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【结 构 式】

【分子编号】51529

【品名】2-Methylbenzimidazole

【CA登记号】615-15-6

【 分 子 式 】C8H8N2

【 分 子 量 】132.165

【元素组成】C 72.7% H 6.1% N 21.2%

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:(I)

The alkylation of 2-methylbenzimidazole (I) with 4-chloro-3-nitrobenzyl chloride (II) provided adduct (III). Displacement of the chlorine atom of (III) with methylamine furnished the nitro aniline (IV), which was further reduced to phenylenediamine (V) by catalytic hydrogenation over Raney-Ni. Acylation of (V) by N-(4-cyanophenyl)glycine (VI) using N,N'-carbonyldiimidazole as the activating reagent yielded amide (VII). The bis-benzimidazole compound (VIII) was then produced by cyclization of (VII) in refluxing HOAc. Finally, Pinner reaction of nitrile (VIII) with ethanolic HCl, followed by treatment of the resulting imidate with ammonium carbonate, provided the target amidine.

1 Kauffmann, I.; Ries, U.; Priepke, H.; Hauel, N.; Stassen, J.M.; Nar, H.; Wienen, W. (Boehringer Ingelheim Pharma KG); Benzimidazoles, production thereof and use thereof as medicaments. DE 19829964; EP 1095025; WO 0001704 .
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) 51529 2-Methylbenzimidazole 615-15-6 C8H8N2 详情 详情
(II) 51530 1-chloro-4-(chloromethyl)-2-nitrobenzene C7H5Cl2NO2 详情 详情
(III) 51531 1-(4-chloro-3-nitrobenzyl)-2-methyl-1H-benzimidazole C15H12ClN3O2 详情 详情
(IV) 51532 N-methyl-4-[(2-methyl-1H-benzimidazol-1-yl)methyl]-2-nitroaniline; N-methyl-N-[4-[(2-methyl-1H-benzimidazol-1-yl)methyl]-2-nitrophenyl]amine C16H16N4O2 详情 详情
(V) 51533 N-[2-amino-4-[(2-methyl-1H-benzimidazol-1-yl)methyl]phenyl]-N-methylamine; N(1)-methyl-4-[(2-methyl-1H-benzimidazol-1-yl)methyl]-1,2-benzenediamine C16H18N4 详情 详情
(VI) 51512 2-(4-cyanoanilino)acetic acid C9H8N2O2 详情 详情
(VII) 51534 2-(4-cyanoanilino)-N-[2-(methylamino)-5-[(2-methyl-1H-benzimidazol-1-yl)methyl]phenyl]acetamide C25H24N6O 详情 详情
(VIII) 51535 4-[([1-methyl-5-[(2-methyl-1H-benzimidazol-1-yl)methyl]-1H-benzimidazol-2-yl]methyl)amino]benzonitrile C25H22N6 详情 详情
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