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【结 构 式】 
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【分子编号】56507 【品名】(4-chloro-3-methoxy-2-pyridinyl)methyl methanesulfonate 【CA登记号】 |
【 分 子 式 】C8H10ClNO4S 【 分 子 量 】251.69044 【元素组成】C 38.18% H 4% Cl 14.09% N 5.57% O 25.43% S 12.74% |
合成路线1
该中间体在本合成路线中的序号：(XXI)In an alternative procedure, the nitropyridine N-oxide (IX) was rearranged to the (mesyloxymethyl)pyridine (XIX) by treatment with methanesulfonic anhydride. Condensation of mesylate (XIX) with mercaptobenzimidazole (V), with concomitant nitro group displacement in the presence of sodium methoxide led to the sulfide precursor (XIV). This was then oxidized to the title sulfoxide employing sodium percarbonate and ammonium molybdate. An analogous synthetic route starting from the chloropyridine N-oxide (XX) provided mesylate (XXI), which was condensed with (V) in the presence of Et3N, leading to the sulfide adduct (XXII). The 4-chloro group of (XXII) was then displaced by sodium methoxide producing the dimethoxypyridine derivative (XIV).
| 【1】 Coppi, L.; Berenguer Maimó, R. (Laboratorios del Dr. Esteve, SA); Method for obtaining derivs. of [[pyridyl substd.)methyl]thio]benzimidazol. ES 2171116; WO 0179194 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 14034 | 5-(Difluoromethoxy)-1H-benzimidazole-2-thiol; 5-(Difluoromethoxy)-1H-benzimidazol-2-ylhydrosulfide; 5-Difluoromethoxy-2-mercapto-1H-benzimidazole | 97963-62-7 | C8H6F2N2OS | 详情 | 详情 |
| (IX) | 56498 | 3-methoxy-2-methyl-4-nitro-1-pyridiniumolate | C7H8N2O4 | 详情 | 详情 | |
| (XIV) | 14036 | 5-(Difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfanyl]-1H-benzimidazole; 2-([[5-(Difluoromethoxy)-1H-benzimidazol-2-yl]sulfanyl]methyl)-3-methoxy-4-pyridinyl methyl ether | 102625-64-9 | C16H15F2N3O3S | 详情 | 详情 |
| (XIX) | 56505 | (3-methoxy-4-nitro-2-pyridinyl)methyl methanesulfonate | C8H10N2O6S | 详情 | 详情 | |
| (XX) | 56506 | 4-chloro-3-methoxy-2-methyl-1-pyridiniumolate | C7H8ClNO2 | 详情 | 详情 | |
| (XXI) | 56507 | (4-chloro-3-methoxy-2-pyridinyl)methyl methanesulfonate | C8H10ClNO4S | 详情 | 详情 | |
| (XXII) | 56508 | 4-chloro-2-({[5-(difluoromethoxy)-1H-benzimidazol-2-yl]sulfanyl}methyl)-3-pyridinyl methyl ether; 2-{[(4-chloro-3-methoxy-2-pyridinyl)methyl]sulfanyl}-5-(difluoromethoxy)-1H-benzimidazole | C15H12ClF2N3O2S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)
| 【1】 Coppi L,Berenguer Maimo R. 2001. Method for obtaining derivatives of[[(substituted-pyridyl) methyl] thio] benzimidazole, useful as intermediates for omeprazole and related antiulcer agents. W0 2001079194 (本专利属于Esteve Quimica,S A, Spain) |
| 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) | 56506 | 4-chloro-3-methoxy-2-methyl-1-pyridiniumolate | C7H8ClNO2 | 详情 | 详情 | |
| (II) | 56507 | (4-chloro-3-methoxy-2-pyridinyl)methyl methanesulfonate | C8H10ClNO4S | 详情 | 详情 | |
| (III) | 66569 | 5-(difluoromethoxy)-1H-benzo[d]imidazole-2(3H)-thione | 97963-62-7 | C8H6F2N2OS | 详情 | 详情 |
| (IV) | 56508 | 4-chloro-2-({[5-(difluoromethoxy)-1H-benzimidazol-2-yl]sulfanyl}methyl)-3-pyridinyl methyl ether; 2-{[(4-chloro-3-methoxy-2-pyridinyl)methyl]sulfanyl}-5-(difluoromethoxy)-1H-benzimidazole | C15H12ClF2N3O2S | 详情 | 详情 |