Hydrogen Peroxide → 4-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-methanesulfonyl-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

HRID 550849Notes

Reaction equation

HRID 550849 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:13]=[C:12]([NH:14][C:15]([N:17]3[CH2:22][CH2:21][C:20]([OH:33])([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)[CH2:19][CH2:18]3)=[O:16])[S:11][C:5]=2[N:6]=[C:7]([S:9][CH3:10])[N:8]=1.OO.[OH2:36].C[OH:38]>[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:10][S:9]([C:7]1[N:8]=[C:3]([O:2][CH3:1])[C:4]2[N:13]=[C:12]([NH:14][C:15]([N:17]3[CH2:22][CH2:21][C:20]([OH:33])([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:32])[F:31])[CH:24]=4)[CH2:19][CH2:18]3)=[O:16])[S:11][C:5]=2[N:6]=1)(=[O:38])=[O:36]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 962WaterHCID 590119534-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-2-yl)-amide

Product 1

HCID 248306134-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-methanesulfonyl-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amideYield 63%

Reagents, catalysts & solvents 1

HCID 26052Sodium tungstateCatalyst

Procedure

A magnetically stirred mixture of 4-hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-2-yl)-amide (375 mg, 0.75 mmol) in methanol (20 mL) was cooled in an ice water bath and treated with sodium tungstate dihyrate (135 mg, 0.04 mmol) followed by hydrogen peroxide (30% solution, 10 mL) The reaction mixture was warmed to room temperature and stirred for 2 h. The reaction was then poured into water and extracted with methylene chloride. The organics were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo to afford 4-hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-methanesulfonyl-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (251 mg, 63%) as a red solid. LRMS for C20H20F3N5O5S2 (M+H)+ at m/z=499. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. temperaturewas cooled in an ice water bath
  2. extractionextracted with methylene chloride
  3. washThe organics were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ce5796a435344a59dd63287bea523c9
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

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