Triethylamine → HCID 23502835, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.018 ml (0.21 mmol) oxalyl chloride in 2.5 ml dichloromethane 0.03 ml (0.4 mmol) dimethylsulfoxide were added at −78° C. After 5 min a solution of 100 mg (0.179 mmol) (RS)-N-(3,5-bis-trifluoromethyl-benzyl)-6-(hydroxy-phenyl-methyl)-N-methyl-4-o-tolyl-nicotinamide (Example 76) in 2.5 ml dichloromethane were added dropwise at −78° C. After stirring for another 30 min at −78° C. 0.15 ml (0.90 mmol) triethylamine were added. The reaction mixture was allowed to warm to room temperature. Dilution with dichloromethane was followed by washing with three portions of 1 M aqueous hydrochloric acid solution and one portion of a saturated aqueous solution of sodium bicarbonate. The organic layer was dried with sodium sulfate and concentrated. Column chromatography afforded 69 mg (70%) of the title compound as a light-yellow foam.

Provenance & Evidence