2-(7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N-methyl-acetamide → 2-[5-Chloro-2-(3-methylcarbamoylmethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-ethyl-3-fluoro-benzamide
Reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:12]([NH:14][CH3:15])=[O:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.Cl[C:19]1[N:24]=[C:23]([NH:25][C:26]2[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:27]=2[C:28]([NH:30][CH2:31][CH3:32])=[O:29])[C:22]([Cl:38])=[CH:21][N:20]=1>>[Cl:38][C:22]1[C:23]([NH:25][C:26]2[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:27]=2[C:28]([NH:30][CH2:31][CH3:32])=[O:29])=[N:24][C:19]([NH:1][C:2]2[CH:17]=[CH:16][C:5]3[CH2:6][CH2:7][N:8]([CH2:11][C:12](=[O:13])[NH:14][CH3:15])[CH2:9][CH2:10][C:4]=3[CH:3]=2)=[N:20][CH:21]=1Participants
3
Reactant 2
Product 1
Procedure
2-[5-Chloro-2-(3-methylcarbamoylmethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-N-ethyl-3-fluoro-benzamide was prepared from 2-(7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N-methyl-acetamide and 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-ethyl-3-fluoro-benzamide in an analogous manner to Example 308c. Product isolated as a yellow foam (117 mg, 52%). LCMS (m/e) 526 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.63 (s, 1H), 8.08 (s, 1H), 7.40-7.33 (m, 1H), 7.33-7.24 (m, 2H), 7.18 (s, 1H), 7.14 (d, 1H, J=8.1 Hz), 6.91 (d, 1H, J=8.1 Hz), 6.85 (s, 1H), 6.20-6.13 (m, 1H), 3.46-3.36 (m, 2H), 3.12 (s, 2H), 2.87 (d, 3H, J=4.9 Hz), 2.87-2.81 (m, 2H), 2.81-2.74 (m, 2H), 2.72-2.63 (m, 4H), 1.15 (t, 3H, J=7.3 Hz).
Sources & evidence
- ORD record
- ord-08731e7048b54492ba179d7aba1b8ba1
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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