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【结 构 式】 
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【分子编号】63668 【品名】5-methoxy-2-methyl-1,3-benzothiazole; methyl 2-methyl-1,3-benzothiazol-5-yl ether 【CA登记号】 |
【 分 子 式 】C9H9NOS 【 分 子 量 】179.2426 【元素组成】C 60.31% H 5.06% N 7.81% O 8.93% S 17.89% |
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：(I)5-Methoxy-2-methylbenzothiazole (I) is hydrolyzed by NaOH in ethylene glycol to furnish 2-amino-4-methoxythiophenol (II), which is further alkylated with iodomethane and potassium tert-butoxide, yielding thioether (III). Condensation of aniline (III) with 2-(chloromethyl)imidazoline (IV) in the presence of phenol provides (V). After oxidation of sulfide (V) to the corresponding sulfone by means of m-chloroperbenzoic acid, the title compound is isolated as its fumarate salt (1,2).
| 【1】 Hodson, S.J.; Bishop, M.J.; Speake, J.D.; Navas, F. III; Garrison, D.T.; Bigham, E.C.; Saussy, D.L. Jr.; Liacos, J.A.; Irving, P. E.; Gobel, M.J.; Sherman, B.W.; 2-(Anilinomethyl)imidazolines as alpha1 adrenergic receptor agonists: The discovery of alpha1a subtype selective 2'-alkylsulfonyl-substituted analogues. J Med Chem 2002, 45, 11, 2229. |
| 【2】 Hodson, S.J.; Navas, F. III; Bishop, M.J.; Bigham, E.C.; Garrison, D.T.; Drewry, D.H.; Speake, J.D. (Glaxo Group Ltd.); Imidazoline derivs. as alpha-1A adrenoceptor ligands. WO 0066563 . |
| 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) | 63668 | 5-methoxy-2-methyl-1,3-benzothiazole; methyl 2-methyl-1,3-benzothiazol-5-yl ether | C9H9NOS | 详情 | 详情 | |
| (II) | 63669 | 2-amino-4-methoxybenzenethiol; 2-amino-4-methoxyphenylhydrosulfide | C7H9NOS | 详情 | 详情 | |
| (III) | 63670 | 5-methoxy-2-(methylsulfanyl)aniline; 5-methoxy-2-(methylsulfanyl)phenylamine | C8H11NOS | 详情 | 详情 | |
| (IV) | 17330 | 2-(chloromethyl)-4,5-dihydro-1H-imidazole | C4H7ClN2 | 详情 | 详情 | |
| (V) | 63671 | N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-5-methoxy-2-(methylsulfanyl)aniline; N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-N-[5-methoxy-2-(methylsulfanyl)phenyl]amine | C12H17N3OS | 详情 | 详情 |
Extended Information