-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】N-[2-[2-[Bis(4-fluorophenyl)methoxy]ethylamino]ethyl]-3-(4-bromophenyl)-2(E)-propenamide

【CA登记号】

【分子式】C₂₆H₂₅BrF₂N₂O₂

【分子量】515.40215

【开发单位】Massachusetts General Hospital (Originator), Northeastern University (Originator)

【药理作用】Treatment of Cocaine Dependency, TREATMENT OF POISONING, DRUG ABUSE & DEPENDENCY, Treatment of Substance Dependency, Dopamine Transporter (DAT) Inhibitors

合成路线1

The precursor bromoether (III) was prepared by condensation of 4,4’-difluorobenzhydrol (I) with 2-bromoethanol (II) under acidic conditions. Treatment of 4-bromocinnamic acid (IV) with thionyl chloride afforded acid chloride (V), which was coupled with ethylenediamine (VI) to furnish mono amide (VII). The title compound was finally obtained by alkylation of amine (VII) with bromide (III) in the presence of K2CO3.

参考文献中间体

【1】 Elmaleh, D.R.; Fischman, A.J.; Hanson, R.N.; Choi, S.-W.; Design, synthesis, and biological evaluation of novel non-piperazine analogues of 1-[2-(diphenylmethoxy]ethyl]- and 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]4-(3-phenylpropyl)piperazines as dopamine transporter inhibitors. J Med Chem 1999, 42, 18, 3647.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	41974	4,4'-Difluorobenzhydrol; bis(4-Fluorophenyl)methanol; alpha-(4-fluorophenyl)benzenemethanol; 4-fluoro-alpha-(4-fluorophenyl)benzenemethanol	365-24-2	C₁₃H₁₀F₂O	详情	详情
(II)	10059	Ethylene bromohydrin; 2-Bromo-1-ethanol	540-51-2	C₂H₅BrO	详情	详情
(III)	41975	1-[(2-bromoethoxy)(4-fluorophenyl)methyl]-4-fluorobenzene; bis(4-fluorophenyl)methyl 2-bromoethyl ether		C₁₅H₁₃BrF₂O	详情	详情
(IV)	41976	(E)-3-(4-bromophenyl)-2-propenoic acid		C₉H₇BrO₂	详情	详情
(V)	41977	(E)-3-(4-bromophenyl)-2-propenoyl chloride		C₉H₆BrClO	详情	详情
(VI)	14754	ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine	107-15-3	C₂H₈N₂	详情	详情
(VII)	41978	(E)-N-(2-aminoethyl)-3-(4-bromophenyl)-2-propenamide		C₁₁H₁₃BrN₂O	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)