Sodium Hydroxide → HCID 58010221, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 4-methyl-3-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)piperidine-1-carboxylate (0.93 g, 1.7 mmol) in 1,4-dioxane (20 mL) was added aqueous NaOH (2 N, 1.0 mL), and the resulting mixture was heated at about 90° C. for about 80 min. The solvents were removed under reduced pressure and the residue was treated with saturated aqueous NH4Cl (26 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine (20 mL), dried over anhydrous MgSO4, filtered, and concentrated to yield the crude product as a brown amorphous solid. The material was purified by silica gel chromatography eluting with a gradient of 5-100% MeOH/DCM to give benzyl 3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylpiperidine-1-carboxylate (0.55 g, 83%) as a yellow solid: LC/MS (Table 2, Method a) Rt=1.94 min; MS m/z: 390 (M+H)+.

Provenance & Evidence