dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-827aca2c99d04cc1a044b4a8bf2652ae | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Oc1ccc2[nH]ccc2c1F>>COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCCN1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C.FC1=C2C=CNC2=CC=C1O.C([O-])([O-])=O.[K+].[K+]>>FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][cH:13][cH:14][c:15]2[c:16]1[F:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Oc1ccc2[nH]ccc2c1F | COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCCN1CCN(C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCNCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 42.2 | [{"value": 42.0, "product": "FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.2, "product": "FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 3 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (232 mg, 0.662 mmol), (prepared as described for the starting material in Examples 176 or 244), and 4-fluoro-5-hydroxyindole (120 mg, 0.794 mmol), (prepared as described for the starting material in Example 242), in DMF (3 ml) containing p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | CN(C)C=O | 95 | 3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Oc1ccc2[nH]ccc2c1F>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f0a21121369d4d2e83e725978514d809 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1.ClCCN1CCCC1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(CCN2CCCC2)CC1 | COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C=C(NC2=CC1)C.ClCCN1CCCC1.C([O-])([O-])=O.[Na+].[Na+].[I-].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCN1CCCC1)OC=1C=C2C=C(NC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][CH:26]1[CH2:27][CH2:28][NH:29][CH2:37][CH2:38]1.Cl[CH2:30][CH2:31][N:32]1[CH2:33][CH2:34][CH2:35][CH2:36]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1.ClCCN1CCCC1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(CCN2CCCC2)CC1 | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCN(CCN4CCCC4)CC3)cc2n1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 20 | [{"value": 20.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCN1CCCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.8, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCN1CCCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of 6-methoxy-4-(2-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline (600 mg, 1.43 mmol), (prepared as described in Example 70), 1-(2-chloroethyl)-pyrrolidine (292 mg, 1.72 mmol) in methanol (14 ml) containing sodium carbonate (262 mg, 4.3 mmol) and potassium iodide (48 mg, 0.29 mmol) was heated at 50°... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1.C1CC[NH]C1 | HCl | CO | 50 | null | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1.ClCCN1CCCC1>CO>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(CCN2CCCC2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fff12c083f2d4e2ab369ffc87bd1d18f | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1cc2cc[nH]c2cc1F>>COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCOCC1 | O.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.FC1=C(C=C2C=CNC2=C1)O.C([O-])([O-])=O.[K+].[K+]>>FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][c:10]2[cH:11][cH:12][nH:13][c:14]2[cH:15][c:16]1[F:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][c:10]4[cH:11][cH:12][nH:13][c:14]... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1cc2cc[nH]c2cc1F | COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCOCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 41 | [{"value": 41.0, "product": "FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.4, "product": "FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (110 mg, 0.325 mmol), (prepared as described for the starting material in Example 1), and 6-fluoro-5-hydroxyindole (59 mg, 0.39 mmol), (prepared as described for the starting material in Example 242), in DMF (1.8 ml) containing potassium carbonate (67 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | 90 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1cc2cc[nH]c2cc1F>CN(C)C=O>COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b8614837fc174298adee985ee2d1dda5 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.OCCN1CCOCC1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCN1CCOCC1 | N(=NC(=O)OCC)C(=O)OCC.OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OCCN1CCOCC1>>N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCOCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[OH:23].O[CH2:24][CH2:25][N:26]1[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3... | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.OCCN1CCOCC1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCN1CCOCC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCN3CCOCC3)cc2n1 | O-[CH2;D2;+0:1]-[C:2]-[#7:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]:[c:5]:[#7;a:4] | 55 | [{"value": 55.0, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.3, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 3 | HOUR | To a solution of 7-hydroxy-4-(indol-5-yloxy)-6-methoxyquinazoline (183 mg, 0.6 mmol), (prepared as described for the starting material in Example 107), triphenylphosphine (235 mg, 0.89 mmol) and 4-(2-hydroxyethyl)morpholine (93 mg, 0.72 mmol) in methylene chloride (4 ml) cooled at 10° C. was added diethyl azodicarboxyl... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HO- | C(Cl)Cl | 10 | 3 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.OCCN1CCOCC1>C(Cl)Cl>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-179d12d1cebe48639e155c74702b58c4 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OC[C@H](O)CN1CCCC1 | C(C)(=O)O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C(=C2C=C(NC2=CC1)C)F)OC)CN1CCCC1.N>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C(=C2C=C(NC2=CC1)C)F)OC)CN1CCCC1 | CC(=O)[O:28][C@@H:27]([CH2:26][O:25][c:24]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[c:17]3[F:18])[n:19][cH:20][n:21][c:22]2[cH:23]1)[CH2:29][N:30]1[CH2:31][CH2:32][CH2:33][CH2:34]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OC[C@H](O)CN1CCCC1 | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | d7acfb2397f2b5b2a83b3bebf3698d6d984dd716982297f62a944222c79ce234 | 19dd58e0f83625e74b4b1375d88cb4c813ee60f593d812516d14eafc4ab68dc7 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[OH;D1;+0:1] | 75 | [{"value": 75.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C(=C2C=C(NC2=CC1)C)F)OC)CN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C(=C2C=C(NC2=CC1)C)F)OC)CN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (2R)-7-(2-acetoxy-3-(pyrrolidin-1-yl)propoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxyquinazoline (570 mg, 1.12 mmol) in methanol saturated with ammonia (7 ml) was stirred overnight at ambient temperature. The volatiles were removed under vacuum and the residue was purified by column chromatography el... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Secondary alcohol | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HO- | CO | null | null | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O>CO>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OC[C@H](O)CN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a5cda6931414ca185c1b2bb674b7242 | CC(=O)OC(C)=O.COc1cc2c(=O)[nH]cnc2cc1OC[C@H](O)CN1CCCC1>>COc1cc2c(=O)[nH]cnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O | O[C@@H](COC1=C(C=C2C(NC=NC2=C1)=O)OC)CN1CCCC1.C(C)(=O)OC(C)=O.O>>C(C)(=O)O[C@@H](COC1=C(C=C2C(NC=NC2=C1)=O)OC)CN1CCCC1 | CC(=O)O[C:24]([CH3:25])=[O:26].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][C@@H:16]([CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1)[OH:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][C@@H:16]([CH2:17][N:18]1[CH2... | CC(=O)OC(C)=O.COc1cc2c(=O)[nH]cnc2cc1OC[C@H](O)CN1CCCC1 | COc1cc2c(=O)[nH]cnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O | null | null | null | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | O=c1[nH]cnc2cc(OCCCN3CCCC3)ccc12 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[C:6])-[OH;D1;+0:7]>>[C:4]-[C:5](-[C:6])-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 65.6 | [{"value": 65.0, "product": "C(C)(=O)O[C@@H](COC1=C(C=C2C(NC=NC2=C1)=O)OC)CN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.6, "product": "C(C)(=O)O[C@@H](COC1=C(C=C2C(NC=NC2=C1)=O)OC)CN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of (2R)-7-(2-hydroxy-3-(pyrrolidin-1-yl)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (803 mg, 2.51 mmol) in acetic anhydride (1.2 ml, 12.5 mmol) was stirred at ambient temperature for 1 hour. Water (360 μl, 20 mmol) was added and stirring was continued for 90 minutes. The mixture was partitioned between aqu... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | c1ccc2ncncc2c1.C1CC[NH]C1 | HO- | null | null | 1 | CC(=O)OC(C)=O.COc1cc2c(=O)[nH]cnc2cc1OC[C@H](O)CN1CCCC1>>COc1cc2c(=O)[nH]cnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47e0365b1812489482b8aa55a39d018c | COc1cc2c(=O)[nH]cnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O | C(C)(=O)O[C@@H](COC1=C(C=C2C(NC=NC2=C1)=O)OC)CN1CCCC1.S(=O)(Cl)Cl>>C(C)(=O)O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)Cl)OC)CN1CCCC1 | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][C@@H:16]([CH2:17][N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[O:23][C:24]([CH3:25])=[O:26])[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][C@@H:16]([CH2:17][N:18]1[C... | COc1cc2c(=O)[nH]cnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O | null | CN(C)C=O | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccc(OCCCN3CCCC3)cc2n1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 90 | [{"value": 90.0, "product": "C(C)(=O)O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)Cl)OC)CN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of (2R)-7-(2-acetoxy-3-(pyrrolidin-1-yl)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (556 mg, 1.54 mmol) in thionyl chloride (6 ml) containing DMF (3 drops) was heated at 80° C. for 4 hours. The volatiles were removed under vacuum. The residue was dissolved in methylene chloride and the organic layer was w... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 80 | null | COc1cc2c(=O)[nH]cnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O.O=S(Cl)Cl>CN(C)C=O>COc1cc2c(Cl)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-15520b7aa20a499bbf62226c8aec6142 | COc1cc2c(Cl)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O.Cc1cc2c(F)c(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O | C(C)(=O)O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)Cl)OC)CN1CCCC1.FC1=C2C=C(NC2=CC=C1O)C.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C(=C2C=C(NC2=CC1)C)F)OC)CN1CCCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][C@@H:27]([CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[O:34][C:35]([CH3:36])=[O:37])[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][c:13]([CH3:14])[cH:15][c:16]2[c:17]1[F:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9... | COc1cc2c(Cl)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O.Cc1cc2c(F)c(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 81.5 | [{"value": 81.0, "product": "C(C)(=O)O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C(=C2C=C(NC2=CC1)C)F)OC)CN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.5, "product": "C(C)(=O)O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C(=C2C=C(NC2=CC1)C)F)OC)CN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 90 | CELSIUS | 2 | HOUR | A suspension of (2R)-7-(2-acetoxy-3-(pyrrolidin-1-yl)propoxy)4-chloro-6-methoxyquinazoline (530 mg, 1.4 mmol) and 4-fluoro-5-hydroxy-2-methylindole (277 mg, 1.68 mmol), (prepared as described for the starting material in Example 237), in DMF (8 ml) containing potassium carbonate (290 mg, 2.1 mmol) was stirred at 90° C.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 90 | 2 | COc1cc2c(Cl)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O.Cc1cc2c(F)c(O)ccc2[nH]1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OC[C@@H](CN1CCCC1)OC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-62f3670c972f42379d1e7979ccdd61ac | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Nc1ccc2[nH]ccc2c1>>COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCC1 | Cl.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.NC=1C=C2C=CNC2=CC1>>Cl.N1C=CC2=CC(=CC=C12)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[cH:21][c:20]2[n:19][cH:18][n:17]1.[NH2:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][cH:13][cH:14][c:15]2[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Nc1ccc2[nH]ccc2c1 | COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCC1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1nc(Nc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 92.8 | [{"value": 72.0, "product": "Cl.N1C=CC2=CC(=CC=C12)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.8, "product": "Cl.N1C=CC2=CC(=CC=C12)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of 4-chloro-6-methoxy-7(3-(pyrrolidin-1-yl)propoxy)quinazoline (61 mg, 0.19 mmol), (prepared as described for the starting material in Example 9), and 5-aminoindole (30 mg, 0.23 mmol) in isopropanol (2 ml) containing 6.2 N hydrogen chloride in isopropanol (33 μl) was heated at 80° C. for 6 hours. After cooli... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | C(C)(C)O | 80 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Nc1ccc2[nH]ccc2c1>C(C)(C)O>COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-931c61833c834a56a0de166465458f50 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2cc(F)cnc2c1>>COc1cc2c(Oc3ccc4cc(F)cnc4c3)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].FC=1C=NC2=CC(=CC=C2C1)O>>FC=1C=NC2=CC(=CC=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][c:13]([F:14])[cH:15][n:16][c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][c:... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2cc(F)cnc2c1 | COc1cc2c(Oc3ccc4cc(F)cnc4c3)ncnc2cc1OCCCN1CCCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCCCN5CCCCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 44 | [{"value": 44.0, "product": "FC=1C=NC2=CC(=CC=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.7, "product": "FC=1C=NC2=CC(=CC=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (144 mg, 0.43 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (91 mg, 0.66 mmol) and 3-fluoro-7-hydroxyquinoline (77 mg, 0.47 mmol), (prepared as described for the starting material in Example 157), in DMF (3 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CN(C)C=O | 100 | 2 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2cc(F)cnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cc(F)cnc4c3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-11607c9d8b494044a8e8e7d5f2e20c30 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2cc(F)cnc2c1>>COc1cc2c(Oc3ccc4cc(F)cnc4c3)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.C([O-])([O-])=O.[K+].[K+].FC=1C=NC2=CC(=CC=C2C1)O>>FC=1C=NC2=CC(=CC=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][c:13]([F:14])[cH:15][n:16][c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][c:13]([F:1... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2cc(F)cnc2c1 | COc1cc2c(Oc3ccc4cc(F)cnc4c3)ncnc2cc1OCCCN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCCCN5CCCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 28.2 | [{"value": 28.0, "product": "FC=1C=NC2=CC(=CC=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.2, "product": "FC=1C=NC2=CC(=CC=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (218 mg, 0.68 mmol), (prepared as described for the starting material in Example 9), potassium carbonate (138 mg, 1.13 mmol) and 3-fluoro-7-hydroxyquinoline (117 mg, 0.72 mmol), (prepared as described for the starting material in Example 157), in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 100 | 4 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2cc(F)cnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cc(F)cnc4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b48f576b22e64091bd7a8f6512fa62ec | CC1=CCC(CC2CCN(C)C(=O)C2)(S(=O)(=O)[O-])C=C1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C)C(=O)C1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.C([O-])([O-])=O.[K+].[K+].CN1C(CC(CC1)CC1(CC=C(C=C1)C)S(=O)(=O)[O-])=O>>COC=1C=C2C(=NC=NC2=CC1OCC1CC(N(CC1)C)=O)OC=1C=C2C=C(NC2=CC1)C | CC1=CCC(S(=O)(=O)[O-])([CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([CH3:30])[C:31](=[O:32])[CH2:33]2)C=C1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:... | CC1=CCC(CC2CCN(C)C(=O)C2)(S(=O)(=O)[O-])C=C1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C)C(=O)C1 | null | null | CC(=O)C.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f2d5edccac2080b2c6539c229872a63825a11125de9eb3381e8b7cab2bd888c2 | d784cc625c03ea59ddf5ea6c0b5bb33b10fce3b4e0d8e178af93294c63ad5e22 | O=C1CC(COc2ccc3c(Oc4ccc5[nH]ccc5c4)ncnc3c2)CCN1 | C-C1=C-C-C(-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7])(-S(=O)(=O)-[O-])-C=C-1.[#7;a:8]:[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7:7]-[C:5](=[O;D1;H0:6])-[C:4]-[C:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]:[c:9]:[#7;a:8])-[C:3] | 17 | [{"value": 17.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CC(N(CC1)C)=O)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CC(N(CC1)C)=O)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 4 | HOUR | A mixture of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (280 mg, 0.87 mmol), (prepared as described in Example 49), potassium carbonate (370 mg, 2.68 mmol) and 4-(1-methyl-2-oxopiperidin-4-yl)methyl-4-toluene sulphonate (260 mg, 0.87 mmol) in DMF (8 ml) was stirred at 95° C. for 4 hours and allowed to coo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Sulfonic acid | Ether | C1=CCCC=C1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | CC(=O)C.CN(C)C=O | 95 | 4 | CC1=CCC(CC2CCN(C)C(=O)C2)(S(=O)(=O)[O-])C=C1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>CC(=O)C.CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C)C(=O)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-17c4b1ea3f47418e894ce9c36802c1b3 | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H](O)CN1CCN(C)CC1 | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C=C(NC2=CC1)C.CN1CCNCC1>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCN(CC1)C | [NH:29]1[CH2:30][CH2:31][N:32]([CH3:33])[CH2:34][CH2:35]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][C@@H:26]1[O:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[... | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H](O)CN1CCN(C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 17ab6d3921429d49d85a9af124942b034c73e1fe2f69930f0392bbbfc9046e12 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCNCC3)cc2n1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[#8:7]-[C:8]-[C@H;D3;+0:9]1-[CH2;D2;+0:10]-[O;H0;D2;+0:11]-1>>[#8:7]-[C:8]-[C@H;D3;+0:9](-[OH;D1;+0:11])-[CH2;D2;+0:10]-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 91.2 | [{"value": 91.