Phosphate → HCID 86666695, compound

HRID 338178Notes

Reaction equation

HRID 338178 reaction equation
P([O-])([O-])([O-])=O.[Na].[F:7][C:8]1[C:13]([F:14])=[C:12]([C:15]([F:18])([F:17])[F:16])[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[C:35]3[C:34](=[O:36])[N:33]([CH3:37])[C:32](=[O:38])[N:31]([CH3:39])[C:30]=3[O:29][C:28]=2[CH3:40])[S:22][CH:23]=1.[P:42]([O:54][CH2:55]Cl)([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43].[I-].[Na+]>CC(C)=O>[P:42]([O:54][CH2:55][N:20]1[C:19]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:18])[F:17])=[C:13]([F:14])[C:8]=2[F:7])=[CH:23][S:22][C:21]1=[N:24][C:25](=[O:41])[CH2:26][C:27]1[C:35]2[C:34](=[O:36])[N:33]([CH3:37])[C:32](=[O:38])[N:31]([CH3:39])[C:30]=2[O:29][C:28]=1[CH3:40])([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])([O:49][C:50]([CH3:51])([CH3:52])[CH3:53])=[O:43]

Participants

7

Reactant 5

HCID 1061PhosphateHCID 5238Sodium IodideHCID 5360545SodiumHCID 11701630Di-tert-butyl (chloromethyl) phosphate2×HCID 86666696HCID 86666696, compound

Product 1

HCID 86666695HCID 86666695, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The title compound was prepared according to the general procedure as described in method C for the preparation of phosphate derivatives by coupling reaction of sodium salt of N1-[4-(2,3-Difluoro-4-trifluoromethylphenyl)-1,3-thiazol-2-yl]-2-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydrofuro[2,3-d]pyrimidin-5-yl)acetamide (2.0 g, 3.73 mmol) with di-tert-butyl chloromethyl phosphate (Intermediate 1) (2.41 g, 9.328 mmol) in presence of sodium iodide (559 mg, 3.731 mmol) in dry acetone (50 ml) to obtain 3.0 g of a product as a pale yellow solid; ESI-MS (m/z): 736.70 (M+H)+.

Sources & evidence

ORD record
ord-6699a4f1c7be4bae9b1d48dee65d342f
Source dataset
uspto-grants-2014_11
Patent number
US08889862B2

Reaction notes

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