Diethyl Ether → HCID 57929906, compound

Participants

Reaction Steps

A 100 mL flask was charged with tert-butyl 4-(4-(2,4-difluorophenyl)-5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)thiazol-2-yl)piperidine-1-carboxylate (1.05 g, 1.94 mmol, prepared using General Procedure O from Preparation #A.2 and tert-butyl 4-(aminocarbothioyl) tetrahydropyridine-1-(2H)-carboxylate) in DCM (10 mL) to give a yellow solution. To the solution was added TFA (1.50 mL, 19.4 mmol) and the mixture was stirred at ambient temperature. After about 19 h, the reaction was concentrated under reduced pressure to give a yellow oil which was redissolved in DCM and washed sequentially with 10% aqueous NaOH, water, and brine. The organic solution was dried over MgSO4, filtered, and concentrated to dryness under reduced pressure to give a yellow oil. Upon addition of Et2O, a cloudy solution was formed. Concentration of this solution yielded the title compound as a yellow powder (0.65 g, 76%): LC/MS (Table 1, Method a) Rt=1.54 min; MS m/z: 441.2 (M+H)+.

Provenance & Evidence