新产品编号:454543
Chemical Name: 2-(4-Chlorophenoxy)-1-[4-(4-fluorobenzyl)-2(R)-methylpiperazin-1-yl]ethanone
CAS No. 217646-35-0, 217645-39-1 ((S)-isomer), 217645-38-0 (undefined isomer)
项目整合开发状态: Preclinical
项目研究机构: Berlex (Originator)
合成路线:Condensation of chloroacetyl derivative (I) with phenolic compound (II) by means of K2CO3 in DMF affords the desired compound.
合成路线:Alkylation of (R)-2-methylpiperazine (I) with 4-fluorobenzyl bromide (II) provides 1-(4-fluorobenzyl)-3-methylpiperazine (III).Subsequent acylation of piperazine (III) with (4-chlorophenoxy)acetyl chloride (IV) furnishes the title amide.
合成路线:In a further method,1-(4-fluorobenzyl)-3-methylpiperazine (I) is acylated by chloroacetyl chloride to provide the chloroacetamide (II).Subsequent chloride displacement with 4-chlorophenol (III) leads to the target chlorophenoxy acetamide.
📌 参考资料/链接：
参考文献标题:Piperazine derivs.and their use as anti-inflammatory agents
文献作者:Monahan,S.D.; Xu,W.; Morissey,M.M.; Bauman,J.G.; Ng,H.P.; Hesselgesser,J.E.; Liang,M.; Zheng,W.; Islam,I.; May,K.B.; Ghannam,A.F.; Buckman,B.O.; Horuk,R.; Wei,G.P.(Schering AG)
参考来源:US 6207665; WO 9856771
📄 详细内容
合成路线:In an alternative procedure,N-Boc-D-alanine (I) is activated as the mixed anhydride (II) by treatment with isobutyl chloroformate.Coupling of anhydride (II) with N-(4-fluorobenzyl)glycine methyl ester (III) produces dipeptide (IV).Further cleavage of the N-Boc protecting group of (IV) under acidic conditions proceeds with concomitant cyclization to the diketopiperazine (V).This is then reduced by means of LiAlH4 to piperazine (VI).Finally,acylation of piperazine (VI) with (4-chlorophenoxy)acetyl chloride (VII) provides the title compound.
参考文献标题:Synthesis and SAR of CCR1-specific non-peptide antagonists
文献作者:Islam,I.; May,K.; Bauman,J.; et al.
参考来源:224th ACS Natl Meet (Aug 18 2002,Boston) 2002,Abst MEDI 334