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【结 构 式】 
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【分子编号】57754 【品名】10-(4-chlorobutyl)-10H-phenothiazine 【CA登记号】 |
【 分 子 式 】C16H16ClNS 【 分 子 量 】289.82848 【元素组成】C 66.31% H 5.56% Cl 12.23% N 4.83% S 11.06% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(VII)4-Chloro-1-butanol (I) is protected as the tetrahydropyranyl ether (III) by treatment with dihydropyran (II) in the presence of pyridinium p-toluenesulfonate (PPTS). Alkylation of the sodium derivative of phenothiazine (IV) with chloride (III) yields adduct (V), which is subsequently deprotected to alcohol (VI) with PPTS in MeOH-THF. The free alcohol (VI) is then chlorinated to (VII) by using SOCl2 in benzene. Finally, condensation of chloride (VII) with pyrrolidine (VIII) in THF at 100 C in a sealed tube provides the title compound.
| 【1】 Guan, J.; et al.; Design, synthesis, and evaluation of new chemosensitizers in multi-drug-resistant Plasmodium falciparum. J Med Chem 2002, 45, 13, 2741. |
| 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) | 22336 | 4-chloro-1-butanol | 928-51-8 | C4H9ClO | 详情 | 详情 |
| (II) | 13684 | 3,4-Dihydro-2H-pyran;2,3-Dihydro-4H-pyran; 5,6-Dihydro-4H-pyran;Dihydropyran | 110-87-2 | C5H8O | 详情 | 详情 |
| (III) | 57750 | 2-(4-Chlorobutoxy)tetrahydropyran | C9H17ClO2 | 详情 | 详情 | |
| (IV) | 57751 | 10H-Phenothiazine; 2,3,5,6-Dibenzo-1,4-thiazine; Dibenzo-1.4-thiazine; Dibenzothiazine; Phenothiazine; Thiodiphenylamine | 92-84-2 | C12H9NS | 详情 | 详情 |
| (V) | 57752 | 4-(10H-phenothiazin-10-yl)butyl tetrahydro-2H-pyran-2-yl ether; 10-[4-(tetrahydro-2H-pyran-2-yloxy)butyl]-10H-phenothiazine | C21H25NO2S | 详情 | 详情 | |
| (VI) | 57753 | 4-(10H-phenothiazin-10-yl)-1-butanol | C16H17NOS | 详情 | 详情 | |
| (VII) | 57754 | 10-(4-chlorobutyl)-10H-phenothiazine | C16H16ClNS | 详情 | 详情 | |
| (VIII) | 11376 | Pyrrolidine | 123-75-1 | C4H9N | 详情 | 详情 |
Extended Information