N-(5,5-Dimethyl-8-nitro-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-acetamide → 3-[2-(3-Acetylamino-5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-8-ylamino)-5-chloro-pyrimidin-4-ylamino]-thiophene-2-carboxylic acid methylamide
Reaction equation
[CH3:1][C:2]1([CH3:21])[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=O)=[CH:12][C:7]=2[NH:6][C:5](=[O:16])[CH:4]([NH:17][C:18](=[O:20])[CH3:19])[CH2:3]1.[CH3:22][NH:23][C:24]([C:26]1[S:27][CH:28]=[CH:29][C:30]=1[NH:31][C:32]1[C:37]([Cl:38])=[CH:36][N:35]=[C:34](Cl)[N:33]=1)=[O:25]>>[CH3:22][NH:23][C:24]([C:26]1[S:27][CH:28]=[CH:29][C:30]=1[NH:31][C:32]1[C:37]([Cl:38])=[CH:36][N:35]=[C:34]([NH:13][C:11]2[CH:10]=[CH:9][C:8]3[C:2]([CH3:21])([CH3:1])[CH2:3][CH:4]([NH:17][C:18](=[O:20])[CH3:19])[C:5](=[O:16])[NH:6][C:7]=3[CH:12]=2)[N:33]=1)=[O:25]Participants
3
Reactant 2
Product 1
Procedure
Title compound was prepared from N-(5,5-Dimethyl-8-nitro-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-acetamide and 3-(2,5-Dichloro-pyrimidin-4-ylamino)-thiophene-2-carboxylic acid methylamide in an analogous manner to Example 1221d. Title compound was isolated as a brown solid. (51 mg, 36%) MP=205-210, LCMS 530 (M+H), 1H-NMR (DMSO-d6, 400 MHz) δ 11.70 (s, 1H), 9.80 (s, 1H), 9.63 (s, 1H), 8.47 (d, J=4.8 Hz, 1H), 8.26-8.24 (m, 2H), 8.08 (d, J=8.2 Hz, 1H), 7.76 (d, J=5.6 Hz, 1H), 7.47 (s, 1H), 7.35-7.30 (m, 2H), 4.32-4.29 (m, 1H), 2.78 (d, J=4.1 Hz, 3H), 2.14-2.10 (m, 1H), 1.94-1.90 (m, 1H), 1.87 (s, 3H), 1.38 (s, 3H), 1.27 (s, 3H).
Sources & evidence
- ORD record
- ord-cbdaa6fcd82a4f8cbacf8288ac12c365
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148391B2
Reaction notes
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