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-764201f239bd4d3e97dad5d5a4b1d001 | CCNCC.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1>>CCN(CC)CC(O)COc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC | O1C(COC2=C(C=C3C(=NC=NC3=C2)OC=2C=C3C=C(NC3=CC2)C)OC)C1.C(C)NCC>>C(C)N(CC)CC(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[CH: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][CH:7]([OH:8])[CH2:9][O:10][c:11]1[cH:12][c:... | CCNCC.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1 | CCN(CC)CC(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 | [C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C;D1;H3:5].[C:6]-[C:7]1-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1>>[C:6]-[C:7](-[OH;D1;+0:9])-[CH2;D2;+0:8]-[N;H0;D3;+0:3](-[C:2]-[C;D1;H3:1])-[C:4]-[C;D1;H3:5] | 46 | [{"value": 46.0, "product": "C(C)N(CC)CC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.2, "product": "C(C)N(CC)CC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture of 7-(2,3-epoxypropoxy)-6-methoxy-4-(2-methylindol-5-yloxy) quinazoline (100 mg, 0.27 mmol), (prepared as described for the starting material in Example 162), and diethylamine (100 ul, 0.8 mmol) in DMF (4 ml) was heated at 70° C. for 24 hours. The solvent was removed by evaporation and the residue was purifie... | 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 | null | CCNCC.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1>CN(C)C=O>CCN(CC)CC(O)COc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-df2ac05840054c5486acbdaca480a418 | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCN(C)CC1 | O1C(COC2=C(C=C3C(=NC=NC3=C2)OC=2C=C3C=C(NC3=CC2)C)OC)C1.CN1CCNCC1>>OC(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][CH: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... | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(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.[C:7]-[C:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1>>[C:7]-[C:8](-[OH;D1;+0:10])-[CH2;D2;+0:9]-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 32 | [{"value": 32.0, "product": "OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.8, "product": "OC(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 | null | null | A mixture of 7-(2,3-epoxypropoxy)-6-methoxy-4-(2-methylindol-5-yloxy) quinazoline (100 mg, 0.27 mmol), (prepared as described for the starting material in Example 162), and N-methylpiperazine (200 ul, 1.8 mmol) in DMF (4 ml) was heated at 70° C. for 24 hours. The solvent was removed by evaporation and the residue was r... | 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 | null | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7c1252df20534aecbea6a4ad46e7aa95 | CC(C)N.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CNC(C)C | O1C(COC2=C(C=C3C(=NC=NC3=C2)OC=2C=C3C=C(NC3=CC2)C)OC)C1.C(C)(C)N>>OC(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][CH: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)ncnc2cc1OCC1CO1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CNC(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:4].[C:5]-[C:6]1-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-1>>[C:5]-[C:6](-[OH;D1;+0:8])-[CH2;D2;+0:7]-[NH;D2;+0:4]-[C:2](-[C;D1;H3:1])-[C;D1;H3:3] | 16 | [{"value": 16.0, "product": "OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CNC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.3, "product": "OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CNC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture of 7-(2,3-epoxypropoxy)-6-methoxy-4-(2-methylindol-5-yloxy) quinazoline (100 mg, 0.27 mmol), (prepared as described for the starting material in Example 162), and isopropylamine (100 ul, 0.8 mmol) in DMF (4 ml) was heated at 70° C. for 24 hours. The solvent was removed by evaporation and the residue was purif... | 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 | 70 | null | CC(C)N.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CNC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9ffd160700234287a5acf4978eea8324 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cc2cc[nH]c2cc1C(F)(F)F>>COc1cc2c(Oc3cc4cc[nH]c4cc3C(F)(F)F)ncnc2cc1OCCCN1CCCCC1 | CC(=O)N(C)C.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC=1C=C2C=CNC2=CC1C(F)(F)F>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C=CNC2=CC1C(F)(F)F | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[cH:25][c:24]2[n:23][cH:22][n:21]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[C:17]([F:18])([F:19])[F:20]>>[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... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cc2cc[nH]c2cc1C(F)(F)F | COc1cc2c(Oc3cc4cc[nH]c4cc3C(F)(F)F)ncnc2cc1OCCCN1CCCCC1 | null | null | ClCCl | 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] | 25 | [{"value": 25.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C=CNC2=CC1C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.8, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C=CNC2=CC1C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 1.5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (168 mg, 0.5 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (276 mg, 2.0 mmol) and 5-hydroxy-6-trifluoromethylindole (110 mg, 0.55 mmol) and DMA (4.0 ml) were stirred at 95° C. for 1.5 hours and allowed to co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | ClCCl | 95 | 1.5 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cc2cc[nH]c2cc1C(F)(F)F>ClCCl>COc1cc2c(Oc3cc4cc[nH]c4cc3C(F)(F)F)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12783713139945e38ae19dee0a14a42e | O=[N+]([O-])c1ccc(Cl)c(C(F)(F)F)c1.OCc1ccccc1>>O=[N+]([O-])c1ccc(OCc2ccccc2)c(C(F)(F)F)c1 | C(C)(=O)O.[H-].[Na+].C(C1=CC=CC=C1)O.ClC1=C(C=C(C=C1)[N+](=O)[O-])C(F)(F)F>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)[N+](=O)[O-])C(F)(F)F | Cl[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:21][c:16]1[C:17]([F:18])([F:19])[F:20].[OH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1 | O=[N+]([O-])c1ccc(Cl)c(C(F)(F)F)c1.OCc1ccccc1 | O=[N+]([O-])c1ccc(OCc2ccccc2)c(C(F)(F)F)c1 | null | null | ClCCl.CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(COc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[OH;D1;+0:10]-[C:11]-[c:12]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[C:11]-[c:12]):[c:2]:[c:3] | 49 | [{"value": 49.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C(C=C1)[N+](=O)[O-])C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.4, "product": "C(C1=CC=CC=C1)OC1=C(C=C(C=C1)[N+](=O)[O-])C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium hydride (1.8 g, of a 60% dispersion in oil, 45 mmol) was added in portions to a stirred solution of benzyl alcohol (10.8 g, 100 mmol) in DMA (100 ml) with vigorous stirring under an atmosphere of nitrogen at ambient temperature. After warming to 45° C. for 30 minutes the mixture was cooled to ambient temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | ClCCl.CC(=O)N(C)C | null | null | O=[N+]([O-])c1ccc(Cl)c(C(F)(F)F)c1.OCc1ccccc1>ClCCl.CC(=O)N(C)C>O=[N+]([O-])c1ccc(OCc2ccccc2)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fc3145e35b4460c87d0579c588585ed | N#CCc1ccc(Cl)cc1.O=[N+]([O-])c1ccc(OCc2ccccc2)c(C(F)(F)F)c1>>N#CCc1cc(OCc2ccccc2)c(C(F)(F)F)cc1[N+](=O)[O-] | Cl.C(C1=CC=CC=C1)OC1=C(C=C(C=C1)[N+](=O)[O-])C(F)(F)F.ClC1=CC=C(C=C1)CC#N.CC(C)([O-])C.[K+]>>C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)CC#N)[N+](=O)[O-])C(F)(F)F | Clc1cc[c:4]([CH2:3][C:2]#[N:1])[cH:5]c1.c1c[c:21]([N+:22](=[O:23])[O-:24])[cH:20][c:15]([C:16]([F:17])([F:18])[F:19])[c:6]1[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][c:21]1... | N#CCc1ccc(Cl)cc1.O=[N+]([O-])c1ccc(OCc2ccccc2)c(C(F)(F)F)c1 | N#CCc1cc(OCc2ccccc2)c(C(F)(F)F)cc1[N+](=O)[O-] | null | null | CN(C)C=O | Miscellaneous | OtherReaction | e1a86e32d8a62056777b80c3d8e217471ab53bfaa0552fe67a867bfc2dce42db | 90896f03fa7176670c6618dd1123693033ce2a8538f8fd8da8706c8a6043dc98 | c1ccc(COc2ccccc2)cc1 | Cl-c1:c:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C:3]-[C:4]#[N;D1;H0:5]):c:c:1.[C:6]-[#8:7]-[c;H0;D3;+0:8]1:c:c:[c;H0;D3;+0:9](-[#7;+:10](-[O;-;D1;H0:11])=[O;D1;H0:12]):[c:13]:[c:14]:1-[C:15](-[F;D1;H0:16])(-[F;D1;H0:17])-[F;D1;H0:18]>>[C:6]-[#8:7]-[c;H0;D3;+0:8]1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C:3]-[C:4]#[N;D1;H0:5]):[c;H0;D3;+0:... | 96 | [{"value": 77.0, "product": "C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)CC#N)[N+](=O)[O-])C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.0, "product": "C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)CC#N)[N+](=O)[O-])C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 1 | HOUR | Potassium tert-butoxide (3.94 g, 35.4 mmol) was dissolved in anhydrous DMF (15 ml) and a mixture of 2-benzyloxy-5-nitro-trifluoromethylbenzene (3.5 g, 16.1 mmol) and 4-chlorophenylacetonitrile (2.96 g, 17.7 mmol) in DMF (20 ml) was added over 30 minutes keeping the temperature at −15C. The mixture was stirred at −10° C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Nitro group | Ether.Nitro group | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | -10 | 1 | N#CCc1ccc(Cl)cc1.O=[N+]([O-])c1ccc(OCc2ccccc2)c(C(F)(F)F)c1>CN(C)C=O>N#CCc1cc(OCc2ccccc2)c(C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6840e0bf182b4e299ed28de5d2ff9819 | N#CCc1cc(OCc2ccccc2)c(C(F)(F)F)cc1[N+](=O)[O-]>>Oc1cc2cc[nH]c2cc1C(F)(F)F | O.C(C)(=O)O.C(C1=CC=CC=C1)OC=1C(=CC(=C(C1)CC#N)[N+](=O)[O-])C(F)(F)F>>OC=1C=C2C=CNC2=CC1C(F)(F)F | N#[C:6][CH2:5][c:4]1[cH:3][c:2]([O:1]Cc2ccccc2)[c:10]([C:11]([F:12])([F:13])[F:14])[cH:9][c:8]1[N+:7](=O)[O-]>>[OH:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][nH:7][c:8]2[cH:9][c:10]1[C:11]([F:12])([F:13])[F:14] | N#CCc1cc(OCc2ccccc2)c(C(F)(F)F)cc1[N+](=O)[O-] | Oc1cc2cc[nH]c2cc1C(F)(F)F | null | [Pd] | C(C)O | Functional Group Interconversion | OtherReaction | d674d6fdb3b5cbb7247a702f066088407269945f41d65ac05ee14f7e0733fdaa | c2e261676da3d876901f8094899a33724e27f2712d56041d0a451c2699036a45 | c1ccc2[nH]ccc2c1 | N#[C;H0;D2;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5](-[O;H0;D2;+0:6]-C-c2:c:c:c:c:c:2):[c:7]:[c:8]:[c:9]:1-[N+;H0;D3:10](=O)-[O-]>>[OH;D1;+0:6]-[c:5]1:[c:7]:[c:8]:[c:9]2:[nH;D2;+0:10]:[cH;D2;+0:1]:[cH;D2;+0:2]:[c:3]:2:[c:4]:1 | 84.4 | [{"value": 84.0, "product": "OC=1C=C2C=CNC2=CC1C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.4, "product": "OC=1C=C2C=CNC2=CC1C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Benzyloxy-2-nitro-4(trifluoromethyl)phenylacetonitrile (2.22 g, 6.6 mmol) was dissolved in ethanol (45 ml), water (5 ml) and acetic acid (0.32 ml) then hydrogenated with 10% palladium on carbon at 1 atmosphere pressure for 2 hours. The catalyst was filtered off and filtrate evaporated to give 5-hydroxy-6-trifluoromet... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile.Nitro group | Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | [Pd].C(C)O | null | null | N#CCc1cc(OCc2ccccc2)c(C(F)(F)F)cc1[N+](=O)[O-]>[Pd].C(C)O>Oc1cc2cc[nH]c2cc1C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1a37df9bbfcc43518a54b12f8978e98f | COc1cc2[nH]ccc2cc1O.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1>>COc1cc2c(Oc3cc4cc[nH]c4cc3OC)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC=1C=C2C=CNC2=CC1OC>>COC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1 | [OH:7][c:8]1[cH:9][c:10]2[cH:11][cH:12][nH:13][c:14]2[cH:15][c:16]1[O:17][CH3:18].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>>[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... | COc1cc2[nH]ccc2cc1O.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1 | COc1cc2c(Oc3cc4cc[nH]c4cc3OC)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] | 38.2 | [{"value": 38.0, "product": "COC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.2, "product": "COC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 2.5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (200 mg, 0.6 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (248 mg, 1.8 mmol) and 5-hydroxy-6-methoxyindole (127 mg, 0.78 mmol) in DMA (4.0 ml) was stirred at 95° C. for 2.5 hours. The reaction mixture was a... | 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 | 95 | 2.5 | COc1cc2[nH]ccc2cc1O.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1>CC(=O)N(C)C>COc1cc2c(Oc3cc4cc[nH]c4cc3OC)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6c40b817a99245b5ae1c0af10020a5d8 | COc1cc2[nH]ccc2cc1OCc1ccccc1>>COc1cc2[nH]ccc2cc1O | C(C1=CC=CC=C1)OC=1C=C2C=CNC2=CC1OC>>OC=1C=C2C=CNC2=CC1OC | c1ccc(C[O:12][c:11]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[nH:6][cH:7][cH:8][c:9]3[cH:10]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[nH:6][cH:7][cH:8][c:9]2[cH:10][c:11]1[OH:12] | COc1cc2[nH]ccc2cc1OCc1ccccc1 | COc1cc2[nH]ccc2cc1O | null | [Pd] | CO | 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] | 87 | [{"value": 87.0, "product": "OC=1C=C2C=CNC2=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 7.9, "product": "OC=1C=C2C=CNC2=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Benzyloxy-6-methoxyindole (253 mg, 11.0 mmol) was hydrogenated at 1 atmosphere pressure in methanol (10 ml) with 10% palladium on carbon (50 mg) for 2 hours at 25° C. The catalyst was filtered off and the filtrate evaporated to give 5-hydroxy-6-methoxylindole (141 mg, 87%).
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1 | Other | [Pd].CO | null | null | COc1cc2[nH]ccc2cc1OCc1ccccc1>[Pd].CO>COc1cc2[nH]ccc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9267b799df84f46929e357a34a8a5a4 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cccc2[nH]ccc12>>COc1cc2c(Oc3cc4ccccc4[nH]3)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC1=C2C=CNC2=CC=C1>>N1C(=CC2=CC=CC=C12)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: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:11]1[c:10]2[cH:9][cH:8][nH:16][c:15]2[cH:14][cH:13][cH:12]1>>[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][cH:13][cH:14][c... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cccc2[nH]ccc12 | COc1cc2c(Oc3cc4ccccc4[nH]3)ncnc2cc1OCCCN1CCCCC1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | OtherReaction | 5af8f53eb6fe20519bb1cf399cab4d8844ca0e30f8f4c67b935a221e33f2c4d3 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2[nH]c(Oc3ncnc4cc(OCCCN5CCCCC5)ccc34)cc2c1 | 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;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[c:14]2:[#7;a:15]:[cH;D2;+0:16]:[c:17]:[c:18]:2:1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c;H0;D3;+0:16]2:[#7;a:15]:[c:14]3:[c:13]:[c:12]:[c:11]:[cH;D2;+0:10]:[c:18]:3:... | 51 | [{"value": 51.0, "product": "N1C(=CC2=CC=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.9, "product": "N1C(=CC2=CC=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 3 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (200 mg, 0.595 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (411 mg, 2.98 mmol) and 4-hydroxyindole (103 mg, 0.774 mmol) in DMA (2.0 ml) was stirred at 85° C. for 3 hours and allowed to cool to ambient temp... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CC(=O)N(C)C | 85 | 3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cccc2[nH]ccc12>CC(=O)N(C)C>COc1cc2c(Oc3cc4ccccc4[nH]3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ed001413ff043fca1378b9ad403d778 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]c3ccccc3c2c1>>COc1cc2c(Oc3ccc4[nH]c5ccccc5c4c3)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC=1C=CC=2NC3=CC=CC=C3C2C1>>C1=CC(=CC=2C3=CC=CC=C3NC12)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:26]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[cH:25][c:24]2[n:23][cH:22][n:21]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]2[cH:20]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... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]c3ccccc3c2c1 | COc1cc2c(Oc3ccc4[nH]c5ccccc5c4c3)ncnc2cc1OCCCN1CCCCC1 | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2c(c1)[nH]c1ccc(Oc3ncnc4cc(OCCCN5CCCCC5)ccc34)cc12 | 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] | 74 | [{"value": 74.0, "product": "C1=CC(=CC=2C3=CC=CC=C3NC12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "C1=CC(=CC=2C3=CC=CC=C3NC12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 3 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (200 mg, 0.595 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (411 mg, 2.98 mmol) and 3-hydroxycarbazole (142 mg, 0.774 mmol) in DMA (2.0 ml) was stirred at 85° C. for 3 hours then allowed to cool to ambient ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)[nH]c1ccccc12.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CC(=O)N(C)C | 85 | 3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]c3ccccc3c2c1>CC(=O)N(C)C>COc1cc2c(Oc3ccc4[nH]c5ccccc5c4c3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5420ffa646cf4180bb04913a9b4e2ddb | CCOC(=O)c1cc2cc(O)cc(Cl)c2[nH]1.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1>>COc1ncc2ccc(OCCCN3CCCCC3)cc2n1.N | ClC=1C=C(C=C2C=C(NC12)C(=O)OCC)O.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+]>>N.COC1=NC2=CC(=CC=C2C=N1)OCCCN1CCCCC1 | CCOC(=O)c1cc2cc(O)cc(Cl)c2[nH:23]1.Cl[c:3]1[n:4][cH:5][n:22][c:21]2[c:6]1[cH:7][c:8]([O:2][CH3:1])[c:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[cH:20]2>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]2[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:... | CCOC(=O)c1cc2cc(O)cc(Cl)c2[nH]1.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1 | COc1ncc2ccc(OCCCN3CCCCC3)cc2n1.N | null | null | CC(=O)N(C)C | Heteroatom Alkylation and Arylation | OtherReaction | 1f4a078a87a2cd24f5427d4b035f6072255d15c9e66b3a1d7b1eefefb95252f6 | 94b25ed96cf8c349fb5ad11a6cf51873bfff33948c723a93839df0af98ec2286 | c1ncc2ccc(OCCCN3CCCCC3)cc2n1 | C-C-O-C(=O)-c1:[nH;D2;+0:1]:c2:c(-Cl):c:c(-O):c:c:2:c:1.Cl-[c;H0;D3;+0:2]1:[#7;a:3]:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[c:6]2:[c:7]:[c:8](-[#8:9]):[c;H0;D3;+0:10](-[O;H0;D2;+0:11]-[C;D1;H3:12]):[c:13]:[c;H0;D3;+0:14]:2:1>>[#8:9]-[c:8]1:[c:7]:[c:6]2:[n;H0;D2;+0:5]:[c;H0;D3;+0:2](-[O;H0;D2;+0:11]-[C;D1;H3:12]):[#7;a:3]:[cH;D2;+... | 215.7 | [{"value": 2.0, "product": "N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.0, "product": "COC1=NC2=CC(=CC=C2C=N1)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 215.7, "product": "COC1=NC2=CC(=CC=C2C=N1)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}... | 100 | CELSIUS | 2 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (84 mg, 0.24 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (162 mg, 1.18 mmol) and ethyl 7-chloro-5-hydroxyindole-2-carboxylate (62 mg, 0.26 mmol) in DMA (2.0 ml) was stirred at 100° C. for 2 hours and allow... