Triethylamine → HCID 10236927, compound

Participants

Reaction Steps

Triethylamine (0.78 mL, 5.6 mmol) was added to a solution of 1-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine (1.00 g, 4.3 mmol) in chloroform (50 mL). The solution was cooled in an ice bath and then 4-morpholinecarbonyl chloride (0.55 mL, 4.7 mmol) was added. After 15 minutes the reaction mixture was removed from the ice bath and allowed to stir at ambient temperature for 2 days. The reaction mixture was diluted with water (30 mL) and the pH was adjusted to 11 with potassium carbonate. The resulting precipitate was isolated by filtration and then recrystallized from isopropanol/water to provide 0.61 g of N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]morpholine-4-carboxamide as a white solid, m.p. 128.9-129.7° C. Analysis: Calculated for C17H26N6O2.1.00 H2O: %C, 56.03; %H, 7.74; %N, 23.06; Found: %C, 56.10; %H, 7.92; %N, 23.31. 1H NMR (Bruker 300 MHz, DMSO-d6) δ6.63 (t, J=4.9 Hz, 1H), 5.56 (s, 2 H), 4.19 (t, J=8.1 Hz, 2 H), 3.53 (t, J=4.4 Hz, 4 H), 3.25 (t, J=4.9 Hz, 4 H), 3.14 (q, J=6.2 Hz, 2 H), 2.45 (s, 3 H), 2.35 (s, 3 H), 2.29 (s, 3 H), 1.81 (p, J=7.4 Hz, 2 H). MS(CI) m/e 347 (M+H).

Provenance & Evidence