Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Steps

Pd/C (45 mg, 0.042 mmol) 10% wet was added to a solution of (3R,4R)-naphthalen-2-ylmethyl 3-fluoro-4-(6-fluoro-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate (270 mg, 0.42 mmol) in a 1:1 mixture of EtOH/EtOAc (10 mL) and 500 uL of 6 N HCl. The mixture was purged with H2, and then allowed to stir under a balloon of hydrogen for 48 hours. The mixture was filtered through GF paper removing the desired product salt as a precipitate, with the palladium catalyst. The combined solids were washed into a beaker with 30 mL of MeOH and the palladium removed by subsequent filtration through GF filter paper. The organic phase was concentrated in vacuo, followed by flash column chromatography (1-20% MeOH/DCM (4% NH4OH). The resulting product was dissolved in chloroform and subject to four equivalents of 4 M HCl in dioxane. The desired product was then isolated as the bis-HCl salt. MS APCI (+) m/z 455.2 (M+1) detected.

Provenance & Evidence