6-(6,7-Dimethoxyquinazolin-4-yloxy)-1-naphthoic acid → N-(3-((2-aminophenyl)carbamoyl)benzyl)-6-(6,7-dimethoxyquinazolin-4-yloxy)-1-naphthamide

HRID 1510008Notes

Reaction equation

HRID 1510008 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([C:26](O)=[O:27])=[CH:21][CH:20]=[CH:19]2.[NH2:29][CH2:30][C:31]1[CH:32]=[C:33]([CH:44]=[CH:45][CH:46]=1)[C:34]([NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH2:43])=[O:35]>>[NH2:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[NH:36][C:34]([C:33]1[CH:32]=[C:31]([CH:46]=[CH:45][CH:44]=1)[CH2:30][NH:29][C:26]([C:22]1[C:23]2[C:18](=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=1)=[O:27])=[O:35]

Participants

3

Reactant 2

HCID 248237346-(6,7-Dimethoxyquinazolin-4-yloxy)-1-naphthoic acidHCID 595905533-(aminomethyl)-N-(2-aminophenyl)benzamide

Product 1

HCID 49821846N-(3-((2-aminophenyl)carbamoyl)benzyl)-6-(6,7-dimethoxyquinazolin-4-yloxy)-1-naphthamideYield 81%

Procedure

The title compound (48.5 mg, 81% yield) was prepared as a brown solid from 6-(6,7-dimethoxyquinazolin-4-yloxy)-1-naphthoic acid (37.6 mg, 0.1 mmol) and 3-(aminomethyl)-N-(2-aminophenyl)benzamide (28.9 mg, 0.12 mmol) by an analogous procedure to that described in example 16. LC-MS (m/z) 600 (M+1).

Sources & evidence

ORD record
ord-ad76498a26ba4bcca46869f35316ffaf
Source dataset
uspto-grants-2012_07
Patent number
US08211901B2

Reaction notes

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