4-(Aminomethyl)-N-(2-aminophenyl)benzamide → HCID 49805500, compound

HRID 1510022Notes

Reaction equation

HRID 1510022 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([C:23]([OH:25])=O)=[CH:18][CH:17]=[CH:16]4)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[NH2:26][CH2:27][C:28]1[CH:43]=[CH:42][C:31]([C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[NH2:41])=[O:33])=[CH:30][CH:29]=1>>[NH2:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[NH:34][C:32]([C:31]1[CH:42]=[CH:43][C:28]([CH2:27][NH:26][C:23]([C:19]2[C:20]3[C:15](=[CH:14][C:13]([O:12][C:6]4[C:5]5[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=5)[N:9]=[CH:8][CH:7]=4)=[CH:22][CH:21]=3)[CH:16]=[CH:17][CH:18]=2)=[O:25])=[CH:29][CH:30]=1)=[O:33]

Participants

3

Reactant 2

HCID 588172504-(Aminomethyl)-N-(2-aminophenyl)benzamideHCID 59590548HCID 59590548, compound

Product 1

HCID 49805500HCID 49805500, compoundYield 74%

Procedure

The title compound (42.4 mg, 74% yield) was prepared as a brown solid from 6-(7-chloroquinolin-4-yloxy)-1-naphthoic acid (35.0 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 4.64 (d, J=5.8 Hz, 2H, —CH2), 4.87 (s, 2H, benzene-NH2), 6.60 (t, J=7.0 Hz, 1H, Ar—H), 6.75-6.79 (m, 2H, Ar—H), 6.97 (t, J=7.5 Hz, 1H, Ar—H), 7.18 (d, J=7.7 Hz, 1H, Ar—H), 7.53-7.59 (m, 3H, Ar—H), 7.66 (t, J=8.0 Hz, 1H, Ar—H), 7.70-7.74 (m, 2H, Ar—H), 7.92 (d, J=2.0 Hz, 1H, Ar—H), 7.99 (d, J=7.9 Hz, 2H, Ar—H), 8.06 (d, J=8.2 Hz, 1H, Ar—H), 8.13 (s, 1H, Ar—H), 8.39-8.42 (m, 2H, Ar—H), 8.75 (d, J=5.1 Hz, 1H, Ar—H), 9.22 (t, J=5.6 Hz, 1H, —CONH), 9.62 (s, 1H, benzene-NH). LC-MS (m/z) 573 (M+1).

Sources & evidence

ORD record
ord-bdbbbb1bdcb3466e860f5bdd9a24ed97
Source dataset
uspto-grants-2012_07
Patent number
US08211901B2

Reaction notes

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