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【结 构 式】

【分子编号】53370

【品名】5-amino-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile

【CA登记号】n/a

【 分 子 式 】C16H24N2O2

【 分 子 量 】276.37884

【元素组成】C 69.53% H 8.75% N 10.14% O 11.58%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

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.

1 Dei, S.; et al.; 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. Bioorg Med Chem 2001, 9, 10, 2673.
2 Teodori, E.; Dei, S.; Quidu, P.; et al.; Design, synthesis, and in vitro activity of catamphiphilic reverters of multidrug resistance: Discovery of a selective, highly efficacious chemosensitizer with potency in the nanomolar range. J Med Chem 1999, 42, 10, 1687.
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) 30391 2-(3,4-dimethoxyphenyl)-3-methylbutanenitrile; alpha-Isopropylveratryl cyanide 20850-49-1 C13H17NO2 详情 详情
(II) 12581 1,3-Dibromopropane 109-64-8 C3H6Br2 详情 详情
(III) 30392 5-bromo-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile C16H22BrNO2 详情 详情
(IV) 27890 Potassium phthalimide 1074-82-4 C8H4KNO2 详情 详情
(V) 53369 2-(3,4-dimethoxyphenyl)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-isopropylpentanenitrile n/a C24H26N2O4 详情 详情
(VI) 53370 5-amino-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile n/a C16H24N2O2 详情 详情
(VII) 53371 2-Bromo-9-fluorenone 3096-56-8 C13H7BrO 详情 详情
(VIII) 53372 5-({2-bromo-9-[(triisopropylsilyl)oxy]-9H-fluoren-9-yl}amino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile n/a C38H51BrN2O3Si 详情 详情
Extended Information