Triethylamine → N-{2-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]-oxadiazol-3-yl]-phenyl}-2-(4-methyl-piperazin-1-yl)-acetamide

Participants

Reaction Steps

A solution of 3-(3-amino-4-chloro-phenyl)-5-(3-chlorothiophen-2-yl)-[1,2,4]-oxadiazole (56.5 mg, 0.181 mmol), triethylamine (75.0 μL, 0.540 mmol), and bromo-acetyl bromide (48.0 μL, 0.549 mmol) and dichloromethane (15.0 mL) was stirred at room temperature for 30 min. The solution was washed with 5% hydrochloric acid solution, dried over sodium sulfate, and rotary evaporated to dryness. To the residue was added ethanol (10 mL), tetrahydrofuran (10 mL), and 1-methyl-piperazine (525 μL, 4.73 mmol) and the resulting solution was refluxed for 20 min under argon. The solution was partitioned between ethyl acetate (25 mL) and 10% sodium bicarbonate (15 mL). The ethyl acetate layer was washed with water (15 mL), dried over sodium sulfate and rotary evaporated to dryness to yield 68.7 mg (84%) of the title compound as a white solid. 1H NMR (CDCl3): 10.04 (s, 1H), 9.25 (d, J=1.92 Hz, 1H), 7.85 (dd, J1=8.24 Hz, J2=1.64 Hz, 1H), 7.60 (d, J=5.22 Hz, 1H), 7.52 (d, J=8.24 Hz, 1H), 7.12 (d, J=5.49 Hz, 1H), 3.24 (s, 2H), 2.73 (s, 4H), 2.57 (s, 4H), 2.35 (s, 3H).

Provenance & Evidence