Hydrochloric Acid → HCID 69675581, compound

Participants

Reaction Steps

To a solution of 2-{5-[4-(6-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (0.10 g, 0.0.14 mmol) in CH2Cl2 (1.3 mL) and MeOH (0.1 mL) was added HCl (in dioxanes, 4 M, 0.35 mL, 1.4 mmol). The solution was stirred at room temperature for 2 h and concentrated to dryness. The resulting solid was dissolved in DMF (1.5 mL). Methoxycarbonylamino-pyridin-2-yl-acetic acid (assumed 0.23 g, 1.1 mmol), HATU (0.06 g, 0.15 mmol) and DIPEA (0.12 mL, 0.69 mmol) were added. The solution was stirred at room temperature for 2 h. Additional HATU (0.13 g, 0.30 mmol) was added and the solution was stirred for 2 h. LiOH (2.5 M, 0.1 mL) was added and the reaction was concentrated. The crude oil was purified by preparative HPLC (Gemini, 15→40% MeCN in H2O (0.1% formic acid)) and lyophilized to provide [1-(2-{5-[6-(4-{2-[1-(2-Methoxycarbonylamino-2-pyridin-2-yl-acetyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester (0.02 g, 22%). LCMS-ESI+: calc'd for C46H49N9O6: 823.38 (M+); Found: 824.88 (M+H+).

Provenance & Evidence