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 24 | HOUR | A mixture of (2R)-6-methoxy-4-(2-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (300 mg, 0.79 mmol), and 1-methylpiperazine (0.26 ml, 2.38 mmol) in DMF (10 ml) was stirred at 70° C. for 24 hours and allowed to cool to ambient temperature. The solvents were removed in vacuo and the residue purified by silica col... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CNCC[NH]1.C1CO1 | C1C[NH]CC[NH]1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | null | CN(C)C=O | 70 | 24 | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H](O)CN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5dc63d9ad4014b659f77e59b495d353f | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.C([O-])([O-])=O.[K+].[K+].CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]2CO2>>COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C=C(NC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].Cc1ccc(S(=O)(=O)O[CH2:25][C@H:26]2[CH2:27][O:28]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OC[C@H]3CO3)cc2n1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:c:1.[#7;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:10] | 53 | [{"value": 53.0, "product": "COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.7, "product": "COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | A mixture of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (300 mg, 0.93 mmol), (prepared as described in Example 49), potassium carbonate (385 mg, 2.79 mmol) and (2R)-(−)-glycidyl tosylate (426 mg, 2.79 mmol) in DMF (15 ml) was stirred at 60° C. for 2 hours and allowed to cool to ambient temperature. The re... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CO1 | TsOH.HO- | CN(C)C=O | 60 | 2 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ecdf3e68612844bfb6627c1e01714b97 | CCNCC.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1>>CCN(CC)C[C@@H](O)COc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C=C(NC2=CC1)C.C(C)NCC>>C(C)N(CC)C[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)O | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].[CH2:6]1[C@H:7]([CH2:9][O:10][c:11]2[cH:12][c:13]3[n:14][cH:15][n:16][c:17]([O:18][c:19]4[cH:20][cH:21][c:22]5[nH:23][c:24]([CH3:25])[cH:26][c:27]5[cH:28]4)[c:29]3[cH:30][c:31]2[O:32][CH3:33])[O:8]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][C@@H:7]([OH:8])[CH2:9][O:10][c:11]1[cH:12]... | CCNCC.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1 | CCN(CC)C[C@@H](O)COc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C;D1;H3:10]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:8](-[C:7]-[C;D1;H3:6])-[C:9]-[C;D1;H3:10] | 81 | [{"value": 81.0, "product": "C(C)N(CC)C[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "C(C)N(CC)C[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 24 | HOUR | A mixture of (2R)-6-methoxy-4-(2-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (300 mg, 0.79 mmol), (prepared as described for the starting material in Example 269), and diethylamine (0.25 ml, 2.38 mmol) in DMF (10 ml) was stirred at 70° C. for 24 hours and allowed to cool to ambient temperature. The solvents ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1 | null | CN(C)C=O | 70 | 24 | CCNCC.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1>CN(C)C=O>CCN(CC)C[C@@H](O)COc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-54e6fc74c4e14c9d92b6ddf607c1544c | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC.C(=O)[O-].[NH4+]>>OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC | c1ccc(C[O:24][c:23]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([O:7][c:8]4[cH:9][cH:10][c:11]5[nH:12][cH:13][c:14]([CH3:15])[c:16]5[cH:17]4)[n:18][cH:19][n:20][c:21]3[cH:22]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22]... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCc1ccccc1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O | null | [Pd] | CN(C)C=O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 91 | [{"value": 91.0, "product": "OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 7-benzyloxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (7.76 g, 18.9 mmol), ammonium formate (17.82 g, 282 mmol) and 10% palladium on charcoal (800 mg) in DMF (350 ml) was stirred at ambient temperature for 1 hour. The catalyst was filtered off through celite and the cake washed with DMF. The solvent w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | Other | [Pd].CN(C)C=O | null | 1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCc1ccccc1>[Pd].CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bac32f0e58ec4ba1a4f44945696ebe84 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1c[nH]c2ccc(O)cc12>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC.C([O-])([O-])=O.[K+].[K+].OC=1C=C2C(=CNC2=CC1)C>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][cH:13][c:14]([CH3:15])[c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1c[nH]c2ccc(O)cc12 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCc1ccccc1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(COc2ccc3c(Oc4ccc5[nH]ccc5c4)ncnc3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 73 | [{"value": 73.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.5, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 2 | HOUR | A mixture of 7-benzyloxy-4-chloro-6-methoxyquinazoline (7.859 g, 26.1 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (18.03 g, 130 mmol) and 5-hydroxy-3-methylindole (5.00 g, 34.0 mmol), (Journal of Organic Chemistry 1993, 58, 3757), in DMA (600 ml) was stirred at 75° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CC(=O)N(C)C | 75 | 2 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1c[nH]c2ccc(O)cc12>CC(=O)N(C)C>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0787e9c37224c8d8c58490f573822c5 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.ClCCCN1CCOCC1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCCN1CCOCC1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC.C([O-])([O-])=O.[K+].[K+].ClCCCN1CCOCC1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2C(=CNC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].Cl[CH2:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:1... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.ClCCCN1CCOCC1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCOCC3)cc2n1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:9] | 51 | [{"value": 51.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2C(=CNC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2C(=CNC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | A mixture of 7-hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (800 mg, 2.49 mmol), (prepared as described in Example 271), potassium carbonate (687 mg, 4.98 mmol) and 1-chloro-3-morpholinopropane (448 mg, 2.74 mmol), (prepared as described for the starting material in Example 1), in DMF (20 ml) was stirred at 8... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | 80 | 2 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.ClCCCN1CCOCC1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f92e71d9fffa455aa45f519e5336c685 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.ClCCN1CCOCC1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCN1CCOCC1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC.C([O-])([O-])=O.[K+].[K+].Cl.ClCCN1CCOCC1>>COC=1C=C2C(=NC=NC2=CC1OCCN1CCOCC1)OC=1C=C2C(=CNC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].Cl[CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.ClCCN1CCOCC1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCN3CCOCC3)cc2n1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]:[c:5]:[#7;a:4] | 47.1 | [{"value": 47.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCN1CCOCC1)OC=1C=C2C(=CNC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.1, "product": "COC=1C=C2C(=NC=NC2=CC1OCCN1CCOCC1)OC=1C=C2C(=CNC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | A mixture of 7-hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (800 mg, 2.49 mmol), (prepared as described for the starting material in Example 271), potassium carbonate (1.031 g, 7.47 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (510 mg, 2.74 mmol) in DMF (25 ml) was stirred at 80° C. for 2 hours and all... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | 80 | 2 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.ClCCN1CCOCC1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac332f7b11bd4d39b5c3a40f2bb40dd0 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC.C([O-])([O-])=O.[K+].[K+].CC1=CC=C(C=C1)S(=O)(=O)OCC1CCN(CC1)C(=O)OC(C)(C)C>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)OC=1C=C2C(=CNC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].Cc1ccc(S(=O)(=O)O[CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]2)cc1>>[CH3:1][O:2][c:3]1[cH:4]... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):c:c:1.[#7;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):[c:10] | 63 | [{"value": 63.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)OC=1C=C2C(=CNC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.7, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)OC=1C=C2C(=CNC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | A mixture of 7-hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (1.00 g, 3.11 mmol), (prepared as described for the starting material in Example 271), potassium carbonate (1.288 g, 9.33 mmol) and 4-(4-methylphenylsulphonyloxymethyl)-1-tert-butoxycarbonylpiperidine (1.264 g, 3.42 mmol), (prepared as described for ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | TsOH.HO- | CN(C)C=O | 80 | 2 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-233237a2c74449d28a2d406ee16b0bd3 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OOCCCN2CCS(=O)(=O)CC2)cc1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC.C([O-])([O-])=O.[K+].[K+].S(=O)(=O)(OOCCCN1CCS(CC1)(=O)=O)C1=CC=C(C)C=C1>>O=S1(CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].Cc1ccc(S(=O)(=O)OO[CH2:25][CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][S:31](=[O:32])(=[O:33])[CH2:34][CH2:35]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OOCCCN2CCS(=O)(=O)CC2)cc1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | fedcb14b605772e360ae1ed30c4604b3d84b43339d9ff4d2021d0434b5dd15ef | c6ee87f63e41bd18f606223ec6576e0792ab2fd4ec5b723604eae1f551dc5463 | O=S1(=O)CCN(CCCOc2ccc3c(Oc4ccc5[nH]ccc5c4)ncnc3c2)CC1 | C-c1:c:c:c(-S(=O)(=O)-O-O-[CH2;D2;+0:1]-[C:2]-[C:3]):c:c:1.[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:9] | 56.5 | [{"value": 56.0, "product": "O=S1(CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.5, "product": "O=S1(CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | A mixture of 7-hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (600 mg, 1.87 mmol), (prepared as described for the starting material in Example 271), potassium carbonate (773 mg, 5.60 mmol) and 3-(1,1-dioxothiomorphlino)propoxy tosylate (1.296 g, 3.74 mmol) in DMF (30 ml) was stirred at 75° C. overnight and allo... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol.Peroxide | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CSCC[NH]1 | TsOH.HO- | CN(C)C=O | 75 | 8 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OOCCCN2CCS(=O)(=O)CC2)cc1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fa7099ef0614cd4af04d9806122a0ab | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCNCC1 | COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)OC=1C=C2C(=CNC2=CC1)C>>COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C(=CNC2=CC1)C | CC(C)(C)OC(=O)[N:29]1[CH2:28][CH2:27][CH:26]([CH2:25][O:24][c:23]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([O:7][c:8]4[cH:9][cH:10][c:11]5[nH:12][cH:13][c:14]([CH3:15])[c:16]5[cH:17]4)[n:18][cH:19][n:20][c:21]3[cH:22]2)[CH2:31][CH2:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCNCC1 | null | null | FC(C(=O)O)(F)F | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 62.2 | [{"value": 62.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C(=CNC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.2, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C(=CNC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 6-methoxy-4-(3-methylindol-5-yloxy)-7-(1-tert-butoxycarbonylpiperidin-4-ylmethoxy)quinazoline (1.290 g, 2.49 mmol), (prepared as described in Example 274), in 25% trifluoroacetic acid/75% dichloromethane solution (75 ml) was stirred at ambient temperature for 2 hours. The solvents were then removed in vacu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CCNCC1 | HO- | FC(C(=O)O)(F)F | null | 2 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1>FC(C(=O)O)(F)F>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af9c13b920d74909b69f5bc1fb670bf3 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCNCC1.N#CCCl>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCN(CC#N)CC1 | COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C(=CNC2=CC1)C.C(C)N(CC)CC.ClCC#N>>C(#N)CN1CCC(CC1)COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][CH:26]1[CH2:27][CH2:28][NH:29][CH2:33][CH2:34]1.Cl[CH2:30][C:31]#[N:32]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:1... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCNCC1.N#CCCl | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCN(CC#N)CC1 | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | Cl-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[C:7]-[C:8] | 35 | [{"value": 35.0, "product": "C(#N)CN1CCC(CC1)COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 6-methoxy-4-(3-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline (460 mg, 1.10 mmol), (prepared as described in Example 276), triethylamine (5 ml) and chloroacetonitrile (0.38 ml, 6.05 mmol) in methanol (5 ml) was stirred at ambient temperature for 24 hours. The solvents were removed in vacuo and t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CO | null | 24 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCNCC1.N#CCCl>CO>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCN(CC#N)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c89511f52ee846f4a5080b1f6e515de3 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC.C([O-])([O-])=O.[K+].[K+].CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]2CO2>>COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].Cc1ccc(S(=O)(=O)O[CH2:25][C@H:26]2[CH2:27][O:28]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OC[C@H]3CO3)cc2n1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:c:1.[#7;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:10] | 53.1 | [{"value": 53.0, "product": "COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.1, "product": "COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | A mixture of 7-hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (1.35 g, 4.2 mmol), (prepared as described for the starting material in Example 271), potassium carbonate (1.74 g, 12.6 μmmol) and (2R)-(−)-glycidyl tosylate (1.92 g, 8.4 mmol) in DMF (25 ml) was stirred at 60° C. for 2 hours and allowed to cool to a... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CO1 | TsOH.HO- | CN(C)C=O | 60 | 2 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ba7a97d699e4b688bca43eee5c7f5b7 | C1CCNC1.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN1CCCC1 | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C.N1CCCC1>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CN1CCCC1 | [NH:29]1[CH2:30][CH2:31][CH2:32][CH2:33]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][C@@H:26]1[O:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:... | C1CCNC1.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 76b1810a18be65e42ea157c2729971f505df73ec247c72e2192a1e56ead5967f | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1 | 88.2 | [{"value": 88.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.2, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 24 | HOUR | A mixture of (2R)-6-methoxy-4-(3-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (300 mg, 0.65 mmol), (prepared as described in Example 278), and pyrrolidine (0.17 ml, 2.04 mmol) in DMF (5 ml) was stirred at 60° C. for 24 hours and allowed to cool to ambient temperature. The solvents were removed in vacuo and th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CCNC1.C1CO1 | C1CC[NH]C1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | null | CN(C)C=O | 60 | 24 | C1CCNC1.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2069c05e6da748919de375efa853f1c2 | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN1CCN(C)CC1 | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C.CN1CCNCC1.CN(C)C=O>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CN1CCN(CC1)C | [NH:29]1[CH2:30][CH2:31][N:32]([CH3:33])[CH2:34][CH2:35]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][C@@H:26]1[O:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[... | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 17ab6d3921429d49d85a9af124942b034c73e1fe2f69930f0392bbbfc9046e12 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCNCC3)cc2n1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[#8:7]-[C:8]-[C@H;D3;+0:9]1-[CH2;D2;+0:10]-[O;H0;D2;+0:11]-1>>[#8:7]-[C:8]-[C@H;D3;+0:9](-[OH;D1;+0:11])-[CH2;D2;+0:10]-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 80 | [{"value": 80.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 24 | HOUR | A mixture of (2R)-6-methoxy-4-(3-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (350 mg, 0.93 mmol), (prepared as described in Example 278), and 1-methylpiperazine (0.31 ml, 2.78 mmol) in DMF (5 ml) was stirred at 60° C. for 24 hours and allowed to cool to ambient temperature. The solvents were removed in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CNCC[NH]1.C1CO1 | C1C[NH]CC[NH]1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | null | null | 60 | 24 | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-128583cbc4174050a3b7291e19927c4c | CNC.