Hydrochloric Acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-8-(1H-pyrazol-4-yl)-chromen-4-one hydrochloride

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Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, (1-{4-[4-oxo-2-phenyl-8-(1H-pyrazol-4-yl)-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was dissolved in a mixture of MeOH (7 mL), water (7 mL) and 1 M HCl (0.6 mL) and chromatographed on a 20 g C18 cartridge {gradient 10 to 60% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (73 mg, 83%). 1H NMR (400 MHz, DMSO-d6): δ 8.59 (s, 3H), 8.14-8.08 (m, 3H), 7.95 (dd, J=7.9 and 1.8 Hz, 1H), 7.53-7.32 (m, 8H), 7.25 (d, J=8.3 Hz, 2H), 3.83 (bs, 1H), 2.57-2.43 (m, 4H), 2.19-2.06 (m, 1H), 1.82-1.69 (m, 1H). LCMS (Method E): RT=3.03 min, [M+H]+=434.

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