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【结 构 式】 
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【分子编号】32386 【品名】3-[3-[4-(6-chloro-5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl]-5-fluoro-1H-indole; 4-chloro-6-[4-[3-(5-fluoro-1H-indol-3-yl)propyl]-1-piperazinyl]-5-pyrimidinyl methyl ether 【CA登记号】 |
【 分 子 式 】C20H23ClFN5O 【 分 子 量 】403.8868232 【元素组成】C 59.48% H 5.74% Cl 8.78% F 4.7% N 17.34% O 3.96% |
合成路线1
该中间体在本合成路线中的序号：(VI)The cyclization of dimethyl 2-methoxymalonate (I) with formamidine (II) by means of sodium methoxide in methanol gives the dihydroxypyrimidine (III), which by reaction with POCl3 is converted into the dichloropyrimidine (IV). The condensation of (IV) with 5-fluoro-3-[3-(1-piperazinyl)propyl]-1H-indole (V) by means of DIPEA in refluxing acetonitrile affords intermediate (VI), which is finally dechlorinated by hydrogenation with H2 over Pd/C in aqueous ethanol.
| 【1】 Anderson, N.G.; et al.; Process development of 5-fluoro-3[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl]-1H-indole dihydrochloride. Org Process Res Dev 1997, 1, 4, 300. |
| 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) | 32382 | dimethyl 2-methoxymalonate | 5018-30-4 | C6H10O5 | 详情 | 详情 |
| (II) | 15369 | Iminoformamide; Methanimidamide | 463-52-5 | CH4N2 | 详情 | 详情 |
| (III) | 32383 | 5-methoxy-4,6-pyrimidinediol | C5H6N2O3 | 详情 | 详情 | |
| (IV) | 32384 | 4,6-dichloro-5-pyrimidinyl methyl ether; 4,6-dichloro-5-methoxypyrimidine | C5H4Cl2N2O | 详情 | 详情 | |
| (V) | 32385 | 5-fluoro-3-[3-(1-piperazinyl)propyl]-1H-indole | C15H20FN3 | 详情 | 详情 | |
| (VI) | 32386 | 3-[3-[4-(6-chloro-5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl]-5-fluoro-1H-indole; 4-chloro-6-[4-[3-(5-fluoro-1H-indol-3-yl)propyl]-1-piperazinyl]-5-pyrimidinyl methyl ether | C20H23ClFN5O | 详情 | 详情 |