Hydrochloric Acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-chromen-4-one O-methyl-oxime hydrochloride

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Reaction Steps

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(4-methoxyimino-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 (2 mL), water (6 mL) and 1 M HCl (0.1 mL) and chromatographed on a 5 g C18 cartridge {35 to 80% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (13.3 mg, 69%). 1H NMR (400 MHz, CD3OD): δ 8.89 (dd, J=8.4 and 1.4 Hz, 1H), 7.54-7.50 (m, 1H), 7.39 (d, J=8.4 Hz, 2H), 7.33-7.16 (m, 9H), 3.77 (s, 3H), 2.80-2.73 (m, 2H), 2.60-2.52 (m, 2H), 2.28-2.17 (m, 1H), 2.01-1.90 (m, 1H). LCMS (Method E): RT=4.10 min, [M+H]+=397.

Provenance & Evidence