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>>[CH2:20]([O:19][P:18]([CH2:17][C:16]1[CH:26]=[CH:27][C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([CH:42]4[CH2:43][CH2:44][CH:45]([N:48]([CH3:49])[CH3:50])[CH2:46][CH2:47]4)=[C:35]4[C:39]=3[C:38](=[O:40])[N:37]([CH3:41])[CH2:36]4)[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[C:14]([O:28][CH3:29])[CH:15]=1)(=[O:25])[O:22][CH2:23][CH3:24])[CH3:21]Participants
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, 6H), 1.75-1.85 (m, 2H), 1.85-2.02 (m, 4H), 2.39 (d, J=14.15 Hz, 2H), 2.77-2.88 (m, 1H), 3.04 (s, 6H), 3.18 (s, 3H), 3.38-3.50 (m, 3H), 3.86 (s, 3H), 4.07-4.20 (m, 4H), 4.51 (s, 2H), 7.01-7.07 (m, 1H), 7.12 (t, J=2.15 Hz, 1H), 7.62 (d, J=8.59 Hz, 2H), 8.32-8.42 (m, 2H). MS (ES+): m/z 705.26 [MH+] (TOF, polar).
Sources & evidence
- ORD record
- ord-31528afa14f04d5ba8e32ce387afd0b0
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399433B2
Reaction notes
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