[C@@H]1CC[C@H](CC1)CN(C(=O)NC1=CC=C(C=C1)N)C1CCCCC1", "details": "CALCULATEDPERCENTYIELD", ... | null | null | null | null | A 0.6 g quantity of 10% palladium carbon was added to 100 ml of a DMF solution containing 5.7 g of trans-1,4-bis[[1-cyclohexyl-3-(4-nitrophenyl)ureido]-metyl]cyclohexane synthesized in accordance with Example 2. Hydrogen was added at ordinal pressure and normal temperature for 15 hours. After completion of the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccccc1.C1CCCCC1.c1ccccc1.C1CCCCC1.C1CCCCC1 | Other | [Pd].[C].[Pd].CN(C)C=O | null | null | O=C(Nc1ccc([N+](=O)[O-])cc1)N(C[C@@H]1CC[C@@H](CN(C(=O)Nc2ccc([N+](=O)[O-])cc2)C2CCCCC2)CC1)C1CCCCC1>[Pd].[C].[Pd].CN(C)C=O>Nc1ccc(NC(=O)N(C[C@@H]2CC[C@@H](CN(C(=O)Nc3ccc(N)cc3)C3CCCCC3)CC2)C2CCCCC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cf112f9f981e4357be02e4ddbd112b54 | C#CCBr.CONC(=O)OC>>C#CCN(OC)C(=O)OC | O.[H-].[Na+].CONC(OC)=O.C(C#C)Br>>CON(C(OC)=O)CC#C | Br[CH2:3][C:2]#[CH:1].[NH:4]([O:5][CH3:6])[C:7](=[O:8])[O:9][CH3:10]>>[CH:1]#[C:2][CH2:3][N:4]([O:5][CH3:6])[C:7](=[O:8])[O:9][CH3:10] | C#CCBr.CONC(=O)OC | C#CCN(OC)C(=O)OC | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5da873da5e065666521679df8db5a1d2754540edd93ae40997847c9a24dedeb3 | c05cd517c346aa4e8e8e58218c491edaea33d354b5dba9eb90dac8ad97104f73 | null | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[#8:9]-[C;D1;H3:10]>>[C;D1;H1:3]#[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8](-[#8:9]-[C;D1;H3:10])-[C:6](=[O;D1;H0:7])-[#8:5]-[C;D1;H3:4] | 58.7 | [{"value": 58.7, "product": "CON(C(OC)=O)CC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.43 g of sodium hydride (60% in oil) was suspended in 10 ml of tetrahydrofuran, and 1.0 g of methyl N-methoxycarbamate and 1.36 g of propargyl bromide were added to the suspension in this order while being cooled with ice. The mixture was heat-refluxed for 4 hours. After completion of the reaction, water was added to ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester | null | null | null | HBr | O1CCCC1 | null | null | C#CCBr.CONC(=O)OC>O1CCCC1>C#CCN(OC)C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b317ab1e31f1484d8c7fa6fc2ad9a7be | C#CCOCCl.CONC(=O)OC>>C#CCOCN(OC)C(=O)OC | O.[H-].[Na+].CONC(OC)=O.ClCOCC#C>>CON(C(OC)=O)COCC#C | Cl[CH2:5][O:4][CH2:3][C:2]#[CH:1].[NH:6]([O:7][CH3:8])[C:9](=[O:10])[O:11][CH3:12]>>[CH:1]#[C:2][CH2:3][O:4][CH2:5][N:6]([O:7][CH3:8])[C:9](=[O:10])[O:11][CH3:12] | C#CCOCCl.CONC(=O)OC | C#CCOCN(OC)C(=O)OC | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 86848dd2159c6006fdcfad1637821bff7ec5e51fc9ab33fa406eeb0ccd5d29e2 | b12b7f91cf142e2ddad8d1f02ba972615b69f606a979e2c6ca26037ba95d3adf | null | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3]-[C:4]#[C;D1;H1:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[NH;D2;+0:10]-[#8:11]-[C;D1;H3:12]>>[C;D1;H1:5]#[C:4]-[C:3]-[#8:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10](-[#8:11]-[C;D1;H3:12])-[C:8](=[O;D1;H0:9])-[#8:7]-[C;D1;H3:6] | 75.9 | [{"value": 75.9, "product": "CON(C(OC)=O)COCC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.37 