Phosphate → HCID 86666692, compound
Reaction equation
P([O-])([O-])([O-])=O.[F:6][C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[C:11]([F:17])[CH:10]=[CH:9][C:8]=1[C:18]1[N:19]=[C:20]([NH:23][C:24](=[O:39])[CH2:25][C:26]2[C:34]3[C:33](=[O:35])[N:32]([CH3:36])[C:31](=[O:37])[N:30]([CH3:38])[C:29]=3[S:28][CH:27]=2)[S:21][CH:22]=1.[P:40]([O:52][CH2:53]I)([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41].[H-].[Na+].[CH3:57]N(C=O)C>>[P:40]([O:52][CH2:53][N:19]1[C:18]([C:8]2[CH:9]=[CH:10][C:11]([F:17])=[C:12]([C:13]([F:15])([F:14])[F:16])[C:7]=2[F:6])=[CH:22][S:21][C:20]1=[N:23][C:24](=[O:39])[CH2:25][C:26]1[C:34]2[C:33](=[O:35])[N:32]([CH3:36])[C:31](=[O:37])[N:30]([CH3:38])[C:29]=2[S:28][C:27]=1[CH3:57])([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]Participants
Procedure
The title compound was prepared according to the general procedure as described in method A for the preparation of phosphate derivatives by coupling N-{4-[2,4-Difluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}-2-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)acetamide (1.10 g, 2.07 mmol) with freshly prepared di-tert-butyl iodomethyl phosphate (intermediate 2) (1.459 g, 4.15 mmol) in dry DMF (11 ml) in presence of sodium hydride (60% dispersion in mineral oil, 0.0745 g, 3.113 mmol) to yield 0.85 g of pure product as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 1.46 (s, 18H), 2.42 (s, 3H), 3.33 (s, 3H), 3.52 (s, 3H), 4.40 (s, 2H), 6.47 (d, J=7.8 Hz, 2H), 7.07 (t, J=8.7 Hz, 1H), 7.46 (s, 1H), 8.47 (q, J=9.0 Hz, 1H); APCI (m/z): 752.72 (M+H)+.
Sources & evidence
- ORD record
- ord-e6163fc0865946a7b20f52df43a7a1b5
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592398B2
Reaction notes
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