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-ab7b8d70f4d6495f995fc35087a3a344 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2c(Cl)ccnc2c1>>COc1cc2c(Oc3ccc4c(Cl)ccnc4c3)ncnc2cc1OCCCN1CCOCC1 | ClC1=CC=NC2=CC(=CC=C12)O.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=CC=NC2=CC(=CC=C12)O.C([O-])([O-])=O.[K+].[K+]>>ClC1=CC=NC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][O: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[c:12]([Cl:13])[cH:14][cH:15][n:16][c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([Cl:... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2c(Cl)ccnc2c1 | COc1cc2c(Oc3ccc4c(Cl)ccnc4c3)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(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].[#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] | 47 | [{"value": 47.0, "product": "ClC1=CC=NC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.6, "product": "ClC1=CC=NC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 30 | MINUTE | To 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (250 mg, 0.74 mmol), (prepared as described for the starting material in Example 1), in suspension in DMF (4 ml) were successively added 4-chloro-7-hydroxyquinoline (133 mg, 0.74 mmol) and potassium carbonate (153 mg, 1 mmol) and the reaction mixture heated to 10... | 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 | 0.5 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2c(Cl)ccnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4c(Cl)ccnc4c3)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d53e2547fb874bd493ae351e58fef713 | Clc1ccnc2cc(OCc3ccccc3)ccc12>>Oc1ccc2c(Cl)ccnc2c1 | C(C1=CC=CC=C1)OC1=CC=C2C(=CC=NC2=C1)Cl.C(O)([O-])=O.[Na+]>>ClC1=CC=NC2=CC(=CC=C12)O | c1ccc(C[O:1][c:2]2[cH:3][cH:4][c:5]3[c:6]([Cl:7])[cH:8][cH:9][n:10][c:11]3[cH:12]2)cc1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[cH:8][cH:9][n:10][c:11]2[cH:12]1 | Clc1ccnc2cc(OCc3ccccc3)ccc12 | Oc1ccc2c(Cl)ccnc2c1 | null | null | C(=O)(C(F)(F)F)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2ncccc2c1 | [#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] | 98 | [{"value": 98.0, "product": "ClC1=CC=NC2=CC(=CC=C12)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "ClC1=CC=NC2=CC(=CC=C12)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 7-benzyloxy-4-chloroquinoline (17 g, 56 mmol), (Konishi et al. WO 96/11187), in TFA (170 ml) was heated at reflux for 2 hours. The solvent was removed under vacuum and the residue was triturated with ether, filtered and washed with ether. The solid was suspended in an aqueous solution of sodium hydrogen c... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2ncccc2c1 | Other | C(=O)(C(F)(F)F)O | null | 0.5 | Clc1ccnc2cc(OCc3ccccc3)ccc12>C(=O)(C(F)(F)F)O>Oc1ccc2c(Cl)ccnc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea6322402661414aa9a77b99040c3dc8 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2ccccc2c1>>COc1cc2c(Oc3ccc4ccccc4c3)ncnc2cc1OCC1CCN(C)CC1 | C(Cl)Cl.ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.OC1=CC2=CC=CC=C2C=C1.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC2=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][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[cH:12][cH:13][cH:14][cH: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][c... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2ccccc2c1 | COc1cc2c(Oc3ccc4ccccc4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2cc(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].[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 | [{"value": 83.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC2=CC=CC=C2C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC2=CC=CC=C2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3.5 | HOUR | A solution of 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (74 mg, 0.23 mmol), (prepared as described for the starting material in Example 10), and 2-hydroxynaphthalene (40 mg, 0.28 mmol) in DMF (1.5 ml) containing potassium carbonate (48 mg, 0.35 mmol) was stirred at 100° C. for 3.5 hours. After c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ccccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CN(C)C=O | 100 | 3.5 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2ccccc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4ccccc4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ead54da921b4c8c9f7bda41c38444cd | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1ccc2c(c1)OCO2>>COc1cc2c(Nc3ccc4c(c3)OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.C1OC=2C=C(N)C=CC2O1.Cl>>O1COC2=C1C=CC(=C2)NC2=NC=NC1=CC(=C(C=C21)OC)OCCCN2CCOCC2 | 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][O:30][CH2:31][CH2:32]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[c:12]([cH:13]1)[O:14][CH2:15][O:16]2>>[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[c:12]([cH:13]3)[O:14]... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1ccc2c(c1)OCO2 | COc1cc2c(Nc3ccc4c(c3)OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1nc(Nc2ccc3c(c2)OCO3)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].[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] | 81.3 | [{"value": 76.0, "product": "O1COC2=C1C=CC(=C2)NC2=NC=NC1=CC(=C(C=C21)OC)OCCCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.3, "product": "O1COC2=C1C=CC(=C2)NC2=NC=NC1=CC(=C(C=C21)OC)OCCCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (74 mg, 0.23 mmol), (prepared as described for the starting material in Example 1), and 3,4-(methylenedioxy)aniline (53 mg, 0.24 mmol) in a solution of isopropanol (3.5 ml) containing 5.5M hydrogen chloride in isopropanol (42 μl) was heated for 3 hours... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | C(C)(C)O | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Nc1ccc2c(c1)OCO2>C(C)(C)O>COc1cc2c(Nc3ccc4c(c3)OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b3882d707985453f8a9340c245ee6b06 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc(=O)c2ccc(O)cc2o1>>COc1cc2c(Oc3ccc4c(=O)cc(C)oc4c3)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.OC1=CC=C2C(C=C(OC2=C1)C)=O.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC=C2C(C=C(OC2=C1)C)=O | 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[c:12](=[O:13])[cH:14][c:15]([CH3:16])[o: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[c:12](... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc(=O)c2ccc(O)cc2o1 | COc1cc2c(Oc3ccc4c(=O)cc(C)oc4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | O=c1ccoc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc12 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#8;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] | 92.1 | [{"value": 92.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC=C2C(C=C(OC2=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC=C2C(C=C(OC2=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A suspension of 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (130 mg, 0.4 mmol), (prepared as described for the starting material in Example 10), 7-hydroxy-2-methylchromone (88 mg, 0.5 mmol), (Bull Soc. Chim. Fr. 1995, 132, 233), and potassium carbonate (83 mg, 0.6 mmol) was heated at 100° C. for 1.5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2cccoc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | 100 | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc(=O)c2ccc(O)cc2o1>>COc1cc2c(Oc3ccc4c(=O)cc(C)oc4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-733f6a2c3eaf44c49e3d49aebedf0468 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2[nH]ccc2c1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCC1CCN(C)CC1 | O.ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.OC=1C=C2C=CNC2=CC1.C([O-])([O-])=O.[K+].[K+]>>N1C=CC2=CC(=CC=C12)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:22]([O:23][CH2:24][CH:25]3[CH2:26][CH2:27][N:28]([CH3:29])[CH2:30][CH2:31]3)[cH:21][c:20]2[n:19][cH:18][n:17]1.[OH:7][c:8]1[cH:9][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:14][c:15]4[c... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2[nH]ccc2c1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)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] | 64 | [{"value": 64.0, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.3, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (110 mg, 0.34 mmol), (prepared as described for the starting material in Example 10), and 5-hydroxyindole (55 mg, 0.41 mmol) in DMF (1.5 ml) containing potassium carbonate (70 mg, 0.51 mmol) was heated at 100° C. for 2 hours. After cooling, w... | 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 | 100 | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2[nH]ccc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c7c6aa780474464098c7bfbbaec7ba8d | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1[nH]c2ccc(O)cc2c1C>>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.CC=1NC2=CC=C(C=C2C1C)O>>CC=1NC2=CC=C(C=C2C1C)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: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])[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... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1[nH]c2ccc(O)cc2c1C | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | 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] | 40 | [{"value": 40.0, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.5, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 34, 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (110 mg, 0.34 mmol), (prepared as described for the starting material in Example 10), was reacted with 2,3-dimethyl-5-hydroxyindole (66 mg, 0.41 mmol), (Arch. Pharm. 1972, 305, 159). The crude p... | 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)ncnc2cc1OCC1CCN(C)CC1.Cc1[nH]c2ccc(O)cc2c1C>>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c40490e235804b9f9e191e661cd968ee | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2[nH]ccc2c1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.OC=1C=C2C=CNC2=CC1>>N1C=CC2=CC(=CC=C12)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: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][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:14][c:15]4[cH... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2[nH]ccc2c1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)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 | [{"value": 50.0, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.2, "product": "N1C=CC2=CC(=CC=C12)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 34, 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline (10 mg, 0.34 mmol), (prepared as described for the starting material in Example 9), was reacted with 5-hydroxyindole (55 mg, 0.41 mmol). The crude product was purified by chromatography on alumina, e... | 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.Oc1ccc2[nH]ccc2c1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-19ddd9522a2c45959f0bb35aaef8f53e | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1[nH]c2ccc(N)cc2c1C>>COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCC1CCN(C)CC1 | Cl.ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.NC=1C=C2C(=C(NC2=CC1)C)C>>Cl.CC=1NC2=CC=C(C=C2C1C)NC1=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: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.[NH2:7][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]([NH:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1[nH]c2ccc(N)cc2c1C | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1nc(Nc2ccc3[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].[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] | 79 | [{"value": 74.0, "product": "Cl.CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.0, "product": "Cl.CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A suspension of 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (100 mg, 0.31 mmol), (prepared as described for the starting material in Example 10), and 5-amino-2,3-dimethylindole (55 mg, 0.34 mmol) in isopropanol (6 ml) containing 5.5M hydrogen choride in isopropanol (60 μL) was heated for 30 minutes ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | C(C)(C)O | 70 | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1[nH]c2ccc(N)cc2c1C>C(C)(C)O>COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a64612f1488145b3a1017e0a6b4aac55 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1[nH]c2ccc(N)cc2c1C>>COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCCN1CCCC1.Cl | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.NC=1C=C2C(=C(NC2=CC1)C)C>>Cl.CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:34])[n:19][cH:20][n:21][c:22]2[cH:23][c:24]1[O:25][CH2:26][CH2:27][CH2:28][N:29]1[CH2:30][CH2:31][CH2:32][CH2:33]1.[NH2:7][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]([NH:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1[nH]c2ccc(N)cc2c1C | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCCN1CCCC1.Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1nc(Nc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | [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] | 76.3 | [{"value": 72.0, "product": "Cl.CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.3, "product": "Cl.CC=1NC2=CC=C(C=C2C1C)NC1=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 37, 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline (100 mg, 0.31 mmol), (prepared as described for the starting material in Example 9), was reacted with 5-amino-2,3-dimethylindole (55 mg, 0.34 mmol) to give 4(2,3-dimethylindol-5-ylamino)-6-methoxy-7-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | null | null | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1[nH]c2ccc(N)cc2c1C>>COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCCN1CCCC1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f0c1a689d76a40c7a36e8a94ad814beb | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2cc(N)ccc2[nH]1>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCCC1.Cl | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.NC=1C=C2C=C(NC2=CC1)C>>Cl.COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)NC=1C=C2C=C(NC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:33])[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][CH2:31][CH2:32]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]([CH... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2cc(N)ccc2[nH]1 | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCCC1.Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1nc(Nc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | [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] | 95.1 | [{"value": 89.0, "product": "Cl.COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)NC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.1, "product": "Cl.COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)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 38, 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline (100 mg, 0.31 mmol), (prepared as described for the starting material in Example 9), was reacted with 5-amino-2-methylindole (50 mg, 0.34 mmol) to give 6-methoxy-4-(2-methylindol-5-ylamino)-7-(3-pyrr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | null | null | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2cc(N)ccc2[nH]1>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCCC1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aabebf6e59a24b7097a02e84c979c5a4 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc(C)c2ccc(O)cc2n1>>COc1cc2c(Oc3ccc4c(C)cc(C)nc4c3)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.OC1=CC=C2C(=CC(=NC2=C1)C)C.C([O-])([O-])=O.[K+].[K+]>>CC1=NC2=CC(=CC=C2C(=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:25]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][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[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[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[c:12](... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc(C)c2ccc(O)cc2n1 | COc1cc2c(Oc3ccc4c(C)cc(C)nc4c3)ncnc2cc1OCCCN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCCCN5CCCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 35.2 | [{"value": 35.0, "product": "CC1=NC2=CC(=CC=C2C(=C1)C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.2, "product": "CC1=NC2=CC(=CC=C2C(=C1)C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline (100 mg, 0.31 mmol), (prepared as described for the starting material in Example 9), and 7-hydroxy-2,4-dimethylquinoline (64 mg, 0.36 mmol), (Chem. Berichte, 1903, 36, 4016), in DMF (3 ml) containing potassium carbonate (86 mg, 0.62 mmol) was heate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 90 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc(C)c2ccc(O)cc2n1>CN(C)C=O>COc1cc2c(Oc3ccc4c(C)cc(C)nc4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bda7ad14238d46d198d97acd5d1b374a | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc2cc(N)ccc2[nH]1>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C)CC1.Cl | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.NC=1C=C2C=C(NC2=CC1)C>>Cl.COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)NC=1C=C2C=C(NC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:33])[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][N:29]([CH3:30])[CH2:31][CH2:32]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]([C... