【结 构 式】 |
【分子编号】21939 【品名】1-[bis(4-propylphenyl)methyl]-1H-benzimidazole-5-carboxylic acid 【CA登记号】 |
【 分 子 式 】C27H28N2O2 【 分 子 量 】412.5316 【元素组成】C 78.61% H 6.84% N 6.79% O 7.76% |
合成路线1
该中间体在本合成路线中的序号:(VI)The condensation of methyl 4-chloro-3-nitrobenzoate (I) with dipropylbenzhydryl amine (II), followed by reduction of the nitro group of the resulting (III) with H2 in the presence of PtO2 yielded diamine (IV). Treatment of (IV) with triethyl orthoformate and formic acid at 120 C produced the benzimidazole (V), which was hydrolyzed with NaOH to the benzimidazolecarboxylic (VI). Finally, acid (VI) was condensed with aniline (VII) using 2-chloro-1-methylpyridinium iodide (CMP) and Bu3N to furnish the target amide.
【1】 Takami, H.; Kishibayashi, N.; Ishii, A.; Kumazawa, T.; Indole and benzimidazole derivatives as steroid 5alpha-reductase inhibitors in the rat prostate. Bioorg Med Chem 1998, 6, 12, 2441. |
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) | 21934 | methyl 4-chloro-3-nitrobenzoate | 14719-83-6 | C8H6ClNO4 | 详情 | 详情 |
(II) | 21935 | bis(4-propylphenyl)methanamine; bis(4-propylphenyl)methylamine | C19H25N | 详情 | 详情 | |
(III) | 21936 | N-[4-(methoxymethyl)-2-nitrophenyl]-N-[phenyl(4-propylphenyl)methyl]amine; 4-(methoxymethyl)-2-nitro-N-[phenyl(4-propylphenyl)methyl]aniline | C24H26N2O3 | 详情 | 详情 | |
(IV) | 21937 | methyl 3-amino-4-[[bis(4-propylphenyl)methyl]amino]benzoate | C27H32N2O2 | 详情 | 详情 | |
(V) | 21938 | methyl 1-[bis(4-propylphenyl)methyl]-1H-benzimidazole-5-carboxylate | C28H30N2O2 | 详情 | 详情 | |
(VI) | 21939 | 1-[bis(4-propylphenyl)methyl]-1H-benzimidazole-5-carboxylic acid | C27H28N2O2 | 详情 | 详情 | |
(VII) | 21940 | ethyl 4-(2-aminophenoxy)butanoate | C12H17NO3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(VI)The intermediate benzimidazolecarboxylic acid (VI) cal also be obtained as follows: Alkylation of benzimidazole-5-carboxylic acid (VIII) with 4,4'-dipropylbenzhydryl bromide (XI) afforded a mixture of alkylated benzimidazoles (VI) and (X), which were separated by column chromatography.
【1】 Takami, H.; Kishibayashi, N.; Ishii, A.; Kumazawa, T.; Indole and benzimidazole derivatives as steroid 5alpha-reductase inhibitors in the rat prostate. Bioorg Med Chem 1998, 6, 12, 2441. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VI) | 21939 | 1-[bis(4-propylphenyl)methyl]-1H-benzimidazole-5-carboxylic acid | C27H28N2O2 | 详情 | 详情 | |
(VIII) | 21941 | 1H-benzimidazole-5-carboxylic acid | 15788-16-6 | C8H6N2O2 | 详情 | 详情 |
(IX) | 21942 | 1-[bromo(4-propylphenyl)methyl]-4-propylbenzene | C19H23Br | 详情 | 详情 | |
(X) | 21943 | 1-[bis(4-propylphenyl)methyl]-1H-benzimidazole-6-carboxylic acid | C27H28N2O2 | 详情 | 详情 |