Potassium Hydroxide → HCID 178494285, compound

HRID 550850Notes

Reaction equation

HRID 550850 reaction equation
CS([C:5]1[N:6]=[C:7]([O:34][CH3:35])[C:8]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:9]=2[N:10]=1)(=O)=O.[OH-:36].[K+]>C1COCC1.O>[OH:36][C:5]1[N:6]=[C:7]([O:34][CH3:35])[C:8]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:9]=2[N:10]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 248306134-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-methanesulfonyl-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

Product 1

HCID 178494285HCID 178494285, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A magnetically stirred mixture of 4-hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-methanesulfonyl-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (250 mg, 0.47 mmol) in THF (10 mL) and water (5 mL) was treated with a 2N aqueous KOH solution (0.5 mL, 0.94 mmol). The reaction mixture was stirred at 75° C. for 4 h. The reaction was then cooled to room temperature and 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-hydroxy-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (32 mg, 15%) as a white solid. LRMS for C19H18F3N5O4S2 (M+H)+ at m/z=469. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  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-f6b31592a9ae435893220359cb726dbe
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

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