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【结 构 式】

【分子编号】38448

【品名】2-(trifluoromethyl)-1H-benzimidazol-4-ylamine; 2-(trifluoromethyl)-1H-benzimidazol-4-amine

【CA登记号】

【 分 子 式 】C8H6F3N3

【 分 子 量 】201.1510696

【元素组成】C 47.77% H 3.01% F 28.33% N 20.89%

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:(III)

Condensation of 3-nitro-1,2-phenylenediamine (I) with trifluoroacetic acid provided benzimidazole (II). Reduction of the nitro group of (II) by means of hydrazine in the presence of FeCl3 and activated carbon gave amine (III), which was coupled with 2,6-dichlorobenzoyl chloride (IV) yielding amide (V). Alkylation of (V) with tert-butyl bromoacetate afforded benzimidazoleacetic acid tert-butyl ester (VI). After trifluoroacetic acid-promoted cleavage of the tert-butyl ester of (VI) the resulting carboxylic acid (VII) was coupled with morpholine (VIII) using EDC to furnish the title morpholide.

1 Oku, T.; Kawai, Y.; Yatabe, T.; Sato, S.; Yamazaki, H.; Kayakiri, N.; Yoshihara, K. (Fujisawa Pharmaceutical Co., Ltd.); Benzimidazole derivs. and their use in the prevention and/or the treatment of bone diseases. EP 0863881; JP 1999513364; WO 9710219 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
17430 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate 5292-43-3 C6H11BrO2 详情 详情
(I) 38446 2-amino-3-nitrophenylamine; 3-nitro-1,2-benzenediamine 3694-52-8 C6H7N3O2 详情 详情
(II) 38447 4-nitro-2-(trifluoromethyl)-1H-benzimidazole C8H4F3N3O2 详情 详情
(III) 38448 2-(trifluoromethyl)-1H-benzimidazol-4-ylamine; 2-(trifluoromethyl)-1H-benzimidazol-4-amine C8H6F3N3 详情 详情
(IV) 25087 2,6-dichlorobenzoyl chloride 4659-45-4 C7H3Cl3O 详情 详情
(V) 38449 2,6-dichloro-N-[2-(trifluoromethyl)-1H-benzimidazol-4-yl]benzamide C15H8Cl2F3N3O 详情 详情
(VI) 38450 tert-butyl 2-[4-[(2,6-dichlorobenzoyl)amino]-2-(trifluoromethyl)-1H-benzimidazol-1-yl]acetate C21H18Cl2F3N3O3 详情 详情
(VII) 38451 2-[4-[(2,6-dichlorobenzoyl)amino]-2-(trifluoromethyl)-1H-benzimidazol-1-yl]acetic acid C17H10Cl2F3N3O3 详情 详情
(VIII) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
Extended Information