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc2cc(N)ccc2[nH]1 | COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C)CC1.Cl | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1nc(Nc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | [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] | 99.3 | [{"value": 99.3, "product": "Cl.COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)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 37, 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (50 mg, 0.155 mmol), (prepared as described for the starting material in Example 10), was reacted with 5-amino-2-methylindole (0.171 mmol) to give 6-methoxy-4-(2-methylindol-5-ylamino)-7-(1-meth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | null | null | null | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc2cc(N)ccc2[nH]1>>COc1cc2c(Nc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C)CC1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d7023257e4b74c068b11b0748425a934 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1ccc2ccc(O)cc2n1>>COc1cc2c(Oc3ccc4ccc(C)nc4c3)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.OC1=CC=C2C=CC(=NC2=C1)C.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C=CC(=NC2=C1)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[cH:12][cH:13][c:14]([CH3:15])[n:16][c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][cH:13][c... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1ccc2ccc(O)cc2n1 | COc1cc2c(Oc3ccc4ccc(C)nc4c3)ncnc2cc1OCCCN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCCCN5CCCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 69 | [{"value": 69.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C=CC(=NC2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.9, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C=CC(=NC2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A suspension of 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline (100 mg, 0.31 mmol), (prepared as described for the starting material in Example 9), and 7-hydroxy-2-methylquinoline (54 mg, 0.34 mmol), (J. Med. Chem. 1998, 41, 4062), in DMF (3 ml) containing potassium carbonate (86 mg, 0.62 mmol) was heated a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 90 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1ccc2ccc(O)cc2n1>CN(C)C=O>COc1cc2c(Oc3ccc4ccc(C)nc4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f8b1220b3c543f5aee2364d26d2c395 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1.Cc1ccc2ccc(O)cc2n1>>COc1cc2c(Oc3ccc4ccc(C)nc4c3)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)CCS(=O)(=O)C.OC1=CC=C2C=CC(=NC2=C1)C>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)OC1=CC=C2C=CC(=NC2=C1)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]([CH2:31][CH2:32][S:33]([CH3:34])(=[O:35])=[O:36])[CH2:37][CH2:38]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][c:14]([CH3:15])[n:16][c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1.Cc1ccc2ccc(O)cc2n1 | COc1cc2c(Oc3ccc4ccc(C)nc4c3)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | null | null | null | 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] | 82 | [{"value": 82.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)OC1=CC=C2C=CC(=NC2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)OC1=CC=C2C=CC(=NC2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 42, 4-chloro-6-methoxy-7-(1-(2-methylsulphonylethyl)piperidin-4-ylmethoxy)quinazoline (156 mg, 0.38 mmol), (prepared as described for the starting material in Example 12), was reacted with 7-hydroxy-2-methylquinoline (66 mg, 0.4 mmol), (J. Med. Chem. 1998, 41, 4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1.Cc1ccc2ccc(O)cc2n1>>COc1cc2c(Oc3ccc4ccc(C)nc4c3)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-62bde8e5c40c43e7be7f0f6a31a9b042 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2[nH]c(C(F)(F)F)cc2c1>>COc1cc2c(Oc3ccc4[nH]c(C(F)(F)F)cc4c3)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.OC=1C=C2C=C(NC2=CC1)C(F)(F)F.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C=C(NC2=CC1)C(F)(F)F | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH2:28][CH:29]3[CH2:30][CH2:31][N:32]([CH3:33])[CH2:34][CH2:35]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]([C:14]([F:15])([F:16])[F:17])[cH:18][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:11]4[... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2[nH]c(C(F)(F)F)cc2c1 | COc1cc2c(Oc3ccc4[nH]c(C(F)(F)F)cc4c3)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] | 48 | [{"value": 48.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C=C(NC2=CC1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C=C(NC2=CC1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A suspension of 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (50 mg, 0.155 mmol), (prepared as described for the starting material in Example 10), and 5-hydroxy-2-trifluoromethylindole (34 mg, 0.17 mmol) in DMF (1.5 ml) containing potassium carbonate (43 mg, 0.31 mmol) was heated at 90° 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 | 90 | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2[nH]c(C(F)(F)F)cc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C(F)(F)F)cc4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2fc861487edd4918bf21ab23242d9513 | COc1ccc2[nH]c(C(F)(F)F)cc2c1>>Oc1ccc2[nH]c(C(F)(F)F)cc2c1 | COC=1C=C2C=C(NC2=CC1)C(F)(F)F.B(Br)(Br)Br.C(O)([O-])=O.[Na+]>>OC=1C=C2C=C(NC2=CC1)C(F)(F)F | C[O:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]2[cH:14]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]2[cH:14]1 | COc1ccc2[nH]c(C(F)(F)F)cc2c1 | Oc1ccc2[nH]c(C(F)(F)F)cc2c1 | 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] | 39 | [{"value": 39.0, "product": "OC=1C=C2C=C(NC2=CC1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.0, "product": "OC=1C=C2C=C(NC2=CC1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A solution of 5-methoxy-2-trifluoromethylindole (800 mg, 3.7 mmol) in methylene chloride (6 ml) was cooled to −15° C. and a solution of 1M boron tribromide in methylene chloride (7.44 ml, 7.4 mmol) was added in portions. The mixture was allowed to warm to ambient temperature and was stirred for 45 minutes. After coolin... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | C(Cl)Cl | null | 0.75 | COc1ccc2[nH]c(C(F)(F)F)cc2c1>C(Cl)Cl>Oc1ccc2[nH]c(C(F)(F)F)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a3c232ef77384535b4420dbb140115b3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2[nH]c(C(F)(F)F)cc2c1>>COc1cc2c(Oc3ccc4[nH]c(C(F)(F)F)cc4c3)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.OC=1C=C2C=C(NC2=CC1)C(F)(F)F>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C=C(NC2=CC1)C(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]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]([C:14]([F:15])([F:16])[F:17])[cH:18][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:11]4[n... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2[nH]c(C(F)(F)F)cc2c1 | COc1cc2c(Oc3ccc4[nH]c(C(F)(F)F)cc4c3)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] | 71.9 | [{"value": 70.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C=C(NC2=CC1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.9, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C=C(NC2=CC1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 44, 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline (100 mg, 0.3 mmol), (prepared as described for the starting material in Example 9), was reacted with 5-hydroxy-2-trifluoromethylindole (75 mg, 0.37 mmol), (prepared as described for the starting mate... | 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.Oc1ccc2[nH]c(C(F)(F)F)cc2c1>>COc1cc2c(Oc3ccc4[nH]c(C(F)(F)F)cc4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2e01c4278d8a4ffc9f7a54bfa168e355 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1ccc2ccc(O)cc2n1>>COc1cc2c(Oc3ccc4ccc(C)nc4c3)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.OC1=CC=C2C=CC(=NC2=C1)C>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC=C2C=CC(=NC2=C1)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[cH:12][cH:13][c:14]([CH3:15])[n:16][c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][cH:13][... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1ccc2ccc(O)cc2n1 | COc1cc2c(Oc3ccc4ccc(C)nc4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | 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] | 63 | [{"value": 63.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC=C2C=CC(=NC2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC=C2C=CC(=NC2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 42, 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (100 mg, 0.31 mmol), (prepared as described for the starting material in Example 10), was reacted with 7-hydroxy-2-methylquinoline (54 mg, 0.34 mmol), (J. Med. Chem. 1998, 41, 4062), to give 6-m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1ccc2ccc(O)cc2n1>>COc1cc2c(Oc3ccc4ccc(C)nc4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6cee24b781e3485797a09bfb9bcee4b3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1[nH]c2ccc(O)cc2c1C>>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.CC=1NC2=CC=C(C=C2C1C)O.C([O-])([O-])=O.[K+].[K+]>>CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[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]... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1[nH]c2ccc(O)cc2c1C | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)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] | 33 | [{"value": 33.0, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.9, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A suspension of 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline (10 mg, 0.34 mmol), (prepared as described for the starting material in Example 9), and 2,3-dimethyl-5-hydroxyindole (66 mg, 0.41 mmol), (Arch. Pharm. 1972, 305, 159), in DMF (1.5 ml) containing potassium carbonate (70 mg, 0.51 mmol) was heated ... | 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 | 100 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1[nH]c2ccc(O)cc2c1C>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e83fe1a1497148cb93f5b986bef58f5f | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1cc2cc(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC.OC=1C=C2C=C(NC2=CC1)C>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][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]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1cc2cc(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1 | null | null | null | 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] | 91.2 | [{"value": 91.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 32, 7-benzyloxy-4-chloro-6-methoxyquinazoline (1 g, 3.33 mmol), (prepared as described for the starting material in Example 1), was reacted with 5-hydroxy-2-methylindole (0.59 g, 4 mmol) to give 7-benzyloxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (1.25 g,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ccccc1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1cc2cc(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c969e0ea9f6645219c26c1d9c55db636 | COc1ccc2[nH]c(C)cc2c1>>Cc1cc2cc(O)ccc2[nH]1 | [OH-].[Na+].B(Br)(Br)Br.COC=1C=C2C=C(NC2=CC1)C.O>>OC=1C=C2C=C(NC2=CC1)C | C[O:7][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]([OH:7])[cH:8][cH:9][c:10]2[nH:11]1 | COc1ccc2[nH]c(C)cc2c1 | Cc1cc2cc(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] | 93 | [{"value": 93.0, "product": "OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -45 | CELSIUS | 15 | MINUTE | A solution of boron tribromide (32.5 ml, 341 mmol) in methylene choride (60 ml) was added in portions to a solution of 5-methoxy-2-methylindole (25 g, 155 mmol) in methylene chloride (250 ml) cooled at −45° C. After stirring for 15 minutes at −30° C., the mixture was warmed up to ambient temperature and stirred for 1 h... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | C(Cl)Cl | -45 | 0.25 | COc1ccc2[nH]c(C)cc2c1>C(Cl)Cl>Cc1cc2cc(O)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-89f73e14acf541e39c05386c43425075 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.[H][H]>>OC1=C(C=C2C(=NC=NC2=C1)OC=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]([O: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]([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]... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O | null | [Pd] | CN(C)C=O.C(Cl)Cl | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 89 | [{"value": 89.0, "product": "OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.1, "product": "OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-benzyloxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (0.2 g, 0.5 mmol), (prepared as described in Example 48), in a mixture of methylene chloride (5 ml) and DMF (2 ml) containing 10% palladium-on-charcoal (50 mg) was treated with hydrogen at 1.8 atmospheres pressure for 2 hours. The suspension was f... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | Other | [Pd].CN(C)C=O.C(Cl)Cl | null | null | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCc1ccccc1>[Pd].CN(C)C=O.C(Cl)Cl>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-96273fe54ce24254ab4ef9d0098e7fb3 | COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O.Oc1ccc2[nH]c(C(F)(F)F)cc2c1>>COc1cc2c(Oc3ccc4[nH]c(C(F)(F)F)cc4c3)ncnc2cc1OCCCS(C)(=O)=O | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)C.OC=1C=C2C=C(NC2=CC1)C(F)(F)F.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCCCS(=O)(=O)C)OC=1C=C2C=C(NC2=CC1)C(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][S:31]([CH3:32])(=[O:33])=[O:34])[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]([C:14]([F:15])([F:16])[F:17])[cH:18][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:11]4[nH:12][c:... | COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O.Oc1ccc2[nH]c(C(F)(F)F)cc2c1 | COc1cc2c(Oc3ccc4[nH]c(C(F)(F)F)cc4c3)ncnc2cc1OCCCS(C)(=O)=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[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] | 87.5 | [{"value": 87.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCS(=O)(=O)C)OC=1C=C2C=C(NC2=CC1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.5, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCS(=O)(=O)C)OC=1C=C2C=C(NC2=CC1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A suspension of 4-chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (150 mg, 0.45 mmol) and 5-hydroxy-2-trifluoromethylindole (109 mg, 0.54 mmol), (prepared as described for the starting material in Example 44), in DMF (1.5 ml) containing potassium carbonate (94 mg, 0.67 mmol) was heated at 100° C. for 1 hour. A... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | HCl | CN(C)C=O | 100 | null | COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O.Oc1ccc2[nH]c(C(F)(F)F)cc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C(F)(F)F)cc4c3)ncnc2cc1OCCCS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1ad020d43b3342738f15a32411be44bc | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.CS(=O)(=O)CCCO>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCS(C)(=O)=O | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.CS(=O)(=O)CCCO.N(=NC(=O)OCC)C(=O)OCC>>COC=1C=C2C(N(C=NC2=CC1OCCCS(=O)(=O)C)COC(C(C)(C)C)=O)=O | [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][S:26]([CH3:27])(=[O:28])=[O: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... | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.CS(=O)(=O)CCCO | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCS(C)(=O)=O | 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] | 91 | [{"value": 91.0, "product": "COC=1C=C2C(N(C=NC2=CC1OCCCS(=O)(=O)C)COC(C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "COC=1C=C2C(N(C=NC2=CC1OCCCS(=O)(=O)C)COC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Triphenylphosphine (8.9 g, 35.2 mmol) was added to a suspension of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (6 g, 19.6 mmol), (prepared as described for the starting material in Example 12), in methylene chloride (150 ml). This was followed by the addition of 3-(methylsulphonyl)-1-propano... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1 | HO- | C(Cl)Cl | null | null | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.CS(=O)(=O)CCCO>C(Cl)Cl>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f76face8e9de472a8b5987c3e4ec04f2 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCS(C)(=O)=O>>COc1cc2c(=O)[nH]cnc2cc1OCCCS(C)(=O)=O | Cl.COC=1C=C2C(N(C=NC2=CC1OCCCS(=O)(=O)C)COC(C(C)(C)C)=O)=O.[OH-].[Na+].CC1=CC=C(C=C1)COC(=O)NNC(=O)C2=NC=CN=C2>>COC=1C=C2C(NC=NC2=CC1OCCCS(=O)(=O)C)=O | 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][S:18]([CH3:19])(=[O:20])=[O:21])[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][S:18]([CH3:19])(=[O:20])=[O:21] | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCS(C)(=O)=O | COc1cc2c(=O)[nH]cnc2cc1OCCCS(C)(=O)=O | null | null | O.CO | 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 | 94.2 | [{"value": 90.0, "product": "COC=1C=C2C(NC=NC2=CC1OCCCS(=O)(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.2, "product": "COC=1C=C2C(NC=NC2=CC1OCCCS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 6-Methoxy-7-(3-methylsulphonylpropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (7 g, 17 mmol) was suspended in methanol and 2M sodium hydroxide (3.3 ml, 6.6 mmol) was added with continuous stirring. The reaction mixture became homogeneous after 15 minutes. After a further 45 minutes water was added (7 ml) a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HO- | O.CO | null | 0.25 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCS(C)(=O)=O>O.CO>COc1cc2c(=O)[nH]cnc2cc1OCCCS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ccd25b557cf14e1f8fe5ba6a11a356ea | COc1cc2c(=O)[nH]cnc2cc1OCCCS(C)(=O)=O.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O | COC=1C=C2C(NC=NC2=CC1OCCCS(=O)(=O)C)=O.S(=O)(Cl)Cl.C1(=CC=CC=C1)C.C(O)([O-])=O.[Na+].S(=O)(Cl)Cl.CN(C)C=O>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)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][S:18]([CH3:19])(=[O:20])=[O:21])[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][S:18]([CH3:19])(=[O:20])=[O:21] | COc1cc2c(=O)[nH]cnc2cc1OCCCS(C)(=O)=O.