Hydrogen Peroxide → 1H-1,3-benzodiazole-2-carboxamide

Participants

Reaction Steps

6-(2-(4-(Trifluoromethyl)phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-1H-benzo[d]imidazole-2-carboxamide. A mixture of 6-(2-(4-(trifluoromethyl)phenylamino)-[1,2,4]triazolo[1,5-c]pyridin-5-yl)-1H-benzo[d]imidazole-2-carbonitrile (300 mg, 0.5 mmol), hydrogen peroxide (30%, 1.0 mL) and sodium hydroxide (40 mg, 1.0 mmol) in dimethylsulfoxide (5 mL) was stirred at room temperature for 3 h. The reaction mixture was poured into water (15 mL), and the mixture was extracted with ethyl acetate (15 mL×3). The combined organic layer was dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was purified by reverse-phase preparatory HPLC (35-65% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, over 15 min.) to give 64244-(trifluoromethyl)phenylamino)-[1,2,4]triazolo[1,5-c]pyridin-5-yl)-1H-benzo[d]imidazole-2-carboxamide (65 mg, 29.7% yield) as a trifluoroacetic acid salt, which was converted to the hydrochloride salt with methanolic hydrochloride solution. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 10.19 (s, 1H), 8.37 (s, 1H), 7.95 (m, 5H), 7.73 (m, 4H), 7.29 (d, J=7.2 Hz, 1H); MS (ESI): m/z 438.1 [M+1]+.

Provenance & Evidence