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester.Ether.Aromatic alcohol | Ether | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CC(=O)N(C)C | 100 | 2 | CCOC(=O)c1cc2cc(O)cc(Cl)c2[nH]1.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1>CC(=O)N(C)C>COc1ncc2ccc(OCCCN3CCCCC3)cc2n1.N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b720bf58d91e480d8483df4e9d3bbf50 | CCC(C)OC(=O)CC(C)=O.COc1ccc(N)c(Cl)c1>>CCOC(=O)c1cc2cc(OC)cc(Cl)c2[nH]1 | ClC1=C(N)C=CC(=C1)OC.Cl.C(C)(=O)[O-].[Na+].S(O)(O)(=O)=O.N(=O)[O-].[Na+].C(CC(=O)C)(=O)OC(C)CC.[OH-].[K+]>>ClC=1C=C(C=C2C=C(NC12)C(=O)OCC)OC | C[CH2:1][CH:2](C)[O:3][C:4](=[O:5])[CH2:6][C:7](C)=O.[cH:8]1[cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]([Cl:15])[c:16]1[NH2:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]([Cl:15])[c:16]2[nH:17]1 | CCC(C)OC(=O)CC(C)=O.COc1ccc(N)c(Cl)c1 | CCOC(=O)c1cc2cc(OC)cc(Cl)c2[nH]1 | null | null | O.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 82a2f84f83ec62d512cf1b75ad27b27172bebc89925485b01b04151288b3e16b | c45a7acb285da3123c5d22eec0ca0a66ba4c84503de7af0b65f8f37d8156499c | c1ccc2[nH]ccc2c1 | C-[CH2;D2;+0:1]-[CH;D3;+0:2](-C)-[#8:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C;H0;D3;+0:7](-C)=O.[NH2;D1;+0:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:9](:[c:10]):[nH;D2;+0:8]:1 | 4 | [{"value": 4.0, "product": "ClC=1C=C(C=C2C=C(NC12)C(=O)OCC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 3.5, "product": "ClC=1C=C(C=C2C=C(NC12)C(=O)OCC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | 4 | HOUR | 2-Chloro-4-methoxyaniline (2.719 g, 14 mmol) was added to 8.0M aqueous hydrochloric acid (15 ml) and the suspension cooled to −5° C. Sodium nitrite (1.063 g, 15.4 mmol) was added as a solution in water (3 ml). After addition the pH was brought to pH 4–5 by addition of sodium acetate. In a separate flask, ethyl-α-ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Ester | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | O.C(C)O | -5 | 4 | CCC(C)OC(=O)CC(C)=O.COc1ccc(N)c(Cl)c1>O.C(C)O>CCOC(=O)c1cc2cc(OC)cc(Cl)c2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b84b0cbdfc1d47a3b0b638876f5a0ba5 | CCOC(=O)c1cc2cc(OC)cc(Cl)c2[nH]1>>CCOC(=O)c1cc2cc(O)cc(Cl)c2[nH]1 | O.ClC=1C=C(C=C2C=C(NC12)C(=O)OCC)OC.B(Br)(Br)Br.[OH-].[Na+]>>ClC=1C=C(C=C2C=C(NC12)C(=O)OCC)O | C[O:11][c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:16][c:15]2[c:13]([Cl:14])[cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([OH:11])[cH:12][c:13]([Cl:14])[c:15]2[nH:16]1 | CCOC(=O)c1cc2cc(OC)cc(Cl)c2[nH]1 | CCOC(=O)c1cc2cc(O)cc(Cl)c2[nH]1 | null | null | ClCCl.C(Cl)Cl | 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] | 71.1 | [{"value": 71.0, "product": "ClC=1C=C(C=C2C=C(NC12)C(=O)OCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.1, "product": "ClC=1C=C(C=C2C=C(NC12)C(=O)OCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of ethyl 7-chloro-5-methoxyindole-2-carboxylate (82 mg, 0.323 mmol) in dichloromethane (5 ml) at −78° C. was added boron tribromide (1.07 ml of a 1.0M solution in DCM, 1.07 mmol) and the reaction stirred at −78° C. for 30 minutes then allowed to warm to ambient temperature overnight. Water was carefully a... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | ClCCl.C(Cl)Cl | -78 | 0.5 | CCOC(=O)c1cc2cc(OC)cc(Cl)c2[nH]1>ClCCl.C(Cl)Cl>CCOC(=O)c1cc2cc(O)cc(Cl)c2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4221763137304788ad96c9204309b884 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1[nH]c2ccc(O)cc2c1C>>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC.C([O-])([O-])=O.[K+].[K+].CC=1NC2=CC=C(C=C2C1C)O>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=C(NC2=CC1)C)C)OC | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]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])[c:15]([CH3:16])[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[nH:12][c:13]([CH3:14])[c:... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1[nH]c2ccc(O)cc2c1C | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1 | null | null | CN(C)C=O | 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] | 46 | [{"value": 46.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=C(NC2=CC1)C)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=C(NC2=CC1)C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A mixture of 7-benzyloxy-4-chloro-6-methoxyquinazoline (1.5 g, 4.99 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (2.07 g, 15 mmol) and 2,3-dimethyl-5-hydroxyindole (1.21 g, 7.5 mmol), (Arch. Pharm. 1972, 305, 159), in DMF (75 ml) was stirred at 100° C. for 2 hours and allow... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CN(C)C=O | 100 | 2 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1[nH]c2ccc(O)cc2c1C>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5d09da4ac3df44b0980281c44d3d8b4a | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2ccccc2n1>>COc1cc2c(Oc3ccc4ccccc4n3)ncnc2cc1OCCCN1CCOCC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.C([O-])([O-])=O.[K+].[K+].OC1=NC2=CC=CC=C2C=C1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=NC2=CC=CC=C2C=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][cH:13][cH:14][cH:15][c:16]2[n: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][cH:13][cH:1... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2ccccc2n1 | COc1cc2c(Oc3ccc4ccccc4n3)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2nc(Oc3ncnc4cc(OCCCN5CCOCC5)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].[OH;D1;+0:9]-[c:10](:[c:11]):[#7;a:12]:[c:13]>>[c:13]:[#7;a:12]:[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:11] | 11 | [{"value": 11.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=NC2=CC=CC=C2C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=NC2=CC=CC=C2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (225 mg, 0.67 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (106 mg, 0.77 mmol) and 2-hydroxyquinoline (111 mg, 0.76 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient tem... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2ccccc2n1>CN(C)C=O>COc1cc2c(Oc3ccc4ccccc4n3)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e4ec6c08da654f7997c0a4f544c47d32 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1cccc2ncccc12>>COc1cc2c(Oc3cccc4ncccc34)ncnc2cc1OCCCN1CCOCC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.C([O-])([O-])=O.[K+].[K+].OC1=C2C=CC=NC2=CC=C1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=C2C=CC=NC2=CC=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][cH:11][c:12]2[n:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][cH:11][c:12]4[n:13][cH:14... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1cccc2ncccc12 | COc1cc2c(Oc3cccc4ncccc34)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cc(Oc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2cccnc2c1 | 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] | 59.5 | [{"value": 59.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=C2C=CC=NC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.5, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=C2C=CC=NC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (225 mg, 0.67 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (106 mg, 0.77 mmol) and 5-hydroxyquinoline (111 mg, 0.77 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient tem... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1cccc2ncccc12>CN(C)C=O>COc1cc2c(Oc3cccc4ncccc34)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-38211a4e4b754ee4b088506079758e11 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Oc1ccc2cccnc2c1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCN(C)CC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C=CC=NC2=C1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCN(CC1)C)OC1=CC=C2C=CC=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][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[cH:12][cH: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][c... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Oc1ccc2cccnc2c1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCN(C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCCCN5CCNCC5)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] | 39 | [{"value": 39.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCN(CC1)C)OC1=CC=C2C=CC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.9, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCN(CC1)C)OC1=CC=C2C=CC=NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (200 mg, 0.57 mmol), potassium carbonate (106 mg, 0.77 mmol) and 7-hydroxyquinoline (111 mg, 0.76 mmol) in DMF (7 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient temperature. The reaction mixture was treated with 1.0 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Oc1ccc2cccnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00871006f26b4344bb664f8a0a7014cc | CN1CCN(CCCO)CC1.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OCCCN2CCN(C)CC2)cc1 | OCCCN1CCN(CC1)C.C(C)N(CC)CC.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>CN1CCN(CC1)CCCOS(=O)(=O)C1=CC=C(C=C1)C | [OH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][N:16]([CH3:17])[CH2:18][CH2:19]1.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH3:17])[CH2:18][CH2:19]2)[cH:20][cH:21]1 | CN1CCN(CCCO)CC1.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OCCCN2CCN(C)CC2)cc1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=S(=O)(OCCCN1CCNCC1)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] | null | [] | null | null | 2 | HOUR | A solution of 1-(3-hydroxypropyl)-4-methylpiperazine (2.4 g, 15 mmol), (prepared as described for the starting material in Example 133), in dichloromethane (60 ml) was treated with triethylamine (4.6 ml, 33 mmol) and p-toluenesulphonyl chloride (3.2 g, 17 mmol) and stirred at ambient temperature for 2 hours. The soluti... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.C1C[NH]CC[NH]1 | HCl | ClCCl | null | 2 | CN1CCN(CCCO)CC1.Cc1ccc(S(=O)(=O)Cl)cc1>ClCCl>Cc1ccc(S(=O)(=O)OCCCN2CCN(C)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d9aee196fb0c45a69e6970ec9680d477 | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1>>COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | NC1=C(C(=O)N)C=C(C(=C1)OCC1=CC=CC=C1)OC.CN(C)C=NC=[N+](C)C.[Cl-].C(C)(=O)[O-].[Na+].C(C)(=O)O>>C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH2:8])[c:11]([NH2:10])[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[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:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 0798449d56bc7e7756a703d33bd60780d26c4986e39e1809e15228456c95135b | 3074b6c74bc99545969aa05d42dae7b149d9d6bb1b36a52cec3a362e1e7f7ca0 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[O;D1;H0:7]):[c:8]>>[O;D1;H0:7]=[c;H0;D3;+0:5]1:[nH;D2;+0:6]:[c:9]:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4]:1:[c:8] | 84 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-amino-4-benzyloxy-5-methoxybenzamide (J. Med. Chem. 1977, vol 20, 146–149, 10 g, 0.04 mol) and Gold's reagent (7.4 g, 0.05 mol) in dioxane (100 ml) was stirred and heated at reflux for 24 hours. Sodium acetate (3.02 g, 0.037 mol) and acetic acid (1.65 ml, 0.029 mol) were added to the reaction mixture and... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | Other | O1CCOCC1 | null | null | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1>O1CCOCC1>COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a632f4224c1a43a8b4f45d262cdce4eb | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cl | C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC.S(=O)(Cl)Cl>>Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S([Cl:7])[Cl:22]>>[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:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[ClH:22] | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cl | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(COc2ccc3cncnc3c2)cc1 | O=S(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].O=[c;H0;D3;+0:3]1:[nH;D2;+0:4]:[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10]>>[Cl;H0;D1;+0:2]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10].[ClH;D0;+0:1] | null | [] | null | null | null | null | A mixture of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (2.82 g, 0.01 mol), thionyl chloride (40 ml) and DMF (0.28 ml) was stirred and heated at reflux for 1 hour. The mixture was evaporated and azeotroped with toluene to give 7-benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride (3.45 g).
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | Other | CN(C)C=O | null | null | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>CN(C)C=O>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fdab2a2d61764a5eb1313b4fbd993e77 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc(Cl)cc1F>>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1 | ClC1=CC(=C(C=C1)O)F.Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:20][c:19]2[n:18][cH:17][n:16]1.[OH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[F:15]>>[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]([Cl:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:1... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc(Cl)cc1F | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(COc2ccc3c(Oc4ccccc4)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] | 77 | [{"value": 77.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloro-2-fluoro-phenol (264 mg, 1.8 mmol) was added to a solution of 7-benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride (506 mg, 1.5 mmol) in pyridine (8 ml) and the mixture heated at reflux for 45 minutes. The solvent was removed by evaporation and the residue partitioned between ethyl acetate and water. The or... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | null | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc(Cl)cc1F>N1=CC=CC=C1>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85135f206b204869838501aa1ca971d5 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1>>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC>>ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)O)C=C1)F | c1ccc(C[O:22][c:21]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]([Cl:12])[cH:13][c:14]4[F:15])[n:16][cH:17][n:18][c:19]3[cH:20]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]([Cl:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:19]2[cH:20][c:21]1[OH:22] | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O | null | null | C1(=CC=CC=C1)C.C(=O)(C(F)(F)F)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Oc2ncnc3ccccc23)cc1 | [#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] | 90.7 | [{"value": 90.0, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)O)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)O)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-benzyloxy-4-(4-chloro-2-fluorophenoxy)-6-methoxyquinazoline (451 mg, 1.1 mmol) in TFA (4.5 ml) was heated at reflux for 3 hours. The mixture was diluted with toluene and the volatiles removed by evaporation. The residue was triturated with methylene chloride, collected by filtration, washed with ether a... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccc2ncncc2c1 | Other | C1(=CC=CC=C1)C.C(=O)(C(F)(F)F)O | null | null | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1>C1(=CC=CC=C1)C.C(=O)(C(F)(F)F)O>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc4b8fce3c9d43948548a1d1d49422d6 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.Cc1ccc(S(=O)(=O)OCCCN2CCN(C)CC2)cc1>>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCN(C)CC1 | FC(C(=O)O)(F)F.ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)O)C=C1)F.C([O-])([O-])=O.[K+].[K+].CN1CCN(CC1)CCCOS(=O)(=O)C1=CC=C(C=C1)C>>ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCN(CC2)C)C=C1)F | [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]([Cl:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:19]2[cH:20][c:21]1[OH:22].Cc1ccc(S(=O)(=O)O[CH2:23][CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][N:29]([CH3:30])[CH2:31][CH2:32]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]([Cl:12... | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.Cc1ccc(S(=O)(=O)OCCCN2CCN(C)CC2)cc1 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCN(C)CC1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1ccc(Oc2ncnc3cc(OCCCN4CCNCC4)ccc23)cc1 | C-c1:c:c:c(-S(=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] | 48.1 | [{"value": 48.0, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCN(CC2)C)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.1, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCN(CC2)C)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 5 | HOUR | A mixture of the trifluoroacetic acid salt of 4-(4-chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (3.2 g, 7.4 mmol), potassium carbonate (6.1 g, 44.2 mmol) and 3-(4-methyl-1-piperazinyl)propyl-4-toluene sulphonate (3.0 g, 9.6 mmol) in DMF (60 ml) was stirred at 90° C. for 5 hours and allowed to cool to ambient ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccccc1.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | TsOH.HO- | O.CN(C)C=O | 90 | 5 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.Cc1ccc(S(=O)(=O)OCCCN2CCN(C)CC2)cc1>O.CN(C)C=O>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce966b7d00e34720838fdfe6a72f7ac8 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCN(C)CC1>>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1 | ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCN(CC2)C)C=C1)F.Cl.C(O)([O-])=O.