Dimethylamine → HCID 178433659, compound

Participants

Reaction Conditions

Reaction Steps

Five milliliters of ethanol and 3.5 ml (3.5 mmol) of a 1 N sodium hydroxide aqueous solution were added to 0.48 g (1.0 mmol) of the 4-(5-(4-pyridylsulfenyl)-6-phenoxybenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxylic acid ethyl ester obtained in Comparative Example 1, and the reaction mixture was stirred at 60° C. for 17 hours. The reaction mixture was allowed to cool and concentrated, and the insoluble material was filtered off by adding water. The filtrate was neutralized with a 2 N hydrochloric acid solution, and the precipitate was collected by filtration, washed with water, and dried at reduced pressure to afford crude carboxylic acid (0.22 g). 0.2 g (0.4 mmol) of the crude carboxylic acid was dissolved in 3 ml of N,N-dimethylformamide, and then 92 mg (0.5 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and 0.25 ml (2.2 mmol) of a 40% dimethylamine aqueous solution were added to the solution. The reaction mixture was stirred at 60° C. for 18 hours. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated at reduced pressure. The obtained residue was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:100 to 1:10) to afford (N,N-dimethyl)-4-(5-(4-pyridylsulfenyl)-6-phenoxybenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxamide (83 mg, 43%) as an amorphous.

Provenance & Evidence