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O | null | null | null | 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] | 88 | [{"value": 88.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Methoxy-7-(3-methylsulphonylpropoxy)-3,4-dihydroquinazolin-4-one (3.6 g, 11.5 mmol) was suspended in thionyl chloride (40 ml). DMF (1.8 ml) was added under argon and the mixture was heated at reflux for 1.5 hours. The thionyl chloride was eliminated by several azeotropic distillations using toluene. The solid residue... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | null | null | null | COc1cc2c(=O)[nH]cnc2cc1OCCCS(C)(=O)=O.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e62930fc082348af970119e748626e64 | CN(C)CCO.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)C | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OC(C)C)C(=O)OC(C)C.OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.CN(CCO)C>>CN(C)CCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC | O[CH2:25][CH2:26][N:27]([CH3:28])[CH3:29].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:... | CN(C)CCO.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)C | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | 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] | 38 | [{"value": 38.0, "product": "CN(C)CCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.9, "product": "CN(C)CCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 0.5M Triphenylphosphine in methylene chloride and diisopropyl azodicarboxylate (150 μl, 0.75 mmol) were added in portions to a suspension of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (112 mg, 0.35 mmol), (prepared as described in Example 49), and N,N-dimethylethanolamine (62 mg, 0.7 mmol) in methylene ch... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | HO- | C(Cl)Cl | null | 2 | CN(C)CCO.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>C(Cl)Cl>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cce430dfd4714f8e95b0ff31efa5b976 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cc1cc2cc(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.OC=1C=C2C=C(NC2=CC1)C.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C=C(NC2=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][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]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13](... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cc1cc2cc(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)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] | 54.8 | [{"value": 54.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A solution of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (100 mg, 0.29 mmol), 5-hydroxy-2-methylindole (53 mg, 0.36 mmol), (prepared as described for the starting material in Example 48), and potassium carbonate (62 mg, 0.44 mmol) in DMF (2 ml) was heated at 85° C. for 3 hours, followed by heating at 95° 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 | 85 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Cc1cc2cc(O)ccc2[nH]1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1711a3376bc04eb0afdc44598921f85a | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.OCCCBr>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCBr | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OCC)C(=O)OCC.OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.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] | 86.1 | [{"value": 86.0, "product": "BrCCCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.1, "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 | Diethyl azodicarboxylate (3.9 ml, 24.5 mmol) was added in portions to a suspension of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (5 g, 16.3 mmol), (prepared as described for the starting material in Example 12), 3-bromo-1-propanol (2.21 ml, 24.5 mmol) and triphenylphosphine (6.42 g, 24.5 mm... | 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-4d3b8a10f745466aafe4a2248ae64a91 | C1CCNCC1.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCBr>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCCCC1 | BrCCCOC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.N1CCCCC1>>COC=1C=C2C(N(C=NC2=CC1OCCCN1CCCCC1)COC(C(C)(C)C)=O)=O | [NH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]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:13]([CH3... | C1CCNCC1.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCBr | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=c1[nH]cnc2cc(OCCCN3CCCCC3)ccc12 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 83 | [{"value": 83.0, "product": "COC=1C=C2C(N(C=NC2=CC1OCCCN1CCCCC1)COC(C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-(3-bromopropoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (2.89 g, 6.78 mmol) in piperidine (100 ml) was heated at 100° C. for 1 hour. After cooling, the volatiles were removed under vacuum. The residue was dissolved in methylene chloride, and washed with saturated ammonium chloride... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | HBr | null | null | null | C1CCNCC1.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCBr>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-014b8f0e02a14648ba8ac29a10e872a5 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCCCC1>>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCCCC1 | COC=1C=C2C(N(C=NC2=CC1OCCCN1CCCCC1)COC(C(C)(C)C)=O)=O>>COC=1C=C2C(NC=NC2=CC1OCCCN1CCCCC1)=O | 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][CH2:21][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][CH2:17][N:18]1[CH2:19][CH2:20][CH2:... | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCCCC1 | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCCCC1 | null | null | CO.N | Reduction | OtherReaction | 9f6991089c15fc054898797f1d3a42b158e517f125611bc103acfc00878b3b20 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]cnc2cc(OCCCN3CCCCC3)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 | 95.4 | [{"value": 95.0, "product": "COC=1C=C2C(NC=NC2=CC1OCCCN1CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "COC=1C=C2C(NC=NC2=CC1OCCCN1CCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-methoxy-7-(3-piperidinopropoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (2.35 g, 5.45 mmol) in 7M ammonia in methanol (50 ml) was stirred overnight at ambient temperature. The volatiles were removed under vacuum and the residue was triturated with ether, filtered and washed with ether follow... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | CO.N | null | null | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCCCN1CCCCC1>CO.N>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d897344702e4688b939d67c1d01d492 | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCCCC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1 | COC=1C=C2C(NC=NC2=CC1OCCCN1CCCCC1)=O.CN(C)C=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1 | 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][CH2:21][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][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2... | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCCCC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccc(OCCCN3CCCCC3)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] | 76 | [{"value": 76.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-one (1.5 g, 4.7 mmol) in thionyl chloride (15 ml) containing DMF (1.5 ml) was heated at reflux for 3 hours. After cooling, the volatiles were removed under vacuum. The residue was azeotroped with toluene. The solid was partitioned between methylene... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCCCC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a248418fe27d4b758d9ad8eaa7e43814 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]ccc2c1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.OC=1C=C2C=CNC2=CC1>>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: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:14][c... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2[nH]ccc2c1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)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] | 442.6 | [{"value": 45.0, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 442.6, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 67, 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (10 mg), (prepared as described for the starting material in Example 67), was reacted with 5-hydroxyindole (48 mg, 0.36 mmol) to give 4-(indol-5-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline (57 mg,... | 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.Oc1ccc2[nH]ccc2c1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b096573f55bf4a47bccdbc6229d71106 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 | O.OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.CC1=CC=C(C=C1)S(=O)(=O)OCC1CCN(CC1)C(=O)OC(C)(C)C.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)OC=1C=C2C=C(NC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].Cc1ccc(S(=O)(=O)O[CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]2)cc1>>[CH3:1][O:2][c:3]1[cH:4]... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):c:c:1.[#7;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):[c:10] | 77.1 | [{"value": 77.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.1, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (161 mg, 0.5 mmol), (prepared as described in Example 49), 4-(4-methylphenylsulphonyloxymethyl)-1-tert-butoxycarbonylpiperidine (222 mg, 0.6 mmol), (prepared as described for the starting material in Example 10), and potassium carbonate (188 mg, 1 m... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | TsOH.HO- | CN(C)C=O | 100 | null | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-217d5f891d1e4cc6b69362dc24ec7253 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1 | COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)OC=1C=C2C=C(NC2=CC1)C.C(=O)(C(F)(F)F)O>>COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C=C(NC2=CC1)C | CC(C)(C)OC(=O)[N:29]1[CH2:28][CH2:27][CH:26]([CH2:25][O:24][c:23]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([O:7][c:8]4[cH:9][cH:10][c:11]5[nH:12][c:13]([CH3:14])[cH:15][c:16]5[cH:17]4)[n:18][cH:19][n:20][c:21]3[cH:22]2)[CH2:31][CH2:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 96 | [{"value": 96.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.6, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 6-methoxy-4-(2-methylindol-5-yloxy)-7-(1-tert-butoxycarbonylpiperidin-4-ylmethoxy)quinazoline (155 mg, 0.3 mmol), (prepared as described in Example 69), in methylene chloride (5 ml) containing TFA (1 ml) was stirred at ambient temperature for 30 minutes. The volatiles were removed under vacuum and the res... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CCNCC1 | HO- | C(Cl)Cl | null | 0.5 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1>C(Cl)Cl>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da3ae70f1ddc41818b8f4183bc0df9a3 | COCC=O.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1>>COCCN1CCC(COc2cc3ncnc(Oc4ccc5[nH]c(C)cc5c4)c3cc2OC)CC1 | C(O)([O-])=O.[Na+].COCC=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C=C(NC2=CC1)C>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCOC)OC=1C=C2C=C(NC2=CC1)C | O=[CH:4][CH2:3][O:2][CH3:1].[NH:5]1[CH2:6][CH2:7][CH:8]([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])[CH2:34][CH2:35]1>>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([CH2:9][O:10][c:... | COCC=O.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1 | COCCN1CCC(COc2cc3ncnc(Oc4ccc5[nH]c(C)cc5c4)c3cc2OC)CC1 | null | null | CO.C(Cl)Cl | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | O=[CH;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 47.3 | [{"value": 47.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCOC)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.3, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCOC)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Methoxyacetaldehyde (368 mg, 3.47 mmol) (freshly distilled) followed by sodium triacetoxyborohydride (552 mg, 2.6 mol) were added to a solution of 6-methoxy-4-(2-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline (726 mg, 1.74 mmol), (prepared as described in Example 70), in a mixture of methylene chloride (15 m... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1 | Other | CO.C(Cl)Cl | null | 1.5 | COCC=O.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1>CO.C(Cl)Cl>COCCN1CCC(COc2cc3ncnc(Oc4ccc5[nH]c(C)cc5c4)c3cc2OC)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7541a0616eea4860b1a30bd7bd123fbd | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OS(=O)(=O)C(F)(F)F | FC(S(=O)(=O)OS(=O)(=O)C(F)(F)F)(F)F.ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)O)C=C1)F.N1=CC=CC=C1>>ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OS(=O)(=O)C(F)(F)F)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].O=S(=O)(O[S:23](=[O:24])(=[O:25])[C:26]([F:27])([F:28])[F:29])C(F)(F)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][c... | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OS(=O)(=O)C(F)(F)F | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to triflate conversion | 934d625c86d5da305dd43240eee33b5e46f4d298c87ccdc218e9e2eb60c650b5 | 13e8f5cec02bd6a2d12ae535029c405c270682596231c5c8422ac50b2cb1ec74 | c1ccc(Oc2ncnc3ccccc23)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[#7;a:8]:[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7;a:8]:[c:9]:[c:10]:[c:11](-[O;H0;D2;+0:12]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]):[c:13] | 88.5 | [{"value": 88.0, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OS(=O)(=O)C(F)(F)F)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OS(=O)(=O)C(F)(F)F)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 1 | HOUR | Trifluoromethanesulphonic anhydride (338 mg, 1.2 mmol) was added to a suspension of 4-(4-chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (320 mg, I mmol), (prepared as described for the starting material in Example 5), in methylene chloride (2 ml) containing pyridine (2 ml) cooled at 5° C. When the addition was ... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Triflate.Aromatic alcohol | Triflate | null | null | c1ccccc1.c1ccc2ncncc2c1 | HF | C(Cl)Cl | 5 | 1 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F>C(Cl)Cl>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OS(=O)(=O)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53240fd6758b45f5a0295e2790b9229e | C=CC(=O)OC(C)(C)C.COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OS(=O)(=O)C(F)(F)F>>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)OC(C)(C)C | C(C)N(CC)CC.C(C=C)(=O)OC(C)(C)C.ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OS(=O)(=O)C(F)(F)F)C=C1)F.C1(=CC=CC=C1)C(CCP)C1=CC=CC=C1>>ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)C=CC(=O)OC(C)(C)C)C=C1)F | [CH2:22]=[CH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30].O=S(=O)(O[c:21]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:19]2[cH:20]1)C(F)(F)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[... | C=CC(=O)OC(C)(C)C.COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OS(=O)(=O)C(F)(F)F | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)OC(C)(C)C | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C)C=O | C-C Coupling | OtherReaction | 7100118f57cdacf6652618e075fd189ecc51663a50ff9d5c87cbfd490068fb24 | e84d2ff35b106b73e905407d80ffdd5c53fba81bdf3725d58511290daa9d3d79 | c1ccc(Oc2ncnc3ccccc23)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:2:[c:9]:[c:10]:1-[#8:11].[C;D1;H3:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[#8:16]-[C:17](=[O;D1;H0:18])-[C:19]=[CH2;D1;+0:20]>>[#8:11]-[c:10]1:[c:9]:[c:8]2:[c:7]:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:2:[c:2]:[c;H0;D3;+0:1]:1-[CH;D2;+0:20]... | 49 | [{"value": 49.0, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)C=CC(=O)OC(C)(C)C)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.7, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)C=CC(=O)OC(C)(C)C)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | Triethylamine (33 mg, 0.33 mmol) and tert-butyl acrylate (77 mg, 0.6 mmol) followed by diphenylpropylphosphine (3.4 mg, 0.008 mmol) and palladium(II) acetate (1.7 mg, 0.0075 mmol) were added to a solution of 4-(4-chloro-2-fluorophenoxy)-6-methoxy-7-(trifluoromethylsulphonyloxy)quinazoline (136 mg, 0.3 mmol) in DMF (1.5... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Vinyl | null | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1 | TfOH.HO- | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O | null | 6 | C=CC(=O)OC(C)(C)C.COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OS(=O)(=O)C(F)(F)F>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C)C=O>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-023fa086034942b6ba1d3852ed3912fe | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)OC(C)(C)C>>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)O | ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)C=CC(=O)OC(C)(C)C)C=C1)F>>C(=O)(O)C=CC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC | CC(C)(C)[O:26][C:24]([CH:23]=[CH:22][c:21]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:19]2[cH:20]1)=[O:25]>>[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... | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)OC(C)(C)C | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)O | null | null | C(Cl)Cl.C(=O)(C(F)(F)F)O | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | c1ccc(Oc2ncnc3ccccc23)cc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[C:5]-[c:6]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]=[C:5]-[c:6] | 87.6 | [{"value": 85.0, "product": "C(=O)(O)C=CC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "C(=O)(O)C=CC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution of 4-(4-chloro-2-fluorophenoxy)-6-methoxy-7-(2-(tert-butoxycarbonyl)vinyl)quinazoline (581 mg, 1.31 mmol) in a mixture of methylene chloride/TFA (2.5 ml/2.5 ml) was stirred at ambient temperature for 1.5 hours. After removal of the volatiles under vacuum, the residue was partitioned between ethyl acetate and... