Trifluoroacetic acid → 6-(1,4-Diazepan-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

Participants

Reaction Steps

Trifluoroacetic acid (8 mL, 103.68 mmol) was added to a mixture of tert-butyl 4-[3-(trifluoromethyl)-[1,2,4]triazolo[3,4-f]pyridazin-6-yl]-1,4-diazepane-1-carboxylate (5.9 g, 15.3 mmol) and dichloromethane (80 mL) at ambient temperature and the resulting solution was stirred at ambient temperature for 6 hours. The reaction mixture was evaporated to give an involatile residue that was treated with saturated aqueous sodium bicarbonate solution (100 mL) and then extracted with dichloromethane (4×200 mL). The organic phases were combined and dried over Na2SO4, filtered, and evaporated to give 6-(1,4-diazepan-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[3,4-f]pyridazine (3.8 g, 86.9%) as a white solid. 1H NMR (300.132 MHz, DMSO) δ 1.68-1.84 (m, 2H), 2.69 (t, 2H), 2.88 (t, 2H), 3.60-3.79 (m, 4H), 7.46 (d, 1H), 8.19 (d, 1H); m/z. 287 (M+H)+.

Provenance & Evidence