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【结 构 式】 
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【分子编号】20005 【品名】4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoic acid 【CA登记号】 |
【 分 子 式 】C17H11F3N2O2 【 分 子 量 】332.2818296 【元素组成】C 61.45% H 3.34% F 17.15% N 8.43% O 9.63% |
合成路线1
该中间体在本合成路线中的序号：(III)The earlier synthesis starts with the reaction of 4-chloro-7-(trifluoromethyl)quinoline (I) with 4-aminobenzoic acid (II) in ethanol-HCl giving 4-(4-carboxyphenylamino)-7-(trifluoromethyl)quinoline (III), which is converted to its acyl chloride (IV) by treatment with SOCl2. The reaction of (IV) with piperazine (V) yields 1-[4-[7-(trifluoromethyl)quinolin-4-ylamino]benzoyl]piperazine (VI), which is finally acylated with 4-fluorobenzenesulfonyl chloride (VII) to give U-54669 F. However, this method is not economically efficient, since the most expensive compound [quinoline (I)] is already used in the first step of the synthesis.
| 【1】 McCall, J.M. (Pharmacia Corp.); Aminoquinolines. GB 2021567 . |
| 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) | 20003 | 4-chloro-7-(trifluoromethyl)quinoline | 346-55-4 | C10H5ClF3N | 详情 | 详情 |
| (II) | 20004 | p-aminobenzoic acid; 4-aminobenzoic acid | 150-13-0 | C7H7NO2 | 详情 | 详情 |
| (III) | 20005 | 4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoic acid | C17H11F3N2O2 | 详情 | 详情 | |
| (IV) | 20006 | 4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl chloride | C17H10ClF3N2O | 详情 | 详情 | |
| (V) | 10355 | Diethylenediamine; Piperazine | 110-85-0 | C4H10N2 | 详情 | 详情 |
| (VI) | 20008 | 1-piperazinyl(4-[[7-(trifluoromethyl)-4-quinolinyl]amino]phenyl)methanone | C21H19F3N4O | 详情 | 详情 | |
| (VII) | 12292 | 4-Fluorobenzenesulfonyl chloride | 349-88-2 | C6H4ClFO2S | 详情 | 详情 |