Phosphate → HCID 86666697, compound

HRID 2045896Notes

Reaction equation

HRID 2045896 reaction equation
P([O-])([O-])([O-])=O.[Na].[F:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[C:12]([F:18])[CH:11]=[CH:10][C:9]=1[C:19]1[N:20]=[C:21]([NH:24][C:25](=[O:41])[CH2:26][C:27]2[N:28]([CH3:40])[N:29]=[C:30]3[C:35]=2[C:34](=[O:36])[N:33]([CH3:37])[C:32](=[O:38])[N:31]3[CH3:39])[S:22][CH:23]=1.[P:42]([O:54][CH2:55]I)([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>CN(C=O)C>[P:42]([O:54][CH2:55][N:20]1[C:19]([C:9]2[CH:10]=[CH:11][C:12]([F:18])=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]=2[F:7])=[CH:23][S:22][C:21]1=[N:24][C:25](=[O:41])[CH2:26][C:27]1[N:28]([CH3:40])[N:29]=[C:30]2[C:35]=1[C:34](=[O:36])[N:33]([CH3:37])[C:32](=[O:38])[N:31]2[CH3:39])([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])([O:49][C:50]([CH3:51])([CH3:52])[CH3:53])=[O:43]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 5360545SodiumHCID 46947051HCID 46947051, compoundHCID 58196853Di-Tert-Butyl Iodomethyl Phosphate2×

Product 1

HCID 86666697HCID 86666697, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure as described in step 2 of method B for the preparation of phosphate derivatives by the reaction of sodium salt of N-(4-(2,4-difluoro-3-(trifluoromethyl)phenyl)thiazol-2-yl)-2-(2,5,7-trimethyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl)acetamide (500 mg, 0.93 mmol) with freshly prepared di-tert-butyl iodomethyl phosphate (Intermediate 2) (489 mg, 1.39 mmol) dry DMF (5 ml) to yield 460 mg of product as a white solid. The title compound was also prepared according to the general procedure as described in method A by coupling of N-(4-(2,4-difluoro-3-(trifluoromethyl)phenyl)thiazol-2-yl)-2-(2,5,7-trimethyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl)acetamide (2.50 g, 4.86 mmol) with freshly prepared di-tert-butyl iodomethyl phosphate (Intermediate 2) (5.95 g, 17.02 mmol) in the presence of sodium hydride (60% dispersion in mineral oil, 291 mg, 7.29 mmol) in dry DMF (25 ml) to yield 1.35 g of pure product as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 1.44 (s, 18H), 3.34 (s, 3H), 3.51 (s, 3H), 3.92 (s, 3H), 4.74 (s, 2H), 6.44 (d, J=9.6 Hz, 2H), 7.09 (t, J=9.3 Hz, 1H), 7.51 (s, 1H), 8.45 (q, J=9.0 Hz, 1H). ESI (m/z): 736.56 (M+H)+.

Sources & evidence

ORD record
ord-54676e146b114268b6aea084f413d76e
Source dataset
uspto-grants-2013_11
Patent number
US08592398B2

Reaction notes

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