Hydrochloric Acid → 1-{[4-(3-acetylphenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylic acid

HRID 1257343Notes

Reaction equation

HRID 1257343 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH2:15][N:16]3[CH:20]=[C:19]([C:21]([O:23]CC)=[O:22])[CH:18]=[N:17]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C.O1CCCC1.[Cl-].[Na+].O>[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH2:15][N:16]3[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[N:17]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58127487ethyl 1-{[4-(3-acetylphenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylate

Product 1

HCID 581278951-{[4-(3-acetylphenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylic acidYield 84%

Reagents, catalysts & solvents 2

HCID 21873804Tetrahydrofuran ethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixed solution of the compound (188 mg, 0.53 mmol) obtained in Example 30d in ethanol-tetrahydrofuran (v/v=2/1) was added 2N aqueous sodium hydroxide solution (1.5 mL, 3.0 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 1N aqueous hydrochloric acid solution, saturated brine was added, 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 obtained crude product was purified by recrystallization (ethyl acetate-hexane) to give the title compound (145 mg, 84%) as colorless crystals.

Workup

  1. additionwas added
  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 obtained crude product
  7. customwas purified by recrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-616ff89e8b924bf7ab0e39fe3f9eb6d6
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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