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1.c1ccc2ncncc2c1 | Other | C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 1.5 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)OC(C)(C)C>C(Cl)Cl.C(=O)(C(F)(F)F)O>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c762e8e8205e40a5b0790bfd72e40a24 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)O.Cc1cc2cc(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1C=CC(=O)O | [Na].C[Si](C)(C)N[Si](C)(C)C.C1CCOC1.C(=O)(O)C=CC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC.OC=1C=C2C=C(NC2=CC1)C>>C(=O)(O)C=CC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC | Fc1cc(Cl)ccc1O[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([CH:24]=[CH:25][C:26](=[O:27])[OH:28])[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][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]([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... | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)O.Cc1cc2cc(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1C=CC(=O)O | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 2cfaf3a86d100b1ba78e674d1577e6d6c1e9e8fd22a03032330781c71fecde7c | 123a439cc2c8832d15eb655ab85a8be8bc914ef22c53e79f644ec1c9eb4c6b12 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | Cl-c1:c:c:c(-O-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:2:[c:8]):c(-F):c:1.[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] | 71.4 | [{"value": 71.0, "product": "C(=O)(O)C=CC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.4, "product": "C(=O)(O)C=CC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 1M Sodium HMDS in THF (0.84 ml, 8.4 mmol) was added to a suspension of 7-(2-carboxyvinyl)-4-(4-chloro-2-fluorophenoxy)-6-methoxyquinazoline (105 mg, 0.28 mmol) and 5-hydroxy-2methylindole (82 mg, 0.56 mmol), (prepared as described for the starting material in Example 48), in DMSO (1.5 ml). After stirring for 2 hours at... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Aromatic alcohol | Ether | c1ccccc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | HF | CS(=O)C | null | 2 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1C=CC(=O)O.Cc1cc2cc(O)ccc2[nH]1>CS(=O)C>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1C=CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-28efbc76097047bc91374bc3ed11bac3 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.ClCCCBr>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCCl | O.OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.BrCCCCl.C([O-])([O-])=O.[K+].[K+]>>ClCCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][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].Br[CH2:25][CH2:26][CH2:27][Cl:28]>>[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:1... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.ClCCCBr | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCCl | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:9] | 70.4 | [{"value": 70.0, "product": "ClCCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.4, "product": "ClCCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A suspension of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (321 mg, 1 mmol), (prepared as described in Example 49), 1-bromo-3-chloropropane (120 μl, 1.2 mmol) and potassium carbonate (359 mg, 2.6 mmol) in DMF (5 ml) was stirred at ambient temperature overnight. After addition of water, the precipitate was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | HBr | CN(C)C=O | null | 8 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.ClCCCBr>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2b20ed060b2a4669a6217d9c0f6a18c1 | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCCl>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCN(C)CC1 | ClCCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.CN1CCNCC1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCN(CC1)C)OC=1C=C2C=C(NC2=CC1)C | [NH:28]1[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]1.Cl[CH2:27][CH2:26][CH2:25][O:24][c:23]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22]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... | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCCl | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCNCC3)cc2n1 | Cl-[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 | 32 | [{"value": 32.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCN(CC1)C)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-(3-chloropropoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (150 mg, 0.38 mmol), (prepared as described in Example 73), in 1-methylpiperazine (2 ml) was heated at 100° C. for 2 hours. After cooling, the mixture was partitioned between ethyl acetate and aqueous 5% sodium hydrogen carbonate. The orga... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CN1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCCl>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ee680b06e7f4affbf1c69d8a63a3d10 | CCN(CC)CCO.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>>CCN(CC)CCOc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC | N(=NC(=O)OCC)C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CCO)CC.OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC>>C(C)N(CC)CCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC | O[CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5].[OH:8][c:9]1[cH:10][c:11]2[n:12][cH:13][n:14][c:15]([O:16][c:17]3[cH:18][cH:19][c:20]4[nH:21][c:22]([CH3:23])[cH:24][c:25]4[cH:26]3)[c:27]2[cH:28][c:29]1[O:30][CH3:31]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][c:11]2[n:12][cH:13][n:14][c:15](... | CCN(CC)CCO.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O | CCN(CC)CCOc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | 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] | 70 | [{"value": 70.0, "product": "C(C)N(CC)CCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "C(C)N(CC)CCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Triphenylphosphine (262 mg, 1 mmol) and N,N-diethylethanolamine (88 mg, 0.75 mmol) were added to a suspension of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (160 mg, 0.5 mmol), (prepared as described in Example 49), in methylene chloride (5 ml), followed by the addition, in portions, of diethyl azodicarbox... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1 | HO- | C(Cl)Cl | null | 1 | CCN(CC)CCO.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>C(Cl)Cl>CCN(CC)CCOc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc971279b9e240d087147068c0457939 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.OCCOc1ccncc1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCOc1ccncc1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.OCCOC1=CC=NC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OC(C)C)C(=O)OC(C)C>>COC=1C=C2C(=NC=NC2=CC1OCCOC1=CC=NC=C1)OC=1C=C2C=C(NC2=CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24].O[CH2:25][CH2:26][O:27][c:28]1[cH:29][cH:30][n:31][cH:32][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[c... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.OCCOc1ccncc1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCOc1ccncc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1cc(OCCOc2ccc3c(Oc4ccc5[nH]ccc5c4)ncnc3c2)ccn1 | 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] | 54 | [{"value": 54.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCOC1=CC=NC=C1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.5, "product": "COC=1C=C2C(=NC=NC2=CC1OCCOC1=CC=NC=C1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (193 mg, 0.6 mmol), (prepared as described in Example 49), 4-(2-hydroxyethoxy)pyridine (166 mg, 1.2 mmol), (J. Chem. Soc. Perkin II, 1987, 1867), in methylene chloride (5 ml) containing triphenylphosphine (330 mg, 1.26 mmol) and diisopropyl azodicar... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ccncc1 | HO- | C(Cl)Cl | null | 2 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O.OCCOc1ccncc1>C(Cl)Cl>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCOc1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-82407654665140cd8ab19b027a2616a6 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)C(=O)OC(C)(C)C.CS(=O)(=O)Cl>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)S(C)(=O)=O | CS(=O)(=O)Cl.C(=O)(C(F)(F)F)O.COC=1C=C2C(=NC=NC2=CC1OCCN(C(=O)OC(C)(C)C)C)OC=1C=C2C=C(NC2=CC1)C.C(C)N(CC)CC>>COC=1C=C2C(=NC=NC2=CC1OCCN(S(=O)(=O)C)C)OC=1C=C2C=C(NC2=CC1)C | CC(C)(C)OC(=O)[N:27]([CH2:26][CH2:25][O:24][c:23]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22]1)[CH3:28].Cl[S:29]([CH3:30])(=[O:31])=[O: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... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)C(=O)OC(C)(C)C.CS(=O)(=O)Cl | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)S(C)(=O)=O | null | null | C(Cl)Cl | Acylation | OtherReaction | 2b1ae4c17a0a628d4c79000b5e250235a52882f8aea5522afb71b80acc2e8f07 | 705725ff5b1b5bdebe12db390e8895152ae89941b9a07e00716e981f5b25c654 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].Cl-[S;H0;D4;+0:5](-[C;D1;H3:6])(=[O;D1;H0:7])=[O;D1;H0:8]>>[C:4]-[C:3]-[N;H0;D3;+0:1](-[C;D1;H3:2])-[S;H0;D4;+0:5](-[C;D1;H3:6])(=[O;D1;H0:7])=[O;D1;H0:8] | 38.2 | [{"value": 38.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCN(S(=O)(=O)C)C)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.2, "product": "COC=1C=C2C(=NC=NC2=CC1OCCN(S(=O)(=O)C)C)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A suspension of 6-methoxy-4-(2-methylindol-5-yloxy)-7-(2-(N-methyl-N-tert-butoxycarbonylamino)ethoxy)quinazoline (148 mg, 0.31 mmol), (prepared as described in Example 149), in methylene chloride (4 ml) containing TFA (1 ml) was stirred for 1 hour. After removing the volatiles under vacuum, the residue was azeotroped w... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Tertiary amine | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | HCl | C(Cl)Cl | null | 1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)C(=O)OC(C)(C)C.CS(=O)(=O)Cl>C(Cl)Cl>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)S(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a03dd6dfa1f14dcb9f0a84e8b45e70aa | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCOC1CCNCC1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCOC1CCN(CCC#N)CC1 | COC=1C=C2C(=NC=NC2=CC1OCCOC1CCNCC1)OC=1C=C2C=C(NC2=CC1)C>>C(#N)CCN1CCC(CC1)OCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][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][CH2:26][O:27][CH:28]1[CH2:29][CH2:32][NH:31][CH2:36][CH2:37]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14]... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCOC1CCNCC1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCOC1CCN(CCC#N)CC1 | null | null | C(C=C)#N.CO.C(Cl)Cl | Miscellaneous | OtherReaction | a7099ea97bc43b09bfde1675aaf7ec66651498d865ae483e4bd4d037e726db38 | 78ae9872e848ed8994acd80eff3ed9e4541fcd281499500b75914b57d1abfbba | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCOC3CCNCC3)cc2n1 | [#8:1]-[C:2]1-[C:3]-[C:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1>>[#8:1]-[C:2]1-[C:3]-[C:4]-[N;H0;D3;+0:5](-[CH2;D2;+0:6]-[C:8]-[C:9])-[C:10]-[CH2;D2;+0:7]-1 | 171.2 | [{"value": 86.0, "product": "C(#N)CCN1CCC(CC1)OCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 171.2, "product": "C(#N)CCN1CCC(CC1)OCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-methoxy-4-(2-methylindol-5-yloxy)-7-(2-(piperidin-4-yloxy)ethoxy)quinazoline (76 mg, 0.17 mmol), (prepared as described in Example 77), in acrylonitrile (0.5 ml), methylene chloride (1 ml) and methanol (1 ml) was stirred overnight at ambient temperature. After removal of the volatiles under vacuum the r... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Nitrile.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | Other | C(C=C)#N.CO.C(Cl)Cl | null | null | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCOC1CCNCC1>C(C=C)#N.CO.C(Cl)Cl>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCOC1CCN(CCC#N)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-626a831be92641a784c20f02906b08b3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2cc[nH]c2c1>>COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.OC1=CC=C2C=CNC2=C1.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C=CNC2=C1 | 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][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]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][cH:13][nH:14][c:15]4[cH... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2cc[nH]c2c1 | COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCN1CCCC1 | null | null | C(Cl)Cl.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3cc[nH]c3c2)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]:[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] | 69.4 | [{"value": 69.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C=CNC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C=CNC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A solution of 4-chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline (100 m g, 0.31 mmol), (prepared as described for the starting material in Example 9), 6-hydroxyindole (50 mg, 0.37 mmol) and potassium carbonate (64 mg, 0.466 mmol) in DMF (1 ml) was heated at 95° C. for 4 hours. After cooling, the mixture was dil... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | C(Cl)Cl.CN(C)C=O | 95 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Oc1ccc2cc[nH]c2c1>C(Cl)Cl.CN(C)C=O>COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc11ca25b1654c81a392193d4382e978 | Cc1cc2cc(Oc3ncnc4cc(O)ccc34)ccc2[nH]1.OCCCN1CCCC1>>Cc1cc2cc(Oc3ncnc4cc(OCCCN5CCCC5)ccc34)ccc2[nH]1 | N(=NC(=O)OC(C)C)C(=O)OC(C)C.OC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1(CCCC1)CCCO>>CC=1NC2=CC=C(C=C2C1)OC1=NC=NC2=CC(=CC=C12)OCCCN1CCCC1 | [CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([O:7][c:8]3[n:9][cH:10][n:11][c:12]4[cH:13][c:14]([OH:15])[cH:24][cH:25][c:26]34)[cH:27][cH:28][c:29]2[nH:30]1.O[CH2:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([O:7][c:8]3[n:9][cH:10][n:11][c:12]4[cH:13][c:14]([O:15][CH2:16][CH2... | Cc1cc2cc(Oc3ncnc4cc(O)ccc34)ccc2[nH]1.OCCCN1CCCC1 | Cc1cc2cc(Oc3ncnc4cc(OCCCN5CCCC5)ccc34)ccc2[nH]1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)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] | 35.8 | [{"value": 35.0, "product": "CC=1NC2=CC=C(C=C2C1)OC1=NC=NC2=CC(=CC=C12)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.8, "product": "CC=1NC2=CC=C(C=C2C1)OC1=NC=NC2=CC(=CC=C12)OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Diisopropyl azodicarboxylate (146 mg, 0.72 mmol) was added to a solution of 7-hydroxy-4-(2-methylindol-5-yloxy)quinazoline (100 mg, 0.34 mmol), triphenyl phosphine (189 mg, 0.72 mol), and 3-pyrrolidinopropan-1-ol (89 mg, 0.686 mmol), (J. Org. Chem. 1988, 53, 3164), in methylene chloride (2.5 ml). After stirring overnig... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HO- | C(Cl)Cl | null | 8 | Cc1cc2cc(Oc3ncnc4cc(O)ccc34)ccc2[nH]1.OCCCN1CCCC1>C(Cl)Cl>Cc1cc2cc(Oc3ncnc4cc(OCCCN5CCCC5)ccc34)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2d8b67f1a8a545bd9972d1da6ea7114f | O=c1[nH]cnc2cc(F)ccc12.OCc1ccccc1>>O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | Cl.[Na].C(C1=CC=CC=C1)O.FC1=CC=C2C(NC=NC2=C1)=O>>C(C1=CC=CC=C1)OC1=CC=C2C(NC=NC2=C1)=O | F[c:8]1[cH:7][c:6]2[n:5][cH:4][nH:3][c:2](=[O:1])[c:19]2[cH:18][cH:17]1.[OH:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18][c:19]12 | O=c1[nH]cnc2cc(F)ccc12.OCc1ccccc1 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | ac75d0316beb5e727636a794e424e80db78112f51f640e69f9b28b1404a2e776 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:1.[OH;D1;+0:11]-[C:12]-[c:13]>>[c:13]-[C:12]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:1 | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)OC1=CC=C2C(NC=NC2=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.2, "product": "C(C1=CC=CC=C1)OC1=CC=C2C(NC=NC2=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 148 | CELSIUS | null | null | Sodium (368 mg, 16 mmol) was added to benzyl alcohol (10 ml, 96 mmol) and the mixture was heated at 148° C. for 30 minutes. 7-Fluoro-3,4-dihydroquinazolin-4-one (656 mg, 4 mmol), (J. Chem. Soc. section B 1967, 449), was added and the mixture maintained at 148° C. for 24 hours. The reaction mixture was allowed to cool, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccc2cncnc2c1 | c1ccc2cncnc2c1 | c1ccc2cncnc2c1.c1ccccc1 | HF | O | 148 | null | O=c1[nH]cnc2cc(F)ccc12.OCc1ccccc1>O>O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-386c15b33e43484abe8d4c9e2dced546 | O=S(Cl)Cl.O=c1[nH]cnc2cc(OCc3ccccc3)ccc12>>Clc1ncnc2cc(OCc3ccccc3)ccc12 | C(C1=CC=CC=C1)OC1=CC=C2C(NC=NC2=C1)=O.CN(C)C=O.S(=O)(Cl)Cl>>C(C1=CC=CC=C1)OC1=CC=C2C(=NC=NC2=C1)Cl | O=S(Cl)[Cl:1].O=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18][c:19]12>>[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18][c:19]12 | O=S(Cl)Cl.O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | Clc1ncnc2cc(OCc3ccccc3)ccc12 | null | null | null | Functional Group Interconversion | OtherReaction | 5d38f97f3712b237e9f3fba95a694ccb97b6e400bb6127459a74d91e2bc1ab18 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(COc2ccc3cncnc3c2)cc1 | 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] | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)OC1=CC=C2C(=NC=NC2=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 7-benzyloxy-3,4-dihydroquinazolin-4-one (1 g, 43.6 mmol) and DMF (1 ml) in thionyl chloride (100 ml) was heated at reflux for 1.5 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The residue was partitioned between methylene chloride and water and saturated... