1-(Methoxymethyl)benzoimidazole → (1-(methoxymethyl)-1H-benzo[d]imidazol-2-yl)(3-((3-nitropyridin-2-yl)amino)-cyclobutyl)methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(methoxymethyl)-1H-benzo[d]imidazole (1.5 g, 9.04 mmol) in dry tetrahydrofuran (20 mL) at −78° C. was added butyllithium (2.5 M in hexane, 3.7 mL, 9.16 mmol). The solution was stirred at −78° C. for 30 min and a solution of N-methoxy-N-methyl-3-((3-nitropyridin-2-yl)amino)cyclobutanecarboxamide (1.92 g, 6.87 mmol) in dry tetrahydrofuran (20 mL) was added dropwise via cannula. The reaction mixture was stirred at −78° C. for 30 minutes and then warmed to room temperature and quenched with water. The reaction mixture was extracted with ethyl acetate (3×30 mL) and the organic phases were combined and washed with water (20 mL), then brine (20 mL). The organic was dried over magnesium sulfate and concentrated to get a residue, which was purified by flash column chromatography on silica gel (10% to 40% ethyl acetate in hexanes) to give (1-(methoxymethyl)-1H-benzo[d]imidazol-2-yl)(3-((3-nitropyridin-2-yl)amino)-cyclobutyl)methanone (1.17 g, 3.07 mmol, 80% yield) as solid.

Provenance & Evidence