[Na+]>>COC=1C=C2C(NC=NC2=CC1OCCCN1CCN(CC1)C)=O | Fc1cc(Cl)ccc1[O:7][c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]3)[cH:12][c:11]2[n:10][cH:9][n:8]1>>[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][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N... | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCN(C)CC1 | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1 | null | null | null | Functional Group Interconversion | OtherReaction | 2e331e7f987e2f208a7bb6621e9b7dc6ca9e78c94b181dc5496a50196c7c48fe | a99fd2343850f6fbc4a4d7024846a70661aad8ef3f77938589a06d4940f99c06 | O=c1[nH]cnc2cc(OCCCN3CCNCC3)ccc12 | Cl-c1:c:c:c(-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]2:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:2:[c:9]):c(-F):c:1>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 96.7 | [{"value": 96.0, "product": "COC=1C=C2C(NC=NC2=CC1OCCCN1CCN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "COC=1C=C2C(NC=NC2=CC1OCCCN1CCN(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 2 | HOUR | 4-(4-Chloro-2-fluorophenoxy)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (2.6 g, 5.6 mmol) was treated with 2.0 N aqueous hydrochloric acid (45 ml) and the mixture stirred at 95° C. for 2 hours. The mixture was cooled, basified by the addition of solid sodium hydrogen carbonate and the water removed by a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether | null | c1ccccc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HF | null | 95 | 2 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCN(C)CC1>>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d681da44a84f414cbd789e378199dd48 | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 | COC=1C=C2C(NC=NC2=CC1OCCCN1CCN(CC1)C)=O.CN(C)C=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]3)[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][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:2... | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccc(OCCCN3CCNCC3)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] | 53 | [{"value": 53.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-one (2.15 g, 6.48 mmol) was suspended in thionyl chloride (25 ml) and DMF (0.18 ml) and stirred under reflux for 2 hours. The thionyl chloride was evaporated under vacuum and the residue azeotroped twice with toluene. The residue was taken up in wa... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3eddadf507f41a091a405d3f00e1f6e | COCCOCCOc1cc2ncnc(Cl)c2cc1OC.Oc1ccc2cccnc2c1>>COCCOCCOc1cc2ncnc(Oc3ccc4cccnc4c3)c2cc1OC | O.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCOCCOC.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C=CC=NC2=C1>>COC=1C=C2C(=NC=NC2=CC1OCCOCCOC)OC1=CC=C2C=CC=NC2=C1 | Cl[c:15]1[n:14][cH:13][n:12][c:11]2[cH:10][c:9]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][c:27]21.[OH:16][c:17]1[cH:18][cH:19][c:20]2[cH:21][cH:22][cH:23][n:24][c:25]2[cH:26]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][c:11]2[n:12][cH:13][n:14][c:15]([O:16][c... | COCCOCCOc1cc2ncnc(Cl)c2cc1OC.Oc1ccc2cccnc2c1 | COCCOCCOc1cc2ncnc(Oc3ccc4cccnc4c3)c2cc1OC | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4ccccc34)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] | 55 | [{"value": 55.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCOCCOC)OC1=CC=C2C=CC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.9, "product": "COC=1C=C2C(=NC=NC2=CC1OCCOCCOC)OC1=CC=C2C=CC=NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)quinazoline (200 mg, 0.64 mmol), potassium carbonate (102 mg, 0.74 mmol) and 7-hydroxyquinoline (107 mg, 0.74 mmol) in DMSO (5 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient temperature. The mixture was poured into water, washed with di... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2ncccc2c1 | HCl | CS(=O)C | 100 | 5 | COCCOCCOc1cc2ncnc(Cl)c2cc1OC.Oc1ccc2cccnc2c1>CS(=O)C>COCCOCCOc1cc2ncnc(Oc3ccc4cccnc4c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-35ccd4e13712472a93ab2b61e84e6b9f | COCCOCCO.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O>>COCCOCCOc1cc2ncn(COC(=O)C(C)(C)C)c(=O)c2cc1OC | COCCOCCO.N(=NC(=O)OCC)C(=O)OCC.OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>COC=1C=C2C(N(C=NC2=CC1OCCOCCOC)COC(C(C)(C)C)=O)=O | O[CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1].[OH:8][c:9]1[cH:10][c:11]2[n:12][cH:13][n:14]([CH2:15][O:16][C:17](=[O:18])[C:19]([CH3:20])([CH3:21])[CH3:22])[c:23](=[O:24])[c:25]2[cH:26][c:27]1[O:28][CH3:29]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][c:11]2[n:12][cH:13][n:14]([CH2:15][O:16][C:17](... | COCCOCCO.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O | COCCOCCOc1cc2ncn(COC(=O)C(C)(C)C)c(=O)c2cc1OC | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=c1[nH]cnc2ccccc12 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].[#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]-[#8:3]):[c:9] | 106.7 | [{"value": 100.0, "product": "COC=1C=C2C(N(C=NC2=CC1OCCOCCOC)COC(C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.7, "product": "COC=1C=C2C(N(C=NC2=CC1OCCOCCOC)COC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | Diethyl azodicarboxylate (864 μl, 5.5 mmol) was added dropwise to a mixture of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (1.2 g, 3.9 mmol) (prepared as described for the starting material in Example 12), triphenylphosphine (1.44 g, 5.5 mmol) and 2-(2-methoxyethoxy)ethanol (653 μl, 5.5 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1 | HO- | C(Cl)Cl | 0 | 1.5 | COCCOCCO.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O>C(Cl)Cl>COCCOCCOc1cc2ncn(COC(=O)C(C)(C)C)c(=O)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-784e8afcd41e42f19330f8334793a087 | COCCOCCOc1cc2ncn(COC(=O)C(C)(C)C)c(=O)c2cc1OC>>COCCOCCOc1cc2nc[nH]c(=O)c2cc1OC | N.COC=1C=C2C(N(C=NC2=CC1OCCOCCOC)COC(C(C)(C)C)=O)=O.N>>COC=1C=C2C(NC=NC2=CC1OCCOCCOC)=O | CC(C)(C)C(=O)OC[n:14]1[cH:13][n:12][c:11]2[cH:10][c:9]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:19]([O:20][CH3:21])[cH:18][c:17]2[c:15]1=[O:16]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][c:11]2[n:12][cH:13][nH:14][c:15](=[O:16])[c:17]2[cH:18][c:19]1[O:20][CH3:21] | COCCOCCOc1cc2ncn(COC(=O)C(C)(C)C)c(=O)c2cc1OC | COCCOCCOc1cc2nc[nH]c(=O)c2cc1OC | null | null | C(Cl)Cl.C(C)O | Reduction | OtherReaction | 9f6991089c15fc054898797f1d3a42b158e517f125611bc103acfc00878b3b20 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]cnc2ccccc12 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1=[O;D1;H0:7]>>[O;D1;H0:7]=[c:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:[nH;D2;+0:1]:1 | 78 | [{"value": 78.0, "product": "COC=1C=C2C(NC=NC2=CC1OCCOCCOC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.2, "product": "COC=1C=C2C(NC=NC2=CC1OCCOCCOC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Saturated methanolic ammonia (20 ml) was added to a solution of 6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (2.26 g, 5.5 mmol) in a mixture of ethanol (40 ml) and methylene chloride (15 ml). The mixture was stirred for 24 hours at ambient temperature, and further methanol... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HO- | C(Cl)Cl.C(C)O | null | 24 | COCCOCCOc1cc2ncn(COC(=O)C(C)(C)C)c(=O)c2cc1OC>C(Cl)Cl.C(C)O>COCCOCCOc1cc2nc[nH]c(=O)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-30ee7078ab034fc7a1499a0f7c2a6156 | COCCOCCOc1cc2nc[nH]c(=O)c2cc1OC.O=S(Cl)Cl>>COCCOCCOc1cc2ncnc(Cl)c2cc1OC | COC=1C=C2C(NC=NC2=CC1OCCOCCOC)=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCOCCOC | O=[c:15]1[nH:14][cH:13][n:12][c:11]2[cH:10][c:9]([O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[c:19]([O:20][CH3:21])[cH:18][c:17]21.O=S(Cl)[Cl:16]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][c:11]2[n:12][cH:13][n:14][c:15]([Cl:16])[c:17]2[cH:18][c:19]1[O:20][CH3:21] | COCCOCCOc1cc2nc[nH]c(=O)c2cc1OC.O=S(Cl)Cl | COCCOCCOc1cc2ncnc(Cl)c2cc1OC | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncncc2c1 | 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] | 87 | [{"value": 87.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCOCCOC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)-3,4-dihydroquinazolin-4-one (930 mg, 3.16 mmol) in thionyl chloride (15 ml) and DMF (150 μl) was heated at 60° C. for 1.5 hours. The mixture was allowed to cool and the volatiles were removed by evaporation and by azeotroping with toluene. The residue was dissolved ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | CN(C)C=O | null | null | COCCOCCOc1cc2nc[nH]c(=O)c2cc1OC.O=S(Cl)Cl>CN(C)C=O>COCCOCCOc1cc2ncnc(Cl)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6810790b5ad8493290ee02a8938ad3c6 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cc1c[nH]c2ccc(O)cc12>>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].CC1=CNC2=CC=C(C=C12)O>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C(=CNC2=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[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]... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cc1c[nH]c2ccc(O)cc12 | COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)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] | 69.4 | [{"value": 69.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C(=CNC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C(=CNC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (168 mg, 0.5 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (207 mg, 1.5 mmol), 3-methyl-5-hydroxyindole (88 mg, 0.6 mmol), (Can. J. Chem. 1964, 42, 514), and DMA (2.0 ml) was purged with nitrogen for 5 minut... | 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 | 100 | 3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cc1c[nH]c2ccc(O)cc12>CC(=O)N(C)C>COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f62b14e0a79642679a6502437d71f53f | COc1cc2c(Oc3ccccc3)ncnc2cc1O.ClCCN1CCCCC1>>COc1cc2c(Oc3ccccc3)ncnc2cc1OCCN1CCCCC1 | Cl.ClCCN1CCCCC1.OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=CC=C1)OC.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCCN1CCCCC1)OC1=CC=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[n:14][cH:15][n:16][c:17]2[cH:18][c:19]1[OH:20].Cl[CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][CH2:26][CH2:27][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][cH:11][cH:12][cH:13]3)[n:14][cH:15][n:16][c:17]2[cH:18][c:19... | COc1cc2c(Oc3ccccc3)ncnc2cc1O.ClCCN1CCCCC1 | COc1cc2c(Oc3ccccc3)ncnc2cc1OCCN1CCCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(Oc2ncnc3cc(OCCN4CCCCC4)ccc23)cc1 | 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] | 85 | [{"value": 85.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCN1CCCCC1)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.8, "product": "COC=1C=C2C(=NC=NC2=CC1OCCN1CCCCC1)OC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | 1-(2-Chloroethyl)piperidine hydrochloride (0.83 g, 4.5 mmol) was added to 7-hydroxy-6-methoxy-4-phenoxyquinazoline (1.0 g, 3.73 mmol), (prepared as described for the starting material in Example 1), and potassium carbonate (2.6 g, 18.8 mmol) in DMF (30 ml), and the mixture heated at 110° C. for 2.5 hours and allowed to... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CN(C)C=O | 110 | null | COc1cc2c(Oc3ccccc3)ncnc2cc1O.ClCCN1CCCCC1>CN(C)C=O>COc1cc2c(Oc3ccccc3)ncnc2cc1OCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3a79667529d5461bbfecc7604871592f | COc1cc2c(=O)[nH]cnc2cc1OCCN1CCCCC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCN1CCCCC1.Cl | COC=1C=C2C(NC=NC2=CC1OCCN1CCCCC1)=O.S(=O)(Cl)Cl>>Cl.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCCCC1 | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S([Cl:7])[Cl:23]>>[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][CH2:16][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22... | COc1cc2c(=O)[nH]cnc2cc1OCCN1CCCCC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCN1CCCCC1.Cl | null | CN(C)C=O | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccc(OCCN3CCCCC3)cc2n1 | O=S(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].O=[c;H0;D3;+0:3]1:[nH;D2;+0:4]:[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10]>>[Cl;H0;D1;+0:2]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[c:5]:[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10].[ClH;D0;+0:1] | null | [] | null | null | null | null | A mixture of 6-methoxy-7-(2-piperidinoethoxy)-3,4-dihydroquinazolin-4-one (440 mg, 1.45 mmol), thionyl chloride (15 ml) and DMF (3 drops) was heated at reflux for 3 hours then allowed to cool. The excess thionyl chloride was removed by evaporation and the residue was azeotroped with toluene to give a crude 4-chloro-6-m... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | Other | CN(C)C=O | null | null | COc1cc2c(=O)[nH]cnc2cc1OCCN1CCCCC1.O=S(Cl)Cl>CN(C)C=O>COc1cc2c(Cl)ncnc2cc1OCCN1CCCCC1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ea6bc0fd8994e49ab3fba60f5e7f91b | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1cnc2[nH]ccc2c1>>COc1cc2c(Oc3cnc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.OC=1C=C2C(=NC1)NC=C2.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)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]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:15]4[cH:1... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1cnc2[nH]ccc2c1 | COc1cc2c(Oc3cnc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCC1 | null | null | ClCCl.CO.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2cnc3[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].[#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] | 18 | [{"value": 18.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C(=NC1)NC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.5, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C(=NC1)NC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 6 | 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), 5-hydroxy-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.75 mmol) and potassium carbonate (280 mg, 2.0 mmol) in DMF (4 ml) was stirred at 95° C. for 6 hours and allowed to... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1cnc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | ClCCl.CO.CN(C)C=O | 95 | 6 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1cnc2[nH]ccc2c1>ClCCl.CO.CN(C)C=O>COc1cc2c(Oc3cnc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1fd4ad30bad489e975d720d33a26162 | COc1cnc2[nH]ccc2c1>>Oc1cnc2[nH]ccc2c1 | [OH-].[Na+].B(Br)(Br)Br.COC=1C=C2C(=NC1)NC=C2>>OC=1C=C2C(=NC1)NC=C2 | C[O:1][c:2]1[cH:3][n:4][c:5]2[nH:6][cH:7][cH:8][c:9]2[cH:10]1>>[OH:1][c:2]1[cH:3][n:4][c:5]2[nH:6][cH:7][cH:8][c:9]2[cH:10]1 | COc1cnc2[nH]ccc2c1 | Oc1cnc2[nH]ccc2c1 | null | null | ClCCl.O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1cnc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 57 | [{"value": 57.0, "product": "OC=1C=C2C(=NC1)NC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.7, "product": "OC=1C=C2C(=NC1)NC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 5-methoxy-1H-pyrrolo[2,3-b]pyridine (210 mg, 1.42 mmol), (Heterocycles 50, (2), 1065–1080, (1999)), in dichloromethane (10 ml) was stirred in an inert atmosphere, a 1.0M solution of boron tribromide in dichloromethane (4.3 ml, 4.3 mmol) added dropwise and the mixture stirred at ambient temperature overn... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cnc2[nH]ccc2c1 | Other | ClCCl.O | null | null | COc1cnc2[nH]ccc2c1>ClCCl.O>Oc1cnc2[nH]ccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ac2b6b888ce48e0b972662119896213 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.O=C(O)c1cc2cc(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C(=O)O)cc4c3)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC=1C=C2C=C(NC2=CC1)C(=O)O>>C(=O)(O)C=1NC2=CC=C(C=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: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:21][n:20]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][c:18]2[cH:19]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... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.O=C(O)c1cc2cc(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C(=O)O)cc4c3)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] | 36 | [{"value": 36.0, "product": "C(=O)(O)C=1NC2=CC=C(C=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.7, "product": "C(=O)(O)C=1NC2=CC=C(C=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (168 mg, 0.5 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (345 mg, 5.0 mmol), 5-hydroxy-2-indolecarboxylic acid (106 mg, 0.6 mmol) and DMA (2.0 ml) was purged with nitrogen for 5 minutes at 25° C. This mixt... | 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 | 100 | 3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.O=C(O)c1cc2cc(O)ccc2[nH]1>CC(=O)N(C)C>COc1cc2c(Oc3ccc4[nH]c(C(=O)O)cc4c3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1fbb2e166abe4a4db5cbd7ef9f602cf1 | COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O.Oc1ccc2cccnc2c1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCS(C)(=O)=O | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)C.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C=CC=NC2=C1>>COC=1C=C2C(=NC=NC2=CC1OCCCS(=O)(=O)C)OC1=CC=C2C=CC=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][S:28]([CH3:29])(=[O:30])=[O:31])[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][cH: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][cH:13][cH:14][n:15][c:16]... | COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O.Oc1ccc2cccnc2c1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCS(C)(=O)=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4ccccc34)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] | 81.4 | [{"value": 81.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCS(=O)(=O)C)OC1=CC=C2C=CC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCS(=O)(=O)C)OC1=CC=C2C=CC=NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | 4-Chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (0.15 g, 0.45 mmol), (prepared as described for the starting material in Example 50), potassium carbonate (94 mg, 0.68 mmol) and 7-hydroxyquinoline (79 mg, 0.54 mmol) were suspended in anhydrous DMF (1.5 ml) and heated to 90° C. overnight. The compound was prec... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1 | HCl | CN(C)C=O | 90 | null | COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O.Oc1ccc2cccnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1131f735f61548db8b31112a26f39582 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2nc(Cl)[nH]c2c1>>COc1cc2c(Oc3ccc4nc(Cl)[nH]c4c3)ncnc2cc1OCC1CCN(C)CC1 | [Cl-].[NH4+].ClC=1NC2=C(N1)C=CC(=C2)O.[H-].[Na+].ClC=1NC2=C(N1)C=CC(=C2)O.[H-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C>>ClC1=NC2=C(N1)C=C(C=C2)OC2=NC=NC1=CC(=C(C=C21)OC)OCC2CCN(CC2)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([CH3:30])[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[n:12][c:13]([Cl:14])[nH: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[n:12][c:13]([Cl:14])[n... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2nc(Cl)[nH]c2c1 | COc1cc2c(Oc3ccc4nc(Cl)[nH]c4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | ClCCl.CO.CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3nc[nH]c3c2)c2ccc(OCC3CCNCC3)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] | 16.3 | [{"value": 16.0, "product": "ClC1=NC2=C(N1)C=C(C=C2)OC2=NC=NC1=CC(=C(C=C21)OC)OCC2CCN(CC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.3, "product": "ClC1=NC2=C(N1)C=C(C=C2)OC2=NC=NC1=CC(=C(C=C21)OC)OCC2CCN(CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1 | HOUR | To a portion of 2-chloro-5-hydroxybenzimidazole (191 mg, 0.75 mmol) in DMF (3 ml) was added sodium hydride (60 mg, 1.5 mmol) under argon at ambient temperature. Ten minutes later 4-chloro-6-methoxy-7-(1-methylpiperidin-4-yl)methoxyquinazoline (200 mg, 0.62 mmol), (prepared as described for the starting material in Exam... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]cnc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | ClCCl.CO.CN(C)C=O.C(C)(=O)OCC | 100 | 1 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2nc(Cl)[nH]c2c1>ClCCl.CO.CN(C)C=O.C(C)(=O)OCC>COc1cc2c(Oc3ccc4nc(Cl)[nH]c4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bbbd1dbdf3be47caba036b8ede78a409 | COc1ccc2nc(Cl)[nH]c2c1>>Oc1ccc2nc(Cl)[nH]c2c1 | ClC=1NC2=C(N1)C=CC(=C2)OC.B(Br)(Br)Br>>ClC=1NC2=C(N1)C=CC(=C2)O | C[O:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([Cl:8])[nH:9][c:10]2[cH:11]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([Cl:8])[nH:9][c:10]2[cH:11]1 | COc1ccc2nc(Cl)[nH]c2c1 | Oc1ccc2nc(Cl)[nH]c2c1 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]cnc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 159.1 | [{"value": 99.0, "product": "ClC=1NC2=C(N1)C=CC(=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 159.1, "product": "ClC=1NC2=C(N1)C=CC(=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2-Chloro-5-methoxybenzimidazole (0.3 g, 1.64 mmol) was suspended in dichloromethane (20 ml) under argon followed by the addition of boron tribromide (233 ul, 2.46 mmol). The reaction mixture was stirred for 2 hours at ambient temperature. The solvent was evaporated and the resulting powder was added in portions to meth... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]cnc2c1 | Other | ClCCl | null | 2 | COc1ccc2nc(Cl)[nH]c2c1>ClCCl>Oc1ccc2nc(Cl)[nH]c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bc76adc5b0bd4925b3e61eaf2710b807 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1nc2ccc(O)cc2[nH]1>>COc1cc2c(Oc3ccc4nc(C)[nH]c4c3)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.OC1=CC2=C(N=C(N2)C)C=C1>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=CC2=C(NC(=N2)C)C1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([CH3:30])[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[n:12][c:13]([CH3:14])[nH: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[n:12][c:13]([CH3:14])... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1nc2ccc(O)cc2[nH]1 | COc1cc2c(Oc3ccc4nc(C)[nH]c4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3nc[nH]c3c2)c2ccc(OCC3CCNCC3)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] | 25 | [{"value": 25.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=CC2=C(NC(=N2)C)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 189, 4-chloro-6-methoxy-7-(1-methylpiperidin-4-yl)methoxyquinazoline, (prepared as described for the starting material in Example 10); was reacted with 5-hydroxy-2-methylbenzimidazole (200 mg, 0.62 mmol) and after work-up and purification on a 10 g silica ISOLUT... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]cnc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1nc2ccc(O)cc2[nH]1>>COc1cc2c(Oc3ccc4nc(C)[nH]c4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-41d9e16042814ca791d6477877ee112e | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.N#Cc1cnc2cc(O)ccc2c1>>COc1cc2c(Oc3ccc4cc(C#N)cnc4c3)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.C(#N)C=1C=NC2=CC(=CC=C2C1)O.C([O-])([O-])=O.[K+].[K+]>>C(#N)C=1C=NC2=CC(=CC=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH2:27][CH:28]3[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]3)[cH:24][c:23]2[n:22][cH:21][n:20]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][c:13]([C:14]#[N:15])[cH:16][n:17][c:18]2[cH:19]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)ncnc2cc1OCC1CCN(C)CC1.N#Cc1cnc2cc(O)ccc2c1 | COc1cc2c(Oc3ccc4cc(C#N)cnc4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | ClCCl.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCC5CCNCC5)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] | 86.4 | [{"value": 86.0, "product": "C(#N)C=1C=NC2=CC(=CC=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "C(#N)C=1C=NC2=CC(=CC=C2C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | 4-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (200 mg, 0.62 mmol), (prepared as described for the starting material in Example 10), was suspended in DMF (3 ml) under argon. 3-Cyano-7-hydroxyquinoline (116 mg, 0.68 mmol) and potassium carbonate (129 mg, 0.93 mmol) were added and the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | ClCCl.CN(C)C=O | 95 | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.N#Cc1cnc2cc(O)ccc2c1>ClCCl.CN(C)C=O>COc1cc2c(Oc3ccc4cc(C#N)cnc4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07f135c27d114ba88260201d5ae6735d | CCOC(=O)c1c[nH]c2cc(OC)ccc2c1=O.O=P(Cl)(Cl)Cl>>CCOC(=O)c1cnc2cc(OC)ccc2c1Cl | P(=O)(Cl)(Cl)Cl.COC1=CC=C2C(C(=CNC2=C1)C(=O)OCC)=O>>ClC1=C(C=NC2=CC(=CC=C12)OC)C(=O)OCC | O=[c:17]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][nH:8][c:9]2[cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15][c:16]21.O=P(Cl)(Cl)[Cl:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15][c:16]2[c:17]1[Cl:18] | CCOC(=O)c1c[nH]c2cc(OC)ccc2c1=O.O=P(Cl)(Cl)Cl | CCOC(=O)c1cnc2cc(OC)ccc2c1Cl | null | null | null | Functional Group Interconversion | OtherReaction | cc4352f89fc20313a06e82f7021393e5d431acffd8627b85ca094d4e9dc6ea22 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[nH;D2;+0:7]:[c:8]:[c:9]:1-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:13]-[#8:12]-[C:10](=[O;D1;H0:11])-[c:9]1:[c:8]:[n;H0;D2;+0:7]:[c:5](:[c:6]):[c:3](:[c:4]):[c;H0;D3;+0:2]:1-[Cl;H0;D1;+0:1] | 73 | [{"value": 73.0, "product": "ClC1=C(C=NC2=CC(=CC=C12)OC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Phosphorus oxychloride (88 ml) was added to ethyl 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (58 g, 235 mmol) and the mixture was heated at reflux for 45 minutes under anhydrous conditions. Upon cooling to ambient temperature, phosphorus oxychloride was evaporated and the solid residue was added in portions to ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cc2ccccc2nc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | null | null | null | CCOC(=O)c1c[nH]c2cc(OC)ccc2c1=O.O=P(Cl)(Cl)Cl>>CCOC(=O)c1cnc2cc(OC)ccc2c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9ba942eb8037492287f433c1fa78f7e6 | CCOC(=O)c1cnc2cc(OC)ccc2c1Cl>>CCOC(=O)c1cnc2cc(OC)ccc2c1 | ClC1=C(C=NC2=CC(=CC=C12)OC)C(=O)OCC>>C(C)OC(=O)C=1C=NC2=CC(=CC=C2C1)OC | Cl[c:17]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]2[cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15][c:16]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[cH:10][c:11]([O:12][CH3:13])[cH:14][cH:15][c:16]2[cH:17]1 | CCOC(=O)c1cnc2cc(OC)ccc2c1Cl | CCOC(=O)c1cnc2cc(OC)ccc2c1 | null | [Pd] | C(C)(=O)O | Functional Group Interconversion | Aromatic dehalogenation | 9d8b09641537c9b7067a6060cf65ecd110c7af466a7b229ce3601533f966554e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[C:12]-[#8:11]-[C:9](=[O;D1;H0:10])-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[cH;D2;+0:1]:1 | 88.1 | [{"value": 88.0, "product": "C(C)OC(=O)C=1C=NC2=CC(=CC=C2C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.1, "product": "C(C)OC(=O)C=1C=NC2=CC(=CC=C2C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloro-3-ethoxycarbonyl-7-methoxyquinoline (43 g, 162 mmol) was dissolved in acetic acid (250 ml), with 10% palladium on charcoal (1.5 g) and hydrogenated at atmospheric pressure during 8 hours. The catalyst was removed by filtration over a pad of celite and the solvent evaporated. The residue was diluted with water ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | Other | [Pd].C(C)(=O)O | null | null | CCOC(=O)c1cnc2cc(OC)ccc2c1Cl>[Pd].C(C)(=O)O>CCOC(=O)c1cnc2cc(OC)ccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d15a52796345473fb1230ff9d45ea3ac | CCOC(=O)c1cnc2cc(OC)ccc2c1.N>>COc1ccc2cc(C(N)=O)cnc2c1 | C(C)OC(=O)C=1C=NC2=CC(=CC=C2C1)OC.N>>C(N)(=O)C=1C=NC2=CC(=CC=C2C1)OC | CCO[C:9]([c:8]1[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15][c:14]2[n:13][cH:12]1)=[O:11].[NH3:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C:9]([NH2:10])=[O:11])[cH:12][n:13][c:14]2[cH:15]1 | CCOC(=O)c1cnc2cc(OC)ccc2c1.N | COc1ccc2cc(C(N)=O)cnc2c1 | null | null | CO | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc2ncccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[NH3;D0;+0:8]>>[NH2;D1;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 86 | [{"value": 86.0, "product": "C(N)(=O)C=1C=NC2=CC(=CC=C2C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Ethoxycarbonyl-7-methoxyquinoline (28 g, 120 mmol) was added to a methanol solution saturated with ammonia. The suspension was stirred at ambient temperature in a glass pressure vessel for 2 weeks. The white solid was collected by filtration, washed with methanol and dried under vacuum to give 3-carbamoyl-7-methoxyqu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccc2ncccc2c1 | HO- | CO | null | null | CCOC(=O)c1cnc2cc(OC)ccc2c1.N>CO>COc1ccc2cc(C(N)=O)cnc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d77e5cc83ad471fa04f88e630a77a28 | COc1ccc2cc(C#N)cnc2c1>>N#Cc1cnc2cc(O)ccc2c1 | C(#N)C=1C=NC2=CC(=CC=C2C1)OC.[Cl-].[Cl-].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Al+3]>>C(#N)C=1C=NC2=CC(=CC=C2C1)O | C[O:9][c:8]1[cH:7][c:6]2[n:5][cH:4][c:3]([C:2]#[N:1])[cH:13][c:12]2[cH:11][cH:10]1>>[N:1]#[C:2][c:3]1[cH:4][n:5][c:6]2[cH:7][c:8]([OH:9])[cH:10][cH:11][c:12]2[cH:13]1 | COc1ccc2cc(C#N)cnc2c1 | N#Cc1cnc2cc(O)ccc2c1 | null | null | C1=CC=CC=C1 | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2ncccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 68 | [{"value": 68.0, "product": "C(#N)C=1C=NC2=CC(=CC=C2C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "C(#N)C=1C=NC2=CC(=CC=C2C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 3-Cyano-7-methoxyquinoline (380 mg, 2.1 mmol) was suspended in benzene (10 ml), aluminium trichloride (826 mg, 6.2 mmol) was added and the mixture heated at reflux for 30 minutes. More aluminium trichloride (275 mg, 2.1 mmol) was added and the mixture refluxed for a further 2 hours. The solvent was evaporated, the dark... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2ncccc2c1 | Other | C1=CC=CC=C1 | null | 1 | COc1ccc2cc(C#N)cnc2c1>C1=CC=CC=C1>N#Cc1cnc2cc(O)ccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fda18e06f8a245eea32abe311f47265c | COc1cc2c(Oc3ccc4c(c3)CCCN4C(=O)OC(C)(C)C)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Oc3ccc4c(c3)CCCN4)ncnc2cc1OCCCN1CCOCC1 | COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2CCCN(C2=CC1)C(=O)OC(C)(C)C.C(=O)(C(F)(F)F)O>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2CCCNC2=CC1 | CC(C)(C)OC(=O)[N:17]1[c:11]2[cH:10][cH:9][c:8]([O:7][c:6]3[c:5]4[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]5[CH2:29][CH2:30][O:31][CH2:32][CH2:33]5)[cH:22][c:21]4[n:20][cH:19][n:18]3)[cH:13][c:12]2[CH2:14][CH2:15][CH2:16]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:1... | COc1cc2c(Oc3ccc4c(c3)CCCN4C(=O)OC(C)(C)C)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Oc3ccc4c(c3)CCCN4)ncnc2cc1OCCCN1CCOCC1 | null | null | ClCCl | Reduction | Boc amine deprotection | 63a5111cf3995bded3c99cc3b367a6b550d62d47f4aaa59e59daddf6b3bfb17f | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1nc(Oc2ccc3c(c2)CCCN3)c2ccc(OCCCN3CCOCC3)cc2n1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6]>>[C:3]-[C:2]-[NH;D2;+0:1]-[c:4](:[c:5]):[c:6] | 93.2 | [{"value": 93.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2CCCNC2=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2CCCNC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To 6-methoxy-7-(3-morpholinopropoxy)-4-((1-tertbutoxycarbonyl-1,2,3,4-tetrahydroquinolin-6-yl)oxy)quinazoline (110 mg, 0.2 mmol) in solution in dichloromethane (3 ml) was added TFA (0.3 ml) and the mixture stirred for 1 hour at ambient temperature. The solvents were evaporated and the remaining oil was diluted with dic... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2.c1ccc2ncncc2c1.C1COCC[NH]1 | HO- | ClCCl | null | 1 | COc1cc2c(Oc3ccc4c(c3)CCCN4C(=O)OC(C)(C)C)ncnc2cc1OCCCN1CCOCC1>ClCCl>COc1cc2c(Oc3ccc4c(c3)CCCN4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3cc2a4e687ea4f5dbc359a8d76ea9b1e | CC(C)(C)OC(=O)N1CCCc2ccccc21.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Oc3ccc4c(c3)CCCN4C(=O)OC(C)(C)C)ncnc2cc1OCCCN1CCOCC1 | [H-].[Na+].C(C)(C)(C)OC(=O)N1CCCC2=CC=CC=C12.C([O-])([O-])=O.[K+].[K+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2CCCN(C2=CC1)C(=O)OC(C)(C)C | [cH:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[CH2:14][CH2:15][CH2:16][N:17]2[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24].Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)[cH:29][c:28]2[n:27][cH:26][n:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[... | CC(C)(C)OC(=O)N1CCCc2ccccc21.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Oc3ccc4c(c3)CCCN4C(=O)OC(C)(C)C)ncnc2cc1OCCCN1CCOCC1 | null | null | O.CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | d1e86c021d9691a031f3e2141033c42b687d8c898d5b5a9f7608064ec8f667d6 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1nc(Oc2ccc3c(c2)CCCN3)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].[c:9]:[c:10]:[cH;D2;+0:11]:[c:12]:[c:13]>>[c:9]:[c:10]:[c;H0;D3;+0:11](-[#8:14]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12]:[c:13] | 71 | [{"value": 71.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2CCCN(C2=CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2CCCN(C2=CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 2 | HOUR | 6-Hydroxy-4-(1-tertbutoxycarbonyl-1,2,3,4-tetrahydroquinoline (82 mg, 0.32 mmol) was dissolved in anhydrous dimethylformamide under argon, with potassium carbonate (61 mg, 0.44 mmol) and 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (100 mg, 0.3m mmol), (prepared as described for the starting material in Exampl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccc2c(c1)CCC[NH]2.c1ccc2ncncc2c1 | c1ccc2c(c1)CCC[NH]2.c1ccc2ncncc2c1 | c1ccc2c(c1)CCC[NH]2.c1ccc2ncncc2c1.C1COCC[NH]1 | null | O.CN(C=O)C.C(C)(=O)OCC | 120 | 2 | CC(C)(C)OC(=O)N1CCCc2ccccc21.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>O.CN(C=O)C.C(C)(=O)OCC>COc1cc2c(Oc3ccc4c(c3)CCCN4C(=O)OC(C)(C)C)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3489e772959c456aaf5a183afd3c8cc5 | Oc1ccc2[nH]ccc2c1>>Oc1ccc2c(c1)CCN2 | OC=1C=C2C=CNC2=CC1.C(#N)[BH3-].[Na+].B(F)(F)F.CCOCC>>OC=1C=C2CCNC2=CC1 | [OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[cH:8][cH:9][nH:10]2>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][NH:10]2 | Oc1ccc2[nH]ccc2c1 | Oc1ccc2c(c1)CCN2 | null | null | CO | Reduction | OtherReaction | d7c64ff5bdeff25897e9ebfc8baf5f34c2f69037fd4e91a3394e3e20a554de0e | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc2c(c1)CCN2 | [c:1]:[c:2]1:[nH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6]:1:[c:7]>>[c:1]:[c:2]1:[c:6](:[c:7])-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[NH;D2;+0:3]-1 | 73 | [{"value": 73.0, "product": "OC=1C=C2CCNC2=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.5, "product": "OC=1C=C2CCNC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Hydroxyindole (2 g, 15 mmol) was dissolved in methanol (60 ml) under argon. Sodium cyanoborohydride (1.89 g, 30 mmol) and trifluoroboron etherate (4.2 ml, 33 mmol) were added and the mixture was heated at reflux for 3 hours then left to cool to ambient temperature. The solvent was evaporated and the residue was parti... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | null | CO | null | null | Oc1ccc2[nH]ccc2c1>CO>Oc1ccc2c(c1)CCN2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-158a12b79f5b44e38fc23b2c74c8bc3c | COc1cc2c(Cl)ncnc2cc1OCCN1CCCCC1.Oc1ccc2cccnc2c1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C=CC=NC2=C1.[OH-].[Na+]>>COC=1C=C2C(=NC=NC2=CC1OCCN1CCCCC1)OC1=CC=C2C=CC=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][N:27]3[CH2:28][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[cH:12][cH: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][cH:13][cH:14][n:1... | COc1cc2c(Cl)ncnc2cc1OCCN1CCCCC1.Oc1ccc2cccnc2c1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCN1CCCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCCN5CCCCC5)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] | 75 | [{"value": 75.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCN1CCCCC1)OC1=CC=C2C=CC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCCN1CCCCC1)OC1=CC=C2C=CC=NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-chloro-6-methoxy-7-(2-piperidinoethoxy)quinazoline (250 mg, 0.78 mmol), (prepared as described for the starting material in Example 180), in DMF (10 ml) was added anhydrous potassium carbonate (320 mg, 2.30 mmol) and 7-hydroxyquinoline (135 mg, 0.94 mmol), and the reaction heated under reflux at 90... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CN(C)C=O | null | null | COc1cc2c(Cl)ncnc2cc1OCCN1CCCCC1.Oc1ccc2cccnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2c124acdf06481b890ccc98250d1680 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc2cccnc2c1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C=CC=NC2=C1.[OH-].[Na+]>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)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[cH:12][cH: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][cH:13][cH:14][n:15][c:16]4[cH:... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc2cccnc2c1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(COc2ccc3c(Oc4ccc5cccnc5c4)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].