Hydrochloric Acid → HCID 86708747, compound

Participants

Reaction Steps

To a solution of 4,4-Difluoro-2-(5-{4-[6-(2-{1-[2-methoxycarbonylamino-2-(tetrahydro-pyran-4-yl)-acetyl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-naphthalen-2-yl]-phenyl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.04 g, 0.05 mmol) in CH2Cl2 (0.5 mL) and MeOH (0.05 mL) was added HCl (in dioxanes, 4 M, 0.3 mL, 1.2 mmol). The solution was stirred at room temperature for 2 h and concentrated to dryness. The solid was slurried with CH2Cl2 (0.5 mL). Methoxycarbonylamino-phenyl-acetic acid (0.02 g, 0.07 mmol) and Potassium Phosphate (0.03 g, 0.14 mmol) were added and the resulting slurry was cooled to 0° C. (external, ice). COMU (0.03 g, 0.06 mmol) was added and the reaction was stirred at room temperature for 2 h. The slurry was diluted with CH2Cl2 and filtered through celite. The filtrate was concentrated and purified by preparative HPLC (Gemini, 15→50% MeCN in H2O (0.1% TFA)) to provide to provide {2-[4,4-Difluoro-2-(5-{4-[6-(2-{1-[2-methoxycarbonylamino-2-(tetrahydro-pyran-4-yl)-acetyl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-naphthalen-2-yl]-phenyl}-1H-imidazol-2-yl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid methyl ester (0.02 g, 49%). LCMS-ESI+: calc'd for C49H50F2N8O7: 900.38 (M+); Found: 901.4 (M+H+).

Provenance & Evidence