tert-Butyl 4-carbamothioylpiperidine-1-carboxylate → HCID 57929940, compound

Participants

Reaction Steps

A mixture of 2-bromo-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-(2,4,5-trifluorophenyl)ethanone (0.90 g, 2.2 mmol; prepared using General Procedure J from Preparation #F.1 and Preparation #G.1, General Procedure K with H2SO4, and General Procedure A.2), tert-butyl 4-(aminocarbothioyl)tetrahydropyridine-1-(2H)-carboxylate (Maybridge, 0.8 g, 3.3 mmol) and DMF (20 mL) was stirred at ambient temperature for about 24 h. The reaction was quenched with saturated aqueous NaHCO3 and extracted with Et2O (300 mL). The organic layer was dried over Na2SO4, decanted, and concentrated. The crude material was loaded onto a silica gel column and eluted with a gradient of 0-10% MeOH in DCM to give the title compound (0.41 g, 34%): LC/MS (Table 1, Method a) Rt=4.18 min; MS m/z: 559.3 (M+H)+.

Provenance & Evidence