Water → 1-({4-[2-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acid

HRID 1257370Notes

Reaction equation

HRID 1257370 reaction equation
[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[N:13]=[C:14]([CH2:17][N:18]2[CH:22]=[C:21]([C:23]([O:25]CC)=[O:24])[CH:20]=[N:19]2)[S:15][CH:16]=1.[OH-].[Na+].O>C(O)C.O1CCCC1>[F:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[N:13]=[C:14]([CH2:17][N:18]2[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[CH:20]=[N:19]2)[S:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66939677ethyl 1-({4-[2-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 442538521-({4-[2-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acidYield 85,226,936%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a mixed solution of the compound (320 mg, 0.79 nmol) obtained in Example 52a in ethanol/tetrahydrofuran (v/v=1/1, 8 mL) was added 2N aqueous sodium hydroxide solution (1.6 mL, 3.2 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the aqueous layer was washed with diethyl ether, neutralized with 1N aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was recrystallized (ethyl acetate-hexane) to give the title compound (250 mg, 84%) as colorless crystals.

Workup

  1. washthe aqueous layer was washed with diethyl ether
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe resulting crude title compound was recrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c6b0722ba1814048998963fe74ba6fbe
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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