Methanol → HCID 178419531, compound

Participants

Reaction Steps

5,7-Diethyl-3-methoxy-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one (80 mg) was suspended in dichloromethane (1 ml) and a 1M solution of boron tribromide in dichloromethane (0.5 ml) was added. The mixture was stirred for 16 hours then methanol (3 ml) was added dropwise. The mixture was heated at reflux for 5 minutes and volatile material was then removed by evaporation. The residue was recrystallised from ethanol/ether to give 5,7-diethyl-3-hydroxy-1-[(2'-(1H-tetrazole-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one hydrobromide as a solid (45 mg), m.p. 190°-194° C.; NMR (d6 -DMSO): 1.24(t, 3H), 1.30(t, 3H), 2.92(q, 2H), 3.22(q, 2H), 5.64(s, 2H), 7.07(d, 2H), 7.22(d, 2H), 7.45-7.75(m, 6H); mass spectrum (+ve FAB, methanol/NBA): 453 (M+H)+ ; microanalysis, found: C, 57.1; H, 4.9; N, 14.7%; C26H24N6O2.HBr.1.5H2O requires: C, 56.7; H, 5.1; N, 15.2%.

Provenance & Evidence