Water → HCID 19093748, compound

Participants

Reaction Steps

Sodium hydride (50% dispersion in oil; 100 mg) was added to a stirred solution of thiophenol (0.2 ml) in dimethylacetamide (10 ml) and the mixture was stirred until effervescence ceased. 4-Chloro-5,7-diethyl-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one (0.7 g) was added to the solution and the mixture was stirred at 50° C. for 4 hours. The reaction mixture was then poured into water and extracted twice with ethyl acetate. The combined extracts were washed with water, saturated sodium chloride solution and dried (MgSO4). Solvent was removed by evaporation to leave an oil which was purified by flash chromatography, eluting with ethyl acetate/petroleum ether (3:1 v/v, increasing to 2:5 v/v) to give 5,7-diethyl-4-phenylthio-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4yl)methyl[-1,6-naphthyridin-2(1H)-one (A) as a solid (0.53 g); m.p. 166°-168° C. (after recrystallisation from acetonitrile); NMR (d6 -DMSO): 1.07(t, 3H), 1.40(t, 3H), 2.58(q, 2H), 3.47(q, 2H), 5.40(s, 2H), 5.80(s, 1H), 6.8-7.8(complex m, 29H); mass spectrum (+ve FAB): 787 (M+H)+ ; microanalysis, found: C, 78.1; H, 5.1; N, 10.9%; C51H42N6OS requires: C, 77.8; H, 5.4; N, 10.7%.

Provenance & Evidence