MM-36

Chemical Name: 5-(Anthracen-9ylmethylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile hydrochloride
项目整合开发状态: Biological Testing
项目研究机构: Universit?degli Studi di Bologna (Originator), Universit?degli Studi di Firenze (Originator)
合成路线:Reaction of 2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile (I) with 1,3-dibromopropane (II) in the presence of n-butyllithium at -78 C provided bromonitrile (III).Alkylation of potassium phthalimide (V) with 9-(chloromethyl)anthracene (IV) yielded the N-alkylated phthalimide (VI),and subsequent hydrazinolysis gave the aminomethyl compound (VIII).Finally,amine (VIII) was alkylated with bromide (III) in Et3N at 60 C to produce the title compound,which was isolated as the corresponding hydrochloride salt.

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.