Ethyl Acetate → HCID 67396588, compound

Participants

Reaction Steps

To a solution of tert-butyl {[5-(2-cyanopyridin-3-yl)-4-fluoro-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (421 mg) in ethyl acetate (3 mL) and 2-propanol (2 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (6 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=3:7→ethyl acetate) to give a free base of the title compound as a pale-yellow solid (yield 242 mg). A solution of the obtained free base in ethyl acetate (3 mL) was added dropwise to a solution of fumaric acid (74 mg) in ethanol (3 mL) and the mixture was concentrated under reduced pressure. The residue was recrystallized from a mixed solvent of ethanol and water to give the title compound as a white solid (yield 259 mg, 61%).

Provenance & Evidence