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【结 构 式】 
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【药物名称】 【化学名称】trans-7-Bromo-2-methyl-4-oxo-2,3,4,10-tetrahydro-1H-phenothiazine-3-carboxylic acid tert-butyl ester 【CA登记号】 【 分 子 式 】C18H20BrNO3S 【 分 子 量 】410.333 |
【开发单位】3M Pharmaceuticals (Originator), Bristol-Myers Squibb (Originator) 【药理作用】Antiepileptic Drugs, NEUROLOGIC DRUGS |
合成路线1
The reaction of 4-bromoaniline (I) with potassium thiocyanate and bromine in acetic acid gives the benzothiazole (III) through the intermediate (II). The hydrolysis of (III) with NaOH affords 4-bromo-2-sulfanylaniline (IV), which is cyclized with 4-hydroxy-6-methyl-2-oxo-3-cyclohexene-1-carboxylic acid tert-butyl ester (V) in refluxing toluene.
| 【1】 Laws, M.L.; Roberts, R.R.; Nicholson, J.M.; Butcher, R.; Stables, J.P.; Goodwin, A.M.; Smith, C.A.; Scott, K.R.; Synthesis, characterization, and anticonvulsant activity of enaminones. Part 5: Investigations on 3-carboalkoxy-2-methyl-2,3-dihydro-1H-phenothiazin-4[10H]-one derivatives. Bioorg Med Chem 1998, 6, 12, 2289. |
| 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) | 22531 | 4-Bromoaniline; 4-Bromophenylamine | 106-40-1 | C6H6BrN | 详情 | 详情 |
| (II) | 25569 | 2-amino-5-bromobenzenesulfenyl cyanide | C7H5BrN2S | 详情 | 详情 | |
| (III) | 25570 | 6-bromo-1,3-benzothiazol-2-amine; 6-bromo-1,3-benzothiazol-2-ylamine | 15864-32-1 | C7H5BrN2S | 详情 | 详情 |
| (IV) | 25571 | 2-amino-5-bromobenzenethiol; 2-amino-5-bromophenylhydrosulfide | C6H6BrNS | 详情 | 详情 | |
| (V) | 25572 | tert-butyl 4-hydroxy-6-methyl-2-oxo-3-cyclohexene-1-carboxylate | C12H18O4 | 详情 | 详情 |
Extended Information