4-Trifluoromethyl-1,2-phenylenediamine → N-(2-amino-4-trifluoromethylphenyl)-6-(6,7-dimethoxyquinazolin-4-yloxy)-1-naphthamide
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]([OH:28])=O)=[CH:21][CH:20]=[CH:19]2.[F:29][C:30]([F:40])([F:39])[C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[C:33]([NH2:38])[CH:32]=1>>[NH2:38][C:33]1[CH:32]=[C:31]([C:30]([F:29])([F:39])[F:40])[CH:36]=[CH:35][C:34]=1[NH:37][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:28]Participants
3
Procedure
The title compound (42.3 mg, 79% 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-trifluoromethyl-o-phenylenediamine (21.1 mg, 0.12 mmol) by an analogous procedure to that described in example 16. 1H NMR (DMSO-d6) δ 4.01 (s, 6H, 2×OCH3), 5.72 (s, 2H, benzene-NH2), 6.92 (d, J=8.5 Hz, 1H, Ar—H), 7.42 (s, 1H, Ar—H), 7.59-7.65 (m, 3H, Ar—H), 7.90-7.96 (m, 2H, Ar—H), 7.98 (s, 1H, Ar—H), 8.10 (d, J=8.3 Hz, 1H, Ar—H), 8.17 (d, J=7.3 Hz, 1H, Ar—H), 8.39 (d, J=9.2 Hz, 1H, Ar—H), 8.54 (s, 1H, Ar—H), 9.90 (s, 1H, benzene-NH). LC-MS (m/z) 535 (M+1).
Sources & evidence
- ORD record
- ord-0aa80f16f42146c2be13a349b70477ec
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08211901B2
Reaction notes
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