Sodium cyanoborohydride → (S)-6-Bromo-N-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of (S)-6-bromo-N-(5-(2-methylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine hydrobromide 115d (1.05 g, 2.24 mmol), oxetan-3-one (483 mg, 6.7 mmol), and ZnCl2 (914 mg, 6.7 mmol) in methanol (30 mL) was added NaBH3CN (421 mg, 6.7 mmol). The reaction mixture was heated at 50° C. for 14 h and concentrated under reduced pressure. Water (30 mL) was added to the residue and the resulting mixture was extracted with dichloromethane (% X 30 mL). The combined organic phase was dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 40:1 dichloromethane/methanol to afford 115e as a yellow solid (220 mg, 22%). MS-ESI: [M+H]+ 444.1

Provenance & Evidence