Trifluoroacetic acid → HCID 73603575, compound

Participants

Reaction Steps

10% Palladium on carbon (45.1 mg, 0.042 mmol) is added to a degassed solution of the product of step 1, Example 24 (451.0 mg, 0.687 mmol) in ethanol (17.1 mL) and water (3.42 mL). After purging with nitrogen, 1 atm of hydrogen is bubbled through the reaction mixture for 5 min before being left under 1 atm of hydrogen. After 1 hour the reaction mixture is filtered through solka floc, and the cake washed with ethanol. The filtrate is concentrated and azeotroped with ethanol to afford a white foam. The crude intermediate is taken up in methylene chloride (4.51 mL) and cooled at 0° C. before trifluoroacetic acid (1.06 mL, 13.7 mmol) is added and the mixture warmed to room temperature. After 4 hours the mixture is concentrated and azeotroped with methylene chloride then purified by reverse phase CombiFlash (30 g column) eluting with 0-25% acetonitrile in water (with 0.1% trifluoroacetic acid) to afford the title compound (120 mg): 1H NMR (300 MHz, DMSO-6) δ 4.27-4.52 (m, 2.5H), 4.66-4.69 (m, 0.5H), 4.87-4.90 (m, 1H), 4.97 (d, 2H), 5.08 (d, 2H), 6.20 (t, 1H), 7.48 (d, 2H), 7.69 (d, 1H), 7.75 (d, 2H), 8.14-8.17 (dd, 1H), 8.83 (d, 1H), 8.96-8.97 (m, 1H). MS (ESI+) m/z 477.1 [M+H].

Provenance & Evidence