g of sodium hydride (60% in oil) was suspended in 10 ml of tetrahydrofuran, and 0.8 g of methyl N-methoxycarbamate and 0.96 g of chloromethylpropargyl ether were added thereto in this order while being cooled with ice. The mixture was heat-refluxed for 1 hour. After completion of the reaction, water was added to t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester.Ether | null | null | null | HCl | O1CCCC1 | null | null | C#CCOCCl.CONC(=O)OC>O1CCCC1>C#CCOCN(OC)C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-70e031461ff64ee8941f84d430c91d71 | C#CCBr.CONC(=O)c1ccc(Cl)cc1>>C#CCN(OC)C(=O)c1ccc(Cl)cc1 | O.[H-].[Na+].CONC(C1=CC=C(C=C1)Cl)=O.C(C#C)Br>>CON(C(C1=CC=C(C=C1)Cl)=O)CC#C | Br[CH2:3][C:2]#[CH:1].[NH:4]([O:5][CH3:6])[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1>>[CH:1]#[C:2][CH2:3][N:4]([O:5][CH3:6])[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1 | C#CCBr.CONC(=O)c1ccc(Cl)cc1 | C#CCN(OC)C(=O)c1ccc(Cl)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | db9b1b8804b469c037e0a5ba95031d33e73dcd5fc2a6fa79163c623adf75f2a1 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[C;D1;H3:4]-[#8:5]-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[C;D1;H1:3]#[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[#8:5]-[C;D1;H3:4])-[C:7](=[O;D1;H0:8])-[c:9] | 36.5 | [{"value": 36.5, "product": "CON(C(C1=CC=C(C=C1)Cl)=O)CC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.22 g of sodium hydride (60% in oil) was suspended in 10 ml of tetrahydrofuran, and 1.0 g of N-methoxy-p-chlorobenzamide and 0.68 g of propargyl bromide were added thereto in this order while being cooled with ice. The mixture was heat-refluxed for 8 hours. After completion of the reaction, water was added to the reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | null | null | c1ccccc1 | HBr | O1CCCC1 | null | null | C#CCBr.CONC(=O)c1ccc(Cl)cc1>O1CCCC1>C#CCN(OC)C(=O)c1ccc(Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bc47ddbc82764811b755545cf676a4fc | C#CCBr.CONC(=O)c1ccc(Cl)cc1Cl>>C#CCOC(=NOC)c1ccc(Cl)cc1Cl | CONC(C1=C(C=C(C=C1)Cl)Cl)=O.C([O-])([O-])=O.[K+].[K+].C(C#C)Br.CN(C=O)C>>CON=C(C1=C(C=C(C=C1)Cl)Cl)OCC#C | Br[CH2:3][C:2]#[CH:1].[O:4]=[C:5]([NH:6][O:7][CH3:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16]>>[CH:1]#[C:2][CH2:3][O:4][C:5](=[N:6][O:7][CH3:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16] | C#CCBr.CONC(=O)c1ccc(Cl)cc1Cl | C#CCOC(=NOC)c1ccc(Cl)cc1Cl | null | null | O | Acylation | OtherReaction | a42fe6037e9428fb86a68610b95d04d1c80e76840fbd22ac5b494b61dddf5c16 | 1980a023362fbf7fcc752a926f2a644585c21669c0ad54dda0839f321f10887e | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[C;D1;H3:4]-[#8:5]-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[c:9](:[c:10]):[c:11]>>[C;D1;H1:3]#[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[C;H0;D3;+0:7](=[N;H0;D2;+0:6]-[#8:5]-[C;D1;H3:4])-[c:9](:[c:10]):[c:11] | 29.8 | [{"value": 29.8, "product": "CON=C(C1=C(C=C(C=C1)Cl)Cl)OCC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 