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【结 构 式】 
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【分子编号】35167 【品名】benzyl 4-[[[(1R)-1-(2-fluoro-4-pyridinyl)-2-oxo-2-[3-(trifluoromethyl)phenyl]ethyl](methyl)amino]carbonyl]-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C29H27F4N3O4 【 分 子 量 】557.5448128 【元素组成】C 62.47% H 4.88% F 13.63% N 7.54% O 11.48% |
合成路线1
该中间体在本合成路线中的序号：(XVII)Keto oxime (IV) was converted to the syn amino alcohol (XII) by palladium-catalyzed hydrogenation. Subsequent N-methylation of (XII) to give (XIV) was then achieved via formylation of the primary amine to formamide (XIII) in refluxing ethyl formate, followed by borane reduction. Acylation of the secondary amine (XIV) with N-(benzyloxycarbonyl)piperidine-4-carbonyl chloride (XV) provided amide (XVI). After Swern oxidation of the alcohol group of (XVI), the keto amide (XVII) was cyclized to the desired imidazole (VIII) in boiling ammonium formate.
| 【1】 Claiborne, C.F.; et al.; An efficient synthesis of tetrasubstituted imidazoles from N-(2-oxo)-amides. Tetrahedron Lett 1998, 39, 49, 8939. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 16602 | ethyl formate | 109-94-4 | C3H6O2 | 详情 | 详情 | |
| (IV) | 35155 | 1-(2-fluoro-4-pyridinyl)-2-[3-(trifluoromethyl)phenyl]-1,2-ethanedione 1-oxime | C14H8F4N2O2 | 详情 | 详情 | |
| (VIII) | 35159 | benzyl 4-[5-(2-fluoro-4-pyridinyl)-1-methyl-4-[3-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]-1-piperidinecarboxylate | C29H26F4N4O2 | 详情 | 详情 | |
| (XII) | 35162 | (1S,2R)-2-amino-2-(2-fluoro-4-pyridinyl)-1-[3-(trifluoromethyl)phenyl]-1-ethanol | C14H12F4N2O | 详情 | 详情 | |
| (XIII) | 35163 | (1R,2S)-1-(2-fluoro-4-pyridinyl)-2-hydroxy-2-[3-(trifluoromethyl)phenyl]ethylformamide | C15H12F4N2O2 | 详情 | 详情 | |
| (XIV) | 35164 | (1S,2R)-2-(2-fluoro-4-pyridinyl)-2-(methylamino)-1-[3-(trifluoromethyl)phenyl]-1-ethanol | C15H14F4N2O | 详情 | 详情 | |
| (XV) | 35165 | benzyl 4-(chlorocarbonyl)-1-piperidinecarboxylate | C14H16ClNO3 | 详情 | 详情 | |
| (XVI) | 35166 | benzyl 4-[[[(1R,2S)-1-(2-fluoro-4-pyridinyl)-2-hydroxy-2-[3-(trifluoromethyl)phenyl]ethyl](methyl)amino]carbonyl]-1-piperidinecarboxylate | C29H29F4N3O4 | 详情 | 详情 | |
| (XVII) | 35167 | benzyl 4-[[[(1R)-1-(2-fluoro-4-pyridinyl)-2-oxo-2-[3-(trifluoromethyl)phenyl]ethyl](methyl)amino]carbonyl]-1-piperidinecarboxylate | C29H27F4N3O4 | 详情 | 详情 |