Methanol → HCID 70983774, compound

Participants

Reaction Steps

In a 50 mL round-bottomed flask was dissolved (5R,8S,9S)-9-(tert-butoxycarbonylamino)-8-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (38.1 mg, 0.060 mmol) in methylene chloride (1 mL) to give a colorless solution. trifluoroacetic acid (0.5 mL) was added, and the mixture was stirred at rt for 1 h. LCMS showed complete conversion. Volatiles were removed in vacuo, and the residue was partitioned between ethyl acetate/0.5N sodium hydroxide/saturated sodium bicarbonate solution. The layers were separated. The organic layer was dried and concentrated to give a tan oil. flash column chromatography up to 10% methanol (2M ammonia) in methylene chloride afforded the desired product (22 mg, 69%) as a white solid: MS (ESI)[M+H+]=536.2; 1H NMR (400 MHz, CDCl3) δ 8.50 (s, 2H), 8.11 (d, J=4.9 Hz, 1H), 7.42 (s, J=16.5 Hz, 1H), 7.17-6.95 (m, 4H), 6.24-5.97 (m, 2H), 4.69-4.34 (m, 4H), 3.31-2.81 (m, 3H), 2.37 (dd, J=23.5, 13.6 Hz, 4H), 2.17-1.67 (m, 6H); 19F NMR (376 MHz, CDCl3) δ −137.10-−137.50 (m), −142.45 (d, J=20.6 Hz).

Provenance & Evidence