Triethylamine → HCID 44236572, compound

Participants

Reaction Conditions

Reaction Steps

Isonicotinoyl chloride hydrochloride (261 mg, 1.47 mmol) was added to an acetonitrile solution (15 mL) of potassium thiocyanate (70.9 mg, 0.730 mmol) and then the mixture was stirred at 70° C. for 40 minutes. The organic mixture was left to room temperature. An acetonitrile solution (5 mL) of 2-(azacyclooctan-1-yl)-5-(trifluoromethyl)aniline (200 mg, 0.730 mmol) and triethylamine (205 μL, 1.47 mmol) were added sequentially. The reaction solution was heated to 50° C. and then stirred for 1 hour. The organic mixture was left to room temperature and then water was added to the solution. The mixture was subjected to extraction three times with ethyl acetate, washed with saturated sodium chloride solution, dried on anhydrous sodium sulfate, subjected to suction filtration, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1), so that (N-isonicotinoyl-N′-[2-(azacyclooctan-1-yl)-5-(trifluoromethyl)phenyl]thiourea (Compound 7) (149 mg, 46.8%) was obtained as yellow solid.

Provenance & Evidence