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【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
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