4-Methoxy-o-phenylenediamine → N-(2-amino-4-methoxyphenyl)-6-(6,7-dimethoxyquinazolin-4-yloxy)-1-naphthamide

HRID 1510002Notes

Reaction equation

HRID 1510002 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.[CH3:29][O:30][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]([O:30][CH3:29])[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

Reactant 2

HCID 1534044-Methoxy-o-phenylenediamineHCID 248237346-(6,7-Dimethoxyquinazolin-4-yloxy)-1-naphthoic acid

Product 1

HCID 49821756N-(2-amino-4-methoxyphenyl)-6-(6,7-dimethoxyquinazolin-4-yloxy)-1-naphthamideYield 87%

Procedure

The title compound (43.2 mg, 87% 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-methoxy-o-phenylenediamine (16.5 mg, 0.12 mmol) by an analogous procedure to that described in example 16. 1H NMR (DMSO-d6) δ 3.70 (s, 3H, —OCH3), 4.01 (s, 6H, 2×OCH3), 5.00 (s, 2H, benzene-NH2), 6.23 (dd, J=2.6 and 8.6 Hz, 1H, Ar—H), 6.40 (d, J=2.6 Hz, 1H, Ar—H), 7.22 (d, J=8.6 Hz, 1H, Ar—H), 7.41 (s, 1H, Ar—H), 7.59 (dd, J=2.2 and 9.1 Hz, 1H, Ar—H), 7.62-7.66 (m, 2H, Ar—H), 7.86 (d, J=6.9 Hz, 1H, Ar—H), 7.96 (d, J=2.0 Hz, 1H, Ar—H), 8.07 (d, J=8.2 Hz, 1H, Ar—H), 8.38 (d, J=9.2 Hz, 1H, Ar—H), 8.54 (s, 1H, Ar—H), 9.70 (s, 1H, benzene-NH). LC-MS (m/z) 497 (M+1).

Sources & evidence

ORD record
ord-5210fdebd6d64d8ea4af87d2ff6bc5e0
Source dataset
uspto-grants-2012_07
Patent number
US08211901B2

Reaction notes

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