Diethyl (4-{[4-{[4-fluoro-2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate → Diethyl (3-fluoro-5-methoxy-4-{[4-{[2-(methylcarbamoyl)phenyl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]=[C:11]([NH:19][C:20]3[CH:34]=[CH:33][C:23]([CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])=[CH:22][C:21]=3[O:35][CH3:36])[N:10]=2)=[C:4]([C:37](=[O:40])[NH:38][CH3:39])[CH:3]=1.ClC1N=C(NC2C=CC=CC=2C(NC)=O)C(C(F)(F)[F:60])=CN=1.NC1C(OC)=CC(CP(=O)(OCC)OCC)=CC=1F>>[F:60][C:34]1[CH:33]=[C:23]([CH:22]=[C:21]([O:35][CH3:36])[C:20]=1[NH:19][C:11]1[N:10]=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=2[C:37](=[O:40])[NH:38][CH3:39])[C:14]([C:15]([F:18])([F:16])[F:17])=[CH:13][N:12]=1)[CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28]Participants
4
Reactant 3
Product 1
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-methoxybenzyl)phosphonate) with 2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide (Compound 104A) and Diethyl (4-amino-3-fluoro-5-methoxybenzyl)phosphonate (Compound 146A). 1H NMR (CD3OD, 400 MHz): δ=1.30 (t, J=7.07 Hz, 6 H), 2.90 (s, 3 H), 3.33-3.40 (m, 2 H), 3.85 (s, 3 H), 4.06-4.18 (m, 4 H), 6.88 (dt, J=10.11, 2.02 Hz, 1 H), 6.95 (s, 1 H), 7.17 (br. s., 1 H), 7.37 (br. s., 1 H), 7.64 (d, J=6.82 Hz, 1 H), 8.29 (br. s., 2 H). MS (ES+): m/z 586.21 [MH+] (TOF, polar).
Sources & evidence
- ORD record
- ord-0a97517f049d4e5597bee7d054f0cf58
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096624B2
Reaction notes
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