Dimethylacetamide → N-cyclohexyl-5-[(5H-imidazo[4,5-c]pyridin-5-yl)methyl]N-methyl-2-furancarboxamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of imidazopyridine (150 mg, 1.25 mmol) in dimethylacetamide (30 mL) under argon, furfuryl chloride (product of Example H) (320 mg. 1.25 mmol) was added in one portion. The reaction temperature was slowly raised to 75° C. and was stirred for 60 hr. The reaction flask was cooled to room temperature and the solvent was removed under reduced pressure at <45° C. The residue obtained was triturated with excess of dry ether and filtered. The crude product (410 mg) was chromatographed (silica gel, CH2Cl2 :MeOH:NH4OH::90:10:1) to give the title compound (265 mg, 65%) as white solid, mp 189-90° C., 1H NMR (CDCl3) 1H NMR (CDCl3) 0.85 -1.9(m, 13H), 3.6-3.8 & 4.3-4.45(m, 1H), 5.62 (s, 2H), 6.62 (brs, 1H), 6.82 (brs, 1H), 7.73 (dd, J=7 Hz, 1H), 7.85 (dd, J=3,7 Hz, 1H), 8.57 (s, 1H), 8.8 ppm (s, 1H), Anal calcd. for C19H22N4O2 0.5H2O: C, 65.70,H,6.62, N, 16.11. Found: C, 65.65, H, 6.71, N, 16.06.

Provenance & Evidence