Oxalyl chloride → 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxylic acid (2.55 g, 5.87 mmol) (i.e. the product of Example 19, Step C) in 100 mL of dichloromethane was cooled to −10° C. and added 1 drop of N,N-dimethylformamide. The reaction mixture was treated with a dropwise addition of a solution of oxalyl chloride (0.60 mL, 6.8 mmol) in 10 mL of dichloromethane. The reaction mixture was stirred at −10° C. for 30 minutes, allowed to warm to room temperature and stirred an additional 16 h. The resulting homogeneous mixture was evaporated in vacuo and the residue placed under high vacuum for several hours to give 2.46 g of the title compound as a light yellow solid.

Provenance & Evidence