【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% |
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 |