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

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).

1. washThe solution was washed with 5% hydrochloric acid solution
2. dry with materialdried over sodium sulfate
3. customrotary evaporated to dryness
4. temperaturethe resulting solution was refluxed for 20 min under argon
5. customThe solution was partitioned between ethyl acetate (25 mL) and 10% sodium bicarbonate (15 mL)
6. washThe ethyl acetate layer was washed with water (15 mL)
7. dry with materialdried over sodium sulfate
8. customrotary evaporated to dryness

ORD record

ord-d08d517e573546ecbe13cc58c36466e1

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07144876B2