Hydrochloric Acid → HCID 69675391, compound

Participants

Reaction Steps

To a solution of 3-{5-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.25 g, 0.54 mmol) in CH2Cl2 (5 mL) and MeOH (0.5 mL) was added HCl (in dioxane, 4 M, 1.35 mL, 5.40 mmol). The solution was stirred at room temperature for 2 h and concentrated to dryness. The resulting solid was slurried in CH2Cl2 (5 mL) and DMF (1 mL). Methoxycarbonylamino-(tetrahydro-pyran-4-yl)-acetic acid (0.15 g, 0.71 mmol), COMU (0.25 g, 0.59 mmol), and DIPEA (0.50 mL, 0.59 mmol) were added, and the resulting solution was stirred at room temperature for 1 h. The reaction was diluted with EtOAc and washed with saturated sodium bicarbonate and brine. The aqueous layers were back extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The crude oil was purified by column chromatography (SiO2, 10→100% EtOAc (10% MeOH) in Hexanes) to provide [2-Oxo-1-(tetrahydro-pyran-4-yl)-2-(3-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-2-aza-bicyclo[2.2.1]hept-2-yl)-ethyl]-carbamic acid methyl ester (0.24 g, 79%). LCMS-ESI+: calc'd for C30H41BN4O6: 564.31 (M+); Found: 565.40 (M+H+).

Provenance & Evidence