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【结 构 式】 
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【药物名称】IDPH-85184, XZ5481500 【化学名称】5-[(4-Chloro-3-methylphenoxy)methyl]-4-(4-methylphenyl)-3,4-dihydro-2H-1,2,4-triazol-3-one 【CA登记号】 【 分 子 式 】C17H16ClN3O2 【 分 子 量 】329.78897 |
【开发单位】Indian Drugs (Originator) 【药理作用】Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, 5-HT Reuptake Inhibitors |
合成路线1
Chloroacetylation of p-toluidine (I) gives N-chloroacetyl-p-toluidine (II), which by reaction with 3-methyl-4-chlorophenol in refluxing acetone - K2CO3 is converted into 2-(4-chloro-3-methylphenoxy)-N-(p-tolyl)acetamide (III). The reaction of (III) with Lawesson's reagent in boiling toluene affords the thioamide (IV), which is methylated with methyl iodide in refluxing acetone - K2CO3 and the resulting 5-methyl ether without any further purification is finally subjected in situ to cyclocondensation by treating with ethylcarbazate in refluxing DMF to give IDPH-85184 in an overall yield of 40%.
| 【1】 Scheibye, S.; Pedersen, B.S.; Lawesson, S.U.; Bull Soc Chim Belg 1978, 87, 229. |
| 【2】 Arya, V.P.; IDPH-85184. Drugs Fut 1990, 15, 12, 1178. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 31230 | 4-chloro-3-methylphenol | 59-50-7 | C7H7ClO | 详情 | 详情 | |
| (I) | 31228 | p-toluidine; 4-methylphenylamine | 106-49-0 | C7H9N | 详情 | 详情 |
| (II) | 31229 | 2-chloro-N-(4-methylphenyl)acetamide | C9H10ClNO | 详情 | 详情 | |
| (III) | 31231 | 2-(4-chloro-3-methylphenoxy)-N-(4-methylphenyl)acetamide | C16H16ClNO2 | 详情 | 详情 | |
| (IV) | 31232 | 2-(4-chloro-3-methylphenoxy)-N-(4-methylphenyl)ethanethioamide | C16H16ClNOS | 详情 | 详情 |