HCID 24822772, compound → HCID 49821848, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20]([C:24]([OH:26])=O)=[CH:19][CH:18]=[CH:17]4)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[NH2:27][CH2:28][C:29]1[CH:44]=[CH:43][C:32]([C:33]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[NH2:42])=[O:34])=[CH:31][CH:30]=1>>[NH2:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[NH:35][C:33]([C:32]1[CH:43]=[CH:44][C:29]([CH2:28][NH:27][C:24]([C:20]2[C:21]3[C:16](=[CH:15][C:14]([O:13][C:7]4[C:6]5[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=5)[N:10]=[CH:9][CH:8]=4)=[CH:23][CH:22]=3)[CH:17]=[CH:18][CH:19]=2)=[O:26])=[CH:30][CH:31]=1)=[O:34]Participants
Procedure
The title compound (48.3 mg, 85% yield) was prepared as a brown solid from 6-(7-methoxyquinolin-4-yloxy)-1-naphthoic acid (34.5 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 3.95 (s, 3H, —OCH3), 4.64 (d, J=5.6 Hz, 2H, —CH2), 4.87 (s, 2H, benzene-NH2), 6.58-6.62 (m, 2H, Ar—H), 6.78 (dd, J=1.2 and 7.8 Hz, 1H, Ar—H), 6.97 (td, J=1.4 and 8.1 Hz, 1H, Ar—H), 7.18 (d, J=7.0 Hz, 1H, Ar—H), 7.31 (dd, J=2.5 and 9.2 Hz, 1H, Ar—H), 7.44 (d, J=2.4 Hz, 1H, Ar—H), 7.53-7.56 (m, 3H, Ar—H), 7.62 (t, J=8.0 Hz, 1H, Ar—H), 7.72 (d, J=6.1 Hz, 1H, Ar—H), 7.86 (d, J=2.5 Hz, 1H, Ar—H), 7.98-8.06 (m, 3H, Ar—H), 8.24 (d, J=9.1 Hz, 1H, Ar—H), 8.39 (d, J=9.2 Hz, 1H, Ar—H), 8.64 (d, J=5.2 Hz, 1H, Ar—H), 9.21 (t, J=6.0 Hz, 1H, —CONH), 9.61 (s, 1H, benzene-NH). LC-MS (m/z) 569 (M+1).
Sources & evidence
- ORD record
- ord-e277f40c37174a9fb2dcf06ac7e0c057
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08211901B2
Reaction notes
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