新产品编号:2120389
Chemical Name: N-[4-(Dimethylamino)butyl]-4-iodobenzamide
项目整合开发状态: Preclinical
项目研究机构: INSERM (Originator), Univ. Blaise Pascal-Clermont-Ferrand II (Originator)
合成路线:Alkylation of the lithium salt of 2-(3,4-dimethoxyphenyl)isobutyronitrile (I) with 1,3-dibromopropane (II) gave the bromo nitrile (III).Conversion of bromide (III) into the desired primary amine (VI) was achieved through a Gabriel synthesis by condensation with potassium phthalimide (IV),followed by hydrazinolysis of the resultant N-substituted phthalimide (V).A two-step procedure was finally employed for the reductive alkylation of amine (VI),consisting of condensation between amine (VI) and the bromo fluorenone (VII) in the presence of titanium isopropoxide and then reduction of the intermediate (VIII) with NaBH3CN.
合成路线:The title amide is obtained by acylation of N,N-dimethyl-1,4-butanediamine (I) with 4-iodobenzoyl chloride (II) in the presence of Et3N in CH2Cl2.
📌 参考资料/链接:
参考文献标题:Structure-activity relationships and optimisation of the selective MDR modulator 2-(3,4-dimethoxyphenyl)-5-(9-fluorenylamino)-2-(methylethyl) pentanenitrile and its N-methyl derivative
文献作者:Dei,S.; Teodori,E.; Garnier-Suillerot,A.; Gualtieri,F.; Scapecchi,S.; Budriesi,R.; Chiarini,A.
参考来源:Bioorg Med Chem 2001,9(10),2673