Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86592992, compound

Participants

Reaction Steps

To a solution of 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid I-7d (1.31 g, 3.57 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.42 g, 1.2 equiv) in THF (14 ml) were added TEA (4.97 ml, 10 equiv) and 1-propane phosphonic acid cyclic anhydride (3.21 ml, 1.5 equiv). The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate and washed with water, 10% citric acid, and saturated aqueous sodium chloride. The organic phase was dried over anhydrous magnesium sulfate and concentrated to a foam which was purified by flash column chromatography (silica, 70:30 ethyl acetate/hexane grading to ethyl acetate) to give 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid methoxy-methyl-amide I-7e (485 mg, 33%).

Provenance & Evidence