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN(C)C | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C.CNC.C(C)O>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CN(C)C | [NH:29]([CH3:30])[CH3:31].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][C@@H:26]1[O:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:... | CNC.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8] | 78 | [{"value": 78.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 24 | HOUR | A mixture of (2R)-6-methoxy-4-(3-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (350 mg, 0.93 mmol), (prepared as described in Example 278), and 2.0 M dimethylamine in ethanol (4.60 ml, 9.30 mmol) in DMF (5 ml) was stirred at 60° C. for 24 hours and allowed to cool to ambient temperature. The solvents were remo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | null | CN(C)C=O | 60 | 24 | CNC.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e045e7ee22184581a00b2f26425cec95 | CC(C)N.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CNC(C)C | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C.C(C)(C)N>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CNC(C)C | [NH2:29][CH:30]([CH3:31])[CH3:32].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][C@@H:26]1[O:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3... | CC(C)N.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CNC(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[NH;D2;+0:9]-[C:7](-[C;D1;H3:6])-[C;D1;H3:8] | 75.6 | [{"value": 75.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CNC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.6, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CNC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 24 | HOUR | A mixture of (2R)-6-methoxy-4-(3-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (350 mg, 0.93 mmol), (prepared as described in Example 278), and isopropylamine (0.29 ml, 4.65 mmol) in DMF (5 ml) was stirred at 100° C. for 24 hours and allowed to cool to ambient temperature. The solvents were removed in vacuo an... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | null | CN(C)C=O | 100 | 24 | CC(C)N.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CNC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e7731da2f7f243159009b2381ecd2a75 | CC(C)NC(C)C.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN(C(C)C)C(C)C | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C.C(C)(C)NC(C)C>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CN(C(C)C)C(C)C | [NH:29]([CH:30]([CH3:31])[CH3:32])[CH:33]([CH3:34])[CH3:35].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][C@@H:26]1[O:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]... | CC(C)NC(C)C.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN(C(C)C)C(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[C:10](-[C;D1;H3:11])-[C;D1;H3:12]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:9](-[C:7](-[C;D1;H3:6])-[C;D1;H3:8])-[C:10](-[C;D1;H3:11])-[C;D1;H3:12] | 93 | [{"value": 93.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CN(C(C)C)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.4, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CN(C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 24 | HOUR | A mixture of (2R)-6-methoxy-4-(3-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (350 mg, 0.93 mmol), (prepared as described in Example 278), and diisopropylamine (0.78 ml, 5.58 mmol) in DMF (10 ml) was stirred at 130° C. for 24 hours and allowed to cool to ambient temperature. The solvents were removed in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | null | CN(C)C=O | 130 | 24 | CC(C)NC(C)C.COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CN(C(C)C)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-104228acecfb43e6a0a22670d44d151d | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1.NCCCN1CCOCC1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CNCCCN1CCOCC1 | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C.NCCCN1CCOCC1>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CNCCCN1CCOCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][C@@H:26]1[O:27][CH2:28]1.[NH2:29][CH2:30][CH2:31][CH2:32][N:33]1[CH2:34][CH2:35][O:36][CH2:37][CH2:38]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1.NCCCN1CCOCC1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CNCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCNCCCN3CCOCC3)cc2n1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C:6]-[C:7]-[NH2;D1;+0:8]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[NH;D2;+0:8]-[C:7]-[C:6] | 46 | [{"value": 46.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CNCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.9, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CNCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture of (2R)-6-methoxy-4-(3-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (100 mg, 0.28 mmol), (prepared as described in Example 278), and 4-(3-aminopropyl)morpholine (0.12 ml, 0.84 mmol) in DMF (5 ml) was heated to 70° C. for 3 hours. The solvents were removed in vacuo and the residue taken up in dichlor... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | null | CN(C)C=O | 70 | null | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1.NCCCN1CCOCC1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CNCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ad3967b21f84f3588d6a0ac8d52ec97 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>>COc1ccc2ncnc(Oc3ccc4[nH]cc(C)c4c3)c2c1 | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C.NCCCN1CCN(CC1)C>>COC=1C=C2C(=NC=NC2=CC1)OC=1C=C2C(=CNC2=CC1)C | C1O[C@H]1CO[c:4]1[c:3]([O:2][CH3:1])[cH:23][c:22]2[c:6]([cH:5]1)[n:7][cH:8][n:9][c:10]2[O:11][c:12]1[cH:13][cH:14][c:15]2[nH:16][cH:17][c:18]([CH3:19])[c:20]2[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][n:9][c:10]([O:11][c:12]3[cH:13][cH:14][c:15]4[nH:16][cH:17][c:18]([CH3:19])[c:20]4[cH:21]3)[c:22]2[cH:23... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1 | COc1ccc2ncnc(Oc3ccc4[nH]cc(C)c4c3)c2c1 | null | null | CN(C)C=O | Reduction | OtherReaction | a7bf2d7147ce1e3758997759ed14aac4b01a32af045af979a1c7bac98056e4bd | 1556a72485df4201aca96fb7a0c321edf07cb063300030d429a36e916471ff2c | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[c:2]1:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c;H0;D3;+0:11]:1-O-C-[C@@H]1-C-O-1>>[#8:1]-[c:2]1:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[cH;D2;+0:11]:1 | 51.5 | [{"value": 31.0, "product": "COC=1C=C2C(=NC=NC2=CC1)OC=1C=C2C(=CNC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.5, "product": "COC=1C=C2C(=NC=NC2=CC1)OC=1C=C2C(=CNC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture of (2R)-6-methoxy-4-(3-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (100 mg, 0.28 mmol), (prepared as described in Example 278), and 1-(3-aminopropyl)-4-methylpiperazine (132 mg, 0.84 mmol) in DMF (5 ml) was heated to 70° C. for 3 hours. The solvents were removed in vacuo and the residue taken up in... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | C1CO1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1 | HO- | CN(C)C=O | 70 | null | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1>CN(C)C=O>COc1ccc2ncnc(Oc3ccc4[nH]cc(C)c4c3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1bee15e9315e496b8ca9c0c95b460a1c | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1.NCCCN1CCCC1>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CNCCCN1CCCC1 | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C(=CNC2=CC1)C.NCCCN1CCCC1>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CNCCCN1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][c:14]([CH3:15])[c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][C@@H:26]1[O:27][CH2:28]1.[NH2:29][CH2:30][CH2:31][CH2:32][N:33]1[CH2:34][CH2:35][CH2:36][CH2:37]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9]... | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1.NCCCN1CCCC1 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CNCCCN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCNCCCN3CCCC3)cc2n1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C:6]-[C:7]-[NH2;D1;+0:8]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[NH;D2;+0:8]-[C:7]-[C:6] | 68 | [{"value": 68.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CNCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=CNC2=CC1)C)OC)CNCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of (2R)-6-methoxy-4-(3-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (70 mg, 0.19 mmol), (prepared as described in Example 278), and 1-(3-aminopropyl)pyrrolidine (74 mg, 0.58 mmol) in DMF (5 ml) was heated to 60° C. overnight. The solvents were removed in vacuo and the residue purified by column chro... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | null | CN(C)C=O | 60 | null | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H]1CO1.NCCCN1CCCC1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OC[C@H](O)CNCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-156bc0493faf4ea6b372c226721e4d54 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]ccc2c1Br>>COc1cc2c(Oc3ccc4[nH]ccc4c3Br)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].BrC1=C2C=CNC2=CC=C1O>>BrC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][cH:13][cH:14][c:15]2[c:16]1[Br:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]ccc2c1Br | COc1cc2c(Oc3ccc4[nH]ccc4c3Br)ncnc2cc1OCCCN1CCCCC1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 44.3 | [{"value": 44.0, "product": "BrC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.3, "product": "BrC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 3 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (380 mg, 1.13 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (469 mg, 3.4 mmol), 4-bromo-5-hydroxyindole (240 mg, 1.13 mmol) and DMA (4.0 ml) were stirred at 90° C. for 3 hours and allowed to cool to ambient ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CC(=O)N(C)C | 90 | 3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]ccc2c1Br>CC(=O)N(C)C>COc1cc2c(Oc3ccc4[nH]ccc4c3Br)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b0cff2d5040b4c34a8d7dbfcf7338615 | CCO.CCOC(=O)c1cc2c(Br)c(O)ccc2[nH]1>>COc1ccc2[nH]c(C(=O)O)cc2c1Br | BrC1=C2C=C(NC2=CC=C1O)C(=O)OCC.C(C)O.[OH-].[K+]>>BrC1=C2C=C(NC2=CC=C1OC)C(=O)O | OC[CH3:1].CC[O:11][C:9]([c:8]1[nH:7][c:6]2[cH:5][cH:4][c:3]([OH:2])[c:14]([Br:15])[c:13]2[cH:12]1)=[O:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13]2[c:14]1[Br:15] | CCO.CCOC(=O)c1cc2c(Br)c(O)ccc2[nH]1 | COc1ccc2[nH]c(C(=O)O)cc2c1Br | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 0db00e48ffe5800295c995015791d2855681eceda8c116b62320b3c2b225d830 | 9653d63179b641796999681486e0249947865421087fe94dd6954f3668089e9b | c1ccc2[nH]ccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9].O-C-[CH3;D1;+0:10]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[CH3;D1;+0:10]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 96 | [{"value": 96.0, "product": "BrC1=C2C=C(NC2=CC=C1OC)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | Ethyl 4-bromo-5-hydroxyindole-2-carboxylate (1.49 g, 5 mmol.), (Jnl. Org. Chem. 1984, 49, 4761), was dissolved in ethanol (10 ml) and water (3.5 ml). Potassium hydroxide (840 mg) was added and the mixture stirred at 50° C. under an atmosphere of nitrogen for 1 hour then cooled to ambient temperature. The solvent was ev... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccc2[nH]ccc2c1 | HO- | O | 50 | 1 | CCO.CCOC(=O)c1cc2c(Br)c(O)ccc2[nH]1>O>COc1ccc2[nH]c(C(=O)O)cc2c1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d6f2ecd05d344eecbf92022007dacf5d | COc1ccc2[nH]c(C(=O)O)cc2c1Br>>COc1ccc2[nH]ccc2c1Br | BrC1=C2C=C(NC2=CC=C1OC)C(=O)O.N1=CC=CC2=CC=CC=C12>>BrC1=C2C=CNC2=CC=C1OC | O=C(O)[c:8]1[nH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]([Br:12])[c:10]2[cH:9]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][cH:9][c:10]2[c:11]1[Br:12] | COc1ccc2[nH]c(C(=O)O)cc2c1Br | COc1ccc2[nH]ccc2c1Br | null | [Cr](=O)([O-])[O-].[Cu+2] | null | Reduction | Decarboxylation | d5c4709a8d4e49fe37f49e81e5c384f60c93fbbbbfa4eb758c4725d90cd07b32 | 292164ffdf89eeb341ee9424f24084b252a703a26bb77721b558b0f8a8528c45 | c1ccc2[nH]ccc2c1 | O-C(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1>>[#7;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:1]:1 | 67 | [{"value": 60.0, "product": "BrC1=C2C=CNC2=CC=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.0, "product": "BrC1=C2C=CNC2=CC=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 245 | CELSIUS | null | null | 4-Bromo-5-methoxyindole-2-carboxylic acid (1.25 g, 4.19 mmol), quinoline (15 ml) and copper chromite (313 mg) were mixed together. Nitrogen was gently bubbled through the mixture for 5 minutes, then the mixture heated quickly to 245° C. under an atmosphere of nitrogen. After 90 minutes the mixture was cooled to ambient... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | Other | [Cr](=O)([O-])[O-].[Cu+2] | 245 | null | COc1ccc2[nH]c(C(=O)O)cc2c1Br>[Cr](=O)([O-])[O-].[Cu+2]>COc1ccc2[nH]ccc2c1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0fb4521827e14255ad8beb0e5762aff1 | COc1ccc2[nH]ccc2c1Br>>Oc1ccc2[nH]ccc2c1Br | B(Br)(Br)Br.BrC1=C2C=CNC2=CC=C1OC>>BrC1=C2C=CNC2=CC=C1O | C[O:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][cH:8][c:9]2[c:10]1[Br:11]>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][cH:8][c:9]2[c:10]1[Br:11] | COc1ccc2[nH]ccc2c1Br | Oc1ccc2[nH]ccc2c1Br | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 58 | [{"value": 55.0, "product": "BrC1=C2C=CNC2=CC=C1O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.0, "product": "BrC1=C2C=CNC2=CC=C1O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-bromo-5-methoxyindole (540 mg, 2.4 mmol) in dichloromethane (12 ml) was cooled to −40° C. under an atmosphere of nitrogen. Boron tribromide (4.8 ml of a 1M solution in dichloromethane, 4.8 mmol) was added dropwise then the mixture warmed to ambient temperature and stirred for 1 hour. The mixture was dil... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | ClCCl | null | 1 | COc1ccc2[nH]ccc2c1Br>ClCCl>Oc1ccc2[nH]ccc2c1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2653284ecc644473ae51d390ec995ab4 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cn1ccc2cc(O)ccc21>>COc1cc2c(Oc3ccc4c(ccn4C)c3)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC=1C=C2C=CN(C2=CC1)C>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C=CN(C2=CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13][cH:14][n:15]2[CH3:16])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([cH:13]... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cn1ccc2cc(O)ccc21 | COc1cc2c(Oc3ccc4c(ccn4C)c3)ncnc2cc1OCCCN1CCCCC1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 49 | [{"value": 49.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C=CN(C2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.7, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C=CN(C2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 4 | HOUR | Nitrogen was bubbled through a mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (335 mg, 0.68 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (281.5 mg, 2.04 mmol), 5-hydroxy-1methylindole (100 mg, 0.68 mmol) and DMA (4.0 ml) for 5 minutes. The mixture was the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CC(=O)N(C)C | 90 | 4 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cn1ccc2cc(O)ccc21>CC(=O)N(C)C>COc1cc2c(Oc3ccc4c(ccn4C)c3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ab4d48fa8a74ecd8be1088086b8319b | Cn1ccc2cc(OCc3ccccc3)ccc21>>Cn1ccc2cc(O)ccc21 | C(C1=CC=CC=C1)OC=1C=C2C=CN(C2=CC1)C.[H][H]>>OC=1C=C2C=CN(C2=CC1)C | c1ccc(C[O:8][c:7]2[cH:6][c:5]3[cH:4][cH:3][n:2]([CH3:1])[c:11]3[cH:10][cH:9]2)cc1>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([OH:8])[cH:9][cH:10][c:11]12 | Cn1ccc2cc(OCc3ccccc3)ccc21 | Cn1ccc2cc(O)ccc21 | null | [Pd] | C(C)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]ccc2c1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 97 | [{"value": 97.0, "product": "OC=1C=C2C=CN(C2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "OC=1C=C2C=CN(C2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-benzyloxy-1-methylindole (3.5 g, 15.7 mmol), in ethanol (100 ml) was hydrogenated at ambient temperature and 1 atmosphere pressure hydrogen for 4 hours using 10% palladium on carbon (0.5 g) as catalyst. The catalyst was filtered off and the filtrate evaporated in vacuo. The residue was purified by silic... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1 | Other | [Pd].C(C)O | null | null | Cn1ccc2cc(OCc3ccccc3)ccc21>[Pd].C(C)O>Cn1ccc2cc(O)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3241eccbfb14974b801d4e0361b08ed | C1CCNC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN1CCCC1 | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1OC1.N1CCCC1>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCC1 | [NH:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15... | C1CCNC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 76b1810a18be65e42ea157c2729971f505df73ec247c72e2192a1e56ead5967f | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1 | 90.4 | [{"value": 87.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 3 | HOUR | A mixture of (2R)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (300 mg, 0.83 mmol), and pyrrolidine (176 mg, 2.48 mmol) in DMF (5 ml) was stirred at 75° C. for 3 hours under an atmosphere of nitrogen and allowed to cool to ambient temperature. The solvents were removed in vacuo and the residue purified... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CCNC1.C1CO1 | C1CC[NH]C1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | null | CN(C)C=O | 75 | 3 | C1CCNC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6fc7265f2a5a4a41999f37ea8271a87e | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC.C([O-])([O-])=O.[K+].[K+].CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]2CO2>>N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1OC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[OH:23].Cc1ccc(S(=O)(=O)O[CH2:24][C@H:25]2[CH2:26][O:27]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH... | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OC[C@H]3CO3)cc2n1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:c:1.