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【结 构 式】

【分子编号】60798

【品名】ethyl 3-[({2-[(4-cyanoanilino)methyl]-1-methyl-1H-benzimidazol-5-yl}carbonyl)(2-pyridinyl)amino]propanoate

【CA登记号】

【 分 子 式 】C27H26N6O3

【 分 子 量 】482.54208

【元素组成】C 67.21% H 5.43% N 17.42% O 9.95%

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:(VII)

4-Methylamino-3-nitrobenzoic acid (I) is converted into acid chloride (II) by using SOCl2, and subsequently condensed with ethyl 3-(2-pyridylamino)propionate (III) to produce amide (IV). Reduction of the nitro group of (IV) by catalytic hydrogenation yields the phenylenediamine (V). After acylation of diamine (V) with N-(4-cyanophenyl)glycine (VI), cyclization of the resulting amino amide in refluxing AcOH leads to benzimidazole (VII). The cyano group of (VII) is then transformed into amidine (VIII) employing the Pinner reaction. Finally, acylation of the amidino group of (VIII) with hexyl chloroformate gives rise to the target amidine carbamate derivative

1 Hauel, N.H.; et al.; Structure-based design of novel potent nonpeptide thrombin inhibitors. J Med Chem 2002, 45, 9, 1757.
2 Hauel, N.; Wienen, W.; Ries, U.; Priepke, H.; Stassen, J.M. (Boehringer Ingelheim Pharma KG); Disubstd. bicyclic heterocycles, their production and use as medicaments. DE 19706229; DE 19751939; EP 0966454; JP 2001509815; US 2003004181; US 6087380; US 6469039; WO 9837075 .
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) 60793 4-(methylamino)-3-nitrobenzoic acid C8H8N2O4 详情 详情
(II) 60794 4-(methylamino)-3-nitrobenzoyl chloride C8H7ClN2O3 详情 详情
(III) 60795 ethyl 3-(2-pyridinylamino)propanoate C10H14N2O2 详情 详情
(IV) 60796 ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](2-pyridinyl)amino]propanoate C18H20N4O5 详情 详情
(V) 60797 ethyl 3-[[3-amino-4-(methylamino)benzoyl](2-pyridinyl)amino]propanoate C18H22N4O3 详情 详情
(VI) 51512 2-(4-cyanoanilino)acetic acid C9H8N2O2 详情 详情
(VII) 60798 ethyl 3-[({2-[(4-cyanoanilino)methyl]-1-methyl-1H-benzimidazol-5-yl}carbonyl)(2-pyridinyl)amino]propanoate C27H26N6O3 详情 详情
(VIII) 60799 ethyl 3-[{[2-({4-[amino(imino)methyl]anilino}methyl)-1-methyl-1H-benzimidazol-5-yl]carbonyl}(2-pyridinyl)amino]propanoate C27H29N7O3 详情 详情
Extended Information