Diethyl [(5-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-6-methoxypyridin-2-yl)methyl]phosphonate → HCID 178476867, compound
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:14]=[CH:15][C:16]([CH2:21][P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])=[N:17][C:18]=2[O:19][CH3:20])[N:3]=1.[NH2:30][C:31]1[CH:32]=[CH:33][C:34]([C@H:42]2[CH2:47][CH2:46][C@H:45]([OH:48])[CH2:44][CH2:43]2)=[C:35]2[C:39]=1[C:38](=[O:40])[N:37]([CH3:41])[CH2:36]2>>[CH2:24]([O:23][P:22]([CH2:21][C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:4]2[N:3]=[C:2]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([C@H:42]4[CH2:43][CH2:44][C@H:45]([OH:48])[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:18]([O:19][CH3:20])[N:17]=1)(=[O:29])[O:26][CH2:27][CH3:28])[CH3:25]Participants
Procedure
The title compound was prepared according to the procedure for Example 102 using diethyl [(5-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-6-methoxypyridin-2-yl)methyl]phosphonate (Compound 286A, 100 mg, 0.22 mmol) and 7-amino-4-(trans-4-hydroxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one (115 mg, 0.44 mmol). The crude material was purified by MDP to obtain the title compound (82 mg, 55% yield). 1H NMR (400 MHz, methanol-d4) δ=1.31 (t, J=6.9 Hz, 6H), 1.38-1.53 (m, 2H), 1.62-1.77 (m, 2H), 1.84-1.93 (m, 2H), 2.04-2.14 (m, 2H), 2.53-2.64 (m, 1H), 3.17 (s, 3H), 3.44 (d, J=21.7 Hz, 2H), 3.62-3.72 (m, 1H), 4.01 (s, 3H), 4.10-4.21 (m, 4H), 4.51 (s, 2H), 6.99 (dd, J=8.1, 2.8 Hz, 1H), 7.39 (d, J=8.6 Hz, 1H), 8.15 (d, J=7.3 Hz, 1H), 8.37 (s, 2H). MS (ES+): m/z 679.31 (100) [MH+]; HPLC: tR=1.06 min (UPLC, purity).
Workup
- customThe title compound was prepared
- customThe crude material was purified by MDP
Sources & evidence
- ORD record
- ord-5dd28aa6e1ea43408c7cfbf916d33578
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399433B2
Reaction notes
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