【结 构 式】 |
【分子编号】38781 【品名】N-(2-aminoethyl)-N-[2-[(2-aminoethyl)amino]ethyl]amine; N(1),N(2)-bis(2-aminoethyl)-1,2-ethanediamine 【CA登记号】112-24-3 |
【 分 子 式 】C6H18N4 【 分 子 量 】146.23588 【元素组成】C 49.28% H 12.41% N 38.31% |
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:(VIII)Copper-catalyzed coupling of o-toluidine (I) with 2-bromo-3-nitrobenzoic acid (II) gave the N-aryl-3-nitroanthranilic acid (III). Reductive cyclization with NaBH4 in the presence NaOEt produced the desired phenazine (V) along with amino anthranilic acid (VI), which were separated by fractional crystallization. Carboxylic acid (V) was then activated as the imidazolide (VI) upon treatment with carbonyl diimidazole. Finally, coupling of triethylenetetramine (VII) with two equivalents of imidazolide (VI) produced the title diamide.
【1】 Rewcastle, G.W.; et al.; Potential antitumor agents. 51. Synthesis and antitumor activity of substituted phenazine-1-carboxamides. J Med Chem 1987, 30, 5, 843. |
【2】 Denny, W.A.; Gamage, S.A.; Spicer, J.A.; Baguley, B.C.; Finlay, G.J. (Xenova Group plc); Bis(acridinecarboxamide) and bis(phenazinecarboxamide) as antitumour agents. EP 0934278; GB 2334032; WO 9817650 . |
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) | 15511 | o-toluidine; 2-methylphenylamine;2-Methylaniline;2-Aminotoluene;1-Amino-2-methylbenzene;1-Methyl-2-aminobenzene; ortho-Toluidine | 95-53-4 | C7H9N | 详情 | 详情 |
(II) | 38776 | 2-bromo-3-nitrobenzoic acid | C7H4BrNO4 | 详情 | 详情 | |
(III) | 38777 | 3-nitro-2-(2-toluidino)benzoic acid | C14H12N2O4 | 详情 | 详情 | |
(V) | 38778 | 9-methyl-1-phenazinecarboxylic acid | C14H10N2O2 | 详情 | 详情 | |
(VI) | 38779 | 3-amino-2-(2-toluidino)benzoic acid | C14H14N2O2 | 详情 | 详情 | |
(VII) | 38780 | 1H-imidazol-1-yl(9-methyl-1-phenazinyl)methanone | C17H12N4O | 详情 | 详情 | |
(VIII) | 38781 | N-(2-aminoethyl)-N-[2-[(2-aminoethyl)amino]ethyl]amine; N(1),N(2)-bis(2-aminoethyl)-1,2-ethanediamine | 112-24-3 | C6H18N4 | 详情 | 详情 |
Extended Information