[#7;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:10] | 53 | [{"value": 53.0, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1OC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.8, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1OC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | Nitrogen was bubbled through a mixture of 7-hydroxy-4-(indol-5-yloxy)-6-methoxyquinazoline (3.07 g, 10 mmol), (prepared as described for the starting material in Example 107), potassium carbonate (4.14 g, 30 mmol) and (2R)-(−)-glycidyl tosylate (4.57 g, 20 mmol) in DMA (35 ml) for 5 minutes. The mixture was then stirre... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CO1 | TsOH.HO- | CC(=O)N(C)C | 60 | 2 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1>CC(=O)N(C)C>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4ece89f8a164338b014d80355468b69 | C1COCCN1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN1CCOCC1 | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1OC1.N1CCOCC1>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCOCC1 | [NH:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14... | C1COCCN1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 851dfc16280bb8f11cdb75741b500ca1a156bb53c804ef98fc4ef4b1d0f67de0 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCOCC3)cc2n1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1 | 90.4 | [{"value": 85.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 292, (2R)4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (300 mg, 0.83 mmol), (prepared as described for the starting material in Example 292), was reacted with morpholine (211 mg, 2.49 mmol) to give (2R)-7-(2-hydroxy-3-morpholinopropoxy)-4-(indol-... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1COCCN1.C1CO1 | C1COCC[NH]1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | null | null | null | null | C1COCCN1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7e4413bdd67d4bf992102662bce3074b | C1CCNCC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN1CCCCC1 | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1OC1.N1CCCCC1>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCCC1 | [NH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:... | C1CCNCC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | c5753b22446d1ae5dcee7a30af0c7f96061ec363349faf28c9adeaca5e033c6d | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCCC3)cc2n1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:8](-[C:7]-[C:6])-[C:9]-[C:10] | 87.3 | [{"value": 86.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 292, (2R)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (300 mg, 0.83 mmol), (prepared as described for the starting material in Example 292), was reacted with piperidine (211 mg, 2.49 mmol) to give (2R)-7-(2-hydroxy-3-piperidinopropoxy)-4-(indol... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CCNCC1.C1CO1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | null | null | null | null | C1CCNCC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ee337e3d8d924102832727e143fc3d35 | CNC.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN(C)C | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1OC1.CNC>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN(C)C | [NH:28]([CH3:29])[CH3:30].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17... | CNC.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN(C)C | null | null | CN(C)C=O.C1CCOC1 | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8] | 63 | [{"value": 63.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 3 | HOUR | A mixture of (2R)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (300 mg, 0.83 mmol), (prepared as described for the starting material in Example 292), and dimethylamine (1.24 ml of a 2M solution in THF, 2.48 mmol) in DMF (5 ml) was stirred at 75° C. for 3 hours under an atmosphere of nitrogen then allow... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | null | CN(C)C=O.C1CCOC1 | 75 | 3 | CNC.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>CN(C)C=O.C1CCOC1>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1db60d30b6e54133b9e84522d2a3fd09 | CC(C)NC(C)C.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN(C(C)C)C(C)C | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1OC1.C(C)(C)NC(C)C>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN(C(C)C)C(C)C | [NH:28]([CH:29]([CH3:30])[CH3:31])[CH:32]([CH3:33])[CH3:34].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][... | CC(C)NC(C)C.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN(C(C)C)C(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[C:10](-[C;D1;H3:11])-[C;D1;H3:12]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:9](-[C:7](-[C;D1;H3:6])-[C;D1;H3:8])-[C:10](-[C;D1;H3:11])-[C;D1;H3:12] | 89 | [{"value": 86.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN(C(C)C)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN(C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 19 | HOUR | A mixture of (2R)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (300 mg, 0.83 mmol), (prepared as described for the starting material in Example 292), and diisopropylamine (1.35 ml, 9.7 mmol) in DMF (5 ml) was stirred at 70° C. for 19 hours under an atmosphere of nitrogen then allowed to cool to ambient... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | null | CN(C)C=O | 70 | 19 | CC(C)NC(C)C.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CN(C(C)C)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc5529faea7b47769d8e6d36db5af682 | C1CCNC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN1CCCC1 | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@H]1OC1.N1CCCC1>>O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCC1 | [NH:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]... | C1CCNC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 76b1810a18be65e42ea157c2729971f505df73ec247c72e2192a1e56ead5967f | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | [#8:1]-[C:2]-[C@@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#8:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1 | 93.7 | [{"value": 92.0, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 3 | HOUR | A mixture of (2S)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (100 mg, 0.28 mmol), and pyrrolidine (60 mg, 0.84 mmol) in DMF (5 ml) was stirred at 75° C. for 3 hours under an atmosphere of nitrogen and then allowed to cool to ambient temperature. The solvents were removed in vacuo and the residue puri... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CCNC1.C1CO1 | C1CC[NH]C1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | null | CN(C)C=O | 75 | 3 | C1CCNC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b0da29bb5887496a810b39b4a3b863c9 | C1COCCN1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN1CCOCC1 | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@H]1OC1.N1CCOCC1>>O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCOCC1 | [NH:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14]... | C1COCCN1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 851dfc16280bb8f11cdb75741b500ca1a156bb53c804ef98fc4ef4b1d0f67de0 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCOCC3)cc2n1 | [#8:1]-[C:2]-[C@@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#8:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1 | 65 | [{"value": 63.0, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 297, (2S)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (100 mg, 0.28 mmol), (prepared as described for the starting material in Example 297), was reacted with morpholine (73.2 mg, 0.84 mmol) to give (2S)-7-(2-hydroxy-3-morpholinopropoxy)-4-(indo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1COCCN1.C1CO1 | C1COCC[NH]1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | null | null | null | null | C1COCCN1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-21f5092f3fef41deb242548e30deb0d6 | C1CCNCC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN1CCCCC1 | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@H]1OC1.N1CCCCC1>>O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCCC1 | [NH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:1... | C1CCNCC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | c5753b22446d1ae5dcee7a30af0c7f96061ec363349faf28c9adeaca5e033c6d | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCCC3)cc2n1 | [#8:1]-[C:2]-[C@@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[#8:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:8](-[C:7]-[C:6])-[C:9]-[C:10] | 74.1 | [{"value": 73.0, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.1, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 297, (2S)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (100 mg, 0.28 mmol), (prepared as described for the starting material in Example 297), was reacted with piperidine (70 mg, 0.83 mmol), to give (2S)-7-(2-hydroxy-3-piperidinopropoxy)-4-(indol... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CCNCC1.C1CO1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | null | null | null | null | C1CCNCC1.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4990c3bff8344a639ec65aae2792a863 | CNC.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN(C)C | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@H]1OC1.CNC>>O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN(C)C | [NH:28]([CH3:29])[CH3:30].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17]... | CNC.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN(C)C | null | null | CN(C)C=O.C1CCOC1 | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[#8:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C;D1;H3:8] | 85 | [{"value": 85.0, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 3 | HOUR | A mixture of (2S)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (100 mg, 0.28 mmol), (prepared as described for the starting material in Example 297), and dimethylamine (0.42 ml of a 2M solution in THF, 0.84 mmol) in DMF (5 ml) was stirred at 75° C. for 3 hours under an atmosphere of nitrogen and then a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | null | CN(C)C=O.C1CCOC1 | 75 | 3 | CNC.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>CN(C)C=O.C1CCOC1>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2fd1a2e1af44c8d8c05d5b5e3710f46 | CC(C)NC(C)C.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN(C(C)C)C(C)C | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@H]1OC1.C(C)(C)NC(C)C>>O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN(C(C)C)C(C)C | [NH:28]([CH:29]([CH3:30])[CH3:31])[CH:32]([CH3:33])[CH3:34].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c... | CC(C)NC(C)C.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN(C(C)C)C(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 8b0e6adfb78f36f9ea38287644fe13d1ed2aa3ea65e10cc66a65b05c37e2e473 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[C:10](-[C;D1;H3:11])-[C;D1;H3:12]>>[#8:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[N;H0;D3;+0:9](-[C:7](-[C;D1;H3:6])-[C;D1;H3:8])-[C:10](-[C;D1;H3:11])-[C;D1;H3:12] | 33.1 | [{"value": 33.0, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN(C(C)C)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.1, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CN(C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 19 | HOUR | A mixture of (2S)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (100 mg, 0.28 mmol), (prepared as described for the starting material in Example 297), and diisopropylamine (0.45 ml, 3.2 mmol) in DMF (5 ml) was stirred at 70° C. for 19 hours under an atmosphere of nitrogen and then allowed to cool to amb... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | null | CN(C)C=O | 70 | 19 | CC(C)NC(C)C.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CN(C(C)C)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f68e0ecf50514aa08ad37e4da24a1fc8 | CC(C)N.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CNC(C)C | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1OC1.C(C)(C)N>>O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CNC(C)C | [NH2:28][CH:29]([CH3:30])[CH3:31].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16... | CC(C)N.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CNC(C)C | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[NH;D2;+0:9]-[C:7](-[C;D1;H3:6])-[C;D1;H3:8] | 68 | [{"value": 68.0, "product": "O[C@@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CNC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 18 | HOUR | A mixture of (2R)-4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (100 mg, 0.28 mmol), (prepared as described for the starting material in Example 292), and isopropylamine (1.0 ml) in THF (10 ml) was stirred at 75° C. for 18 hours under an atmosphere of nitrogen and then allowed to cool to ambient tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | null | C1CCOC1 | 75 | 18 | CC(C)N.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CO1>C1CCOC1>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H](O)CNC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b59b743b87ef41a7a5284757a346758f | CC(C)N.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CNC(C)C | N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@H]1OC1.C(C)(C)N>>O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CNC(C)C | [NH2:28][CH:29]([CH3:30])[CH3:31].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][C@H:25]1[O:26][CH2:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]... | CC(C)N.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CNC(C)C | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[#8:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[NH;D2;+0:9]-[C:7](-[C;D1;H3:6])-[C;D1;H3:8] | 56 | [{"value": 56.0, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)CNC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 18 | HOUR | A mixture of (2S)4-(indol-5-yloxy)-6-methoxy-7-(oxiran-2-ylmethoxy)quinazoline (100 mg, 0.28 mmol), (prepared as described for the starting material in Example 297), and isopropylamine (1.0 ml) in THF (10 ml) was stirred at 75° C. for 18 hours under an atmosphere of nitrogen and then allowed to cool to ambient temperat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | null | C1CCOC1 | 75 | 18 | CC(C)N.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CO1>C1CCOC1>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H](O)CNC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fddc19d712ef46a598684395e3faf5d2 | CC(C)N.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@@H]1CO1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@@H](O)CNC(C)C | COC=1C=C2C(=NC=NC2=CC1OC[C@H]1OC1)OC=1C=C2C=C(NC2=CC1)C.C(C)(C)N>>O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CNC(C)C | [NH2:29][CH:30]([CH3:31])[CH3:32].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][C@H:26]1[O:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH... | CC(C)N.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@@H]1CO1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@@H](O)CNC(C)C | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[C:2]-[C@@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[#8:1]-[C:2]-[C@@H;D3;+0:3](-[OH;D1;+0:5])-[CH2;D2;+0:4]-[NH;D2;+0:9]-[C:7](-[C;D1;H3:6])-[C;D1;H3:8] | 73 | [{"value": 73.0, "product": "O[C@H](COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CNC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 18 | HOUR | A mixture of (2S)-6-methoxy-4-(2-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (250 mg, 0.66 m.mol), (prepared as described for the starting material in Example 304), and isopropylamine (1.5 ml) in THF (10 ml) was stirred at 75° C. for 18 hours under an atmosphere of nitrogen and then allowed to cool to ambien... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | null | C1CCOC1 | 75 | 18 | CC(C)N.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@@H]1CO1>C1CCOC1>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@@H](O)CNC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e77f24628f9d42b98aee2741e0f2b855 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1>>COc1ccc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2c1 | COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1OC1)OC=1C=C2C=C(NC2=CC1)C.C(C)(C)N>>COC=1C=C2C(=NC=NC2=CC1)OC=1C=C2C=C(NC2=CC1)C | C1O[C@H]1CO[c:4]1[c:3]([O:2][CH3:1])[cH:23][c:22]2[c:6]([cH:5]1)[n:7][cH:8][n:9][c:10]2[O:11][c:12]1[cH:13][cH:14][c:15]2[nH:16][c:17]([CH3:18])[cH:19][c:20]2[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][n:9][c:10]([O:11][c:12]3[cH:13][cH:14][c:15]4[nH:16][c:17]([CH3:18])[cH:19][c:20]4[cH:21]3)[c:22]2[cH:23... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1 | COc1ccc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2c1 | null | null | C1CCOC1 | Reduction | OtherReaction | a7bf2d7147ce1e3758997759ed14aac4b01a32af045af979a1c7bac98056e4bd | 1556a72485df4201aca96fb7a0c321edf07cb063300030d429a36e916471ff2c | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#8:1]-[c:2]1:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[c;H0;D3;+0:11]:1-O-C-[C@@H]1-C-O-1>>[#8:1]-[c:2]1:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[cH;D2;+0:11]:1 | 120.6 | [{"value": 84.0, "product": "COC=1C=C2C(=NC=NC2=CC1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 120.6, "product": "COC=1C=C2C(=NC=NC2=CC1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 18 | HOUR | A mixture of (2R)-6-methoxy-4-(2-methylindol-5-yloxy)-7-(oxiran-2-ylmethoxy)quinazoline (250 mg, 0.66 mmol), (prepared as described for the starting material in Example 269), and isopropylamine (1.5 ml) in THF (10 ml) was stirred at 75° C. for 18 hours under an atmosphere of nitrogen and then allowed to cool to ambient... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | null | C1CO1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1 | HO- | C1CCOC1 | 75 | 18 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CO1>C1CCOC1>COc1ccc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3297ced1472471fa98833a100debdfe | COc1cc2c(Cl)ncnc2cc1OCCN1CCCCC1.Cn1ccc2cc(O)ccc21>>COc1cc2c(Oc3ccc4c(ccn4C)c3)ncnc2cc1OCC(C)N1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC=1C=C2C=CN(C2=CC1)C>>COC=1C=C2C(=NC=NC2=CC1OCC(C)N1CCCCC1)OC=1C=C2C=CN(C2=CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13][cH:14][n:15]2[CH3:16])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([cH:13][cH:14][... | COc1cc2c(Cl)ncnc2cc1OCCN1CCCCC1.Cn1ccc2cc(O)ccc21 | COc1cc2c(Oc3ccc4c(ccn4C)c3)ncnc2cc1OCC(C)N1CCCCC1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | OtherReaction | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCN3CCCCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[C:10]-[CH2;D2;+0:11]-[#7:12](-[C:13])-[C:14].