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

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Reaction Steps

Following the procedure of 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(8-morpholin-4-yl-4-oxo-2-phenyl-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 5 g C18 cartridge {gradient 10 to 50% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (23 mg, 75%). 1H NMR (400 MHz, DMSO-d6): δ 8.47 (bs, 3H), 7.67 (dd, J=7.5 and 2.1 Hz, 1H), 7.45-7.29 (m, 9H), 7.25 (d, J=8.3 Hz, 2H), 3.74 (t, J=4.1 Hz, 4H), 3.13 (t, J=3.6 Hz, 4H), 2.58-2.44 (m, 4H), 2.19-2.06 (m, 1H), 1.82-1.70 (m, 1H). LCMS (Method E): RT=3.44 min, [M+H]+=453.

Provenance & Evidence