Dimethylformamide → HCID 136136825, compound

Participants

Reaction Conditions

Reaction Steps

DMF (1.00 mL, 12.6 mmol) was cooled to about 5° C. then phosphorus oxychloride (0.44 mL, 4.7 mmol) was added dropwise. After about 15 min 1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (0.500 mg, 1.58 mmol, Preparation #K.1) in chloroform (10 mL) was added dropwise. The solution was heated to about 80° C. for about 15 min and then the mixture was cooled to about 5° C. then hydroxylamine hydrochloride (0.330 g, 4.7 mmol) and DMF (0.979 mL, 12.7 mmol) were added. The mixture was stirred at ambient temperature for about 3 h then DCM and saturated aqueous NaHCO3 were added. The organic layer was dried over MgSO4 then filtered and concentrated under reduced pressure. The resulting oil was dissolved in EtOH (4 mL) then hydrazine (0.15 mL, 4.7 mmol) was added. The mixture was refluxed for about 1 h then cooled, diluted with DCM and filtered to give the title compound (0.513 g, 91%): LC/MS (Table 1, Method a) Rt=2.38 min; MS m/z: 356.3 (M+H)+.

Provenance & Evidence