Hydrochloric Acid → HCID 67067981, 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-(2-isopropyl-6-oxo-8-phenyl-2,6-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 (3 mL), water (7 mL) and 1 M HCl (0.2 mL) and chromatographed on a 5 g C18 cartridge {gradient 30 to 70% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound (30.2 mg, 71%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.70 (s, 1H), 8.54 (br s, 3H), 7.74 (d, J=8.8 Hz, 1H), 7.63 (d, J=8.8 Hz, 1H), 7.50-7.38 (m, 7H), 7.32 (d, J=8.3 Hz, 2H), 4.96 (septet, J=6.7 Hz, 1H), 2.61-2.49 (m, 4H), 2.23-2.12 (m, 1H), 1.86-1.75 (m, 1H), 1.60 (d, J=6.7 Hz, 6H). LCMS (Method E): RT=3.58 min, [M+H]+=450.

Provenance & Evidence