Hydrogen chloride-ethyl acetate → HCID 67778231, compound

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Reaction Steps

A mixture of tert-butyl [(1S)-2-{4-[6-(cyclopropylmethoxy)pyrazolo[1,5-a]pyridin-2-yl]-3-fluorophenoxy}-1-methylethyl]carbamate (200 mg), 4 M hydrogen chloride/ethyl acetate (2 mL), and ethyl acetate (2 mL) was stirred at room temperature for 2 hr. The mixture was concentrated under reduced pressure. The residue was mixed with pyridine (2 mL) and acetic anhydride (2 ml). The mixture was stirred at room temperature overnight. 1 M hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and by preparative HPLC (C18, water/acetonitrile (containing 0.1% trifluoroacetic acid)). The desired fraction was neutralized with saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (60.6 mg) as off-white crystals.

Provenance & Evidence