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

HRID 1510011Notes

Reaction equation

HRID 1510011 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:50]=[CH:49][C:34]([C:35]([NH:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][C:39]=2[NH2:48])=[O:36])=[CH:33][CH:32]=1>>[NH2:48][C:39]1[CH:40]=[C:41]([C:44]([F:46])([F:47])[F:45])[CH:42]=[CH:43][C:38]=1[NH:37][C:35]([C:34]1[CH:49]=[CH:50][C:31]([CH2:30][NH:29][C:26]([C:22]2[C:23]3[C:18](=[CH:17][C:16]([O:15][C:6]4[C:5]5[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=5)[N:9]=[CH:8][N:7]=4)=[CH:25][CH:24]=3)[CH:19]=[CH:20][CH:21]=2)=[O:27])=[CH:32][CH:33]=1)=[O:36]

Participants

3

Reactant 2

HCID 248237346-(6,7-Dimethoxyquinazolin-4-yloxy)-1-naphthoic acidHCID 595905434-(aminomethyl)-N-(2-amino-4-trifluoromethylphenyl)benzamide

Product 1

HCID 49805385N-(4-((2-amino-4-trifluoromethylphenyl)carbamoyl)benzyl)-6-(6,7-dimethoxyquinazolin-4-yloxy)-1-naphthamideYield 70%

Procedure

The title compound (46.7 mg, 70% yield) was prepared as a brown solid from 6-(6,7-dimethoxyquinazolin-4-yloxy)-1-naphthoic acid (37.6 mg, 0.1 mmol) and 4-(aminomethyl)-N-(2-amino-4-trifluoromethylphenyl)benzamide (37.1 mg, 0.12 mmol) by an analogous procedure to that described in example 16. LC-MS (m/z) 668 (M+1).

Sources & evidence

ORD record
ord-3d7e8ca6abdb46a6aa4c6731fa584a5a
Source dataset
uspto-grants-2012_07
Patent number
US08211901B2

Reaction notes

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