Methanol → HCID 178501803, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-tert-butyl 4-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-2,2,2-trifluoro-1-(2-methoxy-2-oxoethoxy)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-2,2,2-trifluoro-1-(2-methoxy-2-oxoethoxy)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (510 mg, 0.711 mmol) was dissolved in 1.25 N HCl in MeOH (8.6 mL, 10.75 mmol), and stirred at 60° C. for 7 hours. The reaction mixture was then concentrated to dryness, dissolved in EtOAc, basified with a 15% aq. NH4OH solution at 0° C. and diluted with water. The organic layer was separated, dried over magnesium sulfate, filtered, concentrated and purified via FCC eluting with Heptane/EtOAc (0-60% of EtOAc) to provide the title compound. 1H NMR (400 MHz, Acetone) δ ppm 11.86 (br. s., 1H) 10.15 (br. s., 1H) 7.54-8.07 (m) 7.48 (d, J=8.08 Hz, 1H) 7.25 (t, J=2.91 Hz, 1H) 6.91-7.05 (m, 1H) 6.64 (s, 1H) 4.31 (m, 1H) 3.92-4.05 (m, 1H) 3.30-3.45 (s, 3H) 2.97-3.13 (s, 3H) 2.35-2.46 (s, 3H) HRMS calcd. for C23H19F3N4O4 (M+H)+ 473.1437. found 473.1438.

Provenance & Evidence