Diethyl Ether → HCID 19756360, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 62 mg) was added to a solution of 2-ethyl-6-(2-hydroxyethoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (1.0 g) in THF (10 ml). The mixture was stirred until evolution of hydrogen had ceased and then 1-(4-morpholinocarbonyl)imidazole (285 mg) in THF (10 ml) was added. The solution was heated under reflux for 3 hours and then cooled. Ether (50 ml) was added and the solution was washed with water (2×30 ml) and dried (MgSO4). Volatile material was removed by evaporation an the residue was recrystallised from a mixture of ether and hexane to give 2-ethyl-6-[2-(4-morpholinocarbonyloxy)ethoxy]-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (A) (0.82 g), m.p. 76°-79° C.; NMR (d6 -DMSO): 1.3(t, 3H), 2.85(q, 2H), 3.2-3.3(m, 4H), 3.3-3.5(m, 4H), 4.3-4.4(m, 2H), 4.6-4.7(m, 2H), 5.35(s, 2H), 6.8-6.9(m, 6H), 7.1-7.7(complex m, 18H), 7.8(dd, 1H), 8.15(d, 1H),

Provenance & Evidence