[OH;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[#8:9]-[C:10]-[CH;D3;+0:11](-[C;D1;H3:19])-[#7:12](-[C:13])-[C:14].[c:17]:[c:16](-[O;H0;D2;+0:15]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:... | 83 | [{"value": 83.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC(C)N1CCCCC1)OC=1C=C2C=CN(C2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "COC=1C=C2C(=NC=NC2=CC1OCC(C)N1CCCCC1)OC=1C=C2C=CN(C2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 3 | HOUR | Nitrogen was bubbled through a mixture of 4-chloro-6-methoxy-7-(2-piperidinoethoxy)quinazoline (400 mg, 1.24 mmol), (prepared as described for the starting material in Example 180), potassium carbonate (500 mg, 3.62 mmol), 5-hydroxy-1-methylindole (231 mg, 1.57 mmol), (prepared as described for the starting material in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | null | CC(=O)N(C)C | 90 | 3 | COc1cc2c(Cl)ncnc2cc1OCCN1CCCCC1.Cn1ccc2cc(O)ccc21>CC(=O)N(C)C>COc1cc2c(Oc3ccc4c(ccn4C)c3)ncnc2cc1OCC(C)N1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-db4326c8d5f24bc4a6171f81adaa1aae | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cn1ccc2cc(O)ccc21>>COc1cc2c(Oc3ccc4c(ccn4C)c3)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.C([O-])([O-])=O.[K+].[K+].OC=1C=C2C=CN(C2=CC1)C>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C=CN(C2=CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13][cH:14][n:15]2[CH3:16])[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([cH:13][cH:14][... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cn1ccc2cc(O)ccc21 | COc1cc2c(Oc3ccc4c(ccn4C)c3)ncnc2cc1OCCCN1CCCC1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 46.1 | [{"value": 44.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C=CN(C2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.1, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C=CN(C2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 3 | HOUR | Nitrogen was bubbled through a mixture of 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (400 mg, 1.24 mmol), (prepared as described for the starting material in Example 9), potassium carbonate (500 mg, 3.62 mmol), 5-hydroxy-1-methylindole (231 mg, 1.57 mmol), (prepared as described for the starting mater... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | CC(=O)N(C)C | 90 | 3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cn1ccc2cc(O)ccc21>CC(=O)N(C)C>COc1cc2c(Oc3ccc4c(ccn4C)c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5765a1308ef94c4a807537fe1e5994c7 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.O=[N+]([O-])c1c(O)ccc2[nH]ccc12>>COc1cc2cnc(Oc3ccc4[nH]ccc4c3[N+](=O)[O-])nc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC=1C(=C2C=CNC2=CC1)[N+](=O)[O-]>>COC=1C=C2C=NC(=NC2=CC1OCCCN1CCCCC1)OC=1C(=C2C=CNC2=CC1)[N+](=O)[O-] | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[cH:24][c:23]2[n:22][cH:8][n:7]1.[OH:9][c:10]1[cH:11][cH:12][c:13]2[nH:14][cH:15][cH:16][c:17]2[c:18]1[N+:19](=[O:20])[O-:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[cH:6][n:7][c:8]([O:9][c:10]3[cH:11][c... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.O=[N+]([O-])c1c(O)ccc2[nH]ccc12 | COc1cc2cnc(Oc3ccc4[nH]ccc4c3[N+](=O)[O-])nc2cc1OCCCN1CCCCC1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | OtherReaction | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cc2cc(Oc3ncc4ccc(OCCCN5CCCCC5)cc4n3)ccc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[cH;D2;+0:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:3]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[cH;D2;+0:1]:[#7;a:2]:1):[c:12] | 39 | [{"value": 39.0, "product": "COC=1C=C2C=NC(=NC2=CC1OCCCN1CCCCC1)OC=1C(=C2C=CNC2=CC1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.8, "product": "COC=1C=C2C=NC(=NC2=CC1OCCCN1CCCCC1)OC=1C(=C2C=CNC2=CC1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 4 | HOUR | Nitrogen was bubbled through a mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (114 mg, 0.34 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (141 mg, 1.02 mmol), 5-hydroxy-4-nitroindole (60.5 mg, 0.34 mmol) and DMA (8.5 ml) for 5 minutes at ambient temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1.C1CC[NH]CC1 | HCl | CC(=O)N(C)C | 90 | 4 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.O=[N+]([O-])c1c(O)ccc2[nH]ccc12>CC(=O)N(C)C>COc1cc2cnc(Oc3ccc4[nH]ccc4c3[N+](=O)[O-])nc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0d5244af2d04652bf6b3bc60250d25d | CCOC(=O)c1cc2cc(OC)ccc2[nH]1.O=[N+]([O-])O>>CCOC(=O)c1cc2c([N+](=O)[O-])c(O)ccc2[nH]1 | COC=1C=C2C=C(NC2=CC1)C(=O)OCC.[N+](=O)(O)[O-]>>OC=1C(=C2C=C(NC2=CC1)C(=O)OCC)[N+](=O)[O-] | C[O:14][c:13]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:18][c:17]2[cH:16][cH:15]1.O[N+:10](=[O:11])[O-:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([N+:10](=[O:11])[O-:12])[c:13]([OH:14])[cH:15][cH:16][c:17]2[nH:18]1 | CCOC(=O)c1cc2cc(OC)ccc2[nH]1.O=[N+]([O-])O | CCOC(=O)c1cc2c([N+](=O)[O-])c(O)ccc2[nH]1 | null | null | ClCCl | Functional Group Addition | OtherReaction | 1b904b66dbdc426f37ef7cd0648bda460f21989aad8a862180f4279d1c37170a | f578230051b5bbda6f1c97099de3ba8f9f59ebaead9a0df3d73d663aaddbaf27 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12]:2:[cH;D2;+0:13]:1.O-[N+;H0;D3:14](-[O;-;D1;H0:15])=[O;D1;H0:16]>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#7;a:6]:[c:5]2:[c:4]:[c:3]:[c:2](-[OH;D1;+0:1]):[c;H0;D3;+0:13](-[N+;H0;D3:14](-[O;-;D1;H0:15])=[O;D1;H0:16]):[c:12]:... | 59 | [{"value": 59.0, "product": "OC=1C(=C2C=C(NC2=CC1)C(=O)OCC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of ethyl 5-methoxyindole-2-carboxylate (8.15 g, 37.2 mmol), (prepared by the method described in Heterocycles Vol. 43, No. 2, p. 263–266), nitric acid adsorbed on silica gel (24 g) and dichloromethane (150 ml) was stirred at ambient temperature for 18 hours. The dichloromethane was removed in vacuo and the pr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrate | Nitro group.Aromatic alcohol | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | ClCCl | null | 18 | CCOC(=O)c1cc2cc(OC)ccc2[nH]1.O=[N+]([O-])O>ClCCl>CCOC(=O)c1cc2c([N+](=O)[O-])c(O)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1145bac0a8ef4d079a9ef6503c24f277 | CCO.CCOC(=O)c1cc2c([N+](=O)[O-])c(O)ccc2[nH]1>>COc1ccc2[nH]c(C(=O)O)cc2c1[N+](=O)[O-] | OC=1C(=C2C=C(NC2=CC1)C(=O)OCC)[N+](=O)[O-].C(C)O.[OH-].[K+]>>COC=1C(=C2C=C(NC2=CC1)C(=O)O)[N+](=O)[O-] | OC[CH3:1].CC[O:11][C:9]([c:8]1[nH:7][c:6]2[cH:5][cH:4][c:3]([OH:2])[c:14]([N+:15](=[O:16])[O-:17])[c:13]2[cH:12]1)=[O:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13]2[c:14]1[N+:15](=[O:16])[O-:17] | CCO.CCOC(=O)c1cc2c([N+](=O)[O-])c(O)ccc2[nH]1 | COc1ccc2[nH]c(C(=O)O)cc2c1[N+](=O)[O-] | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 0db00e48ffe5800295c995015791d2855681eceda8c116b62320b3c2b225d830 | 9653d63179b641796999681486e0249947865421087fe94dd6954f3668089e9b | c1ccc2[nH]ccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9].O-C-[CH3;D1;+0:10]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[CH3;D1;+0:10]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | 50 | CELSIUS | 1 | HOUR | Ethyl 5-hydroxy-4-nitroindole-2-carboxylate (1.0 g, 3.8 mmol.) was suspended in a mixture of ethanol (20 ml) and water (5 ml). Potassium hydroxide (840 mg) was added and the mixture stirred at 50° C. under an atmosphere of nitrogen for 1 hour then cooled to ambient temperature. The solvent was evaporated in vacuo and t... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccc2[nH]ccc2c1 | HO- | O | 50 | 1 | CCO.CCOC(=O)c1cc2c([N+](=O)[O-])c(O)ccc2[nH]1>O>COc1ccc2[nH]c(C(=O)O)cc2c1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f52778852eac4e26b387c74570a3fc2c | COc1ccc2[nH]c(C(=O)O)cc2c1[N+](=O)[O-]>>COc1ccc2[nH]ccc2c1[N+](=O)[O-] | COC=1C(=C2C=C(NC2=CC1)C(=O)O)[N+](=O)[O-].N1=CC=CC2=CC=CC=C12>>COC=1C(=C2C=CNC2=CC1)[N+](=O)[O-] | O=C(O)[c:8]1[nH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]([N+:12](=[O:13])[O-:14])[c:10]2[cH:9]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][cH:9][c:10]2[c:11]1[N+:12](=[O:13])[O-:14] | COc1ccc2[nH]c(C(=O)O)cc2c1[N+](=O)[O-] | COc1ccc2[nH]ccc2c1[N+](=O)[O-] | null | [Cr](=O)([O-])[O-].[Cu+2] | null | Reduction | Decarboxylation | d5c4709a8d4e49fe37f49e81e5c384f60c93fbbbbfa4eb758c4725d90cd07b32 | 292164ffdf89eeb341ee9424f24084b252a703a26bb77721b558b0f8a8528c45 | c1ccc2[nH]ccc2c1 | O-C(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1>>[#7;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:1]:1 | 22 | [{"value": 22.0, "product": "COC=1C(=C2C=CNC2=CC1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.0, "product": "COC=1C(=C2C=CNC2=CC1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 225 | CELSIUS | 40 | MINUTE | The crude 5-methoxy-4-nitroindole-2-carboxylic acid (720 mg, 3.05 mmol), quinoline (9 ml) and copper chromite (180 mg) were stirred together. Nitrogen was gently bubbled through the mixture for 5 minutes, then the mixture was heated quickly to 225° C., and stirred at this temperature for 40 minutes under an atmosphere ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | Other | [Cr](=O)([O-])[O-].[Cu+2] | 225 | 0.666667 | COc1ccc2[nH]c(C(=O)O)cc2c1[N+](=O)[O-]>[Cr](=O)([O-])[O-].[Cu+2]>COc1ccc2[nH]ccc2c1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f5f842a0be1424da1f9c5ea19160161 | COc1ccc2[nH]ccc2c1[N+](=O)[O-]>>O=[N+]([O-])c1c(O)ccc2[nH]ccc12 | B(Br)(Br)Br.COC=1C(=C2C=CNC2=CC1)[N+](=O)[O-]>>OC=1C(=C2C=CNC2=CC1)[N+](=O)[O-] | C[O:6][c:5]1[c:4]([N+:2](=[O:1])[O-:3])[c:13]2[c:9]([cH:8][cH:7]1)[nH:10][cH:11][cH:12]2>>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([OH:6])[cH:7][cH:8][c:9]2[nH:10][cH:11][cH:12][c:13]12 | COc1ccc2[nH]ccc2c1[N+](=O)[O-] | O=[N+]([O-])c1c(O)ccc2[nH]ccc12 | null | null | ClCCl.O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 67 | [{"value": 67.0, "product": "OC=1C(=C2C=CNC2=CC1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.0, "product": "OC=1C(=C2C=CNC2=CC1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 5-methoxy-4-nitroindole (110 mg, 0.57 mmol) in dichloromethane (12 ml) was cooled to −30° C. under an atmosphere of nitrogen. Boron tribromide (0.74 ml of a 1M solution in dichloromethane, 0.74 mmol) was added dropwise then the mixture warmed to ambient temperature and stirred for 1 hour. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | ClCCl.O | null | 1 | COc1ccc2[nH]ccc2c1[N+](=O)[O-]>ClCCl.O>O=[N+]([O-])c1c(O)ccc2[nH]ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52ecf86f5b8543e4b0f31151b76f850e | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cnc2[nH]ccc2c1>>COc1cc2c(Oc3cnc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCCC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.OC=1C=C2C(=NC1)NC=C2.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C(=NC1)NC=C2 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]3)[cH:21][c:20]2[n:19][cH:18][n:17]1.[OH:7][c:8]1[cH:9][n:10][c:11]2[nH:12][cH:13][cH:14][c:15]2[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][n:10][c:11]4[nH:12][cH:13][cH:14][c:1... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cnc2[nH]ccc2c1 | COc1cc2c(Oc3cnc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCCC1 | null | null | ClCCl.CO.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2cnc3[nH]ccc3c2)c2ccc(OCCCN3CCCCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13](-[OH;D1;+0:14]):[c:15]>>[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13](-[O;H0;D2;+0:14]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:15] | 20 | [{"value": 20.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C(=NC1)NC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.7, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C(=NC1)NC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 6 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (227 mg, 0.68 mmol), (prepared as described for the starting material in Example 67), 5-hydroxy-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.75 mmol), (prepared as described for the starting material in Example 182), and potassium carbonate (350 mg, 2.5 mmol) i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1cnc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | ClCCl.CO.CN(C)C=O | 95 | 6 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cnc2[nH]ccc2c1>ClCCl.CO.CN(C)C=O>COc1cc2c(Oc3cnc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fb000c2447784f589143e866bd9835aa | BrCCCBr.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCCBr | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC.C([O-])([O-])=O.[K+].[K+].BrCCCBr>>BrCCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC | Br[CH2:24][CH2:25][CH2:26][Br:27].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[OH:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH... | BrCCCBr.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCCBr | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:9] | 66 | [{"value": 66.0, "product": "BrCCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.7, "product": "BrCCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of 7-hydroxy-4-(1H-indol-5-yloxy)-6-methoxyquinazoline (1 g, 3.2 mmol), (prepared as described for the starting material in Example 107), in DMF (50 ml) was added powdered potassium carbonate (1.32 g, 9.6 mmol) and 1,3-dibromopropane (6.43 g, 32 mmol). The reaction was heated at 50° C. for 2 hours. The in... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | HBr | CN(C)C=O | 50 | null | BrCCCBr.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCCBr |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-091fd8723b8d47c0be67dca1b6ab457d | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2C)cc1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@@H]1CCC(=O)N1C | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.C([O-])([O-])=O.[K+].[K+].C1(=CC=C(C=C1)S(=O)(=O)C[C@@H]1CCC(N1C)=O)C>>COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1CCC(N1C)=O)OC=1C=C2C=C(NC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].Cc1ccc(S(=O)(=O)[CH2:25][C@@H:26]2[CH2:27][CH2:28][C:29](=[O:30])[N:31]2[CH3:32])cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2C)cc1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@@H]1CCC(=O)N1C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | O=C1CC[C@@H](COc2ccc3c(Oc4ccc5[nH]ccc5c4)ncnc3c2)N1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4](-[C;D1;H3:5])-[C:6]=[O;D1;H0:7]):c:c:1.[#7;a:8]:[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7;a:8]:[c:9]:[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4](-[C;D1;H3:5])-[C:6]=[O;D1;H0:7]):[c:13] | 33 | [{"value": 33.0, "product": "COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1CCC(N1C)=O)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.0, "product": "COC=1C=C2C(=NC=NC2=CC1OC[C@@H]1CCC(N1C)=O)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | To a solution of 7-hydroxy-6-methoxy-4-(2-methyl-1H-indol-5-yloxy)quinazoline (225 ml, 0.7 mmol), (prepared as described in Example 49), in DMF was added powdered potassium carbonate (290 mg, 2.1 mmol) and (5S)-5-(p-toluenesulphonylmethyl)-1-methyl-2-pyrrolidinone (340 mg, 1.2 mmol). The reaction was then heated at 95°... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | TsOH.HO- | CN(C)C=O | 95 | null | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2C)cc1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@@H]1CCC(=O)N1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3e589ae133f241e1a9ea020855ba8f22 | CI.Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2)cc1>>Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2C)cc1 | C1(=CC=C(C=C1)S(=O)(=O)C[C@@H]1CCC(N1)=O)C.C(C)(C)[N-]C(C)C.[Li+].CI>>C1(=CC=C(C=C1)S(=O)(=O)C[C@@H]1CCC(N1C)=O)C | I[CH3:16].[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[CH2:9][C@@H:10]2[CH2:11][CH2:12][C:13](=[O:14])[NH:15]2)[cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[CH2:9][C@@H:10]2[CH2:11][CH2:12][C:13](=[O:14])[N:15]2[CH3:16])[cH:17][cH:18]1 | CI.Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2)cc1 | Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2C)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 690e4b0724ae1dabd29a2644ea50ad8e32ff966e664aef6e23814fa90ed6067d | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | O=C1CC[C@@H](CS(=O)(=O)c2ccccc2)N1 | I-[CH3;D1;+0:1].[C:2]-[C:3]1-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-1>>[C:2]-[C:3]1-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8]-1-[CH3;D1;+0:1] | 40 | [{"value": 40.0, "product": "C1(=CC=C(C=C1)S(=O)(=O)C[C@@H]1CCC(N1C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | null | null | (5S)-5-(p-Toluenesulphonylmethyl)-2-pyrrolidinone (0.8 g, 3 mmol) was dissolved in dry THF and cooled to −70° C. Lithium diisopropylamide was slowly added and the reaction stirred for 20 minutes before addition of methyl iodide (2 ml, excess). The reaction was allowed to warm to ambient temperature for over 2 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HI | C1CCOC1 | -70 | null | CI.Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2)cc1>C1CCOC1>Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ccca3779f0a24329bf4eb55bf6dab69f | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2)cc1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CCC(=O)N1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC.C([O-])([O-])=O.C1(=CC=C(C=C1)S(=O)(=O)C[C@@H]1CCC(N1)=O)C>>N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1CCC(N1)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[OH:23].Cc1ccc(S(=O)(=O)[CH2:24][C@@H:25]2[CH2:26][CH2:27][C:28](=[O:29])[NH:30]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][... | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2)cc1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CCC(=O)N1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | O=C1CC[C@@H](COc2ccc3c(Oc4ccc5[nH]ccc5c4)ncnc3c2)N1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4]-[C:5]=[O;D1;H0:6]):c:c:1.