A kind of phenylisoxazole carboxylic acid compound with antitumor activity and its synthesis method and application
A synthetic method, the technology of phenyl isocyanate, applied in the field of medicinal chemistry, can solve problems such as threats to human health and treatment failure, and achieve the effects of low production cost, sufficient utilization, and mild reaction conditions
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Embodiment 1
[0032] Example 1 Preparation of 5-((3-fluorophenyl)amino)-3-phenylisoxazole-4-carboxylic acid (1)
[0033]
[0034] Add 1.37g (10mmol) m-fluorophenylisocyanate and 2.30g (12mmol) ethyl benzoylacetate to the reactor, add 50ml of toluene as the reaction solvent, place it on a magnetic stirrer, heat it to 110°C with an electric heating mantle, stir, and reflux React for 2 hours. Then, 1.04 g (15 mmol) of hydroxylamine hydrochloride was added to the reaction system to continue the reflux reaction for 3 hours. After the reaction, the solid-liquid mixture of the above reaction system was concentrated under reduced pressure, diluted with water, acidified with dilute hydrochloric acid, adjusted to neutral pH, cooled to room temperature, then filtered, and the filter cake was washed with warm water to obtain 5-(( Crude 3-fluorophenyl)amino)-3-phenylisoxazole-4-carboxylic acid. The crude product was added to a reactor, and 25ml of ethanol was added for recrystallization, filtered, ...
Embodiment 2
[0036] Example 2 Preparation of 5-((4-chlorophenyl)amino)-3-phenylisoxazole-4-carboxylic acid (2)
[0037]
[0038] Add 1.53g (10mmol) 4-chlorophenylisocyanate and 1.92g (10mmol) ethyl benzoylacetate in the reactor, add 50ml toluene as the reaction solvent, stir on a magnetic stirrer, and heat to 110 with an electric heating mantle. °C, reflux for 2 hours. Then, 0.69 g (10 mmol) of hydroxylamine hydrochloride was added to the reaction system to continue the reflux reaction for 3 hours. After the reaction, the solid-liquid mixture of the above reaction system was concentrated under reduced pressure, diluted with water, acidified with dilute hydrochloric acid, adjusted to neutral pH, cooled to room temperature, then filtered, and the filter cake was washed with warm water to obtain 5-(( Crude 4-chlorophenyl)amino)-3-phenylisoxazole-4-carboxylic acid. The crude product was added to a reactor, 25ml of ethanol was added for recrystallization, filtered, and dried to obtain an o...
Embodiment 3
[0040] Example 3 Preparation of 3-phenyl-5-(m-tolylamino)isoxazole-4-carboxylic acid (3)
[0041]
[0042] Add 1.33g (10 mmol) m-toluene isocyanate and 2.30g (12mmol) ethyl benzoylacetate into the reactor, add 50ml of toluene as the reaction solvent, stir on a magnetic stirrer, heat to 110°C with an electric heating mantle, The reaction was refluxed for 2 hours. Then, 1.04 g (15 mmol) of hydroxylamine hydrochloride was added to the reaction system to continue the reflux reaction for 3 hours. After the reaction, the solid-liquid mixture of the above reaction system was concentrated under reduced pressure, diluted with water, acidified with dilute hydrochloric acid, adjusted to neutral pH, cooled to room temperature, then filtered, and the filter cake was washed with warm water to obtain 3-phenyl - Crude 5-(m-tolylamino)isoxazole-4-carboxylic acid. The crude product was added to a reactor, 25ml of ethanol was added for recrystallization, filtered, and dried to obtain a whit...
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