Hydrochloric Acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-chromene-4-thione 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-(2-phenyl-4-thioxo-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 (3 mL) and 1 M HCl (0.1 mL) and then chromatographed on a 5 g C18 cartridge {40 to 80% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a grey-green solid (17.2 mg, 64% over 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 8.63 (br s, 3H), 8.53 (dd, J=8.3 and 1.4 Hz, 1H), 7.95-7.91 (m, 1H), 7.81 (d, J=8.5 Hz, 1H), 7.61-7.57 (m, 1H), 7.48-7.39 (m, 5H), 7.34-7.26 (m, 4H), 2.57-2.49 (m, 4H), 2.23-2.13 (m, 1H), 1.85-1.74 (m, 1H). LCMS (Method E): RT=3.92 min, [M+H]+=384.

Provenance & Evidence