Dimethylformamide → HCID 59454493, compound

Participants

Reaction Steps

To a solution of 2-chloro-3-(1-cyano-1-methylethyl)benzoic acid (156 mg, 0.697 mmol) in tetrahydrofuran (2 mL) were added oxalyl chloride (75 μL, 0.875 mmol) and N,N-dimethylformamide (20 μL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in N,N-dimethylacetamide (2 mL). N-[6-(3-Amino-4-fluorophenoxy)-7-cyano-1,3-benzothiazol-2-yl]acetamide (200 mg, 0.584 mmol) was added to the solution, and the mixture was stirred at room temperature for 8 hr. The reaction mixture was diluted with ethyl acetate (20 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (20 mL) and saturated brine (20 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was successively purified by basic silica gel column chromatography (ethyl acetate/n-hexane=40/60→100/0) and silica gel column chromatography (ethyl acetate/n-hexane=70/30→100/0), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (164 mg, 51%) as a white powder. 1H-NMR (DMSO-d6, 300 MHz) δ 1.84 (6H, s), 2.24 (3H, s), 7.07 (1H, dt, J=8.8, 3.4 Hz), 7.16 (1H, d, J=9.0 Hz), 7.35-7.46 (1H, m), 7.47-7.61 (2H, m), 7.66 (1H, dd, J=7.7, 1.7 Hz), 7.81 (1H, dd, J=6.3, 3.1 Hz), 8.04 (1H, d, J=9.0 Hz), 10.65 (1H, s), 12.69 (1H, s).

Provenance & Evidence