Hydrochloric Acid → HCID 178435869, compound

Participants

Reaction Conditions

Reaction Steps

A solution of a mixture of (±)-ethyl 2-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)-2,2,2-trifluoroethoxy)acetate and (±)-ethyl 2-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)-2,2,2-trifluoroethoxy)acetate (153 mg, 0.199 mmol) and HCl (1.25 M in MeOH) (1592 μL, 1.990 mmol) was allowed to stir at 60° C. for 0.5 h. The reaction was cooled to rt and concentrated. A suspension of the residue and KOH (112 mg, 1.99 mmol) in EtOH (2 mL) was allowed to stir at 100° C. for 1 h under microwave irradiation. The reaction mixture was concentrated. The crude was purified by HPLC (HC-A) to give the title compound. 1H NMR (TFA salt, 400 MHz, CD3OD) δ 8.05 (s, 1H), 7.71 (br. d, J=8.34 Hz, 1H), 7.61 (dd, J=1.51, 8.59 Hz, 1H), 7.06 (br. s, 1H), 6.92 (s, 1H), 6.11 (br. s, 1H), 4.17 (d, J=16.17 Hz, 1H), 3.95 (d, J=16.17 Hz, 1H), 2.70-2.85 (br. m, 1H), 2.49 (s, 3H), 2.33-2.44 (br. m, 1H) 1.06 (br. t, 3H). HRMS calcd. for C23H19F3N4O3 (M+H)+ 457.1488. found 457.1474.

Provenance & Evidence