Diisopropylethylamine → {3-[3-(2-Methoxyethoxy)-1,2,4-oxadiazol-5-yl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidin-1-yl}-(thiomorpholin-4-yl)methanone

Participants

Reaction Steps

To a solution of 300 mg (0.783 mmol) of the carboxylic acid from Example 56A in 10.0 ml of N,N-dimethylformamide were added, at room temperature, 329 mg (0.864 mmol) of HATU and 0.28 ml (205 mg, 1.59 mmol) of N,N′-diisopropylethylamine, and the mixture was stirred for 30 min. Subsequently, the mixture was admixed with 106 mg (0.792 mmol) of 2-methoxyethyl N′-hydroxyimidocarbamate from Example 44A and stirred at room temperature overnight. The reaction solution was subsequently stirred at 120° C. for 2 h. The reaction solution was purified directly by means of preparative HPLC. Yield: 98.0 mg (26% of theory)

Provenance & Evidence