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【结 构 式】 
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【分子编号】13023 【品名】(Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-amine; (Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-butenylamine 【CA登记号】 |
【 分 子 式 】C15H23N3O 【 分 子 量 】261.36724 【元素组成】C 68.93% H 8.87% N 16.08% O 6.12% |
合成路线1
该中间体在本合成路线中的序号：(III)1) The reaction of 2-bromo-4-(piperidin-1-ylmethyl)pyridine (I) with 4-amino-2(Z)-buten-1-ol (II) by means of NaH in THF gives 4-[4-(piperidin-1-ylmethyl)pyridin-2-yloxy]-2(Z)-buten-1-amine (III), which is then condensed with 2-(2-furylmethylsulfinyl)acetic acid (IV) by means of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (EDCD) in dichloromethane.
| 【1】 Hirakawa, N.; Kashiwaba, N.; Matsumoto, H.; Hosoda, A.; Sekine, Y.; Isowa, Y.; Yamaura, T.; Sekine, A.; Nishikawa, M. (UCB Japan); Pyridyloxy derivs. EP 0282077; JP 1988225371; JP 1989230556; JP 1989230576; US 4912101 . |
| 【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 |
|---|---|---|---|---|---|---|
| (I) | 13021 | 2-Bromo-4-(1-piperidinylmethyl)pyridine | C11H15BrN2 | 详情 | 详情 | |
| (II) | 13022 | (Z)-4-Amino-2-buten-1-ol | C4H9NO | 详情 | 详情 | |
| (III) | 13023 | (Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-amine; (Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-butenylamine | C15H23N3O | 详情 | 详情 | |
| (IV) | 13024 | 2-[(2-Furylmethyl)sulfinyl]acetic acid | C7H8O4S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)The condensation of 4-amino-2(Z)-buten-1-ol (I) with 2-bromo-4-(piperidinomethyl)pyridine (II) by means of NaH in refluxing THF gives 4-[4-(piperidinomethyl)pyridin-2-yloxy]-2(Z)-butenylamine (III), which is allowed to react with 3,4,-dimethoxy-3-cyclobutene-1,2-dione (IV) in methanol to afford 3-methoxy-4-[4-[4-(piperidinomethyl)pyridin-2-yloxy]-2(Z)-butenylamino]-3-cyclobutene-1,2-dione (V). Finally, this compound is treated with dry ammonia in methanol.
| 【1】 Nohara, F.; Fujinawa, T. (Ikeda Mohando); Pyridyloxy derivs.. AU 8548136; EP 0177016; ES 8701161; JP 1986085365; JP 1986207375; JP 1991261766; US 4710498 . |
| 【2】 Prous, J.; Castaner, J.; IT-066. Drugs Fut 1990, 15, 12, 1181. |
| 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) | 13022 | (Z)-4-Amino-2-buten-1-ol | C4H9NO | 详情 | 详情 | |
| (II) | 13021 | 2-Bromo-4-(1-piperidinylmethyl)pyridine | C11H15BrN2 | 详情 | 详情 | |
| (III) | 13023 | (Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-amine; (Z)-4-[[4-(1-Piperidinylmethyl)-2-pyridinyl]oxy]-2-butenylamine | C15H23N3O | 详情 | 详情 | |
| (IV) | 19999 | 3,4-dimethoxy-3-cyclobutene-1,2-dione | 5222-73-1 | C6H6O4 | 详情 | 详情 |
| (V) | 31233 | 3-methoxy-4-[((Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl)amino]-3-cyclobutene-1,2-dione | C20H25N3O4 | 详情 | 详情 |