[#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] | 60.7 | [{"value": 60.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 7-benzyloxy-4-chloro-6-methoxyquinazoline (1.82 g, 6.1 mmol), (prepared as described for the starting material in Example 1), in DMF (50 ml) was added potassium carbonate (2.50 g, 18.1 mmol) and 7-hydroxyquinoline (1.06 g, 7.3 mmol), and the reaction heated under reflux at 90C for 4 hours. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CN(C)C=O | null | null | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc2cccnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5fcd951e2bcd4620b62c72f848929a18 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1O | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)OC>>OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)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[cH:12][cH:13][cH:14][n: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[cH:12][cH:13][cH:14][n:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]... | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCc1ccccc1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1O | null | null | FC(C(=O)O)(F)F | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1cnc2cc(Oc3ncnc4ccccc34)ccc2c1 | [#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] | 76.2 | [{"value": 76.0, "product": "OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.2, "product": "OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-benzyloxy-6-methoxy-4-(quinolin-7-yloxy)quinazoline (1.50 g, 3.70 mmol), (prepared as described in Example 196), in trifluoroacetic acid (50 ml) was heated at reflux for 150 minutes. The reaction was concentrated in vacuo and the reaction neutralised with saturated aqueous ammonium hydroxide. The result... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2ncccc2c1.c1ccc2ncncc2c1 | Other | FC(C(=O)O)(F)F | null | null | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCc1ccccc1>FC(C(=O)O)(F)F>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f583c55c70a04babaa0b691d44c7be83 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1O.OCCN1CCOCC1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCN1CCOCC1 | OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)OC.C([O-])([O-])=O.[K+].[K+].OCCN1CCOCC1>>COC=1C=C2C(=NC=NC2=CC1OCCN1CCOCC1)OC1=CC=C2C=CC=NC2=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[cH:12][cH:13][cH:14][n:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].O[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[cH:12][cH:13][cH:14][n:15][c:... | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1O.OCCN1CCOCC1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1cnc2cc(Oc3ncnc4cc(OCCN5CCOCC5)ccc34)ccc2c1 | 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] | 71.4 | [{"value": 71.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCN1CCOCC1)OC1=CC=C2C=CC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCCN1CCOCC1)OC1=CC=C2C=CC=NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 7-hydroxy-6-methoxy-4-(quinolin-7-yloxy)quinazoline (450 mg, 1.40 mmol), (prepared as described in Example 197), in DMF (50 ml) was added anhydrous potassium carbonate (773 mg, 5.60 mmol) and 4-(2-hydroxyethyl)morpholine (335 mg, 1.80 mmol), and the reaction heated under reflux for 2 hours. The DMF w... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HO- | CN(C)C=O | null | null | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1O.OCCN1CCOCC1>CN(C)C=O>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-08221d9b796a49a8a40abe09d42df29c | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2c(c1)[nH]c1ccccc12>>c1ccc2ncncc2c1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.C([O-])([O-])=O.[K+].[K+].OC1=CC=2NC3=CC=CC=C3C2C=C1>>N1=CN=CC2=CC=CC=C12 | COc1c[c:9]2[c:4]([cH:3]c1OCCCN1CCCC1)[n:5][cH:6][n:7][c:8]2Cl.Oc1ccc2c(c1)[nH]c1c2c[cH:2][cH:1][cH:10]1>>[cH:1]1[cH:2][cH:3][c:4]2[n:5][cH:6][n:7][cH:8][c:9]2[cH:10]1 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2c(c1)[nH]c1ccccc12 | c1ccc2ncncc2c1 | null | null | CN(C)C=O | Miscellaneous | OtherReaction | eea6960b165e3bf92b393c08034a1c42b74c18cdc7433f4b91dbdb50543482d2 | a6c856a27352a45ad86c0cc2b6f73864c00de75080ef629d9dcc8701b1adc73c | c1ccc2ncncc2c1 | C-O-c1:c:[c;H0;D3;+0:1]2:[c:2](:[#7;a:3]:[c:4]:[#7;a:5]:[c;H0;D3;+0:6]:2-Cl):[cH;D2;+0:7]:c:1-O-C-C-C-N1-C-C-C-C-1.O-c1:c:c:c2:c(:[nH]:c3:[cH;D2;+0:8]:[c:9]:[cH;D2;+0:10]:c:c:3:2):c:1>>[#7;a:3]1:[c:4]:[#7;a:5]:[cH;D2;+0:6]:[c;H0;D3;+0:1]2:[cH;D2;+0:8]:[c:9]:[cH;D2;+0:10]:[cH;D2;+0:7]:[c:2]:1:2 | 76.8 | [{"value": 22.0, "product": "N1=CN=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.8, "product": "N1=CN=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (100 mg, 0.31 mmol), (prepared as described for the starting material in Example 9), in DMF (10 ml) was added potassium carbonate (124 mg, 0.9 mmol, 3eq.) followed by 2-hydroxycarbazole (66 mg, 0.36 mmol, 1.2eq.) and the reaction heated at 10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Aromatic alcohol.Tertiary amine | null | C1CCNC1.c1ccc2ncncc2c1.c1ccc2c(c1)[nH]c1ccccc12 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | CN(C)C=O | 100 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2c(c1)[nH]c1ccccc12>CN(C)C=O>c1ccc2ncncc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-01d532ea73d146a0826d5a2a83c5d8b3 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Nc1ccc2[nH]ccc2c1>>COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1 | Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC.NC=1C=C2C=CNC2=CC1>>Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=CNC2=CC1)OC | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]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[cH:16]3)[n:17... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Nc1ccc2[nH]ccc2c1 | COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc3c(Nc4ccc5[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].[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] | 96 | [{"value": 96.0, "product": "Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=CNC2=CC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.0, "product": "Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=CNC2=CC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-benzyloxy-4-chloro-6-methoxyquinazoline (5 g, 16.6 mmol), (prepared as described for the starting material in Example 1), 5-aminoindole (2.4 g, 18.2 mmol) in isopropanol (60 ml) containing 5N hydrogen chloride in isopropanol (260 μl, 1.6 mmol) was refluxed for 90 minutes. After cooling the volatiles wer... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ccccc1 | HCl | C(C)(C)O | null | null | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Nc1ccc2[nH]ccc2c1>C(C)(C)O>COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e850a844177148f189cf982822d768bf | COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1O | Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=CNC2=CC1)OC.C(=O)[O-].[NH4+]>>OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=CNC2=CC1)OC | c1ccc(C[O:23][c:22]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([NH:7][c:8]4[cH:9][cH:10][c:11]5[nH:12][cH:13][cH:14][c:15]5[cH:16]4)[n:17][cH:18][n:19][c:20]3[cH:21]2)cc1>>[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[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[OH:23] | COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1 | COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1O | null | [Pd] | CN(C)C=O.CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(Nc3ccc4[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] | 97 | [{"value": 97.0, "product": "OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=CNC2=CC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.1, "product": "OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=CNC2=CC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of give 7-benzyloxy-4-(indol-5-ylamino)-6-methoxyquinazoline hydrochloride (10 g, 23.1 mmol) in methanol (300 ml) and DMF (100 ml) containing ammonium formate (22gr, 347 mmol) and 10% palladium on charcoal (1 g) was stirred overnight at ambient temperature. The solution was filtered over celite and washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | Other | [Pd].CN(C)C=O.CO | null | 8 | COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1>[Pd].CN(C)C=O.CO>COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-14091c5c560c40b28422ab56234f92cf | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.OCCCN1CCOCC1>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCOCC1 | N(=NC(=O)OCC)C(=O)OCC.OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=C(NC2=CC1)C)OC.OCCCN1CCOCC1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)NC=1C=C2C=C(NC2=CC1)C | [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][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].O[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]([NH:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH... | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.OCCCN1CCOCC1 | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O.C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1nc(Nc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCOCC3)cc2n1 | O-[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] | 44 | [{"value": 44.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)NC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)NC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 4 | CELSIUS | 8 | HOUR | To a solution of 7-hydroxy-6-methoxy-4-(2-methylindol-5-ylamino)quinazoline (102 mg, 0.32 mmol), 4-(3-hydroxypropyl)morpholine (70 mg, 0.48 mmol), (prepared as described for the starting material in Example 60), triphenylphosphine (168 mg, 0.64 mmol) in methylene chloride (1 ml) and DMF (0.5 ml) cooled at 4° C. was add... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HO- | CN(C)C=O.C(Cl)Cl | 4 | 8 | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.OCCCN1CCOCC1>CN(C)C=O.C(Cl)Cl>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e61ba6285aad4ead92197c8467d7a3f8 | Cc1cc2cc([N+](=O)[O-])ccc2[nH]1>>Cc1cc2cc(N)ccc2[nH]1 | CC=1NC2=CC=C(C=C2C1)[N+](=O)[O-].[H][H]>>NC=1C=C2C=C(NC2=CC1)C | O=[N+:7]([O-])[c:6]1[cH:5][c:4]2[cH:3][c:2]([CH3:1])[nH:11][c:10]2[cH:9][cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([NH2:7])[cH:8][cH:9][c:10]2[nH:11]1 | Cc1cc2cc([N+](=O)[O-])ccc2[nH]1 | Cc1cc2cc(N)ccc2[nH]1 | null | [Pd] | C(C)O.C1CCOC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2[nH]ccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.6 | [{"value": 99.6, "product": "NC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-methyl-5-nitroindole (1 g, 5.7 mmol) in ethanol (25 ml) and THF (25 ml) containg 10% palladium on charcoal (128 mg) was hydrogenated until uptake of hydrogen ceased. The mixture was filtered and the filtrate was evaporated to give 5-amino-2-methylindole (830 mg, quant.).
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2[nH]ccc2c1 | Other | [Pd].C(C)O.C1CCOC1 | null | null | Cc1cc2cc([N+](=O)[O-])ccc2[nH]1>[Pd].C(C)O.C1CCOC1>Cc1cc2cc(N)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-70f646d849c74153943d343f766c23b5 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1cc2cc(N)ccc2[nH]1>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1.Cl | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC.NC=1C=C2C=C(NC2=CC1)C>>Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=C(NC2=CC1)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:32])[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.[NH2:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][c:13]([CH3:14])[cH:15][c:16]2[cH:17]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][c:13]([CH3:14])[cH:15]... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1cc2cc(N)ccc2[nH]1 | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1.Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc3c(Nc4ccc5[nH]ccc5c4)ncnc3c2)cc1 | [Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[ClH;D0;+0:1].[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]):[c:13] | 98.3 | [{"value": 98.3, "product": "Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=C(NC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described for the synthesis of the starting material in Example 201, 7-benzyloxy-4-chloro-6-methoxyquinazoline (2 g, 6.6 mmol), (prepared as described for the starting material in Example 1), was reacted with 5-amino-2-methylindole (1.07 g, 7.3 mmol) to give 7-benzyloxy-6-methoxy-4-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ccccc1 | null | null | null | null | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1cc2cc(N)ccc2[nH]1>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2e43e8ff57224e7fac9a2fab2e7da5a0 | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1O | Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=C(NC2=CC1)C)OC.C(=O)[O-].[NH4+]>>OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=C(NC2=CC1)C)OC | c1ccc(C[O:24][c:23]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([NH:7][c:8]4[cH:9][cH:10][c:11]5[nH:12][c:13]([CH3:14])[cH: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]([NH: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:2... | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1 | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1O | null | null | null | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(Nc3ccc4[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] | 93.2 | [{"value": 93.0, "product": "OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=C(NC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=C(NC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described for the synthesis of the starting material in Example 201, 7-benzyloxy-6-methoxy-4-(2-methylindol-5-ylamino)quinazoline hydrochloride (2.87 g, 6.4 mmol) was reacted with ammonium formate (6 g, 9.6 mmol) to give 7-hydroxy-6-methoxy-4-(2-methylindol-5-ylamino)quinazoline (1.... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | Other | null | null | null | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-562f7889a51b4abcb9bf350e35249033 | COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1O.OCCCn1ccnn1>>COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCCCn1ccnn1 | OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=CNC2=CC1)OC.N1(N=NC=C1)CCCO>>N1C=CC2=CC(=CC=C12)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1N=NC=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[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][CH2:26][n:27]1[cH:28][cH:29][n:30][n:31]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[cH:16]3)[... | COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1O.OCCCn1ccnn1 | COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCCCn1ccnn1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1cn(CCCOc2ccc3c(Nc4ccc5[nH]ccc5c4)ncnc3c2)nn1 | O-[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] | 42.1 | [{"value": 42.0, "product": "N1C=CC2=CC(=CC=C12)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1N=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.1, "product": "N1C=CC2=CC(=CC=C12)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1N=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 205, 7-hydroxy-4-(indol-5-ylamino)-6-methoxyquinazoline (98 mg, 0.32 mmol), (prepared as described for the starting material in Example 201), was reacted with 3-(1,2,3-triazol-1-yl)propan-1-ol (61 mg, 0.48 mmol) to give 4-(indol-5-ylamino)-6-methoxy-7-(3-(1,2,3-... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1c[nH]nn1 | HO- | null | null | null | COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1O.OCCCn1ccnn1>>COc1cc2c(Nc3ccc4[nH]ccc4c3)ncnc2cc1OCCCn1ccnn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-379137198887428285f4bb72bff62872 | C=CC(=O)OCC.c1c[nH]nn1>>CCOC(=O)C(C)n1ccnn1 | N1N=NC=C1.C(C=C)(=O)OCC>>N1(N=NC=C1)C(C(=O)OCC)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].[nH:8]1[cH:9][cH:10][n:11][n:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[n:8]1[cH:9][cH:10][n:11][n:12]1 | C=CC(=O)OCC.c1c[nH]nn1 | CCOC(=O)C(C)n1ccnn1 | null | N1=CC=CC=C1 | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d6179ca64e6326d7e717d0f97068c57e14a418c6194f6dfbf857e3013bf810b | 51fad62e29f5f77e8a2cefce7ceeba2655475fda67fa72d63935019e1a813761 | c1c[nH]nn1 | [#7;a:1]1:[#7;a:2]:[nH;D2;+0:3]:[c:4]:[c:5]:1.[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D2;+0:10]=[CH2;D1;+0:11]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[CH3;D1;+0:11])-[n;H0;D3;+0:3]1:[#7;a:2]:[#7;a:1]:[c:5]:[c:4]:1 | 73.2 | [{"value": 73.0, "product": "N1(N=NC=C1)C(C(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.2, "product": "N1(N=NC=C1)C(C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 1,2,3-triazole (5 g, 72.4 mmol) and ethyl acrylate (7.8 ml, 72.4 mmol) containing pyridine (50 drops) was heated at 90° C. for 4 hours. After cooling, the volatiles were removed under vacuum and the residue was purified by column chromatography eluting with methylene chloride/ether to give ethyl (1H-1,2,3-... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Ester | c1c[nH]nn1 | c1c[nH]nn1 | c1c[nH]nn1 | null | N1=CC=CC=C1 | 90 | null | C=CC(=O)OCC.c1c[nH]nn1>N1=CC=CC=C1>CCOC(=O)C(C)n1ccnn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9bcb2b3e3484d9183f9971b312dfb5b | CCOC(=O)C(C)n1ccnn1>>OCCCn1ccnn1 | N1(N=NC=C1)C(C(=O)OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1CCOC1.C1CCOC1.[OH-].[Na+]>>N1(N=NC=C1)CCCO | CCO[C:2](=[O:1])[CH:4]([CH3:3])[n:5]1[cH:6][cH:7][n:8][n:9]1>>[OH:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][n:8][n:9]1 | CCOC(=O)C(C)n1ccnn1 | OCCCn1ccnn1 | null | null | null | Miscellaneous | OtherReaction | 045e3092b4d06245a655f586ed9fcaf6c102267c1323bfa84ee054f5eb72279b | 6c68e56451f63eb914da47d835c80c50f16b8e098a52b924c7914bb1a69fa96c | c1c[nH]nn1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[CH3;D1;+0:4])-[#7;a:5]1:[#7;a:6]:[#7;a:7]:[c:8]:[c:9]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[#7;a:5]1:[#7;a:6]:[#7;a:7]:[c:8]:[c:9]:1 | 92 | [{"value": 92.0, "product": "N1(N=NC=C1)CCCO", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A solution of ethyl (1H-1,2,3-triazol-1-yl)propanoate (8.96 g, 53 mmol) in THF (50 ml) was added dropwise to a suspension of lithium aluminium hydride (3 g, 79 mmol) in THF (250 ml) cooled at 0° C. After stirring for 1 hour at 5° C., the mixture was stirred for 1 hour at ambient temperature. The mixture was cooled at 0... