4-(Bromomethyl)benzonitrile → 1-[2-(4-Cyanobenzyloxy)ethyl]-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole

Participants

Reaction Steps

A mixture of 1-(2-hydroxyethyl)-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole (2.5 g.) and 4-cyanobenzyl bromide (1.96 g.) was heated at 140° for 10 minutes. When cool, the residue was dissolved in a little MeOH and purified by medium pressure chromatography on silica gel using triethylamine/EtOH/EtOAc 1:10:95 v/v/v as eluant to give 1-[2-(4-cyanobenzyloxy)ethyl]-3-[2-(2,2,2-trifluoroethyl)guanidino]pyrazole (yield 55%) having the following n.m.r. spectrum in d6DMSO: 7.5 (br m, 5H); 5.85 (d, 1H); 5.1 (s, 2H); 4.05 (br m, 4H); 3.7 (br t, 2H).

Provenance & Evidence