6-(6,7-Dimethoxyquinolin-4-yloxy)-1-naphthoic acid → HCID 49805387, compound

HRID 1510017Notes

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][CH: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:46]=[CH:45][C:34]([C:35]([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[NH2:44])=[O:36])=[CH:33][CH:32]=1>>[NH2:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[NH:37][C:35]([C:34]1[CH:33]=[CH:32][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][CH:7]=4)=[CH:25][CH:24]=3)[CH:19]=[CH:20][CH:21]=2)=[O:27])=[CH:46][CH:45]=1)=[O:36]

Participants

Reactant 2

HCID 248226036-(6,7-Dimethoxyquinolin-4-yloxy)-1-naphthoic acid

HCID 588172504-(Aminomethyl)-N-(2-aminophenyl)benzamide

Product 1

HCID 49805387HCID 49805387, compoundYield 82%

Procedure

The title compound (49.0 mg, 82% yield) was prepared as a brown solid from 6-(6,7-dimethoxyquinolin-4-yloxy)-1-naphthoic acid (37.5 mg, 0.1 mmol) and 4-(aminomethyl)-N-(2-aminophenyl)benzamide (28.9 mg, 0.12 mmol) by an analogous procedure to that described in example 16. 1H NMR (DMSO-d6) δ 3.93 (s, 3H, —OCH3), 3.95 (s, 3H, —OCH3), 4.63 (d, J=5.6 Hz, 2H, —CH2), 4.90 (s, 2H, benzene-NH2), 6.56-6.59 (m, 2H, Ar—H), 6.78 (d, J=7.6 Hz, 1H, Ar—H), 6.96 (t, J=8.1 Hz, 1H, Ar—H), 7.17 (d, J=7.6 Hz, 1H, Ar—H), 7.42 (s, 1H, Ar—H), 7.53-7.55 (m, 4H, Ar—H), 7.62 (t, J=8.0 Hz, 1H, Ar—H), 7.71 (d, J=6.8 Hz, 1H, Ar—H), 7.87 (s, 1H, Ar—H), 7.98-8.06 (m, 3H, Ar—H), 8.39 (d, J=9.2 Hz, 1H, Ar—H), 8.49 (d, J=5.2 Hz, 1H, Ar—H), 9.26 (t, J=6.0 Hz, 1H, —CONH), 9.66 (s, 1H, benzene-NH). LC-MS (m/z) 599 (M+1).

Sources & evidence

ORD record: ord-50b9e8d22e6a4a118e47b4126d78a182
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211901B2

Reaction notes

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