Dimethylformamide → 2-(4-Chloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetamide

Participants

Reaction Steps

To a mixture of (4-chloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acid (365 mg) and THF (dry) (5 mL) were added oxalyl chloride (0.095 mL) and DMF (6.98 μl) at room temperature. The mixture was stirred at room temperature for 20 min. The mixture was concentrated under reduced pressure. The residue was dissolved in THF (5 mL), and the solution was poured into stirred 28% aqueous ammonium hydroxide (5 mL) at room temperature. After stirring at room temperature for 15 min, the mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The solid was crystallized from MeOH to give the title compound (320 mg).

Provenance & Evidence