Triethylamine → HCID 58379622, compound

Participants

Reaction Steps

A suspension of compound 47 (7.8 g, 15 mmol) and triethylamine (4.1 mL, 29 mmol) in N,N-dimethylformamide (200 mL) was stirred at room temperature for 2 hr. Diphenyl phosphoryl azide (6.5 mL, 29 mmol) was added dropwise to the suspension via a syringe pump. After stirring 2 hours at room temperature the mixture was heated to 60° C., resulting in a solution. After 1.5 hr the reaction was cooled to room temperature overnight. The precipitate was collected by filtration to afford the title compound (4.2 g, 54%). The filtrate was concentrated and the residue was triturated with methanol to afford benzyl 4-(2-oxo-8-quinolin-3-yl-2,3-dihydro-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)piperidine-1-carboxylate (compound 48) (2.7 g, 35%).

Provenance & Evidence