Hydrochloric Acid → HCID 68227506, 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-ethyl-1-methyl-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 (2 mL), water (3 mL) and 1 M HCl (0.1 mL) and chromatographed on a 2 g C18 cartridge {gradient 40 to 65% MeOH in water+1 M HCl (60 μL in each 5 mL of eluent)} to give the title compound (9 mg, 43%, 3 steps) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.38 (br s, 3H), 7.80 (d, J=8.6 Hz, 1H), 7.70 (d, J=8.6 Hz, 1H), 7.55-7.53 (m, 2H), 7.50-7.43 (m, 3H), 7.41-7.37 (m, 2H), 7.32 (d, J=8.3 Hz, 2H), 4.34 (s, 3H), 2.99 (q, J=7.6 Hz, 2H), 2.63-2.52 (m, 4H), 2.22-2.11 (m, 1H), 1.87-1.76 (m, 1H), 1.35 (t, J=7.6 Hz, 3H). LCMS (Method E): RT=3.79 min, [M+H]+=450.

Provenance & Evidence