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2cncnc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HCl | null | null | null | O=S(Cl)Cl.O=c1[nH]cnc2cc(OCc3ccccc3)ccc12>>Clc1ncnc2cc(OCc3ccccc3)ccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-08ed20305afe40bbb64522a1ad4d9b3c | Cc1cc2cc(O)ccc2[nH]1.Clc1ncnc2cc(OCc3ccccc3)ccc12>>Cc1cc2cc(Oc3ncnc4cc(OCc5ccccc5)ccc34)ccc2[nH]1 | C(C1=CC=CC=C1)OC1=CC=C2C(=NC=NC2=C1)Cl.OC=1C=C2C=C(NC2=CC1)C.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C | [CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([OH:7])[cH:26][cH:27][c:28]2[nH:29]1.Cl[c:8]1[n:9][cH:10][n:11][c:12]2[cH:13][c:14]([O:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][cH:24][c:25]12>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([O:7][c:8]3[n:9][cH:10][n:11][c:12]4[cH:13][c:14]([O:15][CH2:16][c:17]5[cH:18][c... | Cc1cc2cc(O)ccc2[nH]1.Clc1ncnc2cc(OCc3ccccc3)ccc12 | Cc1cc2cc(Oc3ncnc4cc(OCc5ccccc5)ccc34)ccc2[nH]1 | 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:6]:[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:7]:1:[c:8] | 81 | [{"value": 81.0, "product": "C(C1=CC=CC=C1)OC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "C(C1=CC=CC=C1)OC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | A solution of 7-benzyloxy-4-chloroquinazoline (2 g, 7.4 mmol), 5-hydroxy-2-methylindole (1.3 g, 8.9 mmol), (prepared as described for the starting material in Example 48), in DMF (20 ml) containing potassium carbonate (1.53 g, 11.1 mmol) was stirred at 80° C. for 3 hours. After cooling, the mixture was poured in portio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CN(C)C=O | 80 | 3 | Cc1cc2cc(O)ccc2[nH]1.Clc1ncnc2cc(OCc3ccccc3)ccc12>CN(C)C=O>Cc1cc2cc(Oc3ncnc4cc(OCc5ccccc5)ccc34)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-66e62c3f593c499ca4a2ecf6732323a2 | Cc1cc2cc(Oc3ncnc4cc(OCc5ccccc5)ccc34)ccc2[nH]1>>Cc1cc2cc(Oc3ncnc4cc(O)ccc34)ccc2[nH]1 | C(=O)[O-].[NH4+].C(C1=CC=CC=C1)OC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C>>OC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C | c1ccc(C[O:15][c:14]2[cH:13][c:12]3[n:11][cH:10][n:9][c:8]([O:7][c:6]4[cH:5][c:4]5[cH:3][c:2]([CH3:1])[nH:22][c:21]5[cH:20][cH:19]4)[c:18]3[cH:17][cH:16]2)cc1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([O:7][c:8]3[n:9][cH:10][n:11][c:12]4[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]34)[cH:19][cH:20][c:21]2[nH:22]1 | Cc1cc2cc(Oc3ncnc4cc(OCc5ccccc5)ccc34)ccc2[nH]1 | Cc1cc2cc(Oc3ncnc4cc(O)ccc34)ccc2[nH]1 | null | [Pd] | CN(C)C=O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 93 | [{"value": 93.0, "product": "OC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "OC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 10% Palladium on charcoal (200 mg) followed by ammonium formate (4.34 g, 69 mmol) were added to a solution of 7-benzyloxy-4-(2-methylindol-5-yloxy)quinazoline (1.75 g, 4.58 mmol) in DMF (60 ml). After stirring for 1 hour at ambient temperature, the mixture was filtered. The filtrate was evaporated. The residue was trit... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | Other | [Pd].CN(C)C=O | null | 1 | Cc1cc2cc(Oc3ncnc4cc(OCc5ccccc5)ccc34)ccc2[nH]1>[Pd].CN(C)C=O>Cc1cc2cc(Oc3ncnc4cc(O)ccc34)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-842f2abcb05746a680def91007ddf757 | CC(C)(C)OC(=O)N1CCC(CO)CC1.Cc1cc2cc(Oc3ncnc4cc(O)ccc34)ccc2[nH]1>>Cc1cc2cc(Oc3ncnc4cc(OCC5CCN(C(=O)OC(C)(C)C)CC5)ccc34)ccc2[nH]1 | N(=NC(=O)OC(C)C)C(=O)OC(C)C.OC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OCC1CCN(CC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCC(CC1)COC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C | O[CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]1.[CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([O:7][c:8]3[n:9][cH:10][n:11][c:12]4[cH:13][c:14]([OH:15])[cH:30][cH:31][c:32]34)[cH:33][cH:34][c:35]2[nH:36]1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([O:7][c:8]3[n:9][cH:... | CC(C)(C)OC(=O)N1CCC(CO)CC1.Cc1cc2cc(Oc3ncnc4cc(O)ccc34)ccc2[nH]1 | Cc1cc2cc(Oc3ncnc4cc(OCC5CCN(C(=O)OC(C)(C)C)CC5)ccc34)ccc2[nH]1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):[c:10] | 68 | [{"value": 68.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)COC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.5, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)COC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 7-hydroxy-4-(2-methylindol-5-yloxy)quinazoline (423 mg, 1.45 mmol), (prepared as described for the starting material in Example 82), triphenylphosphine (685 mg, 2.61 mmol), 4-hydroxymethyl-1-tert-butoxycarbonylpiperidine (500 mg, 2.32 mmol), (prepared as described for the starting material in Example 10),... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)N1CCC(CO)CC1.Cc1cc2cc(Oc3ncnc4cc(O)ccc34)ccc2[nH]1>C(Cl)Cl>Cc1cc2cc(Oc3ncnc4cc(OCC5CCN(C(=O)OC(C)(C)C)CC5)ccc34)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-854ddcf2d8f646d4b6085429f2c86e2c | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O.OCCN1CCCC1>>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCN1CCCC1 | N(=NC(=O)OC(C)C)C(=O)OC(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OCCN1CCCC1.CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)O>>CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCCC1 | [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:15]([CH3:16])[c:17]4[cH:18]3)[n:19][cH:20][n:21][c:22]2[cH:23][c:24]1[OH:25].O[CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[... | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O.OCCN1CCCC1 | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCN1CCCC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCN3CCCC3)cc2n1 | O-[CH2;D2;+0:1]-[C:2]-[#7:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]:[c:5]:[#7;a:4] | 37 | [{"value": 37.0, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.8, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of 4-(2,3-dimethylindol-5-yloxy)-7-hydroxy-6-methoxyquinazoline (124 mg, 0.32 mmol) in methylene chloride (2.5 ml) was added triphenylphosphine (179 mg, 0.628 mmol), 1-(2-hydroxyethyl)pyrrolidine (75 mg, 0.65 mmol) followed by diisopropyl azodicarboxylate (134 μl, 0.68 mmol) in portions. After stirring ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HO- | C(Cl)Cl | null | 8 | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O.OCCN1CCCC1>C(Cl)Cl>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6794c1b8a77945f7839e5559d033a546 | COc1ccc2[nH]c(C)c(C)c2c1>>Cc1[nH]c2ccc(O)cc2c1C | CC=1NC2=CC=C(C=C2C1C)OC.B(Br)(Br)Br.[OH-].[Na+]>>CC=1NC2=CC=C(C=C2C1C)O | C[O:8][c:7]1[cH:6][cH:5][c:4]2[nH:3][c:2]([CH3:1])[c:11]([CH3:12])[c:10]2[cH:9]1>>[CH3:1][c:2]1[nH:3][c:4]2[cH:5][cH:6][c:7]([OH:8])[cH:9][c:10]2[c:11]1[CH3:12] | COc1ccc2[nH]c(C)c(C)c2c1 | Cc1[nH]c2ccc(O)cc2c1C | null | null | O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 77 | [{"value": 77.0, "product": "CC=1NC2=CC=C(C=C2C1C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "CC=1NC2=CC=C(C=C2C1C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2,3-dimethyl-5-methoxyindole (175 mg, 1 mmol), (J. Chem. Soc. 1957, 3175–3180) in methylene (5 ml) cooled at −60° C. was added boron tribromide (210 μl, 2.2 mmol) dropwise. After completion of addition, the mixture was left to warm up to ambient temperature and was stirred for 1 hour. Water was added a... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | O | null | 1 | COc1ccc2[nH]c(C)c(C)c2c1>O>Cc1[nH]c2ccc(O)cc2c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-42046bf8cb5d4a69a8401106f59e4bd4 | 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.CC=1NC2=CC=C(C=C2C1C)O.C([O-])([O-])=O.[K+].[K+]>>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] | 98.8 | [{"value": 95.0, "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": 98.8, "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}] | null | null | 15 | MINUTE | Under nitrogen, to a solution of 2,3-dimethyl-5-hydroxyindole (643 mg, 4 mmol), in DMF (10 ml) was added potassium carbonate (690 mg, 5 mmol). After stirring for 15 minutes at ambient temperature, 7-benzyloxy-4-chloro-6-methoxyquinazoline (1 g, 3.33 mmol), (prepared as described for the starting material in Example 1),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CN(C)C=O | null | 0.25 | 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-3bfd1ba1cd7d48a1aff557104078bbc4 | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C(=C(NC2=CC1)C)C)OC.C(=O)[O-].[NH4+]>>CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)O | c1ccc(C[O:25][c:24]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([O:7][c:8]4[cH:9][cH:10][c:11]5[nH:12][c:13]([CH3:14])[c:15]([CH3:16])[c:17]5[cH:18]4)[n:19][cH:20][n:21][c:22]3[cH:23]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[c:15]([CH3:16])[c:17]4[cH:18]3)[n:19][cH:20][n... | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1 | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O | null | [Pd] | CN(C)C=O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 69.8 | [{"value": 69.0, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.8, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | A solution of 7-benzyloxy-4-(2,3-dimethylindol-5-yloxy)-6-methoxyquinazoline (2 g, 4.7 mmol) in DMF (120 ml) containing ammonium formate (11 gr, 174 mmol) and 10% palladium on charcoal (200 mg) was stirred for 2.5 hours at ambient temperature. The mixture was filtered, and the filtrate was evaporated under vacuum. The ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | Other | [Pd].CN(C)C=O | null | 2.5 | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1>[Pd].CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7c482d15c6cb4a9c8b8c79fb205a2341 | COCCOCCO.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O>>COCCOCCOc1cc2ncnc(Oc3ccc4[nH]ccc4c3)c2cc1OC | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC.COCCOCCO>>N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCOCCOC | 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][c:15]([O:16][c:17]3[cH:18][cH:19][c:20]4[nH:21][cH:22][cH:23][c:24]4[cH:25]3)[c:26]2[cH:27][c:28]1[O:29][CH3:30]>>[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:17]3[cH:... | COCCOCCO.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O | COCCOCCOc1cc2ncnc(Oc3ccc4[nH]ccc4c3)c2cc1OC | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | 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] | 42.2 | [{"value": 42.0, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCOCCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.2, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCOCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 91, 7-hydroxy-4-(indol-5-yloxy)-6-methoxyquinazoline (89 mg) was reacted with 2-(2-methoxyethoxy)ethanol (70 mg) to give 4-(indol-5yloxy)-6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)quinazoline (50 mg, 42%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | COCCOCCO.COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O>>COCCOCCOc1cc2ncnc(Oc3ccc4[nH]ccc4c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-007193818dbc4013a176624a6a5b1660 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc2[nH]ccc2c1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC.OC=1C=C2C=CNC2=CC1.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=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.[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:14][c:15]4[cH:16]3)[n:17][... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc2[nH]ccc2c1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)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] | 88.1 | [{"value": 88.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.1, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | A mixture of 7-benzyloxy-4-chloro-6-methoxyquinazoline (3 g, 10 mmol), (prepared as described for the starting material in Example 1), 5-hydroxyindole (1.46 g, 11 mmol) in DMF (30 ml) containing potassium carbonate (2.75 g, 20 mmol) was heated at 95° C. for 2 hours. After cooling the mixture was poured onto water (100 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CN(C)C=O | 95 | null | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc2[nH]ccc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7667d085405e46f48417935fc1ca117f | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC.[H][H]>>OC1=C(C=C2C(=NC=NC2=C1)OC=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]([O: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]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][cH:13][cH:14][c:15]4[cH:16]3)[n:17][cH:18][n:19][c:20]2[cH:21][c:22]1[OH:23] | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O | null | [Pd] | C(Cl)Cl.CN(C)C=O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 44 | [{"value": 44.0, "product": "OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.9, "product": "OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=CNC2=CC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-benzyloxy-4-(indol-5-yloxy)-6-methoxyquinazoline (8 g, 20 mmol) in DMF (50 ml) and methylene chloride (100 ml) containing 10% palladium on charcoal (2 g) was hydrogenated at 1.8 atmospheres pressure until uptake of hydrogen had ceased. The solution was filtered, the catalyst was washed with DMF and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | Other | [Pd].C(Cl)Cl.CN(C)C=O | null | null | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCc1ccccc1>[Pd].C(Cl)Cl.CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-62cc52a760534c84916822f65748c4c0 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2cc[nH]c2c1>>COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCN1CCCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.OC1=CC=C2C=CNC2=C1.C([O-])([O-])=O.[Cs+].[Cs+]>>N1C=CC2=CC=C(C=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: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]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][cH:13][nH:14][c... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2cc[nH]c2c1 | COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCN1CCCCC1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3cc[nH]c3c2)c2ccc(OCCCN3CCCCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[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] | 94 | [{"value": 93.0, "product": "N1C=CC2=CC=C(C=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.0, "product": "N1C=CC2=CC=C(C=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A solution of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (200 mg, 0.59 mmol), (prepared as described for the starting material in Example 67), 6-hydroxyindole (96 mg, 0.715 mmol) in DMF (3 ml) containing cesium carbonate (291 mg, 0.894 mmol) was heated at 90° C. for 4 hours. After cooling, the mixture was di... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | O.CN(C)C=O | 90 | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2cc[nH]c2c1>O.CN(C)C=O>COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-468fcbe5be244819a8c75295abe707e7 | COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O.Oc1ccc2cc[nH]c2c1>>COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCS(C)(=O)=O | O.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)C.OC1=CC=C2C=CNC2=C1.C([O-])([O-])=O.[K+].[K+]>>N1C=CC2=CC=C(C=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)C | 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][S:27]([CH3:28])(=[O:29])=[O:30])[cH:21][c:20]2[n:19][cH:18][n:17]1.[OH: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]([O: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)ncnc2cc1OCCCS(C)(=O)=O.Oc1ccc2cc[nH]c2c1 | COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCS(C)(=O)=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2c(Oc3ccc4cc[nH]c4c3)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 50.7 | [{"value": 50.0, "product": "N1C=CC2=CC=C(C=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.7, "product": "N1C=CC2=CC=C(C=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A solution of 4-chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (200 mg, 0.6 mmol), (prepared as described for the starting material in Example 50), and 6hydroxyindole (97 mg, 0.73 mmol) in DMF (3 ml) containing potassium carbonate (125 mg, 0.91 mmol) was heated at 90° C. for 2.5 hours. After cooling, water wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | HCl | CN(C)C=O | 90 | null | COc1cc2c(Cl)ncnc2cc1OCCCS(C)(=O)=O.Oc1ccc2cc[nH]c2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f3367ca3df6c40e0a8ab5df5135e4fd7 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2cc[nH]c2c1>>COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCN1CCOCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.OC1=CC=C2C=CNC2=C1>>N1C=CC2=CC=C(C=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH2:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[cH:21][c:20]2[n:19][cH:18][n:17]1.[OH:7][c:8]1[cH:9][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]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][cH:13][nH:14][c:1... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2cc[nH]c2c1 | COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCN1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3cc[nH]c3c2)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].