Reaction #58993

Reaction equation

ethyl 2-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)benzyl]-1,3-thiazole-4-carboxylate

sodium hydroxide

tetrahydrofuran

Hydrochloric acid

→

2-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl }amino)benzyl]-1,3-thiazole-4-carboxylic acid

Yield 83.6%

Solvents

ethanol

water

Conditions

Workup

1. 1
   Filtrationthe precipitated crystals were collected by filtration

Procedure

A mixture of ethyl 2-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl}amino)benzyl]-1,3-thiazole-4-carboxylate (0.52 g), a 1N aqueous sodium hydroxide solution (2 mL), tetrahydrofuran (2 mL) and ethanol (2 mL) was stirred at 50° C. for 30 min. 1N Hydrochloric acid (2 mL) and water were added to the reaction mixture and the precipitated crystals were collected by filtration to give 2-[4-({(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl }amino)benzyl]-1,3-thiazole-4-carboxylic acid as colorless crystals (0.41 g, yield 80%). Recrystallization thereof from acetone-hexane gave colorless prism crystals. melting point: 226-227° C.

Source