S-21663, PMS-812

Chemical Name: 1-(2,4-Dichlorobenzyl)-2-(4,5-dihydro-1H-imidazol-2-yl)-4-methylpiperazine
CAS No. 162510-01-2
项目整合开发状态: Preclinical
项目研究机构: Servier (Originator), Univ. Pierre et Marie Curie - Paris 6 (Originator), University of Li鑗e (Originator)
合成路线:Condensation of N,N'-dibenzylethylenediamine (I) with ethyl 2,3-dibromopropionate (II) in the presence of Et3N in toluene at 80 C gave,after acidification,piperazine (III).Then,hydrogenolytic N-debenzylation in the presence of Pd/C provided ethyl piperazine-2-carboxylate (IV),which was selectively alkylated at position 4 with 1 equivalent of triphenylmethyl chloride in the presence of Et3N at -10 C to give (V).Subsequent alkylation with 2,4-dichlorobenzyl chloride (VI) in the presence of K2CO3 and a catalytic amount of KI provided (VII).Removal of the N-trityl group by treatment with HCl in either acetone or ethanol afforded piperarine (VIII),which was N-methylated by reaction with formaldehyde and formic acid in refluxing MeOH.Finally,the resulting compound (IX) was converted into the imidazoline on treatment with ethylenediamine and trimethylaluminum in refluxing toluene.