Novel triazolols antifungal compound, preparation method and application thereof
A triazole alcohol and compound technology, applied in the field of 1--2--3--2-alcohol compounds and their salts, can solve the problem of large side effects, narrow antibacterial spectrum, lack of antifungal drugs and anti-deep fungal drugs and other problems, to achieve strong antifungal, low toxicity, and wide antifungal spectrum effects
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Embodiment 1
[0043] The intermediate is synthesized according to the reaction scheme of a).
[0044] (1), preparation of 2-chloro-2', 4'-difluoroacetophenone
[0045] Put 200g (1.494mol) of anhydrous aluminum oxide and 150g (1.30mol) of m-difluorobenzene into a 1000mL three-necked bottle, stir at room temperature, slowly add 150g (1.30mol) of chloroacetyl chloride dropwise, and continue to Stir at room temperature for 30 minutes, slowly raise the temperature to 45°C, continue stirring at this temperature for 4.5 hours, pour the reaction solution into ice water as usual, precipitate solids, filter; the filtrate is extracted twice with 800 mL of dichloromethane, and combined Dichloromethane extract, washed with water until neutral, dried over anhydrous sodium sulfate, filtered, and the solvent was recovered to obtain a solid, which was combined twice and recrystallized with ethanol to obtain 2-chloro 2', 4'-difluoroacetophenone 215g, yield 88.2%, melting point: 46-47°C.
[0046] (2), prepa...
Embodiment 2
[0057] Example 2: Preparation of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[N-n-propyl-N-benzylamino ]-2-ol
[0058] Add 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(N-n-propylamino)- 0.55g (0.002mol) of 2-alcohol, 40mL of acetonitrile, 2g (0.019mol) of anhydrous sodium carbonate, 0.54g (0.003mol) of benzyl bromide, heated to reflux in an oil bath for 8 hours, then evaporated to dryness, extracted with 30mL of ethyl acetate, Filtration, ethyl acetate column chromatography (developing solvent chloroform:methanol (60:1), finally give 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-di Fluorophenyl)-3-[(N-n-propyl-N-benzylamino)-2-alcohol 600mg, yield 62.2%. (See compound 1 in Table 1 for specific spectral data)
Embodiment 3
[0059] Example 3: Preparation of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[N-n-propyl-N-(2- Fluorobenzyl)amino]-2-ol
[0060] Add 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(N-n-propylamino)- 0.8g (0.003mol) of 2-alcohol, 40mL of acetonitrile, 2g (0.019mol) of anhydrous sodium carbonate, 0.8g (0.0048mol) of o-fluorochlorobenzyl, heated to reflux in an oil bath for 8 hours, then evaporated to dryness, 30mL of ethyl acetate Extraction, filtration, ethyl acetate column chromatography (developer chloroform: methanol (80:1), finally 1-(1H-1,2,4-triazol-1-yl)-2-(2,4 -difluorophenyl)-3-[(N-n-propyl-N-(2-fluorobenzyl)amino)-2-alcohol 750mg, yield 59.6%. (Specific spectral data see compound 2 in Table 1 ) compound 3, 4 according to the above method.
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