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1c[nH]nn1 | HO- | null | 0 | 1 | CCOC(=O)C(C)n1ccnn1>>OCCCn1ccnn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dcffef0fbd6141e2ae1123294d2ca430 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Nc1ccc2cc[nH]c2c1>>COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1OCc1ccccc1.Cl | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC.NC1=CC=C2C=CNC2=C1>>Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC1=CC=C2C=CNC2=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:31])[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.[NH2:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][nH: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[cH:12][cH:13][nH:14][c:15]4[cH:16]3)[n... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Nc1ccc2cc[nH]c2c1 | COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1OCc1ccccc1.Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc3c(Nc4ccc5cc[nH]c5c4)ncnc3c2)cc1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[NH2;D1;+0:5]):[c:6].[Cl;H0;D1;+0:7]-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[NH;D2;+0:5]-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12](:[c:13]):[c:14]:1:[c:15]):[c:6].[ClH;D0;+0:7] | 89 | [{"value": 89.0, "product": "Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC1=CC=C2C=CNC2=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC1=CC=C2C=CNC2=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described for the preparation of the starting material in Example 201, 7-benzyloxy-4-chloro-6-methoxyquinazoline (2.5 g, 8.3 mmol), (prepared as described for the starting material in Example 1), was reacted with 6-aminoindole (1.5 g, 11.4 mmol) to give 7-benzyloxy-4-(indol-6-ylamin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ccccc1 | null | null | null | null | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Nc1ccc2cc[nH]c2c1>>COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1OCc1ccccc1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-23f127fb712a4282b04e1a0edbe7130f | COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1O | Cl.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC1=CC=C2C=CNC2=C1)OC.C(=O)[O-].[NH4+]>>OC1=C(C=C2C(=NC=NC2=C1)NC1=CC=C2C=CNC2=C1)OC | c1ccc(C[O:23][c:22]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([NH:7][c:8]4[cH:9][cH:10][c:11]5[cH:12][cH:13][nH:14][c:15]5[cH:16]4)[n:17][cH:18][n:19][c:20]3[cH:21]2)cc1>>[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] | COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1OCc1ccccc1 | COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1O | null | null | null | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(Nc3ccc4cc[nH]c4c3)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] | 76 | [{"value": 76.0, "product": "OC1=C(C=C2C(=NC=NC2=C1)NC1=CC=C2C=CNC2=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described for the preparation of the starting material in Example 201, 7-benzyloxy-4-(indol-6-ylamino)-6-methoxyquinazoline hydrochloride was treated with ammonium formate (655 mg, 10.4 mmol) to give 7-hydroxy-4-(indol-6-ylamino)-6-methoxyquinazoline (162 mg, 76%).
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | Other | null | null | null | COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Nc3ccc4cc[nH]c4c3)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1a4ae1a91c574ff4aea685ef8980740d | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1nccn1CCCO>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCn1ccnc1C | OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C=C(NC2=CC1)C)OC.OCCCN1C(=NC=C1)C>>COC=1C=C2C(=NC=NC2=CC1OCCCN1C(=NC=C1)C)NC=1C=C2C=C(NC2=CC1)C | [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][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].O[CH2:25][CH2:26][CH2:27][n:28]1[cH:29][cH:30][n:31][c:32]1[CH3:33]>>[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][c:13]([CH3:14... | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1nccn1CCCO | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCn1ccnc1C | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1cn(CCCOc2ccc3c(Nc4ccc5[nH]ccc5c4)ncnc3c2)cn1 | O-[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] | 37.4 | [{"value": 37.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1C(=NC=C1)C)NC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1C(=NC=C1)C)NC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 224, 7-hydroxy-6-methoxy-4-(2-methylindol-5-ylamino)quinazoline (102 mg, 0.32 mmol), (prepared as described for the starting material in Example 205), was reacted with 1-(3-hydroxypropyl)-2-methylimidazole (67 mg, 0.48 mmol), (EP 0060696 A1), to give 6-methoxy-7... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ncc[nH]1 | HO- | null | null | null | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1nccn1CCCO>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCn1ccnc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f444de9a91244262b159c3de8c35d021 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CC#N)CC1.Oc1ccc2[nH]ccc2c1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC(CC#N)C1CCNCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)CC#N.OC=1C=C2C=CNC2=CC1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C)C=O>>C(#N)CC(OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)C1CCNCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][CH:28]3[CH2:29][CH2:30][N:31]([CH2:25][C:26]#[N:27])[CH2:32][CH2:33]3)[cH:21][c:20]2[n:19][cH:18][n:17]1.[OH: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]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CC#N)CC1.Oc1ccc2[nH]ccc2c1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC(CC#N)C1CCNCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 265b3626c99bc3a4b6d8127566eafee01f77e06cc38538a2f822747cd5c1d8c5 | 3ca54ce149c51cfb6a830420b10afbe007cefb03af2562456f6c0f4c6be5edc1 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]:[c:7]-[#8:8]-[CH2;D2;+0:9]-[C:10]2-[C:11]-[C:12]-[N;H0;D3;+0:13](-[CH2;D2;+0:14]-[C:15]#[N;D1;H0:16])-[C:17]-[C:18]-2):[c:19]:1:[c:20].[OH;D1;+0:21]-[c:22](:[c:23]):[c:24]>>[N;D1;H0:16]#[C:15]-[CH2;D2;+0:14]-[CH;D3;+0:9](-[#8:8]-[c:7]:[c:6]:[c:5]1:[#7;a:4]:[c:3]:[... | 17 | [{"value": 17.0, "product": "C(#N)CC(OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC)C1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 90 | MINUTE | A solution of 4-chloro-6-methoxy-7-((1-cyanomethylpiperidin-4-yl)methoxy)quinazoline (200 mg, 0.58 mmol) and 5-hydroxyindole (85 mg, 0.63 mmol) in DMF (3 ml) containing cesium carbonate (282 mg, 0.86 mmol) was stirred at 90° C. for 90 minutes. After cooling, the mixture was poured onto water (25 ml). The precipitate wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Aromatic alcohol.Tertiary amine | Ether.Ether.Secondary amine | c1ccc2ncncc2c1.C1CC[NH]CC1 | c1ccc2ncncc2c1.C1CCNCC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CCNCC1 | HCl | null | 90 | 1.5 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CC#N)CC1.Oc1ccc2[nH]ccc2c1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OC(CC#N)C1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1fedcee2041d4060b14263b35a021e3b | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCNCC1>>CC(C)(C)C(=O)OCn1cnc2ccccc2c1=O | Cl.COC=1C=C2C(N(C=NC2=CC1OCC1CCNCC1)COC(C(C)(C)C)=O)=O.[OH-].[Na+]>>C(C(C)(C)C)(=O)OCN1C=NC2=CC=CC=C2C1=O | CO[c:15]1[c:14](OCC2CCNCC2)[cH:13][c:12]2[n:11][cH:10][n:9]([CH2:8][O:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[c:18](=[O:19])[c:17]2[cH:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[O:7][CH2:8][n:9]1[cH:10][n:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[c:18]1=[O:19] | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCNCC1 | CC(C)(C)C(=O)OCn1cnc2ccccc2c1=O | null | null | O | Reduction | OtherReaction | 187ea8753b408ee833b3f50b20895b2d8ea8367a707e05bcd98a4b29794fa37f | 690237014162f096d3d1f1269b75c89c1e1fd70eb0c6023c591d469905aa0575 | O=c1[nH]cnc2ccccc12 | C-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9]:[c;H0;D3;+0:10]:1-O-C-C1-C-C-N-C-C-1>>[#7;a:7]1:[c:6]:[#7;a:5]:[c:4]:[c:3]2:[c:2]:[cH;D2;+0:1]:[cH;D2;+0:10]:[c:9]:[c:8]:1:2 | 132.6 | [{"value": 132.6, "product": "C(C(C)(C)C)(=O)OCN1C=NC2=CC=CC=C2C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a suspension of 6-methoxy-7-(piperidin-4-ylmethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one hydrochloride (34 g, 84 mmol), (prepared as described for the starting material in Example 12), in water cooled at 0° C. was added 1N sodium hydroxide until the mixture was at pH8. The solution was extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amine | null | C1CCNCC1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HO- | O | 0 | null | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCNCC1>O>CC(C)(C)C(=O)OCn1cnc2ccccc2c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3050548ff5fe46a1810a9e01baa85851 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc2c(F)c(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(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)OCC1CCN(CC1)C)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH:27]3[CH2:28][CH2:29][N:30]([CH3:31])[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[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][c:13]([C... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc2c(F)c(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCC1CCN(C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)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] | 69.6 | [{"value": 69.0, "product": "FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 2 | HOUR | A solution of 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (2 gr, 6.22 mmol), (prepared as described for the starting material in Example 10), and 4-fluoro-5-hydroxy-2-methylindole (1.23 g, 7.46 mmol) in DMF (30 ml) containing potassium carbonate (1.28 g, 9.33 mmol) was stirred at 95° C. for 2 hour... | 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 | 2 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc2c(F)c(O)ccc2[nH]1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3a3732b9bc3a4e508995ad8b51078eb8 | COc1ccc2[nH]c(C)cc2c1F>>Cc1cc2c(F)c(O)ccc2[nH]1 | FC1=C2C=C(NC2=CC=C1OC)C.B(Br)(Br)Br>>FC1=C2C=C(NC2=CC=C1O)C | C[O:8][c:7]1[c:5]([F:6])[c:4]2[cH:3][c:2]([CH3:1])[nH:12][c:11]2[cH:10][cH:9]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([F:6])[c:7]([OH:8])[cH:9][cH:10][c:11]2[nH:12]1 | COc1ccc2[nH]c(C)cc2c1F | Cc1cc2c(F)c(O)ccc2[nH]1 | null | null | C(Cl)Cl | 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] | 70.7 | [{"value": 70.0, "product": "FC1=C2C=C(NC2=CC=C1O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.7, "product": "FC1=C2C=C(NC2=CC=C1O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-fluoro-5-methoxy-2-methylindole (709 mg, 3.95 mmol) in methylene chloride (9 ml) cooled at −30° C. was added a solution of boron tribromide (2.18 g, 8.7 mmol) in methylene chloride (1 ml). After stirring for 1 hour at ambient temperature, the mixture was poured onto water and was diluted with methyle... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | C(Cl)Cl | null | 1 | COc1ccc2[nH]c(C)cc2c1F>C(Cl)Cl>Cc1cc2c(F)c(O)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb0dcc849300485fb45634be45243899 | CCOC(=O)CC(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F>>CC(=O)Cc1c([N+](=O)[O-])ccc(F)c1F | FC1=C(C(=C(C=C1)[N+](=O)[O-])F)F.C(CC(=O)C)(=O)OCC.[H-].[Na+]>>C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])F)F | CCOC(=O)[CH2:4][C:2]([CH3:1])=[O:3].F[c:5]1[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]([F:13])[c:14]1[F:15]>>[CH3:1][C:2](=[O:3])[CH2:4][c:5]1[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]([F:13])[c:14]1[F:15] | CCOC(=O)CC(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F | CC(=O)Cc1c([N+](=O)[O-])ccc(F)c1F | null | null | C1CCOC1 | C-C Coupling | OtherReaction | ef592c7be4a79a025bc02d41b93309512718a06ea015c1c563159f4a93201859 | 22e57aa13b41a1841299f7cab78227b5ba641493069f77725888e6f7076a1586 | c1ccccc1 | C-C-O-C(=O)-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].F-[c;H0;D3;+0:5](:[c:6](-[F;D1;H0:7]):[c:8]):[c:9](-[#7;+:10]):[c:11]>>[#7;+:10]-[c:9](:[c:11]):[c;H0;D3;+0:5](-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4]):[c:6](-[F;D1;H0:7]):[c:8] | 72 | [{"value": 72.0, "product": "C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.0, "product": "C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 15 | MINUTE | To a suspension of sodium hydride (5.42 g, 226 mmol) (prewashed with pentane) in THF (100 ml) cooled at 101C was added ethyl acetoacetate (29.4 g, 226 mmol) while keeping the temperature below 15C. After completion of addition, the mixture was further stirred for 15 minutes and cooled to 5° C. A solution of 1,2,3-trifl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ester | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C1CCOC1 | 5 | 0.25 | CCOC(=O)CC(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F>C1CCOC1>CC(=O)Cc1c([N+](=O)[O-])ccc(F)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e34a6514760e4fefa10d12665cc4f0f4 | CC(=O)Cc1c([N+](=O)[O-])ccc(F)c1F.COC(OC)OC>>COC(C)(Cc1c([N+](=O)[O-])ccc(F)c1F)OC | C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])F)F.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3].C(OC)(OC)OC.C(Cl)Cl>>FC1=C(C(=C(C=C1)[N+](=O)[O-])CC(C)(OC)OC)F | [O:2]=[C:3]([CH3:4])[CH2:5][c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]([F:14])[c:15]1[F:16].COC(O[CH3:1])[O:17][CH3:18]>>[CH3:1][O:2][C:3]([CH3:4])([CH2:5][c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]([F:14])[c:15]1[F:16])[O:17][CH3:18] | CC(=O)Cc1c([N+](=O)[O-])ccc(F)c1F.COC(OC)OC | COC(C)(Cc1c([N+](=O)[O-])ccc(F)c1F)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cb292cde20c26fa9cc02b1f65c0f8e86f6198a435483943764a6b55b68bc4551 | b458ec6fb4dadeba418f2e59cf38c00d6ac6c678712484b539a4c34cee82ab7a | c1ccccc1 | C-O-C(-O-[CH3;D1;+0:1])-[O;H0;D2;+0:2]-[C;D1;H3:3].[C;D1;H3:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7]-[c:8]>>[C;D1;H3:3]-[O;H0;D2;+0:2]-[C;H0;D4;+0:5](-[C;D1;H3:4])(-[C:7]-[c:8])-[O;H0;D2;+0:6]-[CH3;D1;+0:1] | 88 | [{"value": 88.0, "product": "FC1=C(C(=C(C=C1)[N+](=O)[O-])CC(C)(OC)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 3-acetylmethyl-1,2-difluoro-4-nitrobenzene (500 mg, 2.3 mmol) in methylene chloride (5 ml) containing montmorillonite K10 (1 g) and trimethyl orthoformate (5 ml) was stirred for 24 hours at ambient temperature. The solid was filtered, washed with methylene chloride and the filtrate was evaporated to give ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether | Ether.Ether | null | null | c1ccccc1 | HO- | null | null | 24 | CC(=O)Cc1c([N+](=O)[O-])ccc(F)c1F.COC(OC)OC>>COC(C)(Cc1c([N+](=O)[O-])ccc(F)c1F)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-baab3ef98b5e4254843a1ed88ed2c7f3 | COC(C)(Cc1c([N+](=O)[O-])ccc(F)c1F)OC.OCc1ccccc1>>CC(=O)Cc1c([N+](=O)[O-])ccc(OCc2ccccc2)c1F | FC1=C(C(=C(C=C1)[N+](=O)[O-])CC(C)(OC)OC)F.C(C1=CC=CC=C1)O.[H-].[Na+]>>C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])OCC1=CC=CC=C1)F | CO[C:2]([CH3:1])([O:3]C)[CH2:4][c:5]1[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12](F)[c:21]1[F:22].[OH:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][C:2](=[O:3])[CH2:4][c:5]1[c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]1[F:22] | COC(C)(Cc1c([N+](=O)[O-])ccc(F)c1F)OC.OCc1ccccc1 | CC(=O)Cc1c([N+](=O)[O-])ccc(OCc2ccccc2)c1F | null | null | Cl.CC(=O)N(C)C | Acylation | OtherReaction | c72d3343a35fdee13c620ddc910bc8d1e5f12c9663ce0db0ad6ce5fecdd59870 | 12b430774bc978a28eb866af6898081d50867b776a28f71fa13b31048fc2d903 | c1ccc(COc2ccccc2)cc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C:3]-[c:4]:[c:5](-[F;D1;H0:6]):[c;H0;D3;+0:7](-F):[c:8]:[c:9])-[O;H0;D2;+0:10]-C.[OH;D1;+0:11]-[C:12]-[c:13]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:10])-[C:3]-[c:4]:[c:5](-[F;D1;H0:6]):[c;H0;D3;+0:7](-[O;H0;D2;+0:11]-[C:12]-[c:13]):[c:8]:[c:9] | 56.3 | [{"value": 56.0, "product": "C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])OCC1=CC=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.3, "product": "C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])OCC1=CC=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of benzyl alcohol (221 mg, 2.05 mmol) in DMA (1.5 ml) was added 60% sodium hydride (82 mg, 2.05 mmol). The mixture was stirred for 1 hour at ambient temperature. A solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (534 mg, 2.05 mmol) in DMA (1.5 ml) was added and the mixture was stirred for ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Primary alcohol | Ketone.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | Cl.CC(=O)N(C)C | null | 1 | COC(C)(Cc1c([N+](=O)[O-])ccc(F)c1F)OC.OCc1ccccc1>Cl.CC(=O)N(C)C>CC(=O)Cc1c([N+](=O)[O-])ccc(OCc2ccccc2)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-034204feeb5942f8859af137df3fa766 | CC(=O)Cc1c([N+](=O)[O-])ccc(OCc2ccccc2)c1F>>Cc1cc2c(F)c(O)ccc2[nH]1 | C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])OCC1=CC=CC=C1)F>>FC1=C2C=C(NC2=CC=C1O)C | O=[C:2]([CH3:1])[CH2:3][c:4]1[c:5]([F:6])[c:7]([O:8]Cc2ccccc2)[cH:9][cH:10][c:11]1[N+:12](=O)[O-]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([F:6])[c:7]([OH:8])[cH:9][cH:10][c:11]2[nH:12]1 | CC(=O)Cc1c([N+](=O)[O-])ccc(OCc2ccccc2)c1F | Cc1cc2c(F)c(O)ccc2[nH]1 | null | [Pd] | C(C)(=O)O.C(C)O | Functional Group Interconversion | OtherReaction | 3cfd66aaccb0cd1068889acfd02b7b8ae9adf44c824547ae1bc175897a5df52d | 6868311343724373887f566a45c0a5e9970d44496fd22223969e86834cb40b47 | c1ccc2[nH]ccc2c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[c:4]1:[c:5]:[c:6](-[O;H0;D2;+0:7]-C-c2:c:c:c:c:c:2):[c:8]:[c:9]:[c:10]:1-[N+;H0;D3:11](=O)-[O-]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c:4]2:[c:5]:[c:6](-[OH;D1;+0:7]):[c:8]:[c:9]:[c:10]:2:[nH;D2;+0:11]:1 | null | [] | null | null | 2 | HOUR | A solution of 3-acetylmethyl-1-benzyloxy-2-fluoro-4-nitrobenzene (300 mg, 0.99 mmol) in ethanol (10 ml) and acetic acid (1 ml) containing 10% palladium on charcoal (30 mg) was hydrogenated at 2 atmospheres pressure for 2 hours. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Nitro group | Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | [Pd].C(C)(=O)O.C(C)O | null | 2 | CC(=O)Cc1c([N+](=O)[O-])ccc(OCc2ccccc2)c1F>[Pd].C(C)(=O)O.C(C)O>Cc1cc2c(F)c(O)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-015cb96a7af248c4b21963a09711d662 | COC(C)(Cc1c([N+](=O)[O-])ccc(F)c1F)OC.C[O-]>>COc1ccc([N+](=O)[O-])c(CC(C)=O)c1F | C[O-].[Na+].[Na].FC1=C(C(=C(C=C1)[N+](=O)[O-])CC(C)(OC)OC)F>>C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])OC)F | CO[C:12]([CH2:11][c:10]1[c:6]([N+:7](=[O:8])[O-:9])[cH:5][cH:4][c:3](F)[c:15]1[F:16])([CH3:13])[O:14]C.[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([CH2:11][C:12]([CH3:13])=[O:14])[c:15]1[F:16] | COC(C)(Cc1c([N+](=O)[O-])ccc(F)c1F)OC.C[O-] | COc1ccc([N+](=O)[O-])c(CC(C)=O)c1F | null | null | CO | Acylation | OtherReaction | 62ce2b56333bfce32973170f27f1edca736847b0cf82171fd484e2a7bba55be5 | 5fc8711396a819699ce779336b7bfdeaaaa6fc024e8ddd484dcc51d216e6ca39 | c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C:3]-[c:4]:[c:5](-[F;D1;H0:6]):[c;H0;D3;+0:7](-F):[c:8]:[c:9])-[O;H0;D2;+0:10]-C.[C;D1;H3:11]-[O-;H0;D1:12]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:10])-[C:3]-[c:4]:[c:5](-[F;D1;H0:6]):[c;H0;D3;+0:7](-[O;H0;D2;+0:12]-[C;D1;H3:11]):[c:8]:[c:9] | 90 | [{"value": 90.0, "product": "C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])OC)F", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 3 | DAY | A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5° C. The mixture was left to warm to ambient temperature and was st... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Ketone.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CO | 5 | 72 | COC(C)(Cc1c([N+](=O)[O-])ccc(F)c1F)OC.C[O-]>CO>COc1ccc([N+](=O)[O-])c(CC(C)=O)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f265e1a4fa134689937c53e857f7844e | COc1ccc([N+](=O)[O-])c(CC(C)=O)c1F>>COc1ccc2[nH]c(C)cc2c1F | C(C)(=O)CC=1C(=C(C=CC1[N+](=O)[O-])OC)F.C(C)(=O)[O-].[NH4+]>>FC1=C2C=C(NC2=CC=C1OC)C | O=[N+:7]([O-])[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:12]([F:13])[c:11]1[CH2:10][C:8](=O)[CH3:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]([CH3:9])[cH:10][c:11]2[c:12]1[F:13] | COc1ccc([N+](=O)[O-])c(CC(C)=O)c1F | COc1ccc2[nH]c(C)cc2c1F | null | [Cl-].[Cl-].[Cl-].[Ti+3] | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | e65c65f0f810d0b59dc9184c320c42fa591a551e8b78a8aea60d36d065df7abe | 1c2c81cd7b083137f7463d418ef3bc406dca4f6a8b870047ce0adc41849da5d0 | c1ccc2[nH]ccc2c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6](-[N+;H0;D3:7](=O)-[O-]):[c:8]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:8]):[nH;D2;+0:7]:1 | 91 | [{"value": 90.0, "product": "FC1=C2C=C(NC2=CC=C1OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": "FC1=C2C=C(NC2=CC=C1OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (11.36 g, 50 mmol) in acetone (200 ml) was added 4M aqueous ammonium acetate (700 ml) followed by a solution of titanium trichloride (15% in water, 340 ml) dropwise. The mixture was stirred for 10 minutes at ambient temperature and the mixture was extrac... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | Other | [Cl-].[Cl-].[Cl-].[Ti+3].CC(=O)C | null | 0.166667 | COc1ccc([N+](=O)[O-])c(CC(C)=O)c1F>[Cl-].[Cl-].[Cl-].[Ti+3].CC(=O)C>COc1ccc2[nH]c(C)cc2c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-21f746e8a64044cf85d466f803ad72f9 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cc1cc2c(F)c(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.FC1=C2C=C(NC2=CC=C1O)C>>FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1)C | 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[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][c... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cc1cc2c(F)c(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCCN1CCCCC1 | null | null | null | 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] | 83.6 | [{"value": 83.0, "product": "FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 237, 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (1.65 g, 4.89 mmol), (prepared as described for the starting material in Example 67), was reacted with 4-fluoro-5-hydroxy-2-methylindole (970 mg, 5.88 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]CC1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cc1cc2c(F)c(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a990c8a7c1a3441894bfa8a646697edd | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Cc1cc2c(F)c(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCCN1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C.FC1=C2C=C(NC2=CC=C1O)C>>FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(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][CH2:28][N:29]3[CH2:30][CH2:31][N:32]([CH3:33])[CH2:34][CH2:35]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[... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Cc1cc2c(F)c(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCCN1CCN(C)CC1 | null | null | null | 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] | 70 | [{"value": 70.0, "product": "FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 237, 4-chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (106 mg, 0.30 mmol), (prepared as described for the starting material in Example 176), was reacted with 4-fluoro-5-hydroxy-2methylindole (60 mg, 0.36 mmol), (prepared as described for the s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Cc1cc2c(F)c(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8172a8567c7c4f47b569dad2c8d59417 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2c(F)c(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.FC1=C2C=C(NC2=CC=C1O)C>>FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1)C | 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[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][c:13]([CH... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2c(F)c(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCCN1CCCC1 | null | null | null | 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] | 50.3 | [{"value": 50.0, "product": "FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.3, "product": "FC1=C2C=C(NC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure identical to that described in Example 237, 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (2 g, 6.22 mmol), (prepared as described for the starting material in Example 9), was reacted with 4-fluoro-5-hydroxy-2-methylindole (1.23 g, 7.46 mmol), (prepared as described for the starting mat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2c(F)c(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09b16722bd8d42038922d9843d4354a8 | COc1cc2c(Cl)ncnc2cc1OCCC1CCN(C)CC1.Oc1ccc2[nH]ccc2c1F>>COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCC1CCN(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)OCCC1CCN(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][CH:27]3[CH2:28][CH2:29][N:30]([CH3:31])[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[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:13][cH... | COc1cc2c(Cl)ncnc2cc1OCCC1CCN(C)CC1.Oc1ccc2[nH]ccc2c1F | COc1cc2c(Oc3ccc4[nH]ccc4c3F)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] | 69.6 | [{"value": 69.0, "product": "FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 1 | HOUR | A solution of 4-chloro-6-methoxy-7-(2-(1-methylpiperidin-4-yl)ethoxy)quinazoline (300 mg, 0.9 mmol) and 4-fluoro-5-hydroxyindole (162 mg, 1 mmol), (prepared as described for the starting material in Example 242), in DMF (4.5 ml) containing potassium carbonate (185 mg, 1.3 mmol) was stirred at 90° C. for 1 hour. After c... | 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 | 90 | 1 | COc1cc2c(Cl)ncnc2cc1OCCC1CCN(C)CC1.Oc1ccc2[nH]ccc2c1F>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12857671bd7645b1b73a6f9d93710026 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.Cc1ccc(S(=O)(=O)OCCC2CCN(C(=O)OC(C)(C)C)CC2)cc1>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C(=O)OC(C)(C)C)CC1 | OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.CC1=CC=C(C=C1)S(=O)(=O)OCCC1CCN(CC1)C(=O)OC(C)(C)C.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)OC(=O)N1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]2[cH:20][c:21]1[OH:22].Cc1ccc(S(=O)(=O)O[CH2:23][CH2:24][CH:25]2[CH2:26][CH2:27][N:28]([C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:36][CH2:37]2)cc1>>[CH3:1][O:2][c:3]1[cH:4... | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.Cc1ccc(S(=O)(=O)OCCC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | O=c1[nH]cnc2cc(OCCC3CCNCC3)ccc12 | C-c1:c:c:c(-S(=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] | 88.2 | [{"value": 88.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.2, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | A suspension of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (7 g, 23 mmol), (prepared as described for the starting material in Example 12), 4-(2-(4-methylphenylsulphonyloxy)ethyl)-1-tert-butoxycarbonylpiperidine (11.4 g, 30 mmol) in DMF (70 ml) containing potassium carbonate (6.32 g, 46 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2ncncc2c1.C1CC[NH]CC1 | TsOH.HO- | CN(C)C=O | 100 | 3 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.Cc1ccc(S(=O)(=O)OCCC2CCN(C(=O)OC(C)(C)C)CC2)cc1>CN(C)C=O>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b62228dabf2c4e3f8837fd4882fb76a8 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C(=O)OC(C)(C)C)CC1>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCNCC1 | C(O)([O-])=O.[Na+].O.C(C)(C)(C)OC(=O)N1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.C(=O)(C(F)(F)F)O>>N1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC | CC(C)(C)OC(=O)[N:28]1[CH2:27][CH2:26][CH:25]([CH2:24][CH2:23][O:22][c:21]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]3[cH:20]2)[CH2:30][CH2:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([... | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C(=O)OC(C)(C)C)CC1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCNCC1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]cnc2cc(OCCC3CCNCC3)ccc12 | 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] | 100 | [{"value": 100.0, "product": "N1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.4, "product": "N1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 7-(2-(1-tert-butoxycarbonylpiperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (10.5 g, 20 mmol) in methylene chloride (100 ml) containing TFA (25 ml) was stirred for 1 hour at ambient temperature. Water (50 ml) and methylene chloride (100 ml) were added and the pH of the ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2ncncc2c1.C1CCNCC1 | HO- | C(Cl)Cl | null | 1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C(=O)OC(C)(C)C)CC1>C(Cl)Cl>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53b23347ca994bbbb2fb431adf14d47d | C=O.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCNCC1>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C)CC1 | C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.[BH4-].[Na+].C(C)(=O)O.N1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.C=O>>CN1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC | O=[CH2:29].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]2[cH:20][c:21]1[O:22][CH2:23][CH2:24][CH:25]1[CH2:26][CH2:27][NH:28][CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14... | C=O.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCNCC1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C)CC1 | null | null | C(Cl)Cl.CO | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | e23db47f33553519e7237e30c3b19a21fcbb90bde44fbb5566021920bc9b7164 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=c1[nH]cnc2cc(OCCC3CCNCC3)ccc12 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6] | 68 | [{"value": 68.0, "product": "CN1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.6, "product": "CN1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 7-(2-(piperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (6 g, 14.4 mmol) in methanol (30 ml) and methylene chloride (60 ml) was added 37% aqueous formaldehyde (2.2 ml; 28.9 mmol) followed by acetic acid (990 μl; 17.3 mmol). Sodium borohydride triacetate (4.6 g, 21.6 m... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | Other | C(Cl)Cl.CO | null | 1 | C=O.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCNCC1>C(Cl)Cl.CO>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fdf85d2b5d344a6ab7a1ac655e9bb8a1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C)CC1>>COc1cc2c(=O)[nH]cnc2cc1OCCC1CCN(C)CC1 | CN1CCC(CC1)CCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.N>>CN1CCC(CC1)CCOC1=C(C=C2C(NC=NC2=C1)=O)OC | CC(C)(C)C(=O)OC[n:8]1[c:6](=[O:7])[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH:17]3[CH2:18][CH2:19][N:20]([CH3:21])[CH2:22][CH2:23]3)[cH:12][c:11]2[n:10][cH:9]1>>[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][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([CH3... | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C)CC1 | COc1cc2c(=O)[nH]cnc2cc1OCCC1CCN(C)CC1 | null | null | CO | Reduction | OtherReaction | 9f6991089c15fc054898797f1d3a42b158e517f125611bc103acfc00878b3b20 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]cnc2cc(OCCC3CCNCC3)ccc12 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1=[O;D1;H0:7]>>[O;D1;H0:7]=[c:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:[nH;D2;+0:1]:1 | 101.3 | [{"value": 100.0, "product": "CN1CCC(CC1)CCOC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.3, "product": "CN1CCC(CC1)CCOC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-(2-(1-methylpiperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (4.2 g, 9.7 mmol) in methanol saturated with ammonia (150 ml) was stirred overnight at ambient temperature. The volatiles were removed under vacuum and the residue was triturated with ether. The solid was fi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | CO | null | null | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCC1CCN(C)CC1>CO>COc1cc2c(=O)[nH]cnc2cc1OCCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1821216e182c4f2085528200cb39298b | COc1cc2c(=O)[nH]cnc2cc1OCCC1CCN(C)CC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCC1CCN(C)CC1 | CN1CCC(CC1)CCOC1=C(C=C2C(NC=NC2=C1)=O)OC.CN(C)C=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCC1CCN(CC1)C | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH:17]3[CH2:18][CH2:19][N:20]([CH3:21])[CH2:22][CH2:23]3)[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][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([CH3:21])[C... | COc1cc2c(=O)[nH]cnc2cc1OCCC1CCN(C)CC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCC1CCN(C)CC1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccc(OCCC3CCNCC3)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] | 54 | [{"value": 54.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-(2-(1-methylpiperidin-4-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (3.1 g, 9.8 mmol) in thionyl chloride (40 ml) containing DMF (400 μl) was refluxed for 4 hours. After cooling, the volatiles were removed under vacuum. The residue was partitioned between methylene chloride and water and the pH of ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | COc1cc2c(=O)[nH]cnc2cc1OCCC1CCN(C)CC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb76b60177fc472895a455c1d233b63a | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1cc2cc[nH]c2cc1F>>COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.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)OCC1CCN(CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([CH3:30])[CH2:31][CH2:32]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][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]4[cH:... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1cc2cc[nH]c2cc1F | COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCC1CCN(C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)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] | 46.7 | [{"value": 46.0, "product": "FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.7, "product": "FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 3.5 | HOUR | A solution of 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (213 mg, 0.662 mmol), (prepared as described for the starting material in Example 10), and 6-fluoro-5-hydroxyindole (120 mg, 0.794 mmol) in DMF (3 ml) containing potassium carbonate (137 mg, 0.994 mmol) was stirred at 95° C. for 3.5 hours. ... | 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 | 3.5 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1cc2cc[nH]c2cc1F>CN(C)C=O>COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-564d401599b3426780f7b4dd1bfcdf47 | BrCc1ccccc1.O=[N+]([O-])c1ccc(O)c(F)c1>>O=[N+]([O-])c1ccc(OCc2ccccc2)c(F)c1 | FC1=C(C=CC(=C1)[N+](=O)[O-])O.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>FC1=C(C=CC(=C1)[N+](=O)[O-])OCC1=CC=CC=C1 | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:16]([F:17])[cH:18]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]([F:17])[cH:18]1 | BrCc1ccccc1.O=[N+]([O-])c1ccc(O)c(F)c1 | O=[N+]([O-])c1ccc(OCc2ccccc2)c(F)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 97.4 | [{"value": 97.0, "product": "FC1=C(C=CC(=C1)[N+](=O)[O-])OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "FC1=C(C=CC(=C1)[N+](=O)[O-])OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-fluoro-4-nitrophenol (15 gr, 95.5 mmol) and benzyl bromide (18 g, 105 mmol) in acetone (125 ml) containing potassium carbonate (26.5 gr, 190 mmol) was refluxed for 2 hours. The volatiles were removed and the residue was partitioned between 2N hydrochloric acid and ethyl acetate. The organic layer was sep... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CC(=O)C | null | null | BrCc1ccccc1.O=[N+]([O-])c1ccc(O)c(F)c1>CC(=O)C>O=[N+]([O-])c1ccc(OCc2ccccc2)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9ba4c4b48e2c4954a923bfc60600b34d | N#CCc1c([N+](=O)[O-])ccc(OCc2ccccc2)c1F.N#CCc1cc(OCc2ccccc2)c(F)cc1[N+](=O)[O-]>>Oc1cc2cc[nH]c2cc1F.Oc1ccc2[nH]ccc2c1F | [H][H].C(#N)CC=1C(=C(C=CC1[N+](=O)[O-])OCC1=CC=CC=C1)F.C(#N)CC=1C(=CC(=C(C1)OCC1=CC=CC=C1)F)[N+](=O)[O-]>>FC1=C2C=CNC2=CC=C1O.FC1=C(C=C2C=CNC2=C1)O | N#[C:18][CH2:19][c:20]1[c:16]([N+:17](=O)[O-])[cH:15][cH:14][c:13]([O:12]Cc2ccccc2)[c:21]1[F:22].N#[C:6][CH2:5][c:4]1[cH:3][c:2]([O:1]Cc2ccccc2)[c:10]([F:11])[cH:9][c:8]1[N+:7](=O)[O-]>>[OH:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][nH:7][c:8]2[cH:9][c:10]1[F:11].