[#7;a:7]:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4]-[C:5]=[O;D1;H0:6]):[c:12] | 31 | [{"value": 31.0, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1CCC(N1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.4, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@@H]1CCC(N1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of 7-hydroxy-4-(l H-indol-5-yloxy)-6-methoxyquinazoline (600 mg, 1.95 mmol), (prepared as described for the starting material in Example 107), in DMF (20 ml) was added powdered potassuim carbonate (540 mg, 3.9 mmol) and (5S)-5-(p-toluene-sulphonylmethyl)-2-pyrrolidinone (580 mg, 2.16 mmol). The reaction w... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CCNC1 | TsOH.HO- | CN(C)C=O | 100 | null | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@@H]2CCC(=O)N2)cc1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@@H]1CCC(=O)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7539d0aa4a264d3aae2d635fb64cb2b5 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@H]2CCC(=O)N2)cc1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CCC(=O)N1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC.C([O-])([O-])=O.C1(=CC=C(C=C1)S(=O)(=O)C[C@H]1CCC(N1)=O)C>>N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@H]1CCC(N1)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[OH:23].Cc1ccc(S(=O)(=O)[CH2:24][C@H:25]2[CH2:26][CH2:27][C:28](=[O:29])[NH:30]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c... | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@H]2CCC(=O)N2)cc1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CCC(=O)N1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | O=C1CC[C@H](COc2ccc3c(Oc4ccc5[nH]ccc5c4)ncnc3c2)N1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4]-[C:5]=[O;D1;H0:6]):c:c:1.[#7;a:7]:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4]-[C:5]=[O;D1;H0:6]):[c:12] | 6.7 | [{"value": 6.5, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@H]1CCC(N1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.7, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OC[C@H]1CCC(N1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of 7-hydroxy-4-(1H-indol-5-yloxy)-6-methoxyquinazoline (800 mg, 2.6 mmol), (prepared as described for the starting material in Example 107), in DMF (20 ml) was added powdered potassuim carbonate (1.08 g, 7.8 mmol) and (5R)-5-(p-toluenesulphonylmethyl)-2-pyrrolidinone (1.13 g, 4.2 mmol). The reaction was t... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CCNC1 | TsOH.HO- | CN(C)C=O | 90 | null | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@H]2CCC(=O)N2)cc1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC[C@H]1CCC(=O)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f5c5f32b27054ef198d09aaf03cb0ca3 | Cc1ccc(S(=O)(=O)Cl)cc1.O=C1CC[C@H](CO)N1>>Cc1ccc(S(=O)(=O)C[C@H]2CCC(=O)N2)cc1 | OC[C@H]1CCC(N1)=O.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>C1(=CC=C(C=C1)S(=O)(=O)C[C@H]1CCC(N1)=O)C | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]1)(=[O:7])=[O:8].O[CH2:9][C@H:10]1[CH2:11][CH2:12][C:13](=[O:14])[NH:15]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[CH2:9][C@H:10]2[CH2:11][CH2:12][C:13](=[O:14])[NH:15]2)[cH:16][cH:17]1 | Cc1ccc(S(=O)(=O)Cl)cc1.O=C1CC[C@H](CO)N1 | Cc1ccc(S(=O)(=O)C[C@H]2CCC(=O)N2)cc1 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Acylation | OtherReaction | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=C1CC[C@H](CS(=O)(=O)c2ccccc2)N1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].O-[CH2;D2;+0:7]-[C:8](-[C:9])-[#7:10]-[C:11]=[O;D1;H0:12]>>[C:9]-[C:8](-[CH2;D2;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[#7:10]-[C:11]=[O;D1;H0:12] | 94.6 | [{"value": 89.0, "product": "C1(=CC=C(C=C1)S(=O)(=O)C[C@H]1CCC(N1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.6, "product": "C1(=CC=C(C=C1)S(=O)(=O)C[C@H]1CCC(N1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of (5R)-5-hydroxymethyl-2-pyrrolidinone (5.0 g, 43 mmol) in methylene chloride (100 ml) was added 4-dimethylaminopyridine (15.7 g, 129 mmol) and p-toluenesulphonyl chloride (9.0 g, 47 mmol). The reaction was stirred at ambient temperature for 16 hours. The reaction was then washed with 1M hydrochloric aci... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.C1CCNC1 | HCl | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | 16 | Cc1ccc(S(=O)(=O)Cl)cc1.O=C1CC[C@H](CO)N1>CN(C1=CC=NC=C1)C.C(Cl)Cl>Cc1ccc(S(=O)(=O)C[C@H]2CCC(=O)N2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c6b1ca87ff546b38b050ef8144bce4d | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@H]2CCC(=O)N2)cc1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CCC(=O)N1 | C1(=CC=C(C=C1)S(=O)(=O)C[C@H]1CCC(N1)=O)C.C1(=CC=C(C=C1)S(=O)(=O)C[C@H]1CCC(N1)=O)C.CCOCC.C([O-])([O-])=O.[K+].[K+].CCOCC.OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC>>COC=1C=C2C(=NC=NC2=CC1OC[C@H]1CCC(N1)=O)OC=1C=C2C=C(NC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].Cc1ccc(S(=O)(=O)[CH2:25][C@H:26]2[CH2:27][CH2:28][C:29](=[O:30])[NH:31]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13](... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@H]2CCC(=O)N2)cc1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CCC(=O)N1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | O=C1CC[C@H](COc2ccc3c(Oc4ccc5[nH]ccc5c4)ncnc3c2)N1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4]-[C:5]=[O;D1;H0:6]):c:c:1.[#7;a:7]:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7:4]-[C:5]=[O;D1;H0:6]):[c:12] | 0.3 | [{"value": 0.3, "product": "COC=1C=C2C(=NC=NC2=CC1OC[C@H]1CCC(N1)=O)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a suspension of 7-hydroxy-6-methoxy-4-(2-methyl-1H-indol-5-yloxy)quinazoline (1.36 g, 4.24 mmol), (prepared as described in Example 49), in DMF (70 ml), was added potassium carbonate (2.34 g, 17.0 mmol, 4eq.) followed by (5R)-5-(p-toluenesulphonylmethyl)-2-pyrrolidinone (1.25 g, 4.66 mmol, 1.1 eq.), (prepared as des... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CCNC1 | TsOH.HO- | CN(C)C=O | null | 4 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)C[C@H]2CCC(=O)N2)cc1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC[C@H]1CCC(=O)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7fa8fae7a4d149c49ffe087d086ce4ad | COc1cc2c(Cl)ncnc2cc1OCCC1CCN(C)CC1.Cc1cc2c(F)c(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCC1CCN(CC1)C.FC1=C2C=C(NC2=CC=C1O)C.C([O-])([O-])=O.[K+].[K+]>>FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCC1CCN(CC1)C)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][CH:28]3[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][c:13]([CH3:14])[cH:15][c:16]2[c:17]1[F:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][... | COc1cc2c(Cl)ncnc2cc1OCCC1CCN(C)CC1.Cc1cc2c(F)c(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCC1CCN(C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCC3CCNCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 62.5 | [{"value": 62.0, "product": "FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCC1CCN(CC1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.5, "product": "FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCC1CCN(CC1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 3 | HOUR | A solution of 4-chloro-6-methoxy-7-(2-(1-methylpiperidin-4-yl)ethoxy)quinazoline (1.22 g, 3.65 mmol), (prepared as described for the starting material in Example 241), 4-fluoro-5-hydroxy-2-methylindole (723 mg, 4.38 mmol), (prepared as described for the starting material in Example 237), in DMF (20 ml) containing potas... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CN(C)C=O | 95 | 3 | COc1cc2c(Cl)ncnc2cc1OCCC1CCN(C)CC1.Cc1cc2c(F)c(O)ccc2[nH]1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2efe1d4bfcb84a37bc4f0adf50145c88 | COc1cc2ncnc(Cl)c2cc1OC.Cc1nc2ccc(O)cc2[nH]1>>COc1cc2ncnc(Oc3ccc4nc(C)[nH]c4c3)c2cc1OC | [H-].[Na+].OC1=CC2=C(N=C(N2)C)C=C1.ClC1=NC=NC2=CC(=C(C=C12)OC)OC>>COC=1C=C2C(=NC=NC2=CC1OC)OC=1C=CC2=C(NC(=N2)C)C1 | Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH3:25])[cH:22][c:21]21.[OH:10][c:11]1[cH:12][cH:13][c:14]2[n:15][c:16]([CH3:17])[nH:18][c:19]2[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([O:10][c:11]3[cH:12][cH:13][c:14]4[n:15][c:16]([CH3:17])[nH:18][c:19]4[cH:20]3)[c:21]2[cH:22][... | COc1cc2ncnc(Cl)c2cc1OC.Cc1nc2ccc(O)cc2[nH]1 | COc1cc2ncnc(Oc3ccc4nc(C)[nH]c4c3)c2cc1OC | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2c(Oc3ccc4nc[nH]c4c3)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 48.4 | [{"value": 48.0, "product": "COC=1C=C2C(=NC=NC2=CC1OC)OC=1C=CC2=C(NC(=N2)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.4, "product": "COC=1C=C2C(=NC=NC2=CC1OC)OC=1C=CC2=C(NC(=N2)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Sodium hydride (71 mg, 1.8 mmol) was added to 5-hydroxy-2-methylbenzimidazole (204 mg, 0.89 mmol) in anhydrous DMF (2.5 ml) under an argon atmosphere. The mixture was stirred at ambient temperature for 10 minutes. 4-Chloro-6,7-dimethoxyquinazoline (200 mg, 0.89 mmol) was added and the reaction mixture stirred at 95° C.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2[nH]cnc2c1 | HCl | O.CN(C)C=O | null | 0.166667 | COc1cc2ncnc(Cl)c2cc1OC.Cc1nc2ccc(O)cc2[nH]1>O.CN(C)C=O>COc1cc2ncnc(Oc3ccc4nc(C)[nH]c4c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff90139e3e3341ec989ad20a872b2f67 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2cncnc2c1>>COc1cc2c(Oc3ccc4cncnc4c3)ncnc2cc1OCCCN1CCOCC1 | [Cl-].[NH4+].OC1=CC=C2C=NC=NC2=C1.C([O-])([O-])=O.[K+].[K+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C=NC=NC2=C1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][n:13][cH:14][n:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][n:13][cH:14]... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2cncnc2c1 | COc1cc2c(Oc3ccc4cncnc4c3)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ncc2ccc(Oc3ncnc4cc(OCCCN5CCOCC5)ccc34)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 83.1 | [{"value": 83.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C=NC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C=NC=NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 7-Hydroxyquinazoline (87 mg, 0.6 mmol) and potassium carbonate (110 mg, 0.8 mmol) were added to 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (180 mg, 0.53 mmol), prepared as described for the starting material in Example 1), in suspension in DMF (3 ml) under an argon atmosphere. The reaction mixture was heated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O.C(C)(=O)OCC | 100 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2cncnc2c1>CN(C)C=O.C(C)(=O)OCC>COc1cc2c(Oc3ccc4cncnc4c3)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ca3a6afb71df4486a504fc70cf734f4e | COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1O.Cc1ncsc1CCO>>COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1OCCc1scnc1C | OC1=C(C=C2C(=NC=NC2=C1)NC1=CC=C2C=CNC2=C1)OC.OCCC1=C(N=CS1)C>>COC=1C=C2C(=NC=NC2=CC1OCCC1=C(N=CS1)C)NC1=CC=C2C=CNC2=C1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][cH:13][nH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[OH:23].O[CH2:24][CH2:25][c:26]1[s:27][cH:28][n:29][c:30]1[CH3:31]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][cH:13][nH:14][c:15]4[cH:16]3)[n... | COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1O.Cc1ncsc1CCO | COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1OCCc1scnc1C | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1nc(Nc2ccc3cc[nH]c3c2)c2ccc(OCCc3cncs3)cc2n1 | O-[CH2;D2;+0:1]-[C:2]-[c:3](:[#16;a:4]):[c:5]:[#7;a:6].[#7;a:7]:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#16;a:4]:[c:3](-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:10](:[c:12]):[c:9]:[c:8]:[#7;a:7]):[c:5]:[#7;a:6] | 34 | [{"value": 34.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCC1=C(N=CS1)C)NC1=CC=C2C=CNC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCC1=C(N=CS1)C)NC1=CC=C2C=CNC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 201, 7-hydroxy-4-(indol-6-ylamino)-6-methoxyquinazoline (98 mg, 0.32 mmol), (prepared as described for the starting material in Example 217), was reacted with 5-(2-hydroxyethyl)-4-methylthiazole (69 mg, 0.48 mmol) to give 6-methoxy-4-(indol-6-ylamino)-7-(2-(4-me... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1cscn1 | HO- | null | null | null | COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1O.Cc1ncsc1CCO>>COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1OCCc1scnc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-11a86478d050482fabbb54c90edeca53 | COCCOCCOCCO.O=C(Cl)C1CC1>>COCCOCCOCCOC(=O)C1CC1 | COCCOCCOCCO.C(C)N(CC)CC.C1(CC1)C(=O)Cl>>C1(CC1)C(=O)OCCOCCOCCOC | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11].Cl[C:12](=[O:13])[CH:14]1[CH2:15][CH2:16]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][C:12](=[O:13])[CH:14]1[CH2:15][CH2:16]1 | COCCOCCOCCO.O=C(Cl)C1CC1 | COCCOCCOCCOC(=O)C1CC1 | null | null | ClCCl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1 | null | [] | 0 | CELSIUS | null | null | Triethylene glycol monomethyl ether (1.1 eq, 5.26 mmol, 0.84 ml) and triethylamine (1.1 eq, 5.26 mmol, 0.73 ml) were taken in a 10 ml round bottom flask and dichloromethane (3 ml) was added. This mixture was cooled to 0° C. and then cyclopropanecarbonyl chloride (4.78 mmol, 0.5 g, 0.43 ml) was added in a dropwise fashi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | C1CC1 | HCl | ClCCl | 0 | null | COCCOCCOCCO.O=C(Cl)C1CC1>ClCCl>COCCOCCOCCOC(=O)C1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ba2ecbc665a4759aaf5991b901205ae | O=C(O)C1(c2ccccc2)CC1.O=S(Cl)Cl>>O=C(Cl)C1(c2ccccc2)CC1 | C1(=CC=CC=C1)C1(CC1)C(=O)O.S(=O)(Cl)Cl>>C1(=CC=CC=C1)C1(CC1)C(=O)Cl | O[C:2](=[O:1])[C:4]1([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12]1.O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[C:4]1([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12]1 | O=C(O)C1(c2ccccc2)CC1.O=S(Cl)Cl | O=C(Cl)C1(c2ccccc2)CC1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccc(C2CC2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]1(-[c:5])-[C:6]-[C:7]-1>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]1(-[c:5])-[C:6]-[C:7]-1 | null | [] | 80 | CELSIUS | null | null | 1-Phenyl-cyclopropanecarboxylic acid (0.5 g, 3.1 mmol), was dissolved in thionyl chloride (10 eq, 0.031 mol, 3.68 g, 2.3 ml), and refluxed at 80° C. for 1.5 hours. Then excess of thionyl chloride was evaporated on the rotary evaporator which yielded a dark-yellowish liquid (1-phenyl-cyclopropanecarbonyl chloride A), wh... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1.C1CC1 | HCl | null | 80 | null | O=C(O)C1(c2ccccc2)CC1.O=S(Cl)Cl>>O=C(Cl)C1(c2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-48a20edaaea94c4a9632062988784803 | CC(C)(C)OC(=O)Nc1cccc(O)c1.N#Cc1ccc(CCO)cc1>>CC(C)(C)OC(=O)Nc1cccc(OCCc2ccc(C#N)cc2)c1 | C(C)(C)(C)OC(=O)NC1=CC(=CC=C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(#N)C1=CC=C(C=C1)CCO.CCOC(=O)/N=N/C(=O)OCC>>C(C)(C)(C)OC(=O)NC1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([OH:14])[cH:25]1.O[CH2:15][CH2:16][c:17]1[cH:18][cH:19][c:20]([C:21]#[N:22])[cH:23][cH:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([O:14][CH2:15][CH2:16][c:17]2[cH:18][cH:19][c:20]([... | CC(C)(C)OC(=O)Nc1cccc(O)c1.N#Cc1ccc(CCO)cc1 | CC(C)(C)OC(=O)Nc1cccc(OCCc2ccc(C#N)cc2)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(CCOc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[c:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[c:6]:[c:5](-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[c:3]):[c:7] | 44.3 | [{"value": 44.0, "product": "C(C)(C)(C)OC(=O)NC1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.3, "product": "C(C)(C)(C)OC(=O)NC1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of t-butyloxycarbonylamino-3-hydroxybenzene (418.5 mg; 2 mmol; from step (i) above), triphenylphosphine (629.5 mg; 2.4 mmol) and 2-(4-cyanophenyl)ethanol (353.2 mg; 2.4 mmol) in THF (50 mL), under an atmosphere of nitrogen, was added diethylazodicarboxylate (518 mg; 3 mmol) and the mixture was stirred for... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | null | CC(C)(C)OC(=O)Nc1cccc(O)c1.N#Cc1ccc(CCO)cc1>C1CCOC1>CC(C)(C)OC(=O)Nc1cccc(OCCc2ccc(C#N)cc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d2d5645ed5dc43bbb38599504ef9cde2 | N#Cc1ccc(CCOc2cccc(N)c2)cc1.O=S(=O)(Cl)c1ccccc1>>N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1 | O.NC1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N.Cl.C1(=CC=CC=C1)S(=O)(=O)Cl>>C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)NS(=O)(=O)C1=CC=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([NH2:15])[cH:25]2)[cH:26][cH:27]1.Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]... | N#Cc1ccc(CCOc2cccc(N)c2)cc1.O=S(=O)(Cl)c1ccccc1 | N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1 | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1cccc(OCCc2ccccc2)c1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 87 | [{"value": 87.0, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)NS(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a cold (ice:water temperature) solution of amino-3-[2-(4-cyanophenyl)ethoxy]benzene×HCl (231 mg; 0.84 mmol; from step (iii) above) in pyridine (2 mL) was added benzenesulfonyl chloride (119 μL; 0.93 mmol) and the mixture was allowed to reach room temperature and stirred for three days. The pyridine was removed by ev... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 72 | N#Cc1ccc(CCOc2cccc(N)c2)cc1.O=S(=O)(Cl)c1ccccc1>N1=CC=CC=C1>N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ced6ed214bda408e923e0ec52746946f | N#Cc1ccc(CCO)cc1.O=[N+]([O-])c1cccc(O)c1>>N#Cc1ccc(CCOc2cccc([N+](=O)[O-])c2)cc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)/N=N/C(=O)OCC.[N+](=O)([O-])C=1C=C(C=CC1)O.C(#N)C1=CC=C(C=C1)CCO>>[N+](=O)([O-])C1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N | O[CH2:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:20][cH:19]1.