1.0 g of N-methoxy-2,4-dichlorobenzamide, 0.75 g of potassium carbonate and 0.65 g of propargyl bromide were added to 10 ml of N,N-dimethylformamide, and the mixture was stirred for 3 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Ether | null | null | c1ccccc1 | HBr | O | null | 3 | C#CCBr.CONC(=O)c1ccc(Cl)cc1Cl>O>C#CCOC(=NOC)c1ccc(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-78a2d25f14b9434b93e8ef7743620d47 | C#CCOCCl.CONC(=O)c1ccccc1>>C#CCOCN(OC)C(=O)c1ccccc1 | O.C([O-])([O-])=O.[K+].[K+].ClCOCC#C.CONC(C1=CC=CC=C1)=O>>CON(C(C1=CC=CC=C1)=O)COCC#C | Cl[CH2:5][O:4][CH2:3][C:2]#[CH:1].[NH:6]([O:7][CH3:8])[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH:1]#[C:2][CH2:3][O:4][CH2:5][N:6]([O:7][CH3:8])[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | C#CCOCCl.CONC(=O)c1ccccc1 | C#CCOCN(OC)C(=O)c1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0babe25fdcc7557d9a098e60c4e2635197f8146663a5ec9ff74cb717c3ce944e | 079d538bb08fcdef8e7b0c806871ec3b6fd57947885e03a54265bebefeb48ca6 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3]-[C:4]#[C;D1;H1:5].[C;D1;H3:6]-[#8:7]-[NH;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[C;D1;H1:5]#[C:4]-[C:3]-[#8:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8](-[#8:7]-[C;D1;H3:6])-[C:9](=[O;D1;H0:10])-[c:11] | 91.9 | [{"value": 91.9, "product": "CON(C(C1=CC=CC=C1)=O)COCC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 0.6 g of N-methoxybenzamide was dissolved in 10 ml of acetonitrile, and 0.55 g of potassium carbonate and 0.42 g of chloromethylpropargyl ether were added thereto in this order. The mixture was stirred at room temperature for 3 hours. After completion of the reaction, water was added to the reaction solution, and the m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Secondary amide | Ether.Tertiary amide | null | null | c1ccccc1 | HCl | C(C)#N | null | 3 | C#CCOCCl.CONC(=O)c1ccccc1>C(C)#N>C#CCOCN(OC)C(=O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a7f1a41a70a4d3db418869aba312fea | C#CCOCCl.CONS(=O)(=O)c1ccccc1>>C#CCOCN(OC)S(=O)(=O)c1ccccc1 | O.C([O-])([O-])=O.[K+].[K+].ClCOCC#C.CONS(=O)(=O)C1=CC=CC=C1>>CON(S(=O)(=O)C1=CC=CC=C1)COCC#C | Cl[CH2:5][O:4][CH2:3][C:2]#[CH:1].[NH:6]([O:7][CH3:8])[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH:1]#[C:2][CH2:3][O:4][CH2:5][N:6]([O:7][CH3:8])[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | C#CCOCCl.CONS(=O)(=O)c1ccccc1 | C#CCOCN(OC)S(=O)(=O)c1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c9e6eec230201ae4d7e7b2e419ab36ef0222686e2de8e98691a9c34dce24ce9f | 6e22d2d2df9145a05371d34e8f221134a49014314c48b65ae49b28ba1a406286 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3]-[C:4]#[C;D1;H1:5].