Fluoroquinolone compound as well as preparation method and application thereof
A technology for fluoroquinolones and compounds, which is applied to fluoroquinolones and the fields of their preparation and application, can solve the problems of limited use of antibiotics, increased bacterial resistance and the like, and achieves good inhibitory or bactericidal activity, broad antibacterial spectrum, and good application. Foreground effect
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Embodiment 1
[0124] Example 1: 1-(2-Pyridinyl)-8-chloro-6-fluoro-1,4-dihydro-7-(cyclopropyl(methyl)amino)-4-oxo-3-quinoline Preparation of Carboxylic Acid (Compound 1):
[0125] a) N,N-Dimethylamino ethyl acrylate (3.1 g, 24.0 mmol), triethylamine (2.6 g, 26.2 mmol), and toluene (40 mL) were mixed, and 3-chloro-2,4,5- Trifluorobenzoyl chloride (5g, 21.8mmol) and toluene (20mL) mixed solution, heated to 50°C, monitored by TLC for about 1 hour, the reaction was completed, concentrated to obtain compound II 7.3g, yield 99%. LC / MS[M+H] + =336.05, [M+Na] + =358.08, [M+K] + = 374.04.
[0126] b) Compound II (7g, 20.8mmol), ethanol (70mL), and glacial acetic acid (3mL) were mixed, and the ethanol solution of 2-aminopyridine (2.1g, 22.8mmol) was added dropwise at room temperature, and the dropwise addition was completed and heated to 40° C. , TLC monitoring after the reaction is completed, cool, slowly add an appropriate amount of water to the reaction solution, stir and filter, and dry to obta...
Embodiment 2
[0130] Example 2: 1-(2-Pyridinyl)-8-chloro-6-fluoro-1,4-dihydro-7-(cyclobutyl(methyl)amino)-4-oxo-3-quinoline Preparation of Carboxylic Acid (Compound 2):
[0131] Compound V (1.7 g, 5.0 mmol) was added to a suspension of N-methylcyclopropylamine (0.6 g, 7.5 mmol), triethylamine (1.0 g, 10.0 mmol) and acetonitrile (20 mL), and the mixture was refluxed No starting material was present until detected by TLC (usually 5-8 hours). The solution was cooled to room temperature and filtered, and the filter cake was washed with water and ether to give the crude product. Subsequent purification by recrystallization (DMF / EtOH) gave the desired product 1-(2-pyridyl)-8-chloro-6-fluoro-1,4-dihydro-7-(cyclobutyl(methyl)amino) -4-oxo-3-quinolinecarboxylic acid 1.2 g, yield 60%. LC / MS[M+H] + =402.08, [M+Na] + =424.09, [M+K] + =440.06.
Embodiment 3
[0132] Example 3: Preparation of 1-(2-pyridyl)-8-chloro-6-fluoro-1,4-dihydro-7-pyrrolidinyl-4-oxo-3-quinolinecarboxylic acid (compound 3) preparation:
[0133] Compound V (1.7 g, 5.0 mmol) was added to a suspension of tetrahydropyrrole (0.5 g, 7.5 mmol), triethylamine (1.0 g, 10.0 mmol) and acetonitrile (20 mL), then the mixture was refluxed until by TLC The absence of starting material was detected (usually 5-8 hours). The solution was cooled to room temperature and filtered, and the filter cake was washed with water and ether to give the crude product. Subsequent purification by recrystallization (DMF / EtOH) gave the desired product 1-(2-pyridyl)-8-chloro-6-fluoro-1,4-dihydro-7-(cyclobutyl(methyl)amino) -4-oxo-3-quinolinecarboxylic acid 1.0 g, yield 53%. LC / MS[M+H] + =388.08, [M+Na] + =410.05, [M+K] + = 426.08.
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