2-amino-5-cyano-N-methylbenzamide → Diethyl (4-{[4-{[4-cyano-2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)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][CH:14]=2)[N:3]=1.[NH2:28][C:29]1[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][C:30]=1[C:31]([NH:33][CH3:34])=[O:32]>>[C:39]([C:36]1[CH:37]=[CH:38][C:29]([NH:28][C:2]2[C:7]([C:8]([F:10])([F:9])[F:11])=[CH:6][N:5]=[C:4]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([CH2:17][P:18](=[O:25])([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24])=[CH:26][CH:27]=3)[N:3]=2)=[C:30]([C:31](=[O:32])[NH:33][CH3:34])[CH:35]=1)#[N:40]Participants
Procedure
The title compound was prepared using the procedure from Example 102 (Diethyl (4-{[4-{[4-fluoro-2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-benzyl)phosphonate) with diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate (10.0 mg, 0.0236 mmol) and 2-amino-5-cyano-N-methylbenzamide (Compound 150A, 8.3 mg, 0.0472 mmol). The crude mixture was purified by MDP to obtain the title compound as white solid (2.9 mg, 22% yield). 1H NMR (400 MHz, CD3OD) δ=1.28 (t, J=7.1 Hz, 6 H), 2.92 (s, 3 H), 3.26 (d, J=21.5 Hz, 2 H), 4.07 (qd, J=7.3, 7.1 Hz, 4 H), 7.28 (dd, J=8.8, 2.5 Hz, 2 H), 7.56 (d, J=6.3 Hz, 2 H), 7.76 (d, J=8.6 Hz, 1 H), 8.04 (d, J=1.8 Hz, 1 H), 8.42 (s, 1 H), 8.88 (br. s., 1 H). MS (ES+): m/z 563.17 (100) [MH+]; HPLC: tR=1.04 min (UPLC, purity).
Workup
- customThe title compound was prepared
- customThe crude mixture was purified by MDP
Sources & evidence
- ORD record
- ord-ab5289f6c22a4757b12779eeca600bd8
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096624B2
Reaction notes
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