Preparation method of Delafloxacin and intermediates thereof
A technology of delafloxacin and intermediates, applied in the field of medicine, can solve the problems of amidation reaction, high reaction temperature, multiple impurities and the like, and achieve the effects of simple operation, high purity and high product yield
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Embodiment 1
[0042] Preparation of 3-chloro-2,4,5-fluorobenzoyl chloride (compound 2)
[0043] (1) Compound 1 (5g, 23.7mmol) and dichloromethane (50ml) were mixed and stirred, and thionyl chloride (5.6g, 44.4mmol) was added dropwise at 0-20°C. After the addition was complete, DMF (0.2ml ), heated to reflux, monitored by TLC, it took 8 hours to complete the reaction, cooled, and the solvent was removed under reduced pressure to obtain 5.4 g of compound with a yield of 99.5%.
Embodiment 2
[0045] Preparation of ethyl 2-(3-chloro-2,4,5-trifluorobenzoyl)-3-(dimethylamino)acrylate (compound 3)
[0046] (1) Mix N,N-ethyl dimethylaminoacrylate (4.2g, 32.7mmol), triethylamine (2.6g, 26.2mmol), dichloromethane (40ml), drop compound 1 (5g, 21.8mmol ) dichloromethane (20ml) mixed solution, heated to 1, TLC monitoring, need 3 hours to complete the reaction, concentrated to give compound 3 7.3g yield 99%.
Embodiment 3
[0048] Preparation of ethyl 3-((6-amino-3,5-difluoro-2-pyridyl)amino)-2-(2,4,5-trifluorobenzoyl)acrylate (compound 4)
[0049] (1) Compound 3 (7g, 20.8mmol); acetonitrile (70ml), glacial acetic acid (3ml) was mixed, and 2,4-diamino-3,5-difluoropyridine (3.3g, 22.8 mmol) of acetonitrile solution, heated to 30-40°C after the dropwise addition, monitored by TLC, it took 1 hour to complete the reaction, cooled, slowly added an appropriate amount of water to the reaction solution, stirred, filtered, and dried to obtain 8.6g of compound 4 with a yield of 94.9% . 1H NMR (400MHz, CDCl3) δ11.31(d,1H),9.04(d,1H),7.41(td,1H),7.25(t,1H),4.65(m,2H),4.17(q,2H) ,1.11(s,3H).
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