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【结 构 式】

【分子编号】17931

【品名】ethyl 3-[2-(2-ethoxy-2-oxoethyl)-1H-benzimidazol-1-yl]propanoate

【CA登记号】

【 分 子 式 】C16H20N2O4

【 分 子 量 】304.34588

【元素组成】C 63.14% H 6.62% N 9.2% O 21.03%

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)

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
Extended Information