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

Participants

Reaction Conditions

Reaction Steps

A stirred 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 2, Step C) in dichloromethane (100 mL) was cooled to −10° C., and 1 drop of N,N-dimethyl-formamide was added. A solution of oxalyl chloride (0.60 mL, 6.8 mmol) in dichloromethane (10 mL) was added dropwise to the stirred reaction mixture. The reaction mixture was stirred at −10° C. for 30 minutes more, and then allowed to warm to room temperature and stir an additional 16 h. The resulting homogeneous mixture was evaporated in vacuo, and the residue was placed under high vacuum for several hours to give 2.46 g of the title compound as a light yellow solid. This compound was of sufficient purity to use in subsequent reactions.

Provenance & Evidence