Diethylamine → HCID 14390333, compound

Participants

Reaction Steps

Under nitrogen bubbling, a mixture of 2-(4-methoxyphenyl)-3H-imidazo [4,5-b]pyridine-3-acetic acid (4.2 g, 0.015 mole) and 1,1'-carbonyldiimidazole (2.43 g, 0.015 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 3 hrs. The diethylamine (2.19 g, 0.03 mole) was added and the reaction mixture was allowed to stir at room temperature overnight, then heated at reflux for 3 hrs. The tetrahydrofuran was evaporated to dryness. The residue was treated with hot water, filtered through a Celite pad, and allowed to crystallize upon cooling. The solid was collected by filtration, washed with water, and dried under high vacuum at 50°-60° C. overnight to give 1.0 g, mp (softens at 55° C., resolidified) 133°-35° C. Total yield in 2 crops was 1.9 g (38%). Analysis: Calculated for C19H22N4O2 ·0.5H2O: C, 65.69; H, 6.67; N, 16.13; Found: C, 65.48; H, 6.43; N, 16.13.

Provenance & Evidence