HCID 44434209, compound → HCID 4999172, compound

Participants

Reaction Steps

The 2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(tert-butyl)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (1.57 g, 2.58 mmol) was dissolved in 20 mL of a 4 N HCl in dioxane solution at room temperature, resulting in a modest evolution of gas. After 1 hour stirring at room temperature, the solvent and HCl gas were evaporated in vacuo, then the resulting white solid was resuspended in 75 mL 2:1 EtOAc:dichloromethane and evaporated a second time. The pasty white solid was dissolved in a solution of K2 CO3 (11.2 g) in water (75 mL), dichloromethane was added (75 mL), and the mixture vigorously stirred overnight. The mixture was partitioned, the aqueous layer back-extracted twice with dichloromethane, then the combined organic layers washed with brine. The organic layer was dried and concentrated in vacuo to provide 2-[4-tert-butyl)-2-(piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (1.32 g, 100%) as an off-white crystalline solid.

Provenance & Evidence