BD-1047
BD 1047二氢溴酸Chemical Name: N1-[2-(3,4-Dichlorophenyl)ethyl]-N1,N2,N2-trimethyl-1,2-ethanediamine
CAS No. 138356-20-4
项目整合开发状态: Preclinical
项目研究机构: National Institutes of Health (Originator), Pfizer (Originator)
合成路线:Condensation of 2-(dimethylamino)ethyl chloride hydrochloride (I) with methylamine gave trimethyl ethylenediamine (II),which was coupled with 3,4-dichlorophenylacetic acid (III) in the presence of DCC to afford amide (IV).Subsequent reduction of (IV) with aluminum hydride in THF provided the title diamine.
合成路线:Hexahydroazepine (I) was coupled with N-Boc-glycine (II) by means of EDC and HOBt,and the resulting amide (III) was reduced with LiAlH4 to give diamine (IV).Subsequent coupling of (IV) with 3,4-dichlorophenylacetic acid (V) in the presence of DCC afforded amide (VI).Finally,reduction of (VI) with aluminum hydride in THF provided the title compound.
📌 参考资料/链接：
参考文献标题:N-(Arylethyl)-N-alkyl-2-(1-pyrrolidinyl)ethylamine derivs.for CNS disorders
文献作者:De Costa,B.R.; Radesca,L.; Bowen,W.; Long,J.; Walker,J.M.; Rice,K.C.; Gray,N.M.; Contreras,P.C.(Pharmacia Corp.)
参考来源:EP 0518216; WO 9222279
📄 详细内容
合成路线:Condensation of 2-(dimethylamino)ethyl chloride hydrochloride (I) with methylamine gave trimethyl ethylenediamine (II),which was coupled with 3,4-dichlorophenylacetic acid (III) in the presence of DCC to afford amide (IV).Subsequent reduction of (IV) with aluminum hydride in THF provided the title diamine.
合成路线:Hexahydroazepine (I) was coupled with N-Boc-glycine (II) by means of EDC and HOBt,and the resulting amide (III) was reduced with LiAlH4 to give diamine (IV).Subsequent coupling of (IV) with 3,4-dichlorophenylacetic acid (V) in the presence of DCC afforded amide (VI).Finally,reduction of (VI) with aluminum hydride in THF provided the title compound.
合成路线:Diamine (II) was prepared by reaction of N-(2-chloroethyl)pyrrolidine hydrochloride (I) with ethylamine.Coupling of (II) with 3,4-dichlorophenylacetic acid (III) in the presence of DCC afforded amide (IV).The amide function of (IV) was finally reduced by means of aluminum hydride in THF to furnish the title diamine.
参考文献标题:Synthesis,characterization,and biological evaluation of a novel class of N-(arylethyl)-N-alkyl-2-(1-pyrrolidinyl)ethylamines: Structural requirements and binding affinity at the sigma receptor
文献作者:de Costa,B.R.; Radesca,L..; Di Paolo,L.; Bowen,W.D.
参考来源:J Med Chem 1992,35(1),38
产品链接: CAS No. 138356-20-4››