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【结 构 式】 
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【分子编号】16316 【品名】phenyl N-[4-[4-(4-methoxyphenyl)piperazino]phenyl]carbamate 【CA登记号】 |
【 分 子 式 】C24H25N3O3 【 分 子 量 】403.48092 【元素组成】C 71.44% H 6.25% N 10.41% O 11.9% |
合成路线1
该中间体在本合成路线中的序号：(VII)The intermediate (I) can be obtained as follows:1) The condensation of 1-(4-methoxyphenyl)piperazine (III) with chloronitrobenzene (IV) by means of K2CO3 in DMSO gives 1-(4-methoxyphenyl)-4-(4-nitrophenyl)piperazine (V), which is reduced with H2 over Pt/C to the corresponding amine (VI). The reaction of (VI) with phenyl chloroformate and pyridine in CHCl3 affords the corresponding carbamate (VII), which is treated with hydrazine in dioxane/water yielding the semicarbazide (VIII). The cyclization of (VIII) with formamidine and sodium acetate in butanol gives 4-[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]-3,4-dihydro-2H-1,2,4-triazol-3-one (IX) (2), which is alkylated with 1-ethylpropyl tosylate (X) by means of KOH in DMSO yielding the corresponding 2-alkyl compound (XI). Finally, this compound is demethylated to (I) by refluxing in 48% HBr.
| 【1】 Van Cutsem, J.; Backx, L.J.J.; Heeres, J.; J. Antimycotic azoles. 7. Synthesis and antifungal properties of a series of novel triazol-3-ones. J Med Chem 1984, 27, 7, 894-900. |
| 【2】 Castañer, J.; Fromtling, R.A.; SCH 51048. Drugs Fut 1995, 20, 3, 241. |
| 【3】 Saksena, A.K.; Girijavallabhan, V.M.; Ganguly, A.K.; Lovey, R.G. (Schering Corp.); Tri-substd. tetrahydrofuran antifungals. EP 0610377; JP 1995500605; WO 9309114 . |
| 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) | 16310 | 2-(1-ethylpropyl)-4-[4-[4-(4-hydroxyphenyl)piperazino]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one | C23H29N5O2 | 详情 | 详情 | |
| (III) | 16312 | 1-(4-Methoxyphenyl)piperazine; Methyl 4-piperazinophenyl ether | 38212-30-5 | C11H16N2O | 详情 | 详情 |
| (IV) | 13909 | 1-Chloro-4-nitrobenzene; p-Nitrochlorobenzene | 100-00-5 | C6H4ClNO2 | 详情 | 详情 |
| (V) | 16314 | methyl 4-[4-(4-nitrophenyl)piperazino]phenyl ether; 1-(4-methoxyphenyl)-4-(4-nitrophenyl)piperazine | C17H19N3O3 | 详情 | 详情 | |
| (VI) | 16315 | 4-[4-(4-methoxyphenyl)piperazino]phenylamine; 4-[4-(4-methoxyphenyl)piperazino]aniline; 1-(4-Aminophenyl)-4-(4-methoxyphenyl)piperazine | 74852-62-3 | C17H21N3O | 详情 | 详情 |
| (VII) | 16316 | phenyl N-[4-[4-(4-methoxyphenyl)piperazino]phenyl]carbamate | C24H25N3O3 | 详情 | 详情 | |
| (VIII) | 16317 | N-[4-[4-(4-methoxyphenyl)piperazino]phenyl]-1-hydrazinecarboxamide | C18H23N5O2 | 详情 | 详情 | |
| (IX) | 16318 | 4-[4-[4-(4-methoxyphenyl)piperazino]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one | C19H21N5O2 | 详情 | 详情 | |
| (X) | 16319 | 1-ethylpropyl 4-methylbenzenesulfonate | C12H18O3S | 详情 | 详情 | |
| (XI) | 16320 | 2-(1-ethylpropyl)-4-[4-[4-(4-methoxyphenyl)piperazino]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one | C24H31N5O2 | 详情 | 详情 |