[#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] | 60.5 | [{"value": 60.0, "product": "N1C=CC2=CC=C(C=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.5, "product": "N1C=CC2=CC=C(C=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described for Example 120, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (200 mg, 0.59 mmol), (prepared as described for the starting material in Example 1), was reacted with 6-hydroxyindole (95 mg, 0.71 mmol) to give 4-(indol-6-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinaz... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2cc[nH]c2c1>>COc1cc2c(Oc3ccc4cc[nH]c4c3)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-616c674376af4e3b9af8c59478602e58 | Cc1cc2cc(Oc3ncnc4cc(OCC5CCN(C(=O)OC(C)(C)C)CC5)ccc34)ccc2[nH]1>>Cc1cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2[nH]1 | C(C)(C)(C)OC(=O)N1CCC(CC1)COC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C>>CC=1NC2=CC=C(C=C2C1)OC1=NC=NC2=CC(=CC=C12)OCC1CCNCC1 | CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][CH:17]([CH2:16][O:15][c:14]2[cH:13][c:12]3[n:11][cH:10][n:9][c:8]([O:7][c:6]4[cH:5][c:4]5[cH:3][c:2]([CH3:1])[nH:29][c:28]5[cH:27][cH:26]4)[c:25]3[cH:24][cH:23]2)[CH2:22][CH2:21]1>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([O:7][c:8]3[n:9][cH:10][n:11][c:12]4[cH:13][c:14]([O:15][CH2:16]... | Cc1cc2cc(Oc3ncnc4cc(OCC5CCN(C(=O)OC(C)(C)C)CC5)ccc34)ccc2[nH]1 | Cc1cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2[nH]1 | null | null | C(Cl)Cl.C(=O)(C(F)(F)F)O | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 67 | [{"value": 67.0, "product": "CC=1NC2=CC=C(C=C2C1)OC1=NC=NC2=CC(=CC=C12)OCC1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.4, "product": "CC=1NC2=CC=C(C=C2C1)OC1=NC=NC2=CC(=CC=C12)OCC1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A suspension of 7-(1-tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-(2-methylindol-5-yloxy)quinazoline (150 mg, 0.31 mmol), (prepared as described in Example 90), in methylene chloride (2 ml) and TFA (1.5 ml) was stirred for 1 hour at ambient temperature. After removal of the volatiles under vacuum the residue was azeotro... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CCNCC1 | HO- | C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 1 | Cc1cc2cc(Oc3ncnc4cc(OCC5CCN(C(=O)OC(C)(C)C)CC5)ccc34)ccc2[nH]1>C(Cl)Cl.C(=O)(C(F)(F)F)O>Cc1cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-950ddb65fb7545d7ae9e374e2c9a5445 | COCC=O.Cc1cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2[nH]1>>COCCN1CCC(COc2ccc3c(Oc4ccc5[nH]c(C)cc5c4)ncnc3c2)CC1 | CC=1NC2=CC=C(C=C2C1)OC1=NC=NC2=CC(=CC=C12)OCC1CCNCC1.COCC=O>>COCCN1CCC(CC1)COC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C | O=[CH:4][CH2:3][O:2][CH3:1].[NH:5]1[CH2:6][CH2:7][CH:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([O:16][c:17]4[cH:18][cH:19][c:20]5[nH:21][c:22]([CH3:23])[cH:24][c:25]5[cH:26]4)[n:27][cH:28][n:29][c:30]3[cH:31]2)[CH2:32][CH2:33]1>>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([CH2:9][O:10][c:11]2[cH:12][c... | COCC=O.Cc1cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2[nH]1 | COCCN1CCC(COc2ccc3c(Oc4ccc5[nH]c(C)cc5c4)ncnc3c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | O=[CH;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 46.4 | [{"value": 46.0, "product": "COCCN1CCC(CC1)COC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.4, "product": "COCCN1CCC(CC1)COC1=CC=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described for Example 71, 4-(2-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline (150 mg, 0.386 mmol), (prepared as described in Example 122), was reacted with methoxyacetaldehyde (83 mg, 0.772 mmol), (prepared as described for the starting material in Example 71), to give 7... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | Other | null | null | null | COCC=O.Cc1cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2[nH]1>>COCCN1CCC(COc2ccc3c(Oc4ccc5[nH]c(C)cc5c4)ncnc3c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c3980b4011204cfe93b1fe678c2f67c0 | CCS(=O)(=O)CCCO.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>>CCS(=O)(=O)CCCOc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC | N(=NC(=O)OCC)C(=O)OCC.OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.C(C)S(=O)(=O)CCCO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)S(=O)(=O)CCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC | O[CH2:8][CH2:7][CH2:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5].[OH:9][c:10]1[cH:11][c:12]2[n:13][cH:14][n:15][c:16]([O:17][c:18]3[cH:19][cH:20][c:21]4[nH:22][c:23]([CH3:24])[cH:25][c:26]4[cH:27]3)[c:28]2[cH:29][c:30]1[O:31][CH3:32]>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][c:12]2[n:13][cH:... | CCS(=O)(=O)CCCO.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O | CCS(=O)(=O)CCCOc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | 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] | 55.2 | [{"value": 55.0, "product": "C(C)S(=O)(=O)CCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.2, "product": "C(C)S(=O)(=O)CCCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Diethyl azodicarboxylate (117 mg, 0.67 mmol) was added in portions to a solution of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (120 mg, 0.37 mmol), (prepared as described in Example 49), and 3-(ethylsulphonyl)-1-propanol (74 mg, 0.48 mmol) in methylene chloride (3.5 ml) and triphenylphosphine (176 mg, 0.6... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1 | HO- | C(Cl)Cl | null | 2 | CCS(=O)(=O)CCCO.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>C(Cl)Cl>CCS(=O)(=O)CCCOc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5c132ae4580f451eaf6a3733dd9284dd | CCS(=O)(=O)CCCO.COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O>>CCS(=O)(=O)CCCOc1cc2ncnc(Oc3ccc4[nH]c(C)c(C)c4c3)c2cc1OC | CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)O.C(C)S(=O)(=O)CCCO>>CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)CC | O[CH2:8][CH2:7][CH2:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5].[OH:9][c:10]1[cH:11][c:12]2[n:13][cH:14][n:15][c:16]([O:17][c:18]3[cH:19][cH:20][c:21]4[nH:22][c:23]([CH3:24])[c:25]([CH3:26])[c:27]4[cH:28]3)[c:29]2[cH:30][c:31]1[O:32][CH3:33]>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][c:12]2[... | CCS(=O)(=O)CCCO.COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O | CCS(=O)(=O)CCCOc1cc2ncnc(Oc3ccc4[nH]c(C)c(C)c4c3)c2cc1OC | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | 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] | 57 | [{"value": 57.0, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCS(=O)(=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described for Example 124, 4-(2,3-dimethylindol-5-yloxy)-7-hydroxy-6-methoxyquinazoline (120 mg, 0.36 mol), (prepared as described for the starting material in Example 91), was reacted with 3-(ethylsulphonyl)-1-propanol (71 mg, 0.46 mol), (prepared as described for the starting mate... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1 | HO- | null | null | null | CCS(=O)(=O)CCCO.COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O>>CCS(=O)(=O)CCCOc1cc2ncnc(Oc3ccc4[nH]c(C)c(C)c4c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-96881d55c9224543ab8da979c8651f3b | OCCc1ccncc1>>OCCC1CCNCC1 | OCCC1=CC=NC=C1>>N1CCC(CC1)CCO | [OH:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][n:7][cH:8][cH:9]1>>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]1 | OCCc1ccncc1 | OCCC1CCNCC1 | null | [Pt]=O | C(C)(=O)O | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | C1CCNCC1 | [C:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:1>>[C:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[NH;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-1 | 46 | [{"value": 46.0, "product": "N1CCC(CC1)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.0, "product": "N1CCC(CC1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A solution of 4-(2-hydroxyethyl)pyridine (1.8 g, 14.6 mol) in acetic acid (15 ml) containing platinum oxide (200 mg) was hydrogenated for 20 hours at 3.3–4 atmospheres pressure. After filtration, the filtrate was evaporated and azeotroped twice with toluene. The residue was triturated with 2N sodium hydroxide and solid... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | C1CCNCC1 | null | [Pt]=O.C(C)(=O)O | null | 20 | OCCc1ccncc1>[Pt]=O.C(C)(=O)O>OCCC1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a076f878d6d84a3b975a5319280693d3 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Cc1cc2ccc(O)cc2[nH]1>>COc1cc2c(Oc3ccc4cc(C)[nH]c4c3)ncnc2cc1OCCCN1CCOCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.OC1=CC=C2C=C(NC2=C1)C>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C=C(NC2=C1)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][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][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[cH:12][c:13]([C... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Cc1cc2ccc(O)cc2[nH]1 | COc1cc2c(Oc3ccc4cc(C)[nH]c4c3)ncnc2cc1OCCCN1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3cc[nH]c3c2)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].[#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] | 73 | [{"value": 73.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C=C(NC2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C=C(NC2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described for Example 121, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (160 mg, 0.47 mol), (prepared as described for the starting material in Example 1), was reacted with 6-hydroxy-2-methylindole (84 mg, 0.57 mol), (Eur. J. Med. Chem. 1975, 10, 187), to give 6-methoxy-4-(... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Cc1cc2ccc(O)cc2[nH]1>>COc1cc2c(Oc3ccc4cc(C)[nH]c4c3)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6921e7f806d94a5999c24a7292ff9bf9 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCC1CCN(C(=O)OC(C)(C)C)CC1.Cc1cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2[nH]1>>COc1cc2cnc(Oc3ccc4[nH]c(C)cc4c3)nc2cc1OCCC1CCNCC1 | CC=1NC2=CC=C(C=C2C1)OC1=NC=NC2=CC(=CC=C12)OCC1CCNCC1.C(C)(C)(C)OC(=O)N1CCC(CC1)CCOC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC>>COC=1C=C2C=NC(=NC2=CC1OCCC1CCNCC1)OC=1C=C2C=C(NC2=CC1)C | Cc1cc2cc(O[c:6]3[c:5]4[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH:27]5[CH2:28][CH2:29][N:30](C(=O)OC(C)(C)C)[CH2:31][CH2:32]5)[cH:22][c:21]4[n:20][cH:8][n:7]3)ccc2[nH]1.c1nc([O:9][c:10]2[cH:11][cH:12][c:13]3[nH:14][c:15]([CH3:16])[cH:17][c:18]3[cH:19]2)c2ccc(OCC3CCNCC3)cc2n1>>[CH3:1][O:2][c:3]1[cH:4][c:5]... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCC1CCN(C(=O)OC(C)(C)C)CC1.Cc1cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2[nH]1 | COc1cc2cnc(Oc3ccc4[nH]c(C)cc4c3)nc2cc1OCCC1CCNCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0d140802bf1a07c94371db54b4dff07acf8ee243d07b0abe7af3b6d3e1c97e21 | c689fc1bd5bc1d24ed683f9083af69e41a219bca148131b30f50ea01e2336bac | c1cc2cc(Oc3ncc4ccc(OCCC5CCNCC5)cc4n3)ccc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].C-c1:[nH]:c2:c:c:c(-O-[c;H0;D3;+0:6]3:[#7;a:7]:[cH;D2;+0:8]:[#7;a:9]:[c:10](:[c:11]):[c:12]:3:[c:13]):c:c:2:c:1.[c:14]:[c:15](-[O;H0;D2;+0:16]-c1:n:c:n:c2:c:c(-O-C-C3-C-C-N-C-C-3):c:c:c:1:2):[c:17]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5].[c:14]:[c:15](-[O;H0;D2... | 87 | [{"value": 87.0, "product": "COC=1C=C2C=NC(=NC2=CC1OCCC1CCNCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described for the synthesis of 4-(2-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline, (prepared as described in Example 122), 7-(2-(1-tert-butoxycarbonylpiperidin-4-yl)ethoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (400 mg, 0.75 mmol), (prepared as described in Exam... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Ether.Secondary amine.Boc | Ether.Secondary amine | c1ccc2[nH]ccc2c1.C1CC[NH]CC1.c1ccc2ncncc2c1.c1ccc2ncncc2c1.C1CCNCC1 | c1ccc2ncncc2c1.C1CCNCC1 | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1.C1CCNCC1 | HO- | null | null | null | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCC1CCN(C(=O)OC(C)(C)C)CC1.Cc1cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2[nH]1>>COc1cc2cnc(Oc3ccc4[nH]c(C)cc4c3)nc2cc1OCCC1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2003344db462457e85182b1317dcee08 | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O.OC/C=C/CN1CCCC1>>COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OC/C=C/CN1CCCC1 | N(=NC(=O)OCC)C(=O)OCC.CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1(CCCC1)C/C=C/CO>>CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)OC\C=C\CN1CCCC1 | [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])[c:15]([CH3:16])[c:17]4[cH:18]3)[n:19][cH:20][n:21][c:22]2[cH:23][c:24]1[OH:25].O[CH2:26]/[CH:27]=[CH:28]/[CH2:29][N:30]1[CH2:31][CH2:32][CH2:33][CH2:34]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[cH:9][cH:10][c:11]4[nH:1... | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O.OC/C=C/CN1CCCC1 | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OC/C=C/CN1CCCC1 | null | null | ClCCl.CN(C)C=O | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | C(=C/CN1CCCC1)\COc1ccc2c(Nc3ccc4[nH]ccc4c3)ncnc2c1 | O-[CH2;D2;+0:1]/[C:2]=[C:3]/[C:4]-[#7:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7:5]-[C:4]/[C:3]=[C:2]/[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:8]:[c:7]:[#7;a:6] | 55.7 | [{"value": 55.0, "product": "CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)OC\\C=C\\CN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.7, "product": "CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)OC\\C=C\\CN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | Diethyl azodicarboxylate (65 μl, 0.4 mmol) was added in portions to a suspension of 4-(2,3-dimethylindol-5-ylamino)-7-hydroxy-6-methoxyquinazoline (68 mg, 0.2 mmol), triphenylphosphine (107 mg, 0.4 mmol), (E)-4-(pyrrolidin-1-yl)but-2-en-1-ol (40 mg, 0.28 mmol) in DMF (0.4 ml) and dichloromethane (1.5 ml) cooled at 0° C... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HO- | ClCCl.CN(C)C=O | 0 | 8 | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O.OC/C=C/CN1CCCC1>ClCCl.CN(C)C=O>COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OC/C=C/CN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-92d2445662e34e878073936ee3d26753 | C1CCNC1.OCC#CCCl>>OCC#CCN1CCCC1 | N1CCCC1.ClCC#CCO>>N1(CCCC1)CC#CCO | [NH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1.Cl[CH2:5][C:4]#[C:3][CH2:2][OH:1]>>[OH:1][CH2:2][C:3]#[C:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1 | C1CCNC1.OCC#CCCl | OCC#CCN1CCCC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1CCNC1 | Cl-[CH2;D2;+0:1]-[C:2]#[C:3]-[C:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[C:4]-[C:3]#[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | 69 | [{"value": 69.0, "product": "N1(CCCC1)CC#CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "N1(CCCC1)CC#CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | Pyrrolidine (7.8 ml, 94 mmol) was added dropwise to a solution of 4-chlorobut-2-yn-1-ol (4.74 g, 45 mmol) in toluene (40 ml) and the mixture stirred and heated at 60° C. for 1 hour. The volatiles were removed by evaporation and the residue was purified by chromatography eluting with methylene chloride/methanol (96/4) t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1 | HCl | C1(=CC=CC=C1)C | 60 | null | C1CCNC1.OCC#CCCl>C1(=CC=CC=C1)C>OCC#CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7278cd0e3a4a44c2af3637ec94e801d7 | OCC#CCN1CCCC1>>OC/C=C/CN1CCCC1 | N1(CCCC1)CC#CCO.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>>N1(CCCC1)C/C=C/CO | [OH:1][CH2:2][C:3]#[C:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1>>[OH:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1 | OCC#CCN1CCCC1 | OC/C=C/CN1CCCC1 | null | null | C1CCOC1 | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | C1CCNC1 | [#7:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5]-[O;D1;H1:6]>>[#7:1]-[C:2]/[CH;D2;+0:3]=[CH;D2;+0:4]/[C:5]-[O;D1;H1:6] | 70.6 | [{"value": 70.0, "product": "N1(CCCC1)C/C=C/CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.6, "product": "N1(CCCC1)C/C=C/CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A solution of 4-(pyrrolidin-1-yl)but-2-yn-1-ol (4.3 g, 31 mmol) in THF (20 ml) was added dropwise to a suspension of lithium aluminium hydride (2.35 g, 62 mmol) in anhydrous THF (8 ml) and the mixture stirred and heated at 60° C. for 2 hours. The mixture was cooled to 5° C. and 2M aqueous sodium hydroxide solution (28 ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | C1CC[NH]C1 | null | C1CCOC1 | 60 | null | OCC#CCN1CCCC1>C1CCOC1>OC/C=C/CN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-035104362d2841e8bfe1b89af72f538b | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1[nH]c2ccc(N)cc2c1C>>COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1 | Cl.ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1=CC=CC=C1.NC=1C=C2C(=C(NC2=CC1)C)C>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC=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.[NH2:7][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]([NH:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1[nH]c2ccc(N)cc2c1C | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)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] | 107.5 | [{"value": 107.5, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C(=C(NC2=CC1)C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 4-chloro-6-methoxy-7-benzyloxyquinazoline (7 g, 23 mmol), (prepared as described for the starting material in Example 1), and 5-amino-2,3-dimethylindole (4.5 g, 28 mmol) in isopropanol (90 ml) containing 6.2 N hydrogen chloride in isopropanol (380 μl) was heated at relux for 3 hours and stirred overnight ... | 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 | 8 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Cc1[nH]c2ccc(N)cc2c1C>C(C)(C)O>COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e3fbd87ffc2460d8f1d0cd56bee119e | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O | C(=O)[O-].