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【结 构 式】 
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【分子编号】16140 【品名】1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione 【CA登记号】 |
【 分 子 式 】C10H9N3O2 【 分 子 量 】203.20048 【元素组成】C 59.11% H 4.46% N 20.68% O 15.75% |
合成路线1
该中间体在本合成路线中的序号：(I)The condensation of 1-(benzylideneamino)imidazolidine-2,4-dione (I) with 1-bromo-4-chlorobutane (II) by means of NaH in DMF at 100 C yields 1-(benzylideneamino)-3-(4-chlorobutyl)imidazolidine-2,4-dione (III), which is treated with NaI in refluxing acetone affording the corresponding 4-iodobutyl derivative (IV). The thermal condensation of (IV) with 1-methylpiperazine (V) in refluxing DMF gives the expected condensation product (VI), which is debenzylated by hydrogenation with H2 over Pd/C in 2N HCl giving 1-amino-3-[4-(4-methylpiperazin-1-yl)butyl]imidazolidine-2,4-dione (VII). Finally, this compound is condensed with 5-(4-chlorophenyl)furan-2-carbaldehyde (VIII) in DMF at room temperature.
| 【1】 Robinson, C.P.; Robinson, K.A.; Castaner, J.; Azimilide Hydrochloride. Drugs Fut 1997, 22, 6, 601. |
| 【2】 Pelosi, S.S. Jr.; Yu, C.-NN.; Calcagno, M.A. (The Procter & Gamble Co.); Novel 4-oxocyclic ureas useful as antiarrhythmic and antifibrillatory agents. EP 0598061; JP 1994509804; US 5462940; WO 9304061 . |
| 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) | 16140 | 1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione | C10H9N3O2 | 详情 | 详情 | |
| (II) | 16141 | 1-bromo-4-chlorobutane | 6940-78-9 | C4H8BrCl | 详情 | 详情 |
| (III) | 16142 | 3-(4-chlorobutyl)-1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione | C14H16ClN3O2 | 详情 | 详情 | |
| (IV) | 16143 | 3-(4-iodobutyl)-1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione | C14H16IN3O2 | 详情 | 详情 | |
| (V) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |
| (VI) | 16145 | 3-[4-(4-methylpiperazino)butyl]-1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione | C19H27N5O2 | 详情 | 详情 | |
| (VII) | 16146 | 1-amino-3-[4-(4-methylpiperazino)butyl]-1H-imidazole-2,4(3H,5H)-dione | C12H23N5O2 | 详情 | 详情 | |
| (VIII) | 16147 | 5-(4-Chloro-phenyl)-furan-2-carbaldehyde; 5-(4-Chlorophenyl)-2-furaldehyde | 34035-03-5 | C11H7ClO2 | 详情 | 详情 |