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Synthesizing method of high-purity 3-methyl-N-[4-(trifluoromethyl) phenyl]-4-isoxazol formamide

A technology of dimethylaminomethylene acetoacetamide and trifluoromethyl, which is applied in the field of synthesis of isoxazole compounds to achieve the effects of increased regioselectivity, increased yield, and easier purification

Active Publication Date: 2013-04-10
CHANGZHOU YABANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The object of the present invention is to provide a new method for synthesizing 3-methyl-N-[4-(trifluoromethyl)phenyl]-4-isoxazole carboxamide, aiming at overcoming the shortcoming in the existing synthetic method

Method used

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  • Synthesizing method of high-purity 3-methyl-N-[4-(trifluoromethyl) phenyl]-4-isoxazol formamide
  • Synthesizing method of high-purity 3-methyl-N-[4-(trifluoromethyl) phenyl]-4-isoxazol formamide
  • Synthesizing method of high-purity 3-methyl-N-[4-(trifluoromethyl) phenyl]-4-isoxazol formamide

Examples

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Effect test

Embodiment 1

[0020] Example 1: N-[(4-trifluoromethyl)phenyl]-2-dimethylaminomethyleneacetoacetamide (III)

[0021] N-[(4-trifluoromethyl)phenyl]acetoacetamide (245 g, 1.0 mol) and N,N-dimethylformamide dimethyl acetal (149 g, 1.26 mol) were added to 600 mL of toluene , start stirring, and heat up to reflux until the raw material disappears. Under reflux, slowly mix in 100 mL of isopropanol, continue to stir for 15 minutes, cool down to 0-5°C, crystallize, filter with suction, and dry to obtain 225 g of an off-white solid with a yield of 75%.

Embodiment 2

[0022] Example 2: 3-methyl-N-[4-(trifluoromethyl)phenyl]-4-isoxazole carboxamide (I)

[0023] Add N-[(4-trifluoromethyl)phenyl]-2-dimethylaminomethyleneacetoacetamide (300g, 1.0mol) into 1000ml of methanol, start stirring, and cool the reaction system to -5 After ℃, slowly add 50% aqueous solution of hydroxylamine (66g, 1.0mol) dropwise, keep the stability of the reaction system at -5 ℃ ~ 0 ℃ during the dropwise addition, and add dilute hydrochloric acid dropwise to maintain the pH of the reaction solution at about 6.0 . After the dropwise addition, raise the temperature to 10°C to 15°C to continue the reaction, while maintaining the pH of the reaction solution at about 6.0 until the raw materials disappear. After the reaction was completed, the reaction solution (500ml×3) was extracted with ethyl acetate, and the organic phases were combined. The organic phase was washed once each with saturated aqueous sodium bicarbonate solution (400ml) and water (400ml), dried over anhyd...

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Abstract

The invention relates to a synthesizing method of high-purity 3-methyl-N-[4-(trifluoromethyl) phenyl]-4-isoxazol formamide. The method can enhance the yield of 3-methyl-N-[4-(trifluoromethyl) phenyl]-4-isoxazol formamide greatly, and the product is easy to purify. Therefore, the method is beneficial to preparing the high-purity 3-methyl-N-[4-(trifluoromethyl) phenyl]-4-isoxazol formamide.

Description

technical field [0001] The present invention relates to a method for synthesizing pharmacologically active isoxazole compounds, more specifically to high-purity 3-methyl-N-[4-(trifluoromethyl)phenyl]-4-isoxazole Synthetic method of formamide. Background technique [0002] Leflunomide (leflunomide) is the first new drug approved specifically for the treatment of rheumatoid arthritis in the past ten years. This product has immunosuppressive and anti-inflammatory effects, and its mechanism of action is novel. It inhibits cell adhesion and the activity of acid kinase, affects the information transmission of cytokines, and inhibits the activity of dihydroorotate dehydrogenase, thereby inhibiting the relationship between rheumatoid arthritis and rheumatoid arthritis. Proliferation of activated lymphocytes associated with the pathogenesis of arthritis. [0003] In the process of the production of leflunomide raw materials and preparations, the 3-methyl isomer of leflunomide, name...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D261/18
Inventor 陈再新夏正君蒋龙林送荆小燕史惠忠马堰启于鸿飞王汉元
Owner CHANGZHOU YABANG PHARMA