[C;D1;H3:6]-[#8:7]-[NH;D2;+0:8]-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12]>>[C;D1;H1:5]#[C:4]-[C:3]-[#8:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8](-[#8:7]-[C;D1;H3:6])-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12] | 85.6 | [{"value": 85.6, "product": "CON(S(=O)(=O)C1=CC=CC=C1)COCC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 0.6 g of N-methoxybenzenesulfonamide was dissolved in 10 ml of acetonitrile, and 0.44 g of potassium carbonate and 0.34 g of chloromethylpropargyl ether were added thereto in this order. The mixture was stirred at room temperature for 4 hours. After completion of the reaction, water was added to the reaction solution, ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Ether.Tertiary amine | null | null | c1ccccc1 | HCl | C(C)#N | null | 4 | C#CCOCCl.CONS(=O)(=O)c1ccccc1>C(C)#N>C#CCOCN(OC)S(=O)(=O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-45783ee212a64703af0373922cf64354 | N#CCc1c(Cl)cccc1Cl.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | C(C)OCC[O-].[Na+].[Na].NC1=NC=C(C(=N1)N)C=O.ClC1=C(C(=CC=C1)Cl)CC#N>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N | [CH2:7]([c:8]1[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]1[Cl:15])[C:16]#[N:17].O=[CH:6][c:5]1[cH:4][n:3][c:2]([NH2:1])[n:20][c:19]1[NH2:18]>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16]([NH2:17])[n:18][c:19]2[n:20]1 | N#CCc1c(Cl)cccc1Cl.Nc1ncc(C=O)c(N)n1 | Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | null | null | C(C)OCCO | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16](-[Cl;D1;H0:17]):[c:18]>>[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:... | null | [] | null | null | null | null | (Prepared by the method of U.S. Pat. No. 3,534,039). To a solution of sodium 2-ethoxyethoxide prepared from 0.14 g of sodium and 60 mL of 2-ethoxyethanol was added 2.07 g of 2,4-diamino-5-pyrimidinecarboxaldehyde and 2.79 g of 2,6-dichlorophenylacetonitrile. The mixture is heated at reflux for 4 hours, cooled, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | C(C)OCCO | null | null | N#CCc1c(Cl)cccc1Cl.Nc1ncc(C=O)c(N)n1>C(C)OCCO>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8859698c10bb4c7b910c576bf44215d1 | CC(C)(C)N=C=O.Cc1ccccc1-c1cc2cnc(N)nc2nc1N>>Cc1ccccc1-c1cc2cnc(NC(=O)NC(C)(C)C)nc2nc1NC(=O)NC(C)(C)C | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2)C)N.[H-].[Na+].C(C)(C)(C)N=C=O>>C(C)(C)(C)NC(=O)NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2)C)NC(=O)NC(C)(C)C | [C:15](=[O:16])=[N:17][C:18]([CH3:19])([CH3:30])[CH3:33].[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]2[cH:11][n:12][c:13]([NH2:14])[n:22][c:23]2[n:24][c:25]1[NH2:26]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]2[cH:11][n:12][c:13]([NH:14][C:15](=[O:16])[NH:17][C:18]([CH3:19])([CH3:2... | CC(C)(C)N=C=O.Cc1ccccc1-c1cc2cnc(N)nc2nc1N | Cc1ccccc1-c1cc2cnc(NC(=O)NC(C)(C)C)nc2nc1NC(=O)NC(C)(C)C | null | null | CN(C=O)C | Acylation | OtherReaction | 4cd4a24ba08f7bf502b3150ee8b2fb0c67292b0872d42e763884f695ebc3e7df | 0ec38b10255bbfaa941365846c10b48228a0d7b15bea6d4efd05967a51aa7d5f | c1ccc(-c2cnc3ncncc3c2)cc1 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:[c:13]:[#7;a:14]:[c:15](-[NH2;D1;+0:16]):[c:17]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:18])(-[C;D1;H3:19])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[#... | null | [] | null | null | 1.5 | HOUR | A suspension of 0.5 g of 2,7-diamino-6-o-tolyl-pyrido[2,3-d]pyrimidine, prepared as described above in Example 1, in 10 mL of dimethylformamide is reacted with 0.16 g of 60% sodium hydride and stirred at ambient temperature for 1.5 hours. To the suspension is added 0.49 mL of t-butylisocyanate and the mixture stirred o... