3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → HCID 86671033, compound

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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-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as the free base. The residue was dissolved in a mixture of MeOH (2 mL), water (3 mL) and 1 M HCl (0.1 mL) and then chromatographed on a 5 g C18 cartridge {gradient 40 to 70% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound (12.5 mg, 75%) as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.45 (d, J=5.1 Hz, 1H), 8.02 (d, J=5.1 Hz, 1H), 7.53-7.48 (m, 4H), 7.46-7.41 (m, 1H), 7.39-7.32 (m, 4H), 2.82-2.75 (m, 2H), 2.63-2.55 (m, 2H), 2.30-2.19 (m, 1H), 2.03-1.92 (m, 1H). LCMS (Method E): RT=3.54 min, [M−NH2]−=386/388.

Provenance & Evidence