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【结 构 式】 
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【分子编号】13029 【品名】(Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl methanesulfonate 【CA登记号】 |
【 分 子 式 】C16H24N2O4S 【 分 子 量 】340.44364 【元素组成】C 56.45% H 7.11% N 8.23% O 18.8% S 9.42% |
合成路线1
该中间体在本合成路线中的序号：(IX)The condensation of 2-chloro-4-(piperidin-1-ylmethyl)pyridine (V) with 4-(tetrahydropyranyloxy)-2(Z)-buten-1-ol (VI) by means of NaH in THF gives 4-(piperidin-1-ylmethyl)-2-[4-(tetrahydropyranyloxy)-2(Z)-butenyloxy)pyridine (VII), which is deprotected with 4-methylbenzenesulfonic acid in methanol, yielding the free butenol (VIII). The acylation of (VIII) with methanesulfonyl chloride in toluene affords the corresponding mesylate (IX), which is finally condensed with 2-(2-furylmethylsulfonyl)acetamide (X) (obtained from the corresponding 4-nitrophenyl ester (XI) with ammonia) by means of potassium tert-butoxide in toluene.
| 【1】 Iwata, H.; Matsumoto, H.; Matsumoto, M.; Sekine, Y.; Nishimura, M.; Hosoda, A. (UCB Japan); Methods of producing amino butene derivs. EP 0582304; JP 1994192195 . |
| 【2】 Graul, A.; Prous, J.; Castaner, J.; Lafutidine. Drugs Fut 1994, 19, 9, 835. |
| 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) | 13025 | 2-Chloro-4-(1-piperidinylmethyl)pyridine | C11H15ClN2 | 详情 | 详情 | |
| (VI) | 13026 | (Z)-4-(Tetrahydro-2H-pyran-2-yloxy)-2-buten-1-ol | C9H16O3 | 详情 | 详情 | |
| (VII) | 13027 | 4-(1-Piperidinylmethyl)-2-pyridinyl (Z)-4-(tetrahydro-2H-pyran-2-yloxy)-2-butenyl ether; 4-(1-Piperidinylmethyl)-2-[[(Z)-4-(tetrahydro-2H-pyran-2-yloxy)-2-butenyl]oxy]pyridine | C20H30N2O3 | 详情 | 详情 | |
| (VIII) | 13028 | (Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-ol | C15H22N2O2 | 详情 | 详情 | |
| (IX) | 13029 | (Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl methanesulfonate | C16H24N2O4S | 详情 | 详情 | |
| (X) | 13030 | 2-[(2-Furylmethyl)sulfinyl]acetamide | C7H9NO3S | 详情 | 详情 | |
| (XI) | 13031 | 4-nitrophenyl 2-[(2-furylmethyl)sulfinyl]acetate | C13H11NO6S | 详情 | 详情 |