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【结 构 式】

【分子编号】39238

【品名】4,6-di(1-pyrrolidinyl)-1,3-benzenediamine; 5-amino-2,4-di(1-pyrrolidinyl)phenylamine

【CA登记号】

【 分 子 式 】C14H22N4

【 分 子 量 】246.35564

【元素组成】C 68.26% H 9% N 22.74%

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:(IV)

Treatment of 1,5-dibromo-2,4-dinitrobenzene (I) with pyrrolidine (II) afforded dipyrrolidino derivative (III). Reduction of the nitro groups of (III) by catalytic hydrogenation, followed by acetylation of amine (IV) provided diamide (V). Oxidative cyclization of (V) using H2O2 in the presence of formic acid gave rise to the dipyrroloimidazobenzimidazole system (VI). Quinone elaboration involved nitration of (VI) to (VII), nitro group reduction to amine (VIII), and finally amine oxidation employing Fremy's salt.

1 Skibo, E.B.; Schulz, W.G.; Inhibitors of topoisomerase II based on the benzodiimidazole and dipyrroloimidazobenzimidazole ring systems: Controlling DT-diaphorase reductive inactivation with steric bulk. J Med Chem 2000, 43, 4, 629.
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) 39236 1,5-dibromo-2,4-dinitrobenzene C6H2Br2N2O4 详情 详情
(II) 11376 Pyrrolidine 123-75-1 C4H9N 详情 详情
(III) 39237 1-[2,4-dinitro-5-(1-pyrrolidinyl)phenyl]pyrrolidine C14H18N4O4 详情 详情
(IV) 39238 4,6-di(1-pyrrolidinyl)-1,3-benzenediamine; 5-amino-2,4-di(1-pyrrolidinyl)phenylamine C14H22N4 详情 详情
(V) 39239 N-[5-(acetamido)-2,4-di(1-pyrrolidinyl)phenyl]acetamide C18H26N4O2 详情 详情
(VI) 39240 2,3,8,9-tetrahydro-1H,7H-pyrrolo[1,2-a]pyrrolo[1',2':1,2]imidazo[4,5-f]benzimidazole C14H14N4 详情 详情
(VII) 39241 5-nitro-2,3,8,9-tetrahydro-1H,7H-pyrrolo[1,2-a]pyrrolo[1',2':1,2]imidazo[4,5-f]benzimidazole C14H13N5O2 详情 详情
(VIII) 39242 2,3,8,9-tetrahydro-1H,7H-pyrrolo[1,2-a]pyrrolo[1',2':1,2]imidazo[4,5-f]benzimidazol-5-ylamine; 2,3,8,9-tetrahydro-1H,7H-pyrrolo[1,2-a]pyrrolo[1',2':1,2]imidazo[4,5-f]benzimidazol-5-amine C14H15N5 详情 详情
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