Hydrochloric Acid → HCID 178436792, compound

Participants

Reaction Steps

Concentrated hydrochloric acid (0.4 ml) was added to a suspension of 3-chloro-2,6-diethyl-4-[N-(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl-N-methylamino]pyridine (A) (220 mg) in methanol (5 ml) and the mixture was stirred for 6 hours. Volatile material was removed by evaporation and the residue partitioned between ether and sodium carbonate solution. The aqueous layer was separated, acidified to pH 6 with 4M hydrochloric acid and extracted with dichloromethane (3×25 ml). The combined organic extracts were dried and solvent removed by evaporation. The residue was purified by flash chromatography eluting with dichloromethane/methanol (9:1 v/v) to give 3-chloro-2,6-diethyl-4-[N-(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl-N-methylamino]pyridine as a solid, m.p. 110° C. (decomposition); NMR (d6 -DMSO): 1.1(d, of t, 6H), 2.64(q, 2H), 2.74(s, 3H), 2.84(q, 2H), 4.37(s, 2H), 6.81(s, 1H), 7.07(d, 2H), 7.27(d, 2H), 7.6(m, 4H); mass spectrum (+ve FAB, DMSO): 432,434(M+H)+ ; microanalysis, found: C, 64.6; H, 6.0; N, 17.9%; C24H25N6Cl.0.75H2O.0.125C4H10O requires: C, 64.4; H, 5.9; N, 18.4%.

Provenance & Evidence