7-amino-4-[4-(dimethylamino)cyclohexyl]-2-methyl-2,3-dihydro-1H-isoindol-1-one → Diethyl (4-{[4-({7-[4-(dimethylamino)cyclohexyl]-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate
Reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][C:16]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:15][C:14]=2[O:28][CH3:29])[N:3]=1.[NH2:30][C:31]1[CH:32]=[CH:33][C:34]([CH:42]2[CH2:47][CH2:46][CH:45]([N:48]([CH3:50])[CH3:49])[CH2:44][CH2:43]2)=[C:35]2[C:39]=1[C:38](=[O:40])[N:37]([CH3:41])[CH2:36]2>>[CH3:49][N:48]([CH3:50])[CH:45]1[CH2:44][CH2:43][CH:42]([C:34]2[CH:33]=[CH:32][C:31]([NH:30][C:2]3[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]4[CH:27]=[CH:26][C:16]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:15][C:14]=4[O:28][CH3:29])[N:3]=3)=[C:39]3[C:35]=2[CH2:36][N:37]([CH3:41])[C:38]3=[O:40])[CH2:47][CH2:46]1Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared according to the procedure for Example 102 using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate and 7-amino-4-[4-(dimethylamino)cyclohexyl]-2-methyl-2,3-dihydro-1H-isoindol-1-one (Compound 233A). 1H NMR (CD3OD, 400 MHz): δ=1.30 (t, J=7.07 Hz, 6 H), 1.75-1.85 (m, 2 H), 1.85-2.02 (m, 4 H), 2.39 (d, J=14.15 Hz, 2 H), 2.77-2.88 (m, 1 H), 3.04 (s, 6 H), 3.18 (s, 3 H), 3.38-3.50 (m, 3 H), 3.86 (s, 3 H), 4.07-4.20 (m, 4 H), 4.51 (s, 2 H), 7.01-7.07 (m, 1 H), 7.12 (t, J=2.15 Hz, 1 H), 7.62 (d, J=8.59 Hz, 2 H), 8.32-8.42 (m, 2 H). MS (ES+): m/z 705.26 [MH+] (TOF, polar).
Sources & evidence
- ORD record
- ord-4de5b8e591404d459d5d37d587fb2b7a
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096624B2
Reaction notes
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