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Preparation method of Deracoxib

A cooxib and reaction technology, which is applied in the field of preparation of diracoxib, can solve the problems of a large amount of solvent, high production cost and high price, and achieves the effects of simple operation, mild conditions and high yield

Active Publication Date: 2018-02-13
NORTHEAST AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The solvent methyl tert-butyl ether used in this reaction, the price is higher, needs a large amount of solvents in the process production, and the production cost is high

Method used

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  • Preparation method of Deracoxib
  • Preparation method of Deracoxib
  • Preparation method of Deracoxib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The preparation of embodiment 1 deracoxib

[0041] Step 1 (Step 1): Preparation of 3-fluoro-4-methoxyacetophenone (compound 1): under ice-water bath conditions, put 6.38g (48mmol) aluminum trichloride and 40ml dichloromethane into 100ml circle In the bottom flask, after stirring and dissolving, add 4.68g (60mmol) of acetyl chloride dropwise, maintain the temperature at 5-10°C, stir at 5°C for 10 minutes, and then add 5.04g (40mmol) of 2-fluoroanisole dropwise. The mixture was stirred at 5°C for 1 hour and then poured into 100ml of ice water, the aqueous layer was extracted with dichloromethane (2×30ml), the combined organic phases were washed with water (2×30ml), dried over anhydrous magnesium sulfate, suction filtered, and washed with petroleum ether The product was recrystallized from ethyl acetate with a yield of 92.4%.

[0042] Step 2 (Step 2): Preparation of 4,4-bisfluoro-1-(3-fluoro-4-methoxyphenyl)-1,3-butanedione (compound 2): 1.79g (14.4mmol ) Ethyl difluoroa...

experiment example 1

[0049] Experimental Example 1 Parameter optimization for the preparation of deracoxib

[0050] 1. Optimization of preparation parameters of 3-fluoro-4-methoxyacetophenone

[0051] Operation: Put aluminum trichloride and dichloromethane into a round-bottomed flask in an ice-water bath, stir to dissolve, add acetyl chloride dropwise, keep the temperature at 0-10°C and stir for 10 minutes, then add 2-fluoro Anisole, the mixture continued to stir at this temperature for 0.5-2