[OH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]2)[cH:19][cH:20]1 | N#Cc1ccc(CCO)cc1.O=[N+]([O-])c1cccc(O)c1 | N#Cc1ccc(CCOc2cccc([N+](=O)[O-])c2)cc1 | null | null | O.C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(CCOc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[c:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[c:6]:[c:5](-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[c:3]):[c:7] | 32 | [{"value": 32.0, "product": "[N+](=O)([O-])C1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.9, "product": "[N+](=O)([O-])C1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Triphenylphosphine (11.3 g; 43.1 mmol) and diethylazodicarboxylate (7.5 g; 43 mmol) were dissolved in THF (250 mL) under nitrogen at 0° C. After 5 minutes, 3-nitrophenol (5.00 g; 35.9 mmol) and 2-(4-cyanophenyl)ethanol (6.3 g; 43 mmol) were added. The cooling bath was removed and the mixture stirred for 2 days at room ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HO- | O.C1CCOC1 | null | 0.083333 | N#Cc1ccc(CCO)cc1.O=[N+]([O-])c1cccc(O)c1>O.C1CCOC1>N#Cc1ccc(CCOc2cccc([N+](=O)[O-])c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b973abd038d94f0bb0ea1d8a4c1700bc | N#Cc1ccc(CCOc2cccc([N+](=O)[O-])c2)cc1>>N#Cc1ccc(CCOc2cccc(N)c2)cc1 | [N+](=O)([O-])C1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N.[NH4+].[Cl-]>>NC1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N | O=[N+:15]([O-])[c:14]1[cH:13][cH:12][cH:11][c:10]([O:9][CH2:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18][cH:17]2)[cH:16]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([NH2:15])[cH:16]2)[cH:17][cH:18]1 | N#Cc1ccc(CCOc2cccc([N+](=O)[O-])c2)cc1 | N#Cc1ccc(CCOc2cccc(N)c2)cc1 | null | [Fe] | O.CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCOc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 85 | [{"value": 85.0, "product": "NC1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.7, "product": "NC1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Nitro-3-[2-(4-cyanophenyl)ethoxy]benzene (3.0 g; 11.2 mmol; from step (i) above) and NH4Cl (2.9 g; 55 mmol) were dissolved in a mixture of EtOH (40 mL) and H2O (10 mL) and heated to reflux. Iron powder (3.0 g; 55 mmol) was added and heating was continued for 1 hour. The mixture was filtered, concentrated in vacuo and p... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Fe].O.CCO | null | 1 | N#Cc1ccc(CCOc2cccc([N+](=O)[O-])c2)cc1>[Fe].O.CCO>N#Cc1ccc(CCOc2cccc(N)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a07f8c5795414f378ef03facfd4bc52e | N#Cc1ccc(CCOc2cccc(N)c2)cc1.O=S(=O)(Cl)c1ccccc1Cl>>N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3Cl)c2)cc1 | N1=CC=CC=C1.NC1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N.ClC1=C(C=CC=C1)S(=O)(=O)Cl>>C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)NS(=O)(=O)C1=C(C=CC=C1)Cl | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([NH2:15])[cH:26]2)[cH:27][cH:28]1.Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[Cl:25]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([NH:15][S:16](=[O:17])(=[O:18])... | N#Cc1ccc(CCOc2cccc(N)c2)cc1.O=S(=O)(Cl)c1ccccc1Cl | N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3Cl)c2)cc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1cccc(OCCc2ccccc2)c1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 36.6 | [{"value": 35.0, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)NS(=O)(=O)C1=C(C=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.6, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)NS(=O)(=O)C1=C(C=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Pyridine (0.255 mL; 3.15 mmol) was added to a stirred solution of amino-3-[2-(4-cyanophenyl)ethoxy]benzene (0.15 g; 0.629 mmol; from step (ii) above) and 2-chlorobenzenesulfonyl chloride (0.173 mL; 0.818 mmol) in CH2Cl2 (4 mL). After 45 minutes at room temperature the solvent was removed in vacuo. To remove traces of p... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | N#Cc1ccc(CCOc2cccc(N)c2)cc1.O=S(=O)(Cl)c1ccccc1Cl>C(Cl)Cl>N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3Cl)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2823d9a23038452eb6617bd6e117c0d9 | CC(C)(C)OC(=O)N=Cc1cc(N)ccc1CCOc1cccc([N+](=O)[O-])c1>>CC(C)(C)OC(=O)N=Cc1cc(N)ccc1CCOc1cccc(N)c1 | NC1=CC(=C(C=C1)CCOC=1C=C(C=CC1)[N+](=O)[O-])C=NC(=O)OC(C)(C)C>>NC1=CC(=CC=C1)OCCC1=C(C=C(C=C1)N)C=NC(=O)OC(C)(C)C | O=[N+:25]([O-])[c:24]1[cH:23][cH:22][cH:21][c:20]([O:19][CH2:18][CH2:17][c:16]2[c:10]([CH:9]=[N:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:11][c:12]([NH2:13])[cH:14][cH:15]2)[cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]=[CH:9][c:10]1[cH:11][c:12]([NH2:13])[cH:14][cH:15][c:16]1[CH2:17][CH2:... | CC(C)(C)OC(=O)N=Cc1cc(N)ccc1CCOc1cccc([N+](=O)[O-])c1 | CC(C)(C)OC(=O)N=Cc1cc(N)ccc1CCOc1cccc(N)c1 | null | [Pd] | CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCOc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 25 | MINUTE | A suspension of 3-[2-(4-amino{t-butoxycarbonylimino}methylphenyl)-ethoxy]nitrobenzene (1.47 g; 3.81 mmol; from step (iii) above) and Pd (0.236 g; 5% on charcoal) in EtOH (75 mL) was stirred under H2(g) (1 atm.) for 25 minutes. After filtration through Celite the solvent was evaporated. The residue was purified by prepa... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pd].CCO | null | 0.416667 | CC(C)(C)OC(=O)N=Cc1cc(N)ccc1CCOc1cccc([N+](=O)[O-])c1>[Pd].CCO>CC(C)(C)OC(=O)N=Cc1cc(N)ccc1CCOc1cccc(N)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d57a165596141cbaf972e1129adb4f6 | CC(C)(C)OC(=O)OC(C)(C)C.Cc1c(N)cccc1O>>Cc1c(O)cccc1NC(=O)OC(C)(C)C | NC=1C(=C(C=CC1)O)C.C(C)(C)(C)OC(OC(C)(C)C)=O>>C(C)(C)(C)OC(=O)NC=1C(=C(C=CC1)O)C | CC(C)(C)O[C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16].[CH3:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:8]1[NH2:9]>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:8]1[NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16] | CC(C)(C)OC(=O)OC(C)(C)C.Cc1c(N)cccc1O | Cc1c(O)cccc1NC(=O)OC(C)(C)C | null | null | C1CCOC1 | Protection | Boc amine protection of primary amine | f3c90cf52fa3def89ea52c9439021d67dcb4e78193592b513b9947b2ea03f400 | b95329d3f436e956daff6cdf06b1d304d2b6f26b5a9f436cd33b2f3a6d7b99d2 | c1ccccc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 69 | [{"value": 69.0, "product": "C(C)(C)(C)OC(=O)NC=1C(=C(C=CC1)O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Amino-2-methylphenol (2.0 g; 16 mmol) and di-t-butylcarbonate were dissolved in THF (20 mL) and refluxed overnight. Evaporation of the solvent followed by flash chromatography (SiO2; EtOAc 5–30% in isohexane) afforded 2.48 g (69%) of the sub-title compound.
Conditions: See reaction.notes.procedure_details.
Workup: re... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Primary amine.Boc.Boc | Carbamic ester | null | null | c1ccccc1 | HO- | C1CCOC1 | null | null | CC(C)(C)OC(=O)OC(C)(C)C.Cc1c(N)cccc1O>C1CCOC1>Cc1c(O)cccc1NC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6be99bc338074bd19cfef980b50197e0 | Cc1c(O)cccc1NC(=O)OC(C)(C)C.N#Cc1ccc(CCO)cc1>>Cc1c(NC(=O)OC(C)(C)C)cccc1OCCc1ccc(C#N)cc1 | C(#N)C1=CC=C(C=C1)CCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CCOC(=O)/N=N/C(=O)OCC.C(C)(C)(C)OC(=O)NC=1C(=C(C=CC1)O)C>>C(C)(C)(C)OC(=O)NC1=C(C(=CC=C1)OCCC1=CC=C(C=C1)C#N)C | O[c:15]1[c:2]([CH3:1])[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][cH:13][cH:14]1.[OH:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([C:23]#[N:24])[cH:25][cH:26]1>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][cH:13][cH:14][c:15]1[O:16][CH2:17][CH2:18][c:1... | Cc1c(O)cccc1NC(=O)OC(C)(C)C.N#Cc1ccc(CCO)cc1 | Cc1c(NC(=O)OC(C)(C)C)cccc1OCCc1ccc(C#N)cc1 | null | null | O.C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(CCOc2ccccc2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6] | 77 | [{"value": 77.0, "product": "C(C)(C)(C)OC(=O)NC1=C(C(=CC=C1)OCCC1=CC=C(C=C1)C#N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.2, "product": "C(C)(C)(C)OC(=O)NC1=C(C(=CC=C1)OCCC1=CC=C(C=C1)C#N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Triphenylphosphine (1.31 g, 13.5 mmol) and diethylazodicarboxylate (1.7 mL) were dissolved in THF (20 mL) under nitrogen. After 15 minutes 3-t-butoxycarbonylamino-2-methylphenol (2.48 g; 11.1 mmol; from step (i) above) dissolved in THF (20 mL) and 2-(4-cyanophenyl)ethanol (1.9 g, 13 mmol) were added. After 5 days at ro... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | O.C1CCOC1 | null | 0.5 | Cc1c(O)cccc1NC(=O)OC(C)(C)C.N#Cc1ccc(CCO)cc1>O.C1CCOC1>Cc1c(NC(=O)OC(C)(C)C)cccc1OCCc1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5072aaaf7af947d3ab046709fd2cf87e | Cc1c(NC(=O)OC(C)(C)C)cccc1OCCc1ccc(C#N)cc1>>Cc1c(N)cccc1OCCc1ccc(C#N)cc1 | C(C)(C)(C)OC(=O)NC1=C(C(=CC=C1)OCCC1=CC=C(C=C1)C#N)C>>NC1=C(C(=CC=C1)OCCC1=CC=C(C=C1)C#N)C | CC(C)(C)OC(=O)[NH:4][c:3]1[c:2]([CH3:1])[c:8]([O:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]2)[cH:7][cH:6][cH:5]1>>[CH3:1][c:2]1[c:3]([NH2:4])[cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]1 | Cc1c(NC(=O)OC(C)(C)C)cccc1OCCc1ccc(C#N)cc1 | Cc1c(N)cccc1OCCc1ccc(C#N)cc1 | null | null | Cl.CCOC(=O)C | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(CCOc2ccccc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 21.8 | [{"value": 19.0, "product": "NC1=C(C(=CC=C1)OCCC1=CC=C(C=C1)C#N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.8, "product": "NC1=C(C(=CC=C1)OCCC1=CC=C(C=C1)C#N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene (2.69 g, 7.64 mmol; from step (ii) above) were dissolved in EtOAc, pre-saturated with HCl(g), (150 mL) under nitrogen and stirred at room temperature overnight. After evaporation of the solvent the residue was partitioned between 10% aqueous HCl and EtOA... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | Cl.CCOC(=O)C | null | 8 | Cc1c(NC(=O)OC(C)(C)C)cccc1OCCc1ccc(C#N)cc1>Cl.CCOC(=O)C>Cc1c(N)cccc1OCCc1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e7aa3513f10e42e6a97b30503cbcad8b | Cc1c(N)cccc1OCCc1ccc(C#N)cc1.O=S(=O)(Cl)c1ccccc1>>Cc1c(NS(=O)(=O)c2ccccc2)cccc1OCCc1ccc(C#N)cc1 | C1(=CC=CC=C1)S(=O)(=O)Cl.NC1=C(C(=CC=C1)OCCC1=CC=C(C=C1)C#N)C>>C(#N)C1=CC=C(C=C1)CCOC=1C(=C(C=CC1)NS(=O)(=O)C1=CC=CC=C1)C | [CH3:1][c:2]1[c:3]([NH2:4])[cH:14][cH:15][cH:16][c:17]1[O:18][CH2:19][CH2:20][c:21]1[cH:22][cH:23][c:24]([C:25]#[N:26])[cH:27][cH:28]1.Cl[S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][c:2]1[c:3]([NH:4][S:5](=[O:6])(=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][cH:16][c:17]1[O:... | Cc1c(N)cccc1OCCc1ccc(C#N)cc1.O=S(=O)(Cl)c1ccccc1 | Cc1c(NS(=O)(=O)c2ccccc2)cccc1OCCc1ccc(C#N)cc1 | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1cccc(OCCc2ccccc2)c1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 72 | [{"value": 72.0, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C(=C(C=CC1)NS(=O)(=O)C1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.4, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C(=C(C=CC1)NS(=O)(=O)C1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Benzenesulfonyl chloride (0.24 mL; 1.9 mmol) was added to a stirred solution of amino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene (0.42 g ; 1.7 mmol; from step (iii) above) in dry pyridine (20 mL) under nitrogen. The reaction was left overnight at room temperature. After evaporation of the solvent the residue was parti... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 8 | Cc1c(N)cccc1OCCc1ccc(C#N)cc1.O=S(=O)(Cl)c1ccccc1>N1=CC=CC=C1>Cc1c(NS(=O)(=O)c2ccccc2)cccc1OCCc1ccc(C#N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c02799cee8c540e594b36dee65c595a6 | Cc1ccc(O)cc1[N+](=O)[O-].N#Cc1ccc(CCO)cc1>>Cc1ccc(OCCc2ccc(C#N)cc2)cc1[N+](=O)[O-] | CC1=C(C=C(C=C1)O)[N+](=O)[O-].C(#N)C1=CC=C(C=C1)CCO.CCOC(=O)/N=N/C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(#N)C1=CC=C(C=C1)CCOC1=CC(=C(C=C1)C)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:17][c:18]1[N+:19](=[O:20])[O-:21].O[CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[cH:17][c:18]1[N+:19](=[O:20])[O-:21] | Cc1ccc(O)cc1[N+](=O)[O-].N#Cc1ccc(CCO)cc1 | Cc1ccc(OCCc2ccc(C#N)cc2)cc1[N+](=O)[O-] | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(CCOc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[c:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[c:6]:[c:5](-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[c:3]):[c:7] | null | [] | null | null | 8 | HOUR | 4-Methyl-3-nitrophenol (0.765 g; 5.0 mmol), 2-(4-cyanophenyl)ethanol (0.735 g; 5.0 mmol) and diethylazodicarboxylate (0.87 g; 5.0 mmol) were dissolved in THF (20 mL). Triphenylphosphine (1.31 g; 5.0 mmol), dissolved in THF (5 mL), was added and the solution stirred overnight. Evaporation in vacuo and the addition of di... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 8 | Cc1ccc(O)cc1[N+](=O)[O-].N#Cc1ccc(CCO)cc1>C1CCOC1>Cc1ccc(OCCc2ccc(C#N)cc2)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-97967a60623a4f7b94a70e73c45afd80 | Cc1ccc(OCCc2ccc(C#N)cc2)cc1[N+](=O)[O-]>>Cc1ccc(OCCc2ccc(C#N)cc2)cc1N | [BH4-].[Na+].C(#N)C1=CC=C(C=C1)CCOC1=CC(=C(C=C1)C)[N+](=O)[O-].CCOC(=O)C>>NC1=C(C=CC(=C1)OCCC1=CC=C(C=C1)C#N)C | O=[N+:19]([O-])[c:18]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[cH:17][c:18]1[NH2:19] | Cc1ccc(OCCc2ccc(C#N)cc2)cc1[N+](=O)[O-] | Cc1ccc(OCCc2ccc(C#N)cc2)cc1N | null | S(=O)(=O)([O-])[O-].[Cu+2] | CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCOc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 26 | [{"value": 26.0, "product": "NC1=C(C=CC(=C1)OCCC1=CC=C(C=C1)C#N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.0, "product": "NC1=C(C=CC(=C1)OCCC1=CC=C(C=C1)C#N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Sodium borohydride (0.127 g; 3.35 mmol) was added in portions to a cold suspension (ice:water temperature) of [2-(4-cyanophenyl)ethoxy]-4-methyl-3-nitrobenzene (0.19 g; 0.67 mmol; from step (i) above) and aqueous copper sulfate (1.34 mL; 1 M; 1.34 mmol) in EtOH (5 mL) over five minutes. The temperature was allowed to r... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | S(=O)(=O)([O-])[O-].[Cu+2].CCO | null | 0.5 | Cc1ccc(OCCc2ccc(C#N)cc2)cc1[N+](=O)[O-]>S(=O)(=O)([O-])[O-].[Cu+2].CCO>Cc1ccc(OCCc2ccc(C#N)cc2)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b6cc1b52f1bd4a2782218856645c0bae | Cc1ccc(OCCc2ccc(C#N)cc2)cc1N.O=S(=O)(Cl)c1ccccc1>>Cc1ccc(OCCc2ccc(C#N)cc2)cc1NS(=O)(=O)c1ccccc1 | C1(=CC=CC=C1)S(=O)(=O)Cl.NC1=C(C=CC(=C1)OCCC1=CC=C(C=C1)C#N)C.C(=O)(O)[O-].[Na+]>>C(#N)C1=CC=C(C=C1)CCOC=1C=CC(=C(C1)NS(=O)(=O)C1=CC=CC=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[cH:17][c:18]1[NH2:19].Cl[S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[cH:17][c:18... | Cc1ccc(OCCc2ccc(C#N)cc2)cc1N.O=S(=O)(Cl)c1ccccc1 | Cc1ccc(OCCc2ccc(C#N)cc2)cc1NS(=O)(=O)c1ccccc1 | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1cccc(OCCc2ccccc2)c1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 100 | [{"value": 100.0, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=CC(=C(C1)NS(=O)(=O)C1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.7, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=CC(=C(C1)NS(=O)(=O)C1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Benzenesulfonyl chloride (22 μL; 0.17 mmol) was added to a cold solution (ice:water temperature) of amino-5-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene (0.041 g; 0.16 mmol; from step (ii) above) in pyridine (4 mL) The reaction flask was left overnight in a refrigerator. NaHCO3/aq (sat.) was added and the solution extract... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 8 | Cc1ccc(OCCc2ccc(C#N)cc2)cc1N.O=S(=O)(Cl)c1ccccc1>N1=CC=CC=C1>Cc1ccc(OCCc2ccc(C#N)cc2)cc1NS(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1111fc7a8f8d49969750bc356e38cf41 | Cc1cc(NC(=O)OC(C)(C)C)cc(OCCc2ccc(C#N)cc2)c1>>Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1 | C(C)(C)(C)OC(=O)NC1=CC(=CC(=C1)C)OCCC1=CC=C(C=C1)C#N>>NC1=CC(=CC(=C1)C)OCCC1=CC=C(C=C1)C#N | CC(C)(C)OC(=O)[NH:5][c:4]1[cH:3][c:2]([CH3:1])[cH:19][c:7]([O:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]2)[cH:6]1>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:6][c:7]([O:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]2)[cH:19]1 | Cc1cc(NC(=O)OC(C)(C)C)cc(OCCc2ccc(C#N)cc2)c1 | Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1 | null | null | C(Cl)Cl.FC(C(=O)O)(F)F | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(CCOc2ccccc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | t-Butyloxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-5-methylbenzene (1.55 g; 4.4 mmol; from step (ii) above) was stirred in a mixture of trifluoroacetic acid (10 mL) and methylene chloride (10 mL) for 3 hours. The solvent was removed in vacuo. The residue was dissolved in EtOAc (50 mL), washed with Na2CO3/aq (sat.) and... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.FC(C(=O)O)(F)F | null | null | Cc1cc(NC(=O)OC(C)(C)C)cc(OCCc2ccc(C#N)cc2)c1>C(Cl)Cl.FC(C(=O)O)(F)F>Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d2f2a62a9a7f4a4bbe47ffbd989c1976 | Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1.O=S(=O)(Cl)c1ccccc1>>Cc1cc(NS(=O)(=O)c2ccccc2)cc(OCCc2ccc(C#N)cc2)c1 | C(=O)(O)[O-].[Na+].NC1=CC(=CC(=C1)C)OCCC1=CC=C(C=C1)C#N.C1(=CC=CC=C1)S(=O)(=O)Cl>>C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)NS(=O)(=O)C1=CC=CC=C1 | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:15][c:16]([O:17][CH2:18][CH2:19][c:20]2[cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26][cH:27]2)[cH:28]1.Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]([O:17][C... | Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1.O=S(=O)(Cl)c1ccccc1 | Cc1cc(NS(=O)(=O)c2ccccc2)cc(OCCc2ccc(C#N)cc2)c1 | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1cccc(OCCc2ccccc2)c1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 97 | [{"value": 97.0, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)NS(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.8, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)NS(=O)(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a cold solution (ice:water temperature) of amino-[3-2-(4-cyanophenyl)ethoxy]-5-methylbenzene (0.13 g; 0.50 mmol; from step (iii) above) in pyridine (5 mL) was added benzenesulfonyl chloride (71 μL; 0.55 mmol). After 2 hours stirring, NaHCO3/aq (sat.) was added, and the solution extracted with EtOAc. The combined org... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 2 | Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1.O=S(=O)(Cl)c1ccccc1>N1=CC=CC=C1>Cc1cc(NS(=O)(=O)c2ccccc2)cc(OCCc2ccc(C#N)cc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-737deac25e6e41d4beb1f59e139c081e | Cc1ccc(S(=O)(=O)Cl)cc1.N#Cc1ccc(CCO)cc1>>Cc1ccc(S(=O)(=O)OCCc2ccc(C#N)cc2)cc1 | C(#N)C1=CC=C(C=C1)CCO.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.C(#N)C1=CC=C(C=C1)CCO>>C(#N)C1=CC=C(C=C1)CCOS(=O)(=O)C1=CC=C(C=C1)C | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]1)(=[O:7])=[O:8].