4-Propan-2-ylpiperazine-1-carbothioamide → 4-(2,4-Difluorophenyl)-5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-2-(4-isopropylpiperazin-1-yl)thiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (0.49 g, 1.24 mmol, Preparation #A.2) in EtOH (10 μL) was added 4-isopropylpiperazine-1-carbothioamide (0.21 g, 1.12 mmol, Preparation #AO.1.1). The reaction mixture was stirred at about 40° C. for about 2.5 h. The reaction mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. DCM (35 mL) and water (20 mL) were added. The layers were partitioned and the organic layer was washed with additional water (200 mL). The organic layer was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The crude residue was purified by silica gel column chromatography DCM/MeOH (gradient from 100:0 to 90:10) to afford the title compound (0.34 g, 56%) as a yellow solid: LC/MS (Table 1, Method a) Rt=2.06 min; MS m/z: 484.2 (M+H)+.

Provenance & Evidence