Phosphate → HCID 86666693, compound

HRID 2045891Notes

Reaction equation

HRID 2045891 reaction equation
P([O-])([O-])([O-])=O.[CH2:6]([C:8]1[S:20][C:11]2[N:12]([CH3:19])[C:13](=[O:18])[N:14]([CH3:17])[C:15](=[O:16])[C:10]=2[C:9]=1[CH2:21][C:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[C:32]([F:40])[CH:31]=2)[N:29]=1)=[O:23])[CH3:7].[P:41]([O:53][CH2:54]I)([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].[H-].[Na+]>CN(C=O)C>[P:41]([O:53][CH2:54][N:29]1[C:28]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[C:32]([F:40])[CH:31]=2)=[CH:27][S:26][C:25]1=[N:24][C:22](=[O:23])[CH2:21][C:9]1[C:10]2[C:15](=[O:16])[N:14]([CH3:17])[C:13](=[O:18])[N:12]([CH3:19])[C:11]=2[S:20][C:8]=1[CH2:6][CH3:7])([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:42]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 46926862HCID 46926862, compoundHCID 58196853Di-Tert-Butyl Iodomethyl Phosphate

Product 1

HCID 86666693HCID 86666693, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure as described in method A for the preparation of phosphate derivatives by coupling reaction of 2-(6-Ethyl-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-{4-[3-fluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}acetamide (1.00 g, 1.901 mmol) with freshly prepared intermediate 2 (1.33 g, 3.802 mmol) in presence of sodium hydride (60% dispersion in mineral oil, 115 mg, 2.0851 mmol) in dry DMF (10 ml) to yield 1.15 g of pure product a pale yellow solid. 1H NMR (300 MHz, CDCl3): δ 1.20-1.38 (m, 3H), 1.50 (s, 18H), 2.81 (q, J=7.8 Hz, 2H), 3.32 (s, 3H), 3.53 (s, 3H), 4.40 (s, 2H), 6.47 (d, J=7.2 Hz, 2H), 7.21-7.33 (m, 1H), 7.59-7.81 (m, 3H); ESI (m/z): 748.71 (M)+.

Sources & evidence

ORD record
ord-1e142edcb0304cf995bf4d15b41eae23
Source dataset
uspto-grants-2013_11
Patent number
US08592398B2

Reaction notes

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