[OH:9][CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([C:16]#[N:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | Cc1ccc(S(=O)(=O)Cl)cc1.N#Cc1ccc(CCO)cc1 | Cc1ccc(S(=O)(=O)OCCc2ccc(C#N)cc2)cc1 | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=S(=O)(OCCc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 67 | [{"value": 66.0, "product": "C(#N)C1=CC=C(C=C1)CCOS(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.0, "product": "C(#N)C1=CC=C(C=C1)CCOS(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(4-Cyanophenyl)ethanol (1.46 g; 9.9 mmol) and 4-toluenesulfonyl chloride (1.9 g; 10 mmol) were stirred in pyridine (20 mL) at 5° C. for 3 hours. Work-up was performed by removing the solvent, addition of 2M aqueous HCl and extraction with EtOAc. The organic phase was washed with aqueous citric acid, then passed throu... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | null | Cc1ccc(S(=O)(=O)Cl)cc1.N#Cc1ccc(CCO)cc1>N1=CC=CC=C1>Cc1ccc(S(=O)(=O)OCCc2ccc(C#N)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b6e637c151884c909ff6ec6502860177 | Cc1ccc(S(=O)(=O)OCCc2ccc(C#N)cc2)cc1.Nc1cccc(S)c1>>N#Cc1ccc(CCSc2cccc(N)c2)cc1 | NC=1C=C(C=CC1)S.C(#N)C1=CC=C(C=C1)CCOS(=O)(=O)C1=CC=C(C=C1)C.C(=O)([O-])[O-].[K+].[K+].CCOCC>>NC1=CC(=CC=C1)SCCC1=CC=C(C=C1)C#N | Cc1ccc(S(=O)(=O)O[CH2:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18][cH:17]2)cc1.[SH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([NH2:15])[cH:16]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][S:9][c:10]2[cH:11][cH:12][cH:13][c:14]([NH2:15])[cH:16]2)[cH:17][cH:18]1 | Cc1ccc(S(=O)(=O)OCCc2ccc(C#N)cc2)cc1.Nc1cccc(S)c1 | N#Cc1ccc(CCSc2cccc(N)c2)cc1 | null | null | C(Cl)Cl.CCO | Heteroatom Alkylation and Arylation | OtherReaction | fa9f9600581ef05dca04b54e63c21080ab3037c0f706082a272f2da0c08c4f32 | 8d10c46c4c89029273335615fb077055d8239c352e37ee1740069c99de11581b | c1ccc(CCSc2ccccc2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[c:3]):c:c:1.[SH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[c:6]:[c:5](-[S;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[c:3]):[c:7] | 49 | [{"value": 49.0, "product": "NC1=CC(=CC=C1)SCCC1=CC=C(C=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.8, "product": "NC1=CC(=CC=C1)SCCC1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Aminothiophenol (0.87 g; 7.0 mmol), 4-toluenesulfonic acid-2-(4-cyanophenyl)ethyl ester (2.0 g; 6.6 mmol; from step (i) above) and K2CO3 (1 g) were stirred in a mixture of EtOH (10 mL) and CH2Cl2 for 4 hours. Addition of ether, washing with brine and 2M aqueous NaOH, drying (MgSO4), evaporation of the solvent and fla... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic thiol | Monosulfide | c1ccccc1 | null | c1ccccc1.c1ccccc1 | TsOH.HO- | C(Cl)Cl.CCO | null | null | Cc1ccc(S(=O)(=O)OCCc2ccc(C#N)cc2)cc1.Nc1cccc(S)c1>C(Cl)Cl.CCO>N#Cc1ccc(CCSc2cccc(N)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-900bd1dae3d14db3a3e119f5d642c9f2 | N#Cc1ccc(CCSc2cccc(N)c2)cc1.O=S(=O)(Cl)c1ccccc1>>N#Cc1ccc(CCSc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1 | C1(=CC=CC=C1)S(=O)(=O)Cl.NC1=CC(=CC=C1)SCCC1=CC=C(C=C1)C#N.Cl>>C(#N)C1=CC=C(C=C1)CCSC=1C=C(C=CC1)NS(=O)(=O)C1=CC=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][S:9][c:10]2[cH:11][cH:12][cH:13][c:14]([NH2:15])[cH:25]2)[cH:26][cH:27]1.Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][S:9][c:10]2[cH:11][cH:12][cH:13][c:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]... | N#Cc1ccc(CCSc2cccc(N)c2)cc1.O=S(=O)(Cl)c1ccccc1 | N#Cc1ccc(CCSc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1 | null | null | N1=CC=CC=C1.C(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | O=S(=O)(Nc1cccc(SCCc2ccccc2)c1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 82.1 | [{"value": 82.0, "product": "C(#N)C1=CC=C(C=C1)CCSC=1C=C(C=CC1)NS(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.1, "product": "C(#N)C1=CC=C(C=C1)CCSC=1C=C(C=CC1)NS(=O)(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Benzenesulfonyl chloride (0.62 g; 3.5 mmol) was added to a cold solution (ice:water temperature) of amino-3-[2-(4-cyanophenyl)ethylthio]benzene (0.80 g; 3.15 mmol; from step (ii) above) in a mixture of pyridine (1 mL) and CH2Cl2 (20 mL) over 10 minutes. After 3 hours stirring, 2M aqueous HCl was added and the solution ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1.C(Cl)Cl | null | 3 | N#Cc1ccc(CCSc2cccc(N)c2)cc1.O=S(=O)(Cl)c1ccccc1>N1=CC=CC=C1.C(Cl)Cl>N#Cc1ccc(CCSc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cca034ba033243bb8d279e449cf553e4 | CCOC(=O)CNc1cc(C)cc(OCCc2ccc(C#N)cc2)c1.O=S(=O)(Cl)c1ccccc1Cl>>CCOC(=O)CN(c1cc(C)cc(OCCc2ccc(C#N)cc2)c1)S(=O)(=O)c1ccccc1Cl | C(=O)(O)[O-].[Na+].ClC1=C(C=CC=C1)S(=O)(=O)Cl.C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)NCC(=O)OCC.ClC1=C(C=CC=C1)S(=O)(=O)Cl>>ClC1=C(C=CC=C1)S(=O)(=O)N(C1=CC(=CC(=C1)C)OCCC1=CC=C(C=C1)C#N)CC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][c:8]1[cH:9][c:10]([CH3:11])[cH:12][c:13]([O:14][CH2:15][CH2:16][c:17]2[cH:18][cH:19][c:20]([C:21]#[N:22])[cH:23][cH:24]2)[cH:25]1.Cl[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][cH:32][cH:33][c:34]1[Cl:35]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]([c:8]1[cH:9][c:10]([CH... | CCOC(=O)CNc1cc(C)cc(OCCc2ccc(C#N)cc2)c1.O=S(=O)(Cl)c1ccccc1Cl | CCOC(=O)CN(c1cc(C)cc(OCCc2ccc(C#N)cc2)c1)S(=O)(=O)c1ccccc1Cl | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(Nc1cccc(OCCc2ccccc2)c1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[N;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 62 | [{"value": 62.0, "product": "ClC1=C(C=CC=C1)S(=O)(=O)N(C1=CC(=CC(=C1)C)OCCC1=CC=C(C=C1)C#N)CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "ClC1=C(C=CC=C1)S(=O)(=O)N(C1=CC(=CC(=C1)C)OCCC1=CC=C(C=C1)C#N)CC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2-Chlorobenzenesulfonyl chloride (0.225 g; 1.06 mmol) was added to a cold solution (ice:water temperature) of 3-[2-(4-cyanophenyl)ethoxy]-5-methylphenylaminoacetic acid, ethyl ester (0.30 g; 0.88 mmol; from step (i) above) in pyridine (10 mL). After 2 hours stirring the temperature was allowed to rise to ambient. After... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 2 | CCOC(=O)CNc1cc(C)cc(OCCc2ccc(C#N)cc2)c1.O=S(=O)(Cl)c1ccccc1Cl>N1=CC=CC=C1>CCOC(=O)CN(c1cc(C)cc(OCCc2ccc(C#N)cc2)c1)S(=O)(=O)c1ccccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d998d87bde2546cc85cd8edefb426c90 | C=CC(=O)OCC.Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1>>CCOC(=O)C(C)Nc1cc(C)cc(OCCc2ccc(C#N)cc2)c1 | NC1=CC(=CC(=C1)C)OCCC1=CC=C(C=C1)C#N.C(C=C)(=O)OCC.C(C)(=O)O>>C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)NC(C(=O)OCC)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].[NH2:8][c:9]1[cH:10][c:11]([CH3:12])[cH:13][c:14]([O:15][CH2:16][CH2:17][c:18]2[cH:19][cH:20][c:21]([C:22]#[N:23])[cH:24][cH:25]2)[cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[NH:8][c:9]1[cH:10][c:11]([CH3:12])[cH:13][c:14]([O:15][CH2:16][CH2:17][c:18]2[cH:19][... | C=CC(=O)OCC.Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1 | CCOC(=O)C(C)Nc1cc(C)cc(OCCc2ccc(C#N)cc2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1a11d98577799a07170cd5efd9dd7bb03f34d533a77a248c8322bf305dad4248 | d462df48e06a3b2a50bc83cb7c56b836b8a054b4c300671faa54924b570d58bc | c1ccc(CCOc2ccccc2)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[CH3;D1;+0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 29 | [{"value": 29.0, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)NC(C(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.9, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)NC(C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Amino-3-[2-(4-cyanophenyl)ethoxy]-5-methylbenzene (0.252 g; 1.00 mmol; from Example 17(iii) above), ethyl acrylate (130 μL; 1.2 mmol) and acetic acid (9 μL; 0.15 mmol) were refluxed together for 8 hours. After evaporation in vacuo, the resultant black oil was purified by flash chromatography (SiO2; EtOAc:heptane (3:7))... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Vinyl | Ester.Secondary amine | null | null | c1ccccc1.c1ccccc1 | null | null | null | null | C=CC(=O)OCC.Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1>>CCOC(=O)C(C)Nc1cc(C)cc(OCCc2ccc(C#N)cc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e472ba652644422cb5d716850cd2c733 | Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1.O=S(=O)(Cl)c1ccccc1Cl>>Cc1cc(OCCc2ccc(C#N)cc2)cc(-c2cccc(S(N)(=O)=O)c2Cl)c1 | ClC1=C(C=CC=C1)S(=O)(=O)Cl.NC1=CC(=CC(=C1)C)OCCC1=CC=C(C=C1)C#N.N1=CC=CC=C1.O.CCOC(=O)C>>C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)C=1C(=C(C=CC1)S(=O)(=O)N)Cl | [CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:16][c:17]([NH2:24])[cH:29]1.Cl[S:23]([c:22]1[cH:21][cH:20][cH:19][cH:18][c:27]1[Cl:28])(=[O:25])=[O:26]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([C:12]#[N:13])[cH:14][cH:15]2)[cH:16][c:1... | Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1.O=S(=O)(Cl)c1ccccc1Cl | Cc1cc(OCCc2ccc(C#N)cc2)cc(-c2cccc(S(N)(=O)=O)c2Cl)c1 | null | null | null | Acylation | OtherReaction | 9056a2ae05f3f48721e59db8b9dcb944d8d3e9953d69e7da0ce4e42b3cfd7c9e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc(CCOc2cccc(-c3ccccc3)c2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:1-[Cl;D1;H0:10].[NH2;D1;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[Cl;D1;H0:10]-[c:9]1:[c:4](-[S;H0;D4;+0:1](-[NH2;D1;+0:11])(=[O;D1;H0:2])=[O;D1;H0:3]):[c:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:1-[c;H0;D3;+0:12](:[c:13]:[c:14]... | 78 | [{"value": 78.0, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)C=1C(=C(C=CC1)S(=O)(=O)N)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 2-Chlorophenylsulfonyl chloride (0.152 g; 0.72 mmol) was added to a cooled solution (ice:water temperature) of amino-3-[2-(4-cyanophenyl)ethoxy]-5-methylbenzene (0.16 g; 0.60 mmol; from Example 17(iii) above) in pyridine (5 mL), and the resultant orange solution was stirred for 4 hours. Addition of H2O (30 mL), extract... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | null | null | 4 | Cc1cc(N)cc(OCCc2ccc(C#N)cc2)c1.O=S(=O)(Cl)c1ccccc1Cl>>Cc1cc(OCCc2ccc(C#N)cc2)cc(-c2cccc(S(N)(=O)=O)c2Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8b5caf0ce965422b920c209aacc255dd | CCOC(=O)CBr.N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1>>CCOC(=O)CN(c1cccc(OCCc2ccc(C#N)cc2)c1)S(=O)(=O)c1ccccc1 | C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)NS(=O)(=O)C1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+].BrCC(=O)OCC>>C1(=CC=CC=C1)S(=O)(=O)N(C1=CC(=CC=C1)OCCC1=CC=C(C=C1)C#N)CC(=O)OCC | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:7]([c:8]1[cH:9][cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][c:16]2[cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22][cH:23]2)[cH:24]1)[S:25](=[O:26])(=[O:27])[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]([c:8]1[cH:9][cH:10][cH:11][c:12]([O... | CCOC(=O)CBr.N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1 | CCOC(=O)CN(c1cccc(OCCc2ccc(C#N)cc2)c1)S(=O)(=O)c1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2f528facaf9aa1ab05620b510ae63e5e27715204b772ae8ea86d62f30b49e54b | dc829e3fdfa2d32260f0309a759a8629d6d95173de69dce05d7915b3a870e113 | O=S(=O)(Nc1cccc(OCCc2ccccc2)c1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[O;D1;H0:6]=[#16:7](=[O;D1;H0:8])(-[c:9])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:10](-[c:11](:[c:12]):[c:13])-[#16:7](=[O;D1;H0:6])(=[O;D1;H0:8])-[c:9] | null | [] | null | null | null | null | N-{3-[2-(4-Cyanophenyl)ethoxy]phenyl}benzenesulfonamide (0.179 g; 0.47 mmol; from Example 1(iv) above), K2CO3 (0.082 g; 0.59 mmol) and ethyl bromoacetate (63 μL; 0.57 mmol) were stirred in DMF (10 mL) for 1 hour at room temperature, then 1 hour at 60° C. The mixture was filtered and the solvent removed in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Ester.Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | CCOC(=O)CBr.N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1>CN(C)C=O>CCOC(=O)CN(c1cccc(OCCc2ccc(C#N)cc2)c1)S(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a760ed3aa08d43f0a0a97f8b15340fd1 | N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1.OCCCl>>N#Cc1ccc(CCOc2cccc(N(CCO)S(=O)(=O)c3ccccc3)c2)cc1 | C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)NS(=O)(=O)C1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+].ClCCO.[Na+].[I-]>>C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)N(S(=O)(=O)C1=CC=CC=C1)CCO | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([NH:15][S:19](=[O:20])(=[O:21])[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28]2)[cH:29][cH:30]1.Cl[CH2:16][CH2:17][OH:18]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([N:15]([CH2:16]... | N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1.OCCCl | N#Cc1ccc(CCOc2cccc(N(CCO)S(=O)(=O)c3ccccc3)c2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0fe6648877a29ae177a907a0d252f35d8beab440bf428116c5424a67bc0e72cd | 0b054affe7e4bb904ceae512aabc19d89c93551cb46dfbc6f220fc85e5eeff75 | O=S(=O)(Nc1cccc(OCCc2ccccc2)c1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[O;D1;H0:4]=[#16:5](=[O;D1;H0:6])(-[c:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:4]=[#16:5](=[O;D1;H0:6])(-[c:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3])-[c:9](:[c:10]):[c:11] | 45.2 | [{"value": 45.0, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)N(S(=O)(=O)C1=CC=CC=C1)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.2, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)N(S(=O)(=O)C1=CC=CC=C1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-{3-[2-(4-cyanophenyl)ethoxy]phenyl}benzenesulfonamide (0.093 g; 0.246 mmol; from Example 1(iv) above), K2CO3 (0.047 g, 0.34 mmol), 2-chloroethanol (0.028 g; 0.34 mmol) and NaI (0.052 g; 0.34 mmol) were stirred in DMF (4 mL) for 24 hours at 100° C. The solvent was removed in vacuo. The residue was dissolved in water a... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | null | N#Cc1ccc(CCOc2cccc(NS(=O)(=O)c3ccccc3)c2)cc1.OCCCl>CN(C)C=O>N#Cc1ccc(CCOc2cccc(N(CCO)S(=O)(=O)c3ccccc3)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-715ae417cb214b94910b6d81fbe9317b | CC(C)(N(c1cccc(OCCc2ccc(C#N)cc2)c1)S(=O)(=O)c1ccccc1)P(=O)=O.NO>>CC(C)(N(c1cccc(OCCc2ccc(N)cc2C=NO)c1)S(=O)(=O)c1ccccc1)P(=O)=O | Cl.NO.C(C)N(CC)CC.C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=CC1)N(S(=O)(=O)C1=CC=CC=C1)C(P(=O)=O)(C)C.CCO>>NC1=CC(=C(C=C1)CCOC=1C=C(C=CC1)N(S(=O)(=O)C1=CC=CC=C1)C(P(=O)=O)(C)C)C=NO | [CH3:1][C:2]([CH3:3])([N:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([C:20]#[N:17])[cH:18][cH:19]2)[cH:23]1)[S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[P:33](=[O:34])=[O:35].[NH2:21][OH:22]>>[CH3:1][C:2]([CH3:3])([N:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][... | CC(C)(N(c1cccc(OCCc2ccc(C#N)cc2)c1)S(=O)(=O)c1ccccc1)P(=O)=O.NO | CC(C)(N(c1cccc(OCCc2ccc(N)cc2C=NO)c1)S(=O)(=O)c1ccccc1)P(=O)=O | null | null | null | Functional Group Interconversion | OtherReaction | 9a4199cbda10cf607df9505ac5108b87c80aa46a5446ba42a75d811e5b06fd6e | 5faaa3b624f22840cc937b2c79d5ab2d184e066c323862d533df1ecb9df1680d | O=S(=O)(Nc1cccc(OCCc2ccccc2)c1)c1ccccc1 | [C:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]):[c:8]:[cH;D2;+0:9]:1.[NH2;D1;+0:10]-[O;D1;H1:11]>>[C:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[NH2;D1;+0:7]):[c:8]:[c;H0;D3;+0:9]:1-[CH;D2;+0:6]=[N;H0;D2;+0:10]-[O;D1;H1:11] | 56 | [{"value": 56.0, "product": "NC1=CC(=C(C=C1)CCOC=1C=C(C=CC1)N(S(=O)(=O)C1=CC=CC=C1)C(P(=O)=O)(C)C)C=NO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Hydroxylamine hydrochloride (0.018 g; 0.26 mmol) and triethylamine (45 μL, 0.33 mmol) were added to a solution of N-{3-[2-(4-cyanophenyl)ethoxy]phenyl}-N-(dimethyloxophosphinylmethyl)-benzenesulfonamide (0.090 g; 0.192 mmol; from step (i) above) in EtOH (6 mL). The mixture was heated at reflux for 3 hours, stirred at r... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine.Oxime | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | 8 | CC(C)(N(c1cccc(OCCc2ccc(C#N)cc2)c1)S(=O)(=O)c1ccccc1)P(=O)=O.NO>>CC(C)(N(c1cccc(OCCc2ccc(N)cc2C=NO)c1)S(=O)(=O)c1ccccc1)P(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-328c4fe48c48430ea2808ad405c1e724 | Cc1cc(O)cc(O)c1.N#Cc1ccc(CCO)cc1>>Cc1cc(O)cc(OCCc2ccc(C#N)cc2)c1 | CCOC(=O)/N=N/C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OC=1C=C(C=C(C1)O)C.C(#N)C1=CC=C(C=C1)CCO>>C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)O | O[c:7]1[cH:6][c:4]([OH:5])[cH:3][c:2]([CH3:1])[cH:19]1.[OH:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:6][c:7]([O:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]2)[cH:19]1 | Cc1cc(O)cc(O)c1.N#Cc1ccc(CCO)cc1 | Cc1cc(O)cc(OCCc2ccc(C#N)cc2)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(CCOc2ccccc2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 37 | [{"value": 37.0, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.5, "product": "C(#N)C1=CC=C(C=C1)CCOC=1C=C(C=C(C1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Triphenylphoshine (7.86 g; 30 mmol), 3,5-dihydroxytoluene (2.5 g; 20 mmol) and 2-(4-cyanophenyl)ethanol (4.41 g; 30 mmol) were dissolved in THF (50 mL). Diethylazodicarboxylate (5.22 g; 30 mmol; dissolved in THF (10 mL)), was added and the solution was stirred at room temperature overnight. The solvent was removed in v... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 8 | Cc1cc(O)cc(O)c1.N#Cc1ccc(CCO)cc1>C1CCOC1>Cc1cc(O)cc(OCCc2ccc(C#N)cc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b4f023441e99406caabd808a847bd821 | COc1cc(Cl)cc(OC)c1>>Oc1cc(O)cc(Cl)c1 | B(Br)(Br)Br.ClC1=CC(=CC(=C1)OC)OC>>ClC1=CC(=CC(=C1)O)O | C[O:1][c:2]1[cH:3][c:4]([O:5]C)[cH:6][c:7]([Cl:8])[cH:9]1>>[OH:1][c:2]1[cH:3][c:4]([OH:5])[cH:6][c:7]([Cl:8])[cH:9]1 | COc1cc(Cl)cc(OC)c1 | Oc1cc(O)cc(Cl)c1 | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[O;H0;D2;+0:6]-C):[c:7]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[OH;D1;+0:6]):[c:7] | 207.5 | [{"value": 100.0, "product": "ClC1=CC(=CC(=C1)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 207.5, "product": "ClC1=CC(=CC(=C1)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | BBr3 (26 mL; 0.275 mmol) was added to a solution of chloro-3,5-dimethyoxybenzene (10 g; 30 mmol) in CH2Cl2 (100 mL) at −70° C. The cooling bath was removed and the solution was stirred at room temperature for 4 days. After re-cooling to −70° C., MeOH was added (150 mL). After evaporation of the solvent, toluene was add... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 96 | COc1cc(Cl)cc(OC)c1>C(Cl)Cl>Oc1cc(O)cc(Cl)c1 |
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