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine.Primary amine | Urea.Urea | null | null | c1ccccc1.c1cnc2ncncc2c1 | Other | CN(C=O)C | null | 1.5 | CC(C)(C)N=C=O.Cc1ccccc1-c1cc2cnc(N)nc2nc1N>CN(C=O)C>Cc1ccccc1-c1cc2cnc(NC(=O)NC(C)(C)C)nc2nc1NC(=O)NC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8ab3a8e6f55f47d8b365c3064b07de67 | Nc1ncc2cc(-c3ccccc3)c(N)nc2n1.O=S(=O)([O-])OS(=O)(=O)[O-]>>Nc1ncc2cc(-c3ccccc3)c(O)nc2n1 | Cl.S(=O)(=O)([O-])OS(=O)(=O)[O-].NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC=CC=C2)N>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC=CC=C2)O | N[c:14]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:6][c:5]2[cH:4][n:3][c:2]([NH2:1])[n:18][c:17]2[n:16]1.O=S(=O)([O-])OS(=O)(=O)[O-:15]>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[c:14]([OH:15])[n:16][c:17]2[n:18]1 | Nc1ncc2cc(-c3ccccc3)c(N)nc2n1.O=S(=O)([O-])OS(=O)(=O)[O-] | Nc1ncc2cc(-c3ccccc3)c(O)nc2n1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | f03b70232ecf08fbaaf3a9634857fb15accb640e4f8168b323f472351503e508 | 0faab53fb44f5d790c940e8273c888214a6763f53a41b0c03d0241319b9333e9 | c1ccc(-c2cnc3ncncc3c2)cc1 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:2:[c:9]:[c:10]:1-[c:11].O=S(=O)(-[O-;H0;D1:12])-O-S(=O)(=O)-[O-]>>[OH;D1;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:2:[c:9]:[c:10]:1-[c:11] | null | [] | null | null | 8 | HOUR | To a solution of 2 L of concentrated HCl and 1 L of water is added 300 g of the disulfate salt of 2,7-diamino-6-phenylpyrido[2,3-d]pyrimidine and the resulting mixture refluxed with stirring overnight. The reaction mixture is cooled in an ice bath, filtered, and the insoluble product washed with water, followed by etha... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic alcohol | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | O | null | 8 | Nc1ncc2cc(-c3ccccc3)c(N)nc2n1.O=S(=O)([O-])OS(=O)(=O)[O-]>O>Nc1ncc2cc(-c3ccccc3)c(O)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3fcd707cf920422c9a3f2c314bd98ea8 | Nc1ncc2cc(-c3ccccc3)c(O)nc2n1>>CCCCNc1nc2nc(N)ncc2cc1-c1ccccc1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC=CC=C2)O.ClCCl.S(=O)(Cl)Cl>>C(CCC)NC=1C(=CC2=C(N=C(N=C2)N)N1)C1=CC=CC=C1 | O[c:6]1[n:5][c:8]2[n:9][c:10]([NH2:11])[n:12][cH:13][c:14]2[cH:15][c:16]1-[c:17]1[cH:18][cH:19][cH:1][cH:21][cH:22]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][c:6]1[n:7][c:8]2[n:9][c:10]([NH2:11])[n:12][cH:13][c:14]2[cH:15][c:16]1-[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | Nc1ncc2cc(-c3ccccc3)c(O)nc2n1 | CCCCNc1nc2nc(N)ncc2cc1-c1ccccc1 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 3918fde530e82a2eb40ae9fd955cb7baf7502e7ebe185117a386e4aa64b46462 | 8acaf1912c506977ac2b93b637436f6e9f84e3c03a5886b7706de538665aeb49 | c1ccc(-c2cnc3ncncc3c2)cc1 | O-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:2:[c:9]:[c:10]:1-[c:11]1:[c:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[c:16]:1>>[CH3;D1;+0:14]-[C:17]-[C:18]-[C:19]-[NH;D2;+0:2]-[c;H0;D3;+0:1]1:[#7;a:20]:[c;H0;D3;+0:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:2:[c:9]:[c:10]:1-[c:11]1... | 44.4 | [{"value": 44.4, "product": "C(CCC)NC=1C(=CC2=C(N=C(N=C2)N)N1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a mixture of 23.8 g of 2-amino-6-phenyl-pyrido-[2,3-d]pyrimidin-7-ol prepared above in Example 8, 250 mL of dichloromethane, and 77.5 mL of dimethylformamide was added dropwise with cooling 36 mL of thionyl chloride keeping the temperature below 15° C. Following complete addition, the suspension was heated to reflux... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Secondary amine | c1cnc2ncncc2c1.c1ccccc1 | c1cnc2ncncc2c1.c1ccccc1 | c1cnc2ncncc2c1.c1ccccc1 | null | CN(C=O)C | null | 5 | Nc1ncc2cc(-c3ccccc3)c(O)nc2n1>CN(C=O)C>CCCCNc1nc2nc(N)ncc2cc1-c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e018a58eae26447a85248e2d7c5e33b2 | CN(C)C=O.COc1ccc(-c2cc3cnc(N)nc3nc2O)cc1.O=S(Cl)Cl>>COc1ccc(-c2cc3cnc(N=CN(C)C)nc3nc2Cl)cc1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC=C(C=C2)OC)O.ClCCl.CN(C=O)C.S(=O)(Cl)Cl>>ClC=1C(=CC2=C(N=C(N=C2)N=CN(C)C)N1)C1=CC=C(C=C1)OC | O=[CH:14][N:15]([CH3:16])[CH3:17].O[c:21]1[c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]2)[cH:8][c:9]2[cH:10][n:11][c:12]([NH2:13])[n:18][c:19]2[n:20]1.O=S(Cl)[Cl:22]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[cH:10][n:11][c:12]([N:13]=[CH:14][N:15]([CH3:16])[CH3:17])[n:18][c:19]3[n:20][c:21]2... | CN(C)C=O.COc1ccc(-c2cc3cnc(N)nc3nc2O)cc1.O=S(Cl)Cl | COc1ccc(-c2cc3cnc(N=CN(C)C)nc3nc2Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 38dc813b76ab9bfbc1c3f635b0be6bf536681495974807819197730cbd5961cd | 1e7a2373d3de7893c523befcc507ddda1337e870f8d320e04e5a89e86694733f | c1ccc(-c2cnc3ncncc3c2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]2:[#7;a:5]:[c:6](-[NH2;D1;+0:7]):[#7;a:8]:[c:9]:[c:10]:2:[c:11]:[c:12]:1-[c:13].O=[CH;D2;+0:14]-[#7:15](-[C;D1;H3:16])-[C;D1;H3:17]>>[C;D1;H3:16]-[#7:15](-[C;D1;H3:17])-[CH;D2;+0:14]=[N;H0;D2;+0:7]-[c:6]1:[#7;a:8]:[c:9]:[c:10]2:[c:11]:[c:12](-[c:13]):[c;H0;D3;+0:... | null | [] | null | null | 6 | HOUR | To a mixture of 67.0 g of 2-amino-6-(4-methoxy-phenyl)-pyrido[2,3-d]pyrimidin-7-ol from Example 10, 1 L of dichloromethane, and 155 mL of dimethylformamide was added dropwise with cooling 72 mL of thionyl chloride keeping the temperature below 15° C. The suspension was heated to reflux with stirring for 6 hours. The re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Aromatic alcohol.Primary amine | Aromatic halide | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HCl | null | null | 6 | CN(C)C=O.COc1ccc(-c2cc3cnc(N)nc3nc2O)cc1.O=S(Cl)Cl>>COc1ccc(-c2cc3cnc(N=CN(C)C)nc3nc2Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-86096de2e5674031bab10b49fa871e15 | COc1ccc(-c2cc3cnc(N=CN(C)C)nc3nc2Cl)cc1>>COc1ccc(-c2cc3cnc(N)nc3nc2Cl)cc1 | ClC=1C(=CC2=C(N=C(N=C2)N=CN(C)C)N1)C1=CC=C(C=C1)OC>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC=C(C=C2)OC)Cl | CN(C)C=[N:13][c:12]1[n:11][cH:10][c:9]2[cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]3)[c:17]([Cl:18])[n:16][c:15]2[n:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[cH:10][n:11][c:12]([NH2:13])[n:14][c:15]3[n:16][c:17]2[Cl:18])[cH:19][cH:20]1 | COc1ccc(-c2cc3cnc(N=CN(C)C)nc3nc2Cl)cc1 | COc1ccc(-c2cc3cnc(N)nc3nc2Cl)cc1 | null | null | C(C)O | Deprotection | OtherReaction | 33bcd42056000f3bc2d5907a85ff371ecf8a91697366ae3c95c7cdc536f4e4f7 | 09463156f8971f4e8007d84d8ed410eed1d618bdb6ba7dd05b4970ff2019f62b | c1ccc(-c2cnc3ncncc3c2)cc1 | C-N(-C)-C=[N;H0;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[#7;a:5]:[c:2](-[NH2;D1;+0:1]):[#7;a:3]:[c:4] | 32.2 | [{"value": 32.2, "product": "NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC=C(C=C2)OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 10 g of N'-(7-chloro-6-(4-methoxy-phenyl)-pyrido[2,3-d]pyrimidin-2-yl)-N,N-dimethyl-formamidine from Example 11 and 500 mL of 95% ethanol was refluxed for 3 hours. The solution was concentrated in vacuo and the precipitate collected by filtration. Crystallization from ethanol afforded 2.7 g of the title co... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Primary amine | null | null | c1ccccc1.c1cnc2ncncc2c1 | Other | C(C)O | null | null | COc1ccc(-c2cc3cnc(N=CN(C)C)nc3nc2Cl)cc1>C(C)O>COc1ccc(-c2cc3cnc(N)nc3nc2Cl)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f0d5340aaf840a58a389a03ef389f8c | CN.COc1ccc(-c2cc3cnc(N)nc3nc2Cl)cc1>>CNc1nc2nc(N)ncc2cc1-c1ccc(OC)cc1 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=CC=C(C=C2)OC)Cl.CN>>COC1=CC=C(C=C1)C1=CC2=C(N=C(N=C2)N)N=C1NC | [CH3:1][NH2:2].Cl[c:3]1[n:4][c:5]2[n:6][c:7]([NH2:8])[n:9][cH:10][c:11]2[cH:12][c:13]1-[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][cH:21]1>>[CH3:1][NH:2][c:3]1[n:4][c:5]2[n:6][c:7]([NH2:8])[n:9][cH:10][c:11]2[cH:12][c:13]1-[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][cH:21]1 | CN.COc1ccc(-c2cc3cnc(N)nc3nc2Cl)cc1 | CNc1nc2nc(N)ncc2cc1-c1ccc(OC)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 95363dd4f7eaf5ca3b2b81ca3d4d6901dabfa76417ca700d29bf339c0c5e8fb0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cnc3ncncc3c2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[c:5](-[c:6]):[c:7].[C;D1;H3:8]-[NH2;D1;+0:9]>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C;D1;H3:8]):[c:5](-[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of 3.4 g of 2-amino-7-chloro-6-(4-methoxyphenyl)-pyrido[2,3-d]pyrimidine from Example 12, 40 mL of anhydrous methylamine, and 10 mL of methanol were heated in a bomb on a steam bath for 4 hours. After cooling, the suspension was washed out of the bomb with 50 mL of methanol/water (50:50) and the solvents were... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HCl | CO | null | null | CN.COc1ccc(-c2cc3cnc(N)nc3nc2Cl)cc1>CO>CNc1nc2nc(N)ncc2cc1-c1ccc(OC)cc1 |
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