Hydrochloric Acid → HCID 67067984, 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-[1-(2-hydroxy-ethyl)-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 (8 mL) and 1 M HCl (0.2 mL) and chromatographed on a 5 g C18 cartridge {gradient 20 to 60% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound (33.5 mg, 74%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.60 (br s, 3H), 8.33 (s, 1H), 7.81 (d, J=8.6 Hz, 1H), 7.75 (d, J=8.5 Hz, 1H), 7.57-7.55 (m, 2H), 7.51-7.37 (m, 5H), 7.32 (d, J=8.4 Hz, 2H), 4.95 (t, J=5.1 Hz, 1H), 4.80 (t, J=5.6 Hz, 2H), 3.89 (q, J=5.5 Hz, 2H), 2.63-2.52 (m, 4H), 2.24-2.13 (m, 1H), 1.87-1.76 (m, 1H). LCMS (Method E): RT=3.00 min, [M+H]+=452.

Provenance & Evidence