Triethylamine → HCID 13557454, compound

Participants

Reaction Steps

To an ice-cold suspension of 16.15 g of 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid, 15.75 g of diphenylphosphorylazide, and 10.2 g of 6-(3-pyridyl)-hexanamine in 100 ml of dry dimethylformamide was added 8.0 ml of triethylamine. The reaction mixture was held at 0° C. for 2 hours and allowed to warm to room temperature over night. The resulting clear, yellow solution was diluted with water and 5M sodium hydroxide solution and was extracted with 3×300 ml of dichloromethane. The combined organic layers were dried over potassium carbonate and evaporated to a yellow semi-solid which was recrystallized from ethyl acetate-hexane to give 21.22 g (84%) of N-[6-(3-pyridyl)hexyl]-2-(1-methylethyl)-11-oxo-pyrido[2,1-b]-quinazoline-8-carboxamide, mp 94°-96° C. Recrystallization gave mp 100°-103° C. Conversion to the dihydrochloride salt gave 22.12 g, mp 230°-236° C. (dec.) and recrystallization from ethanol-ether gave 21.06 g, mp 234°-240° C. (dec.).

Provenance & Evidence