[NH4+].C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)NC=1C=C2C(=C(NC2=CC1)C)C)OC.N>>CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)O | c1ccc(C[O:25][c:24]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])[c:15]([CH3:16])[c:17]5[cH:18]4)[n:19][cH:20][n:21][c:22]3[cH:23]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])[c:15]([CH3:16])[c:17]4[cH:18]3)[n:19][cH:20]... | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1 | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O | null | [Pd] | CO.CN(C)C=O | 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] | 75 | [{"value": 75.0, "product": "CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.8, "product": "CC=1NC2=CC=C(C=C2C1C)NC1=NC=NC2=CC(=C(C=C12)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Ammonium formate (20 g, 326 mmol) and 10% palladium on carbon (1 g) were added to a solution of 7-benzyloxy-4-(2,3-dimethylindol-5-ylamino)-6-methoxyquinazoline (10 g, 22 mmol) in DMF (100 ml) and methanol (300 ml). After stirring for 3 hours at ambient temperature, aqueous ammonia (120 ml) was added. The precipitate w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | Other | [Pd].CO.CN(C)C=O | null | 3 | COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCc1ccccc1>[Pd].CO.CN(C)C=O>COc1cc2c(Nc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb4511e2bc87448799845d8aeb098c6f | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2ccc(O)cc2[nH]1>>COc1cc2c(Oc3ccc4cc(C)[nH]c4c3)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.OC1=CC=C2C=C(NC2=C1)C>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C=C(NC2=C1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH: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[cH:12][c:13]([CH3:14]... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2ccc(O)cc2[nH]1 | COc1cc2c(Oc3ccc4cc(C)[nH]c4c3)ncnc2cc1OCCCN1CCCC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3cc[nH]c3c2)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]:[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] | 85 | [{"value": 85.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C=C(NC2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C=C(NC2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described for Example 121, 4-chloro-6-methoxy-7-(3-pyrrolidinopropoxy)quinazoline (150 mg, 0.47 mmol), (prepared as described for the starting material in Example 9), was reacted with 6-hydroxy-2-methylindole (83 mg, 0.56 mol), (Eur. J. Med. Chem. 1975, 10, 187), to give 6-methoxy-4... | 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.Cc1cc2ccc(O)cc2[nH]1>>COc1cc2c(Oc3ccc4cc(C)[nH]c4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c23736e470648e4ac1d23345969519a | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Cc1cc2cc(O)ccc2n1C>>COc1cc2c(Oc3ccc4c(c3)cc(C)n4C)ncnc2cc1OCCCN1CCOCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.CN1C(=CC2=CC(=CC=C12)O)C>>CN1C(=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)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][O: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[c:12]([cH:13]1)[cH:14][c:15]([CH3:16])[n:17]2[CH3:18]>>[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[c:12](... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Cc1cc2cc(O)ccc2n1C | COc1cc2c(Oc3ccc4c(c3)cc(C)n4C)ncnc2cc1OCCCN1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCOCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 74 | [{"value": 74.0, "product": "CN1C(=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.4, "product": "CN1C(=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in Example 120 OR 121 PER PP, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (160 mg, 0.48 mmol), (prepared as described for the starting material in Example 1), was reacted with 1,2-dimethyl-5-hydroxyindole (92 mg, 0.57 mol), (Tetrahedron 1994, 50, 13433), to give ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Cc1cc2cc(O)ccc2n1C>>COc1cc2c(Oc3ccc4c(c3)cc(C)n4C)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ebf27f7d3aa4b389ebd546dabb1ff57 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)C(=O)OC(C)(C)C>>CNCCOc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC | COC=1C=C2C(=NC=NC2=CC1OCCN(C(=O)OC(C)(C)C)C)OC=1C=C2C=C(NC2=CC1)C.C(=O)(C(F)(F)F)O>>COC=1C=C2C(=NC=NC2=CC1OCCNC)OC=1C=C2C=C(NC2=CC1)C | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][n:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]4[nH:18][c:19]([CH3:20])[cH:21][c:22]4[cH:23]3)[c:24]2[cH:25][c:26]1[O:27][CH3:28]>>[CH3:1][NH:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][n:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]4[nH:... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)C(=O)OC(C)(C)C | CNCCOc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | 82 | [{"value": 82.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCNC)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "COC=1C=C2C(=NC=NC2=CC1OCCNC)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 6-methoxy-4-(2-methylindol-5-yloxy)-7-(2-(N-methyl-N-tert-butoxycarbonylamino)ethoxy)quinazoline (550 mg, 1.15 mmol), (prepared as described in Example 149), in methylene chloride (10 ml) containing TFA (12 ml) was stirred for 3 hours at ambient temperature. After removal of the volatiles under vacuum, th... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccc2ncncc2c1.c1ccc2[nH]ccc2c1 | HO- | C(Cl)Cl | null | 3 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCN(C)C(=O)OC(C)(C)C>C(Cl)Cl>CNCCOc1cc2ncnc(Oc3ccc4[nH]c(C)cc4c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5246d30a745044a6a9424dedab8276b3 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1.N#CCCl>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC(CC#N)C1CCNCC1 | COC=1C=C2C(=NC=NC2=CC1OCC1CCNCC1)OC=1C=C2C=C(NC2=CC1)C.ClCC#N.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>C(#N)CC(OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)C1CCNCC1 | [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:29]1[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]1.Cl[CH2:26][C:27]#[N:28]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13... | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1.N#CCCl | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC(CC#N)C1CCNCC1 | null | null | O.CN(C)C=O | C-C Coupling | OtherReaction | 5e2d5f735161ca1f0f824efe0b27c87d9be398df1c44db4f86736c90dd790b94 | 2c1c1647472d7e3cff37f0f3aad955b760f0ad2f8b7aa7e7825b1c0344bab3bb | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | Cl-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5](-[CH2;D2;+0:6]-[#8:7]-[c:8])-[C:9]>>[C:4]-[C:5](-[CH;D3;+0:6](-[#8:7]-[c:8])-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[C:9] | 66.4 | [{"value": 66.0, "product": "C(#N)CC(OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)C1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.4, "product": "C(#N)CC(OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)C1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 6-methoxy-4-(2-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline (419 mg, 1 mmol), (prepared as described in Example 70), in DMF (6 ml) containing chloroacetonitrile (114 mg, 1.5 mmol), potassium carbonate (346 mg, 2.5 mmol) and potassium iodide (50 mg, 0.3 mmol) was stirred at ambient temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CCNCC1 | HCl | O.CN(C)C=O | null | 8 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCNCC1.N#CCCl>O.CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OC(CC#N)C1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c61c81cc31e44983a487963fd3015893 | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Oc1ccc2[nH]ccc2c1>>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C.C([O-])([O-])=O.[K+].[K+].OC=1C=C2C=CNC2=CC1>>N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C | 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]([CH3:28])[S:29]([CH3:30])(=[O:31])=[O:32])[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:14][c... | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Oc1ccc2[nH]ccc2c1 | COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[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] | 17 | [{"value": 17.0, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.9, "product": "N1C=CC2=CC(=CC=C12)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline (360 mg, 1.00 mmol), potassium carbonate (215 mg, 1.56 mmol) and 5-hydroxyindole (147 mg, 1.10 mmol) in DMF (8.0 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient temperature. The solvent was removed by evapora... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Oc1ccc2[nH]ccc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]ccc4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-858dd9b659494367896f342f1efb8810 | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCNC(=O)OC(C)(C)C>>COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN | BrC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCNC(=O)OC(C)(C)C)C=C1)F>>NCCCOC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Br)F)OC | CC(C)(C)OC(=O)[NH:26][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][c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]3[F:15])[n: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][c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:19]2[cH:20]... | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCNC(=O)OC(C)(C)C | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN | null | null | FC(C(=O)O)(F)F | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(Oc2ncnc3ccccc23)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 2,093.6 | [{"value": 100.0, "product": "NCCCOC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Br)F)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 2093.6, "product": "NCCCOC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Br)F)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | 4-(4-Bromo-2-fluorophenoxy)-7-(3-(N-tertbutoxycarbonylamino)propoxy)-6-methoxyquinazoline (5.46 g, 0.5 mmol) was taken up in trifluoroacetic acid (75 ml) and heated at 85° C. for 1.5 hours. The solution was allowed to cool and the excess trifluoroacetic acid removed by evaporation. The residue was then treated with aqu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2ncncc2c1 | HO- | FC(C(=O)O)(F)F | 85 | null | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCNC(=O)OC(C)(C)C>FC(C(=O)O)(F)F>COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c041d7871cb4ad6aa0aa807b48cb8d8 | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN.CS(=O)(=O)Cl>>COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCNS(C)(=O)=O | NCCCOC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Br)F)OC.C(C)N(CC)CC.CS(=O)(=O)Cl>>BrC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCNS(=O)(=O)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]([Br:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:19]2[cH:20][c:21]1[O:22][CH2:23][CH2:24][CH2:25][NH2:26].Cl[S:27]([CH3:28])(=[O:29])=[O:30]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]3[F:15])[n:16][cH:17]... | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN.CS(=O)(=O)Cl | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCNS(C)(=O)=O | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc(Oc2ncnc3ccccc23)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 93.1 | [{"value": 93.0, "product": "BrC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCNS(=O)(=O)C)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "BrC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCNS(=O)(=O)C)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 7-(3-aminopropoxy)-4-(4-bromo-2-fluorophenoxy)-6-methoxyquinazoline (2.71 g, 6.4 mmol) and triethylamine (1.1 ml, 0.80 g, 7.9 mmol) in dichloromethane (15 ml) was treated with a solution of methanesulphonyl chloride (0.53 ml, 0.79 g, 6.9 mmol) in dichloromethane (10 ml) and stirred at ambient temperature,... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2ncncc2c1 | HCl | ClCCl | null | 18 | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN.CS(=O)(=O)Cl>ClCCl>COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCNS(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b6a3a8a1e0ab4c4b8bd8377c4c007bcd | CI.COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCNS(C)(=O)=O>>COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN(C)S(C)(=O)=O | BrC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCNS(=O)(=O)C)C=C1)F.[H-].[Na+].CI>>BrC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN(S(=O)(=O)C)C)C=C1)F | I[CH3:27].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:19]2[cH:20][c:21]1[O:22][CH2:23][CH2:24][CH2:25][NH:26][S:28]([CH3:29])(=[O:30])=[O:31]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]3[F:15])[n:16][... | CI.COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCNS(C)(=O)=O | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN(C)S(C)(=O)=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c6ca050f6d67acb7bc6fc8b4d7848b3f349e4e8db81643cbb6d12b5a34cbf965 | 9d3dfd18cb6410898a6d822a6d80081d602cf34984cafbfa56b84aa4b38ddbf6 | c1ccc(Oc2ncnc3ccccc23)cc1 | I-[CH3;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[#16:5](-[C;D1;H3:6])(=[O;D1;H0:7])=[O;D1;H0:8]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[#16:5](-[C;D1;H3:6])(=[O;D1;H0:7])=[O;D1;H0:8] | 83.6 | [{"value": 83.0, "product": "BrC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN(S(=O)(=O)C)C)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "BrC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN(S(=O)(=O)C)C)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-(4-Bromo-2-fluorophenoxy)-6-methoxy-7-(3-(N-methylsulphonylamino)propoxy)quinazoline (1.0 g, 2 mmol) was taken up in DMF (10 ml), treated with sodium hydride (60% dispersion in mineral oil, 0.11 g, 2.7 mmol) and stirred, under nitrogen for 30 minutes. Methyl iodide (0.16 ml, 2.6 mmol) was added and the mixture stirre... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Tertiary amine | null | null | c1ccccc1.c1ccc2ncncc2c1 | HI | CN(C)C=O | null | 0.5 | CI.COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCNS(C)(=O)=O>CN(C)C=O>COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN(C)S(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cb33bc7bf02042539bf1ac7c3408d1b0 | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN(C)S(C)(=O)=O>>COc1cc2c(=O)[nH]cnc2cc1OCCCN(C)S(C)(=O)=O | BrC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN(S(=O)(=O)C)C)C=C1)F.C(O)([O-])=O.[Na+]>>COC=1C=C2C(NC=NC2=CC1OCCCN(S(=O)(=O)C)C)=O | Fc1cc(Br)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]([CH3:19])[S:20]([CH3:21])(=[O:22])=[O:23])[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]([CH3:19])[S:20]([CH3:21])(... | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN(C)S(C)(=O)=O | COc1cc2c(=O)[nH]cnc2cc1OCCCN(C)S(C)(=O)=O | null | null | Cl | Functional Group Interconversion | OtherReaction | 2e331e7f987e2f208a7bb6621e9b7dc6ca9e78c94b181dc5496a50196c7c48fe | a99fd2343850f6fbc4a4d7024846a70661aad8ef3f77938589a06d4940f99c06 | O=c1[nH]cnc2ccccc12 | Br-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] | 104 | [{"value": 88.0, "product": "COC=1C=C2C(NC=NC2=CC1OCCCN(S(=O)(=O)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.0, "product": "COC=1C=C2C(NC=NC2=CC1OCCCN(S(=O)(=O)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-(4-Bromo-2-fluorophenoxy)-6-methoxy-7-(3-(N-methyl N-methylsulphonylamino)propoxy)quinazoline (4.70 g, 9.1 mmol) was dissolved in 2N aqueous hydrochloric acid solution (85 ml) and heated at reflux for 1 hour. After cooling, the solution was carefully poured into saturated aqueous sodium hydrogen carbonate solution (t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether | null | c1ccccc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HF.Br- | Cl | null | 0.5 | COc1cc2c(Oc3ccc(Br)cc3F)ncnc2cc1OCCCN(C)S(C)(=O)=O>Cl>COc1cc2c(=O)[nH]cnc2cc1OCCCN(C)S(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d7a6b98163b4950bbc754421806b1c0 | COc1cc2c(=O)[nH]cnc2cc1OCCCN(C)S(C)(=O)=O.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O | COC=1C=C2C(NC=NC2=CC1OCCCN(S(=O)(=O)C)C)=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)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]([CH3:19])[S:20]([CH3:21])(=[O:22])=[O:23])[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]([CH3:19])[S:20]([CH3:21])(=[... | COc1cc2c(=O)[nH]cnc2cc1OCCCN(C)S(C)(=O)=O.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O | null | CN(C)C=O | null | 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] | 80 | [{"value": 80.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazolin-4-one (2.24 g, 6.6 mmol) was taken up in thionyl chloride (25 ml) and treated with DMF (5 drops). The resulting solution was then heated at reflux for 1 hour followed by cooling to ambient temperature. The excess thionyl chloride was removed by evaporat... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | CN(C)C=O | null | null | COc1cc2c(=O)[nH]cnc2cc1OCCCN(C)S(C)(=O)=O.O=S(Cl)Cl>CN(C)C=O>COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e6948b52363e4ba1a33f623a63c88dd0 | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Cc1cc2cc(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C.C([O-])([O-])=O.[K+].[K+].OC=1C=C2C=C(NC2=CC1)C>>COC=1C=C2C(=NC=NC2=CC1OCCCN(S(=O)(=O)C)C)OC=1C=C2C=C(NC2=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]([CH3:29])[S:30]([CH3:31])(=[O:32])=[O:33])[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][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]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13](... | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Cc1cc2cc(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[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] | 35.3 | [{"value": 35.