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【结 构 式】 
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【分子编号】12819 【品名】[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methanol 【CA登记号】 |
【 分 子 式 】C11H17NO3 【 分 子 量 】211.26092 【元素组成】C 62.54% H 8.11% N 6.63% O 22.72% |
合成路线1
该中间体在本合成路线中的序号：(V)The condensation of 4-chloro-2,3-dimethylpyridine N-oxide (I) with 3-methoxypropanol (II) by means of NaH in DMSO gives 4-(3-methoxypropoxy)-2,3-dimethylpyridine N-oxide (III), which is treated with acetic anhydride at 90 C yielding 2-(acetoxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (IV). The hydrolysis of (IV) with NaOH in ethanol affords 2-(hydroxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (V), which by treatment with SOCl2 in dichloromethane is converted into 2-(chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine (VI). The condensation of (VI) with 2-mercaptobenzimidazole (VII) by means of NaOH in ethanol gives 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylmethylthio]benzimidazole (VIII), which is oxidized with m-chloroperbenzoic acid in ether - dichloromethane to afford 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylsulfinyl]benzimidazole (IX). Finally, this compound is treated wtih aqueous Na2CO3.
| 【1】 Souda, S.; Ueda, N.; Miyazawa, S.; Tagami, K.; Nomoto, S.; Okita, M.; Shimomura, N.; Kaneko, T.; Fujimoto, M.; Murakami, M.; Oketani, K.; Fujisaki, H.; Shibata, H.; Wakabayashi, T. (Eisai Co., Ltd.); Pyridine derivs., pharmaceutical compsns. comprising the same, the use of the same for the manufacture of medicaments having therapeutic or preventative value, and a process for preparing the same. AU 8781138; EP 0268956; EP 0475456; EP 0654471; EP 0786461; JP 1989006270; JP 1993247035; JP 1995291967; US 5045552; US 5998445 . |
| 【2】 Castaner, J.; Prous, J.; E-3810. Drugs Fut 1991, 16, 1, 19. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 17888 | m-Chloroperbenzoic acid; 3-Chlorobenzenecarboperoxoic acid | 937-14-4 | C7H5ClO3 | 详情 | 详情 | |
| (I) | 12815 | 4-chloro-2,3-dimethyl-1-pyridiniumolate | C7H8ClNO | 详情 | 详情 | |
| (II) | 12816 | 3-Methoxy-1-propanol | 1589-49-7 | C4H10O2 | 详情 | 详情 |
| (III) | 12817 | 4-(3-methoxypropoxy)-2,3-dimethyl-1-pyridiniumolate | C11H17NO3 | 详情 | 详情 | |
| (IV) | 12818 | [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl acetate | C13H19NO4 | 详情 | 详情 | |
| (V) | 12819 | [4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methanol | C11H17NO3 | 详情 | 详情 | |
| (VI) | 12820 | 2-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine; 2-(Chloromethyl)-3-methyl-4-pyridinyl 3-methoxypropyl ether | 117977-20-5 | C11H16ClNO2 | 详情 | 详情 |
| (VII) | 12821 | 2-Mercaptobenzinidiazole; 1H-Benzimidazol-2-ylhydrosulfide; 1H-Benzimidazole-2-thiol; 2-Benzimidazolethiol; o-Phenylenethiourea; 2-Benzimidazolinethione; 1,3-Dihydro-2H-benzimidazole-2-thione | 583-39-1 | C7H6N2S | 详情 | 详情 |
| (VIII) | 12822 | 2-([[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfanyl)-1H-benzimidazole; 2-[(1H-Benzimidazol-2-ylsulfanyl)methyl]-3-methyl-4-pyridinyl 3-methoxypropyl ether | 117977-21-6 | C18H21N3O2S | 详情 | 详情 |
| (IX) | 12823 | 2-([[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl)-1H-benzimidazole; 1H-Benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide | C18H21N3O3S | 详情 | 详情 |