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【结 构 式】 
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【分子编号】31592 【品名】2-[[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]methyl]-3,5-dimethyl-1,4-dihydro-4-pyridinyl methyl ether; 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-1,4-dihydro-2-pyridinyl)methyl]sulfanyl]-1H-benzimidazole 【CA登记号】 |
【 分 子 式 】C17H21N3O2S 【 分 子 量 】331.43876 【元素组成】C 61.61% H 6.39% N 12.68% O 9.65% S 9.67% |
合成路线1
该中间体在本合成路线中的序号：(XXVIII)The reaction of 1-hydroxy-2-butanone (XXIV) with tosyl chloride gives the tosylate (XXV), which is condensed with 5-methoxy-1H-benzimidazole-2-thiol (VIII) yielding 5-methoxy-2-(2-oxobutylsulfanyl)-1H-benzimidazole (XXVI). The reaction of (XXVI) with 3-methoxy-2-methyl-2-propenal (XXI) in basic medium affords the 5-oxohexanal derivative (XXVII), which is cyclized by means of NH4OAc and NH3 to give the dihydropyridine (XXVIII). Finally, this compound is dehydrogenated and oxidized to the target sulfinyl derivative.
| 【1】 Bekhazi, M.; Zoghbi, M. (PDi-Research Laboratories, Inc. ); Synthesis of omeprazole-type pyridine derivs. and intermediates thereof. WO 9729103 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 29924 | 5-Methoxy-1H-benzimidazol-2-ylhydrosulfide; 2-Mercapto-5-methoxybenzimidazole; 5-Methoxy-1H-benzimidazole-2-thiol; 5-Methoxy-2-mercaptbenzimidazole; 5-Methoxy-2-Benzimidazolethiol | 37052-78-1 | C8H8N2OS | 详情 | 详情 |
| (XXI) | 31585 | (E)-3-methoxy-2-methyl-2-propenal | C5H8O2 | 详情 | 详情 | |
| (XXIV) | 31588 | 1-hydroxy-2-butanone | 5077-67-8 | C4H8O2 | 详情 | 详情 |
| (XXV) | 31589 | 2-oxobutyl 4-methylbenzenesulfonate | C11H14O4S | 详情 | 详情 | |
| (XXVI) | 31590 | 1-[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]-2-butanone | C12H14N2O2S | 详情 | 详情 | |
| (XXVII) | 31591 | 3-methoxy-6-[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]-2,4-dimethyl-5-oxohexanal | C17H22N2O4S | 详情 | 详情 | |
| (XXVIII) | 31592 | 2-[[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]methyl]-3,5-dimethyl-1,4-dihydro-4-pyridinyl methyl ether; 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-1,4-dihydro-2-pyridinyl)methyl]sulfanyl]-1H-benzimidazole | C17H21N3O2S | 详情 | 详情 |