[OH:12][c:13]1[cH:14][cH:15][c:16]2[nH:17][cH:18][cH:19][c:20]2[c:... | N#CCc1c([N+](=O)[O-])ccc(OCc2ccccc2)c1F.N#CCc1cc(OCc2ccccc2)c(F)cc1[N+](=O)[O-] | Oc1cc2cc[nH]c2cc1F.Oc1ccc2[nH]ccc2c1F | null | [Pd] | C(C)(=O)O.C(C)O | Functional Group Interconversion | OtherReaction | 05691dbe7c2ab021a56e9125081203d6f1c1149136906e9fc07f5042afff0423 | 4410a65284fe09beb1aa79170ec5752790a66b9caf187a4e992073c911378273 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | N#[C;H0;D2;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5](-[O;H0;D2;+0:6]-C-c2:c:c:c:c:c:2):[c:7]:[c:8]:[c:9]:1-[N+;H0;D3:10](=O)-[O-].N#[C;H0;D2;+0:11]-[CH2;D2;+0:12]-[c:13]1:[c:14]:[c:15](-[O;H0;D2;+0:16]-C-c2:c:c:c:c:c:2):[c:17]:[c:18]:[c:19]:1-[N+;H0;D3:20](=O)-[O-]>>[OH;D1;+0:16]-[c:15]1:[c:17]:[c:18]:[c:19]2:[nH;D2;+0:20... | null | [] | null | null | null | null | A solution of a mixture of 3-cyanomethyl-2-fluoro-4-nitrobenzyloxybenzene and 5-cyanomethyl-2-fluoro-4-nitrobenzyloxybenzene (23 g, 80.4 mmol) in ethanol (220 ml) and acetic acid (30 ml) containing 10% palladium on charcoal (600 mg) was hydrogenated under 3 atmospheres pressure until hydrogen uptake ceased. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Nitrile.Nitrile.Nitro group.Nitro group | Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccc2[nH]ccc2c1 | HO- | [Pd].C(C)(=O)O.C(C)O | null | null | N#CCc1c([N+](=O)[O-])ccc(OCc2ccccc2)c1F.N#CCc1cc(OCc2ccccc2)c(F)cc1[N+](=O)[O-]>[Pd].C(C)(=O)O.C(C)O>Oc1cc2cc[nH]c2cc1F.Oc1ccc2[nH]ccc2c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07a0940d50ee47c797df5fb99135b619 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2[nH]ccc2c1F>>COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(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)OCC1CCN(CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([CH3:30])[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[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:13][cH:14][c:1... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2[nH]ccc2c1F | COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCC1CCN(C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)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] | 26.6 | [{"value": 26.0, "product": "FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.6, "product": "FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 3 | HOUR | A solution of 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (213 mg, 0.662 mmol), (prepared as described for the starting material in Example 10), 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 potassium c... | 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)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2[nH]ccc2c1F>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e608bf7365d449748c1e5ee65ea4dba7 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Oc1cc2cc[nH]c2cc1F>>COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C.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)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][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... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Oc1cc2cc[nH]c2cc1F | COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCN(C)CC1 | null | null | O.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] | 48 | [{"value": 48.0, "product": "FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.7, "product": "FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A mixture of 4-chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (282 mg, 0.662 mmol), 6-fluoro-5-hydroxyindole (120 mg, 0.794 mmol), (prepared as described for the starting material in Example 242), in DMF (3 ml) containing potassium carbonate (137 mg, 0.994 mmol) was heated at 95° C. for 3 hours. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | O.CN(C)C=O | 95 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1.Oc1cc2cc[nH]c2cc1F>O.CN(C)C=O>COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b36d13133fb74c5992bcae9767b50b0e | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.OCCCBr>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCBr | N(=NC(=O)OCC)C(=O)OCC.OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.BrCCCO>>BrCCCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]2[cH:20][c:21]1[OH:22].O[CH2:23][CH2:24][CH2:25][Br:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]2... | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.OCCCBr | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCBr | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=c1[nH]cnc2ccccc12 | O-[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] | 92 | [{"value": 92.0, "product": "BrCCCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "BrCCCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a suspension of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (29 g, 94.7 mmol), (prepared as described for the starting material in Example 12), in methylene chloride (280 ml) colled at 5° C. was added triphenylphosphine (37.1 g, 141.6 mmol) followed by 3-bromo-1-propanol (12.8 ml, 141.6 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1 | HO- | C(Cl)Cl | null | 2 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.OCCCBr>C(Cl)Cl>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCBr |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-39acf0447c3f4b10847017e43e410dc4 | CN1CCNCC1.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCBr>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCN(C)CC1 | BrCCCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.CN1CCNCC1>>CN1CCN(CC1)CCCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC | [NH:26]1[CH2:27][CH2:28][N:29]([CH3:30])[CH2:31][CH2:32]1.Br[CH2:25][CH2:24][CH2:23][O:22][c:21]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]2[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:... | CN1CCNCC1.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCBr | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=c1[nH]cnc2cc(OCCCN3CCNCC3)ccc12 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 83 | [{"value": 83.0, "product": "CN1CCN(CC1)CCCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 90 | MINUTE | A suspension of 7-(3-bromopropoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (36.7 g, 86 mmol) in 1-methylpiperazine (370 ml) was stirred at 100° C. for 90 minutes. After removal of the volatiles under vacuum, the residue was partitioned between methylene chloride and aqueous ammonium chloride. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HBr | null | 100 | 1.5 | CN1CCNCC1.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCBr>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93c9f371cee641829e25238921c4f162 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCN(C)CC1>>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1 | CN1CCN(CC1)CCCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.N>>CN1CCN(CC1)CCCOC1=C(C=C2C(NC=NC2=C1)=O)OC | CC(C)(C)C(=O)OC[n:8]1[c:6](=[O:7])[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]3)[cH:12][c:11]2[n:10][cH:9]1>>[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][CH2:16][CH2:17][N:18]1[CH2:19][CH2:... | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCN(C)CC1 | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1 | null | null | CO | Reduction | OtherReaction | 9f6991089c15fc054898797f1d3a42b158e517f125611bc103acfc00878b3b20 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]cnc2cc(OCCCN3CCNCC3)ccc12 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1=[O;D1;H0:7]>>[O;D1;H0:7]=[c:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:[nH;D2;+0:1]:1 | 95.5 | [{"value": 95.0, "product": "CN1CCN(CC1)CCCOC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.5, "product": "CN1CCN(CC1)CCCOC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A suspension of 7-(3-(4-methylpiperazin-1-yl)propoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (31.8 g, 71.3 mmol) in methanol saturated with ammonia was stirred at ambient temperature overnight. The volatiles were removed under vacuum. The solid was triturated with ether containing about 10% of me... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HO- | CO | null | 8 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCN(C)CC1>CO>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dab3f9c43bc744b18a88b00b23977c4f | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 | CN1CCN(CC1)CCCOC1=C(C=C2C(NC=NC2=C1)=O)OC.CN(C)C=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]3)[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][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:2... | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccc(OCCCN3CCNCC3)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] | 68 | [{"value": 68.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A solution of 7-(3-(4-methylpiperazin-1-yl)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (22.6 g, 68 mmol) in thionyl chloride (300 ml) cotaining DMF (5 ml) was refluxed for 2 hours. After cooling, the volatiles were removed under vacuum and the residue was azeotroped with toluene twice. The solid was dissolved in met... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | null | 0 | null | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCN(C)CC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-699d2ab9eff9457f9c94274b630c1632 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1cc2cc[nH]c2cc1F>>COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.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)OCCCN1CCCC1 | 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][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]4[cH:1... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1cc2cc[nH]c2cc1F | COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCCC1 | 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] | 53.3 | [{"value": 53.0, "product": "FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.3, "product": "FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 243, 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (213 mg, 0.662 mmol), (prepared as described for the starting material in Example 9), was reacted with 6-fluoro-5-hydroxyindole (120 mg, 0.794 mmol), (prepared as described for the starting materi... | 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 | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1cc2cc[nH]c2cc1F>CN(C)C=O>COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-76a63d54b92942e7afe44c57073be5fc | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1.ClCCN1CCOCC1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(CCN2CCOCC2)CC1 | C(O)([O-])=O.[Na+].Cl.ClCCN1CCOCC1.C(O)([O-])=O.[Na+].COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C=C(NC2=CC1)C.[I-].[K+].Cl.ClCCN1CCOCC1>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCN1CCOCC1)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][CH2:38][CH2:39]1.Cl[CH2:30][CH2:31][N:32]1[CH2:33][CH2:34][O:35][CH2:36][CH2:37]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1.ClCCN1CCOCC1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(CCN2CCOCC2)CC1 | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCN(CCN4CCOCC4)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] | 122.8 | [{"value": 73.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCN1CCOCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 122.8, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCN1CCOCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 6-methoxy-4-(2-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline (500 mg, 1.2 mmol), (prepared as described in example 70), in methanol (11.5 ml) containing potassium iodide (99 mg, 0.6 mmol) was added 4-(2chloroethyl)morpholine hydrochloride (134 mg, 0.72 mmol) followed by sodium hydrogen carb... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1.C1COCC[NH]1 | HCl | CO | null | 1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1.ClCCN1CCOCC1>CO>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(CCN2CCOCC2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e31e0ac7b30d415bba4c77699e97c50c | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2[nH]ccc2c1F>>COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.FC1=C2C=CNC2=CC=C1O.C([O-])([O-])=O.[K+].[K+]>>FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1 | 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[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:13][cH:14][c:15... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2[nH]ccc2c1F | COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCCN1CCCC1 | 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] | 52 | [{"value": 52.0, "product": "FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.9, "product": "FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A solution of 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (1.76 g, 5.47 mmol), (prepared as described for the starting material in Example 9), 4-fluoro-5-hydroxyindole (0.992 g, 6.57 mmol), (prepared as described for the starting material in Example 242), in DMF (25 ml) containing potassium carbonate (... | 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 | 95 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2[nH]ccc2c1F>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-04597e881e554ce1a6de9893aef3d4a7 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cc2cc[nH]c2cc1F>>COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.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)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][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:1... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cc2cc[nH]c2cc1F | COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCCCC1 | null | null | CN(C)C=O | 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] | 46.6 | [{"value": 46.0, "product": "FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.6, "product": "FC1=C(C=C2C=CNC2=C1)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (222 mg, 0.662 mmol), (prepared as described for the starting material in Example 67), and 6-fluoro-5-hydroxyindole (120 mg, 0.794 mmol), (prepared as described for the starting material in Example 242), in DMF (3 ml) containing potassium carbonate (137... | 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 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1cc2cc[nH]c2cc1F>CN(C)C=O>COc1cc2c(Oc3cc4cc[nH]c4cc3F)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-574866890c9e4bcfb26604f6e4afbdca | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]ccc2c1F>>COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.FC1=C2C=CNC2=CC=C1O.C([O-])([O-])=O.[K+].[K+]>>FC1=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[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:13][cH:... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]ccc2c1F | COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCCN1CCCCC1 | null | null | CN(C)C=O | 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] | 67.3 | [{"value": 67.0, "product": "FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "FC1=C2C=CNC2=CC=C1OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | Using an analogous procedure to that described in Example 244, 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (407 mg, 1.21 mmol), (prepared as described for the starting material in Example 67), 4-fluoro-5-hydroxyindole (220 mg, 1.45 mmol) (prepared as described for the starting material in Example 242), and po... | 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 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]ccc2c1F>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3F)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-45da1a56bd79459ba378767567fa2054 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2cc(O)c(F)cc2[nH]1>>COc1cc2c(Oc3cc4cc(C)[nH]c4cc3F)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.FC1=C(C=C2C=C(NC2=C1)C)O.C([O-])([O-])=O.[K+].[K+]>>FC1=C(C=C2C=C(NC2=C1)C)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][c:10]2[cH:11][c:12]([CH3:13])[nH:14][c:15]2[cH:16][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][c:10]4[cH:11][c:12]([CH3:13])[... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2cc(O)c(F)cc2[nH]1 | COc1cc2c(Oc3cc4cc(C)[nH]c4cc3F)ncnc2cc1OCCCN1CCCC1 | 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] | 57.3 | [{"value": 57.0, "product": "FC1=C(C=C2C=C(NC2=C1)C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "FC1=C(C=C2C=C(NC2=C1)C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 248, 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (268 mg, 0.833 mmol), (prepared as described for the starting material in Example 9), was reacted with 6-fluoro-5-hydroxy-2-methylindole (165 mg, 1 mmol) in DMF (3.5 ml) containing potassium carbo... | 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 | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2cc(O)c(F)cc2[nH]1>CN(C)C=O>COc1cc2c(Oc3cc4cc(C)[nH]c4cc3F)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a44682b619e34067b2df51e2ad64decc | COc1cc2cc(C)[nH]c2cc1F>>Cc1cc2cc(O)c(F)cc2[nH]1 | FC1=C(C=C2C=C(NC2=C1)C)OC.B(Br)(Br)Br>>FC1=C(C=C2C=C(NC2=C1)C)O | C[O:7][c:6]1[cH:5][c:4]2[cH:3][c:2]([CH3:1])[nH:12][c:11]2[cH:10][c:8]1[F:9]>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([OH:7])[c:8]([F:9])[cH:10][c:11]2[nH:12]1 | COc1cc2cc(C)[nH]c2cc1F | Cc1cc2cc(O)c(F)cc2[nH]1 | null | null | C(Cl)Cl | 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] | 80 | [{"value": 80.0, "product": "FC1=C(C=C2C=C(NC2=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "FC1=C(C=C2C=C(NC2=C1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 90 | MINUTE | To a solution of 6-fluoro-5-methoxy-2-methylindole (1.23 g, 6.86 mmol), (prepared as described for the starting material in Example 237), in methylene chloride (15 ml) cooled at −30° C. was added a solution of boron tribromide (3.78 g, 15.1 mmol) in methylene chloride (2 ml). After stirring for 90 minutes at ambient te... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | C(Cl)Cl | -30 | 1.5 | COc1cc2cc(C)[nH]c2cc1F>C(Cl)Cl>Cc1cc2cc(O)c(F)cc2[nH]1 |
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