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN(S(=O)(=O)C)C)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.3, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN(S(=O)(=O)C)C)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline (360 mg, 1.00 mm ol), (prepared as described for the starting material in Example 152), potassium carbonate (215 mg, 1.56 mmol) and 5-hydroxy-2-methylindole (162 mg, 1.10 mmol) in DMF (8.0 ml) was stirred at 100° C. for 5 hours an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Cc1cc2cc(O)ccc2[nH]1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ac9efacedde4d8d88aa60e0f7a4250b | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Oc1ccc2cccnc2c1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C=CC=NC2=C1>>COC=1C=C2C(=NC=NC2=CC1OCCCN(S(=O)(=O)C)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]([CH3:29])[S:30]([CH3:31])(=[O:32])=[O:33])[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... | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Oc1ccc2cccnc2c1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN(C)S(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] | 63 | [{"value": 63.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN(S(=O)(=O)C)C)OC1=CC=C2C=CC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN(S(=O)(=O)C)C)OC1=CC=C2C=CC=NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline (150 mg, 0.42 mmol), (prepared as described for the starting material in Example 152), potassium carbonate (90 mg, 0.63 mmol) and 7hydroxyquinoline (67 mg, 0.46 mmol) in DMF (5.0 ml) was stirred at 100° C. for 2 hours and allowed ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1 | HCl | CN(C)C=O | 100 | 2 | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Oc1ccc2cccnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-201b31eda4c34809b27034be8982938b | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Cc1ccnc2cc(O)ccc12>>COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C(=CC=NC2=C1)C>>COC=1C=C2C(=NC=NC2=CC1OCCCN(S(=O)(=O)C)C)OC1=CC=C2C(=CC=NC2=C1)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]([CH3:30])[S:31]([CH3:32])(=[O:33])=[O:34])[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([CH3:13])[cH:14][cH:15][n:16][c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([... | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Cc1ccnc2cc(O)ccc12 | COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCCCN(C)S(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] | 42 | [{"value": 42.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN(S(=O)(=O)C)C)OC1=CC=C2C(=CC=NC2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN(S(=O)(=O)C)C)OC1=CC=C2C(=CC=NC2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline (150 mg, 0.42 mmol), (prepared as described for the starting material in Example 152), potassium carbonate (90 mg, 0.63 mmol) and 7-hydroxy-4-methylquinoline (71 mg, 0.46 mmol), (Chem. Berich. 1967, 100, 2077), in DMF (5.0 ml) was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1 | HCl | CN(C)C=O | 100 | 2 | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Cc1ccnc2cc(O)ccc12>CN(C)C=O>COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e66ac03e03f84c75ad3ea3256f26e11f | COc1ccc2cc(F)c(=O)[nH]c2c1.O=S(Cl)Cl>>COc1ccc2cc(F)c(Cl)nc2c1 | FC=1C(NC2=CC(=CC=C2C1)OC)=O.S(=O)(Cl)Cl>>ClC1=NC2=CC(=CC=C2C=C1F)OC | O=[c:10]1[c:8]([F:9])[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][c:13]2[nH:12]1.O=S(Cl)[Cl:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([F:9])[c:10]([Cl:11])[n:12][c:13]2[cH:14]1 | COc1ccc2cc(F)c(=O)[nH]c2c1.O=S(Cl)Cl | COc1ccc2cc(F)c(Cl)nc2c1 | null | CN(C)C=O | null | Functional Group Interconversion | OtherReaction | 608f63cb1f4eb5f8ff4f6128056e651e12d8905ddec242decf5bdb71da52a2d7 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncccc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](:[c:5]):[c:6]:[c:7]:[c:8]:1-[F;D1;H0:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4](:[c:5]):[c:6]:[c:7]:[c:8]:1-[F;D1;H0:9] | 97 | [{"value": 97.0, "product": "ClC1=NC2=CC(=CC=C2C=C1F)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Fluoro-7-methoxyquinol-2(1H)-one (300 mg, 1.55 mmol), (prepared as in Tetrahedron, Vol. 52, No. 9, pp. 3223–3228, 1996), was dissolved in thionyl chloride (3 ml), treated with DMF (1 drop) and heated at reflux for 1 hour. The excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene (... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2ccccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | CN(C)C=O | null | null | COc1ccc2cc(F)c(=O)[nH]c2c1.O=S(Cl)Cl>CN(C)C=O>COc1ccc2cc(F)c(Cl)nc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47c36ea540f04f7688920621e4f1f72a | COc1ccc2cc(F)c(Cl)nc2c1>>COc1ccc2cc(F)cnc2c1 | ClC1=NC2=CC(=CC=C2C=C1F)OC.C(C)N(CC)CC>>FC=1C=NC2=CC(=CC=C2C1)OC | Cl[c:10]1[c:8]([F:9])[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:13][c:12]2[n:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([F:9])[cH:10][n:11][c:12]2[cH:13]1 | COc1ccc2cc(F)c(Cl)nc2c1 | COc1ccc2cc(F)cnc2c1 | null | [Pd] | C(C)O | Functional Group Interconversion | Aromatic dehalogenation | 9d8b09641537c9b7067a6060cf65ecd110c7af466a7b229ce3601533f966554e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6]>>[F;D1;H0:5]-[c:4](:[c:6]):[cH;D2;+0:1]:[#7;a:2]:[c:3] | 54 | [{"value": 54.0, "product": "FC=1C=NC2=CC(=CC=C2C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.9, "product": "FC=1C=NC2=CC(=CC=C2C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 2-chloro-3-fluoro-7-methoxyquinoline (310 mg, 1.47 mmol), triethylamine (310 mg, 0.4 ml, 3.07 mmol) and 10% palladium on activated charcoal (50 mg) in dry ethanol (5 ml) was stirred under hydrogen gas at ambient temperature for 24 hours. The mixture was then filtered through celite. The celite was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | Other | [Pd].C(C)O | null | 24 | COc1ccc2cc(F)c(Cl)nc2c1>[Pd].C(C)O>COc1ccc2cc(F)cnc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-76e7e2024c9c4fb4b22242708b9a260b | COc1ccc2cc(F)cnc2c1>>Oc1ccc2cc(F)cnc2c1 | CO.FC=1C=NC2=CC(=CC=C2C1)OC.B(Br)(Br)Br>>FC=1C=NC2=CC(=CC=C2C1)O | C[O:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([F:8])[cH:9][n:10][c:11]2[cH:12]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([F:8])[cH:9][n:10][c:11]2[cH:12]1 | COc1ccc2cc(F)cnc2c1 | Oc1ccc2cc(F)cnc2c1 | null | null | ClCCl | 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] | null | [] | null | null | 24 | HOUR | 3-Fluoro-7-methoxyquinoline (130 mg, 0.74 mmol) was taken up in dichloromethane (2 ml) under nitrogen and treated with boron tribromide (4 ml of a 11.0M solution of in dichloromethane). The reaction mixture was stirred for 24 hours at ambient temperature followed by quenching the reaction by the slow addition of excess... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2ncccc2c1 | Other | ClCCl | null | 24 | COc1ccc2cc(F)cnc2c1>ClCCl>Oc1ccc2cc(F)cnc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-14533589759940e8bcf11c574ca1a8a0 | COc1ccc2cc(F)c(Cl)nc2c1>>COc1ccc2cc(F)c(C)nc2c1 | C[Mg]Br.ClC1=NC2=CC(=CC=C2C=C1F)OC.[Cl-].[NH4+].[OH-].[Na+]>>FC=1C(=NC2=CC(=CC=C2C1)OC)C | Cl[c:10]1[c:8]([F:9])[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][c:13]2[n:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([F:9])[c:10]([CH3:11])[n:12][c:13]2[cH:14]1 | COc1ccc2cc(F)c(Cl)nc2c1 | COc1ccc2cc(F)c(C)nc2c1 | null | [Cu]Br | C1CCOC1 | Functional Group Interconversion | OtherReaction | 9d8b09641537c9b7067a6060cf65ecd110c7af466a7b229ce3601533f966554e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6]>>[C;D1;H3:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 91 | [{"value": 91.0, "product": "FC=1C(=NC2=CC(=CC=C2C1)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.9, "product": "FC=1C(=NC2=CC(=CC=C2C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | 2-Chloro-3-fluoro-7-methoxyquinoline (210 mg, 1 mmol), (prepared as described for the starting material in Example 157), in anhydrous THF (1 ml) was added to a mixture of copper(I)bromide (570 mg, 4.0 mmol) and methylmagnesium bromide (3.0M solution in diethyl ether, 2.7 ml, 8 mmol) in anhydrous THF (20 ml) at −78° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | null | [Cu]Br.C1CCOC1 | -78 | 1 | COc1ccc2cc(F)c(Cl)nc2c1>[Cu]Br.C1CCOC1>COc1ccc2cc(F)c(C)nc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0f5554e13f848dbb8c550eef8f5d8a3 | COc1ccc2cc(F)c(C)nc2c1>>Cc1nc2cc(O)ccc2cc1F | CO.FC=1C(=NC2=CC(=CC=C2C1)OC)C.B(Br)(Br)Br>>FC=1C(=NC2=CC(=CC=C2C1)O)C | C[O:7][c:6]1[cH:5][c:4]2[n:3][c:2]([CH3:1])[c:12]([F:13])[cH:11][c:10]2[cH:9][cH:8]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([OH:7])[cH:8][cH:9][c:10]2[cH:11][c:12]1[F:13] | COc1ccc2cc(F)c(C)nc2c1 | Cc1nc2cc(O)ccc2cc1F | null | null | ClCCl | 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] | null | [] | null | null | 24 | HOUR | 3-Fluoro-7-methoxy-2-methylquinoline (0.16 g, 0.85 mmol) was taken up in dichloromethane (4 ml) under nitrogen and treated with boron tribromide solution (4 ml of a 11.0M solution in dichloromethane, 4.0 mmol). The reaction was stirred for 24 hours at ambient temperature followed by the slow addition of excess methanol... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2ncccc2c1 | Other | ClCCl | null | 24 | COc1ccc2cc(F)c(C)nc2c1>ClCCl>Cc1nc2cc(O)ccc2cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-918c932a36024ae5be2f60ed5afdc35b | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2cccnc2c1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCCCC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C=CC=NC2=C1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)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][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[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... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2cccnc2c1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCCCN5CCCCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 52 | [{"value": 52.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC1=CC=C2C=CC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCCC1)OC1=CC=C2C=CC=NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (400 mg, 1.19 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (255 mg, 1.84 mmol) and 7-hydroxyquinoline (180 mg, 1.32 mmol) in DMF (10 ml) was stirred at 100° C. for 4 hours and then allowed to cool to ambien... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CN(C)C=O | 100 | 4 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCCC1.Oc1ccc2cccnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a947657169974ce492a4995d6fbad691 | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Cc1[nH]c2ccc(O)cc2c1C>>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C.C([O-])([O-])=O.[K+].[K+].CC=1NC2=CC=C(C=C2C1C)O>>CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)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]([CH3:30])[S:31]([CH3:32])(=[O:33])=[O:34])[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:1... | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Cc1[nH]c2ccc(O)cc2c1C | COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2c(Oc3ccc4[nH]ccc4c3)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 42 | [{"value": 42.0, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.5, "product": "CC=1NC2=CC=C(C=C2C1C)OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN(S(=O)(=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline (360 mg, 1.00 mmol), (prepared as described for the starting material in Example 152), potassium carbonate (215 mg, 1.56 mmol) and 2,3-dimethyl-5-hydroxyindole (177 mg, 1.10 mmol), (Arch. Pharm. 1972, 305, 159), in DMF (8.0 ml) wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN(C)S(C)(=O)=O.Cc1[nH]c2ccc(O)cc2c1C>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)c(C)c4c3)ncnc2cc1OCCCN(C)S(C)(=O)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b33bc77474b14b988eedcc8eb51a757b | BrCC1CO1.C1COCCN1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCOCC1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.C([O-])([O-])=O.[K+].[K+].C(Br)C1CO1.N1CCOCC1>>OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCOCC1 | Br[CH2:25][CH:26]1[O:27][CH2:28]1.[NH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c... | BrCC1CO1.C1COCCN1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 9e8854a5ecfdc8b15022d98dbe1f2eae1fc393a2fececee6fd576a5ba2e5b3ae | eb518202353ad700a277551600b1491d8d2c7644482abd04ae296bc3a44ea97b | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCOCC3)cc2n1 | Br-[CH2;D2;+0:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[#7;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10].[#8:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#8:11]-[C:16]-[C:15]-1):[c:10] | 45.6 | [{"value": 27.0, "product": "OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.6, "product": "OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | A mixture of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (322 mg, 1.00 mmol), (prepared as described in Example 49), potassium carbonate (414 mg, 3.00 mmol) and epibromohydrin (274 mg, 2.00 mmol) in DMF (7.0 ml) was stirred at 60° C. for 2 hours and allowed to cool to ambient temperature. The solvent was r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol.Secondary amine | Ether.Secondary alcohol.Tertiary amine | C1CO1.C1COCCN1 | C1COCC[NH]1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HBr | CN(C)C=O | 60 | 2 | BrCC1CO1.C1COCCN1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-750ad2dfc2884ea3999ef546c21a1e4d | C1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCCCC1 | O1C(COC2=C(C=C3C(=NC=NC3=C2)OC=2C=C3C=C(NC3=CC2)C)OC)C1.N1CCCCC1>>OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCCCC1 | [NH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][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:1... | C1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | c5753b22446d1ae5dcee7a30af0c7f96061ec363349faf28c9adeaca5e033c6d | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCCC3)cc2n1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C: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:1])-[C:4]-[C:5] | 65 | [{"value": 65.0, "product": "OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.1, "product": "OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCCCC1", "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) and piperidine (79ul, 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 recrystallised from acetonitrile. The solid was filtered, washed with diethyl e... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CCNCC1.C1CO1 | C1CC[NH]CC1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | null | CN(C)C=O | 70 | null | C1CCNCC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0bf01e89cf524f49a043d2019db3ed3b | BrCC1CO1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1 | OC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC.C([O-])([O-])=O.[K+].[K+].C(Br)C1CO1>>O1C(COC2=C(C=C3C(=NC=NC3=C2)OC=2C=C3C=C(NC3=CC2)C)OC)C1 | Br[CH2:25][CH:26]1[CH2:27][O: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:15][c:16]4[cH:17]3)[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[OH:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14])[cH:15][c:16]4[cH:17]3)[n:18][cH:1... | BrCC1CO1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CO3)cc2n1 | Br-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[#7;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:10] | 89 | [{"value": 89.0, "product": "O1C(COC2=C(C=C3C(=NC=NC3=C2)OC=2C=C3C=C(NC3=CC2)C)OC)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "O1C(COC2=C(C=C3C(=NC=NC3=C2)OC=2C=C3C=C(NC3=CC2)C)OC)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | A mixture of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (1.89 g, 5.90 mmol), (prepared as described in Example 49), potassium carbonate (2.43 g, 17.6 mmol) and epibromohydrin (1.61 g, 11.7 mmol) in DMF (40 ml) was stirred at 60° C. for 2 hours and allowed to cool to ambient temperature. The insoluble inor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CO1 | HBr | CN(C)C=O | 60 | 2 | BrCC1CO1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1O>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ed7e7184230d4f159c3035aff7748ca7 | C1CCNC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCCC1 | O1C(COC2=C(C=C3C(=NC=NC3=C2)OC=2C=C3C=C(NC3=CC2)C)OC)C1.N1CCCC1>>OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCCC1 | [NH:29]1[CH2:30][CH2:31][CH2:32][CH2:33]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][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:... | C1CCNC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ring opening of epoxide with amine | 76b1810a18be65e42ea157c2729971f505df73ec247c72e2192a1e56ead5967f | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | [C:1]-[C:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[C:1]-[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:3]-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | 37 | [{"value": 37.0, "product": "OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.3, "product": "OC(COC1=C(C=C2C(=NC=NC2=C1)OC=1C=C2C=C(NC2=CC1)C)OC)CN1CCCC1", "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 pyrrolidine (67 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 purified by s... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CCNC1.C1CO1 | C1CC[NH]C1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | null | CN(C)C=O | 70 | null | C1CCNC1.COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CO1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC(O)CN1CCCC1 |
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