8-Amino-1-(2-methoxyethyl)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one → 3-Fluoro-2-{2-[1-(2-methoxy-ethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-8-ylamino]-5-trifluoromethyl-pyrimidin-4-ylamino]-N-methyl-benzamide
Reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([C:20]([F:23])([F:22])[F:21])=[CH:4][N:3]=1.[NH2:24][C:25]1[CH:26]=[CH:27][C:28]2[CH2:34][CH2:33][CH2:32][C:31](=[O:35])[N:30]([CH2:36][CH2:37][O:38][CH3:39])[C:29]=2[CH:40]=1>>[F:19][C:18]1[C:9]([NH:8][C:6]2[C:5]([C:20]([F:23])([F:22])[F:21])=[CH:4][N:3]=[C:2]([NH:24][C:25]3[CH:26]=[CH:27][C:28]4[CH2:34][CH2:33][CH2:32][C:31](=[O:35])[N:30]([CH2:36][CH2:37][O:38][CH3:39])[C:29]=4[CH:40]=3)[N:7]=2)=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([NH:13][CH3:14])=[O:12]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from 2-(2-chloro-5-trifluoromethyl-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide and 8-amino-1-(2-methoxyethyl)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one in an analogous manner to Example 195 (microwave: 120° C., 2 hours) to afford a white solid (30 mg, 50%). Mp: 142-4° C. LCMS (m/e) 547 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 9.03 (s, 1H), 8.35 (s, 1H), 7.56 (s, 1H), 7.47 (br s, 1H), 7.36 (m, 1H), 7.28 (m, 1H), 7.20 (m, 1H), 7.01 (br s, 2H), 3.40 (m, 2H), 3.26 (s, 3H), 2.94 (d, J=5 Hz, 3H), 2.66 (br m, 2H), 2.23 (br s, 2H).
Sources & evidence
- ORD record
- ord-adba622b1c6e4533b9406dfacfccb459
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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