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【结 构 式】

【分子编号】47916

【品名】(2R)-N(1),N(1)-dimethyl-1,2-propanediamine; N-[(2R)-2-aminopropyl]-N,N-dimethylamine

【CA登记号】

【 分 子 式 】C5H14N2

【 分 子 量 】102.17964

【元素组成】C 58.77% H 13.81% N 27.42%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(V)

The oxidation of 5-methoxy-1-tetralone (I) with SeO2 gives 5-methoxy-1,2-naphthoquinone (II), which is cyclized with 2,3-diaminobenzoic acid (II) by means of HCl in refluxing ethanol to yield 4-methoxybenzo[a]phenazine-11-carboxylic acid (IV). Finally, this acid is converted into the target amide by its condensation with N1,N1,2(R)-trimethylethane-1,2-diamine (V) by means of CDI in DMF.

1 Vicker, N.; Burgess, L.; Chuckowree, I.S.; et al.; Novel angular benzophenazines: Dual topoisomerase I and topoisomerase II inhibitors as potential anticancer agents. J Med Chem 2002, 45, 3, 721.
2 Vicker, N.; Folkes, A.J.; Wang, S.; Milton, J.; Denny, W.A. (Xenova Group plc); Benzo[a]phenazin-11-carboxamide derivs. and their use as joint inhibitors of topomerase I and II. WO 0146157 .
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) 18568 5-methoxy-3,4-dihydro-1(2H)-naphthalenone 33892-75-0 C11H12O2 详情 详情
(II) 47913 5-methoxy-1,2-naphthalenedione C11H8O3 详情 详情
(III) 47914 2,3-diaminobenzoic acid C7H8N2O2 详情 详情
(IV) 47915 4-methoxybenzo[a]phenazine-11-carboxylic acid C18H12N2O3 详情 详情
(V) 47916 (2R)-N(1),N(1)-dimethyl-1,2-propanediamine; N-[(2R)-2-aminopropyl]-N,N-dimethylamine C5H14N2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

The intermediate chiral diamine (IV) (see Scheme no. 28794701a, intermediate (V)) is prepared as follows: Reduction of N-Boc-D-alanine methyl ester (I) with DIBAL affords N-Boc-alaninal (II), which is reductively aminated with dimethylamine in the presence of NaBH3CN to afford the Boc-protected diamine (III). The N-Boc group of (III) is finally removed under acidic conditions to provide the target (R)-diamine (IV).

1 Vicker, N.; Burgess, L.; Chuckowree, I.S.; et al.; Novel angular benzophenazines: Dual topoisomerase I and topoisomerase II inhibitors as potential anticancer agents. J Med Chem 2002, 45, 3, 721.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 47916 (2R)-N(1),N(1)-dimethyl-1,2-propanediamine; N-[(2R)-2-aminopropyl]-N,N-dimethylamine C5H14N2 详情 详情
(VI) 55655 methyl (2R)-2-[(tert-butoxycarbonyl)amino]propanoate C9H17NO4 详情 详情
(VII) 55656 tert-butyl (1R)-1-methyl-2-oxoethylcarbamate C8H15NO3 详情 详情
(VIII) 55657 tert-butyl (1R)-2-(dimethylamino)-1-methylethylcarbamate C10H22N2O2 详情 详情
Extended Information