Hydrochloric Acid → HCID 178483311, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-tert-butyl 4-(1-((tert-butoxycarbonyl)(methyl)amino)-1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-(1-((tert-butoxycarbonyl)(methyl)amino)-1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (0.21 g, 0.304 mmol) was dissolved in anhydrous MeOH (0.61 mL) and cooled to 0° C. A 4 M HCl solution in dioxane (1.52 mL, 6.09 mmol) was added and the reaction was stirred in the ice bath for 5 hours. Anhydrous MeOH (0.6 mL) was added to the reaction followed by cesium carbonate (2.98 g, 9.13 mmol). The mixture was heated at 60° C. for 1 hour. At this point the reaction was concentrated and diluted with a saturated solution of aq. ammonium chloride and ethyl acetate. The layers were separated and the organic phase was dried over magnesium sulfate, concentrated and purified by flash chromatography [0-5% MeOH (containing 10% ammonium hydroxide) in DCM] to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.87 (br. s., 1H) 7.93 (m) 7.56 (m) 7.43-7.50 (m, 1H) 7.22 (br. s., 1H) 6.69 (s, 1H) 6.57 (br. s., 1H) 3.22 (s, 3H) 2.44 (s, 3H) 2.06 (s, 3H) 1.91 (s, 3H). HRMS calcd. for C21H21N5O (M+H) 360.1824. found 360.1831.

Provenance & Evidence