|
【结 构 式】 
|
【分子编号】28033 【品名】4-[2-(3,5-dioxo-1-piperazinyl)ethyl]-2,6-piperazinedione 【CA登记号】 |
【 分 子 式 】C10H14N4O4 【 分 子 量 】254.24572 【元素组成】C 47.24% H 5.55% N 22.04% O 25.17% |
合成路线1
该中间体在本合成路线中的序号：(I)4,4'-Ethane-1,2-diylbis(piperazine-2,6-dione) in DMF is heated at 130 C for 10 min. Aqueous formaldehyde is then gradually added, and the mixture is heated at 130 C for 1.5 h. 4,4'-Ethane-1,2-diylbis[1-(hydroxymethyl)piperazine-2,6-dione] precipitates from the solution on cooling. It can be purified by recrystallization from dioxane. The hydroxymethyl compound (II) is then stirred with pyridine and chloroform at 10 C. Isobutoxycarbonyl chloride is gradually added, and the mixture is stirred for 6 h at room temperature. The resulting solution is diluted with chloroform. The combined solution is washed with water and then dried. Evaporation of the chloroform gives MST-16. It can be purified by recrystallization from ethylene glycol monomethyl ether.
| 【1】 Ruyun, J.; MST-16. Drugs Fut 1986, 11, 4, 267. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 13423 | 1-[(Chlorocarbonyl)oxy]-2-methylpropane; Isobutyl chloroformate;isobutyl carbonochloridate | 543-27-1 | C5H9ClO2 | 详情 | 详情 |
| (I) | 28033 | 4-[2-(3,5-dioxo-1-piperazinyl)ethyl]-2,6-piperazinedione | C10H14N4O4 | 详情 | 详情 | |
| (II) | 28034 | 1-(hydroxymethyl)-4-[2-[4-(hydroxymethyl)-3,5-dioxo-1-piperazinyl]ethyl]-2,6-piperazinedione | C12H18N4O6 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)Ethylenediaminetetraacetic acid (EDTA) (I) on heating with formamide (A), afforded IGRF-154 (II). The latter compound was suspended in dimethylformamide (C), heated with morpholine (B) in ethanol and then refluxed with formalin. The final product crystallized on cooling.
| 【1】 Ren, Y.F.; et al.; An investigation of a new antineoplastic agent bimolane (AT-1727). Kexue Tongbao 1980, 23, 4, 189-190. |
| 【2】 Ji Ru-Yun; Bimolane. Drugs Fut 1981, 6, 11, 667. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 |
| (A) | 16598 | Formamide | 75-12-7 | CH3NO | 详情 | 详情 |
| (I) | 39018 | 2-[[2-[bis(carboxymethyl)amino]ethyl](carboxymethyl)amino]acetic acid | C10H16N2O8 | 详情 | 详情 | |
| (II) | 28033 | 4-[2-(3,5-dioxo-1-piperazinyl)ethyl]-2,6-piperazinedione | C10H14N4O4 | 详情 | 详情 | |
| (C) | 33491 | Dimethylformamide | 68-12-2 | C3H7NO | 详情 | 详情 |