Dimethylformamide → 1-benzyl-4-amino-1H-imidazole-5-carboxamide

Participants

Reaction Steps

1.4 ml (10 mmol) of triethylamine, 1.5 g (11 mmol) of 1-hydroxybenzotriazole, and 2.3 g (12 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added to a solution of 1.7 g (10 mmol) of 3-pyridylacetic acid hydrochloride in 100 ml of N,N-dimethylformamide under cooling with ice. The mixture was stirred for one hour while cooling with ice. 2.05 g (9.5 mmol) of 4-amino-1-benzyl-5-imidazole carboxamide which was obtained in Reference Example 2 was added to the reaction solution, followed by stirring overnight. The reaction solution was concentrated under vacuum and 5% aqueous solution of sodium hydrogencarbonate was added to the concentrate to deposite a solid precipitate. The precipitate was collected by filtration through a funnel with a glass filter. The resulting solid was washed with 5% aqueous solution of sodium hydrogencarbonate, then with distilled water, and dried under vacuum to obtain a crude product, which was recrystallized from hot methanol to obtain 1.83 g of 1-benzyl-4-(3-pyridylacetylamino)-5-imidazolecarboxamide (yield 57%).

Provenance & Evidence