Triethylamine → HCID 71811867, compound

Participants

Reaction Steps

(E)-4,4,4-Trifluorobut-2-enoic acid (14 mg, 0.1 mmol) was dissolved in DCM (1 ml containing one drop of dimethyl formamide), oxalyl chloride was added (9 μl, 0.1 mmol) and the solution was stirred at room temperature for 10 minutes. This solution was added to a solution of N′-(2-quinolyl)ethane-1,2-diamine hydrochloride (22 mg, 0.1 mmol) in DMF (0.5 ml) followed by triethylamine (42 μl, 0.3 mmol) and the resulting mixture was stirred at room temperature for 40 minutes. Then another equivalent of the acid chloride solution (prepared from 14 mg (E)-4,4,4-trifluorobut-2-enoic acid, 1 ml DCM/DMF and 9 μl oxalyl chloride as described above) was added and stirring was continued for additional 40 minutes. The reaction mixture was diluted with ethyl acetate, washed with sat. sodium bicarbonate solution and brine and dried over magnesium sulfate. The volatiles were removed under reduced pressure and the residue obtained was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 5% to 100% acetonitrile) to yield 13 mg (0.042 mmol, 42%).

Provenance & Evidence