Trifluoroacetic acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-7-methoxy-2-phenyl-8-(1H-pyrazol-4-yl)-chromen-4-one

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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-[7-methoxy-4-oxo-2-phenyl-8-(1H-pyrazol-4-yl)-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester (50 mg, 0.088 mmol) 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 30 to 80% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to yield the title compound as a white solid (14 mg, 32%). 1H NMR (300 MHz, DMSO-d6): δ 8.75 (s, 3H), 8.12-8.01 (m, 3H), 7.50-7.24 (m, 9H), 7.11 (s, 1H), 4.01 (s, 3H), 2.62-2.48 (m, 4H), 2.27-2.10 (m, 1H), 1.87-1.72 (m, 1H). LCMS (Method E): RT=2.99 min, [M+H]+=464.

Provenance & Evidence