Trifluoroacetic acid → HCID 178479013, compound

Participants

Reaction Steps

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(3-chloro-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was dissolved in a mixture of MeOH (1.25 mL), water (3.75 mL) and 1 M HCl (0.15 mL) and chromatographed on a 2 g C18 cartridge {gradient 25 to 60% MeOH in water+1 M HCl (60 μL in each 5 mL of eluent)} to give the title compound (10.2 mg, 72%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.54 (br s, 3H), 7.82 (d, J=8.6 Hz, 1H), 7.72 (d, J=8.6 Hz, 1H), 7.57-7.55 (m, 2H), 7.51-7.44 (m, 3H), 7.41-7.37 (m, 2H), 7.34 (d, J=8.3 Hz, 2H), 2.63-2.49 (m, 4H), 2.23-2.12 (m, 1H), 1.87-1.76 (m, 1H). LCMS (Method E): RT=3.51 min, [M+H]+=442/444.

Provenance & Evidence