7-(2,5-Dichloropyrimidin-4-ylamino)-4-(4-isopropylpiperazin-1-yl)-2-methyl-2,3-dihydroisoindol-1-one → 2-(7-{5-Chloro-4-[7-(4-isopropyl-piperazin-1-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-ylamino]-pyrimidin-2-ylamino}-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-N,N-dimethyl-acetamide
Reaction equation
[NH2:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.Cl[C:22]1[N:27]=[C:26]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([N:40]3[CH2:45][CH2:44][N:43]([CH:46]([CH3:48])[CH3:47])[CH2:42][CH2:41]3)=[C:33]3[C:37]=2[C:36](=[O:38])[N:35]([CH3:39])[CH2:34]3)[C:25]([Cl:49])=[CH:24][N:23]=1>>[Cl:49][C:25]1[C:26]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([N:40]3[CH2:45][CH2:44][N:43]([CH:46]([CH3:47])[CH3:48])[CH2:42][CH2:41]3)=[C:33]3[C:37]=2[C:36](=[O:38])[N:35]([CH3:39])[CH2:34]3)=[N:27][C:22]([NH:1][C:2]2[C:18]([O:19][CH3:20])=[CH:17][C:5]3[CH2:6][CH2:7][N:8]([CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH2:9][CH2:10][C:4]=3[CH:3]=2)=[N:23][CH:24]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from 2-(7-amino-8-methoxy-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl)-N,N-dimethylacetamide (41 mg, 0.15 mmol) and 7-(2,5-dichloropyrimidin-4-ylamino)-4-(4-isopropylpiperazin-1-yl)-2-methyl-2,3-dihydroisoindol-1-one (60 mg, 0.1 mmol) in an analogous manner to Example 946 to afford a tan foam (79 mg, 80%). Mp: 78-80° C. LCMS (m/e) 676 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 10.58 (s, 1H), 8.68 (d, J=9 Hz, 1H), 8.10 (s, 2H), 7.39 (s, 1H), 7.09 (d, J=9 Hz, 1H), 6.68 (s, 1H), 4.40 (s, 2H), 3.91 (s, 3H), 3.54 (s, 3H), 3.35 (s, 2H), 3.24 (s, 3H), 3.20 (s, 3H), 3.11-2.88 (m, 6H), 2.80-2.65 (m, 8H), 1.82 (m, 1H), 1.12 (d, J=6 Hz, 6H).
Sources & evidence
- ORD record
- ord-8f92c5155e864155a6cd28d21f0dc931
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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