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【结 构 式】 
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【分子编号】17927 【品名】3-(2-aminoanilino)propanenitrile 【CA登记号】 |
【 分 子 式 】C9H11N3 【 分 子 量 】161.20656 【元素组成】C 67.06% H 6.88% N 26.07% |
合成路线1
该中间体在本合成路线中的序号：(IV)Conjugated addition of 2-nitroaniline (I) to acrylonitrile (II) in the presence of Triton B in dioxane yielded propionitrile (III), which was hydrogenated to the phenylenediamine (IV). Treatment of ethyl cyanoacetate (V) with a cold saturated solution of HCl in absolute ethanol gave ethyl ethoxycarbonylacetimidate hydrochloride (VI). Reaction of this acetimidate (VI) with phenylenediamine (IV) in refluxing ethanol afforded the benzimidazole (VII), which was converted to the diester (VIII) on treatment with ethanolic HCl. Dieckmann condensation of diester (VIII) in the presence of sodium ethoxide furnished the tricyclic ketoester (IX), which was finally condensed with 2,6-difluoroaniline (X) in refluxing xilene to afford the target carboxamide.
| 【1】 Maryanoff, B.E.; et al.; Potential anxiolytic agents. Pyrido[1, 2-a]benzimidazoles: A new structural class of ligands for the benzodiazepine binding site on GABA-A receptors. J Med Chem 1995, 38, 1, 16. |
| 【2】 Maryanoff, B.E.; McComsey, D.F.; Winston, H. (Ortho-McNeil Pharmaceutical, Inc.); 3-Oxo-pyrido(1,2-a)benzimidazole-4-carboxyl and 4-oxo-azepino(1,2-a)benzimidazole-5-carboxyl derivs. useful in treating central nervous system disorders. EP 0656002; WO 9404532 . |
| 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) | 11608 | o-Nitroaniline; 2-Nitroaniline; 2-Nitrophenylamine | 88-74-4 | C6H6N2O2 | 详情 | 详情 |
| (II) | 10847 | Acrylonitrile | 107-13-1 | C3H3N | 详情 | 详情 |
| (III) | 17926 | 3-(2-nitroanilino)propanenitrile | C9H9N3O2 | 详情 | 详情 | |
| (IV) | 17927 | 3-(2-aminoanilino)propanenitrile | C9H11N3 | 详情 | 详情 | |
| (V) | 11877 | Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate | 105-56-6 | C5H7NO2 | 详情 | 详情 |
| (VI) | 17929 | ethyl 3-ethoxy-3-iminopropanoate | 2318-25-4 | C7H13NO3 | 详情 | 详情 |
| (VII) | 17930 | ethyl 2-[1-(2-cyanoethyl)-1H-benzimidazol-2-yl]acetate | C14H15N3O2 | 详情 | 详情 | |
| (VIII) | 17931 | ethyl 3-[2-(2-ethoxy-2-oxoethyl)-1H-benzimidazol-1-yl]propanoate | C16H20N2O4 | 详情 | 详情 | |
| (IX) | 17932 | ethyl 3-oxo-1,2,3,5-tetrahydropyrido[1,2-a]benzimidazole-4-carboxylate | C14H14N2O3 | 详情 | 详情 | |
| (X) | 17933 | 2,6-Difluorophenylamine; 2,6-Difluoroaniline | 5509-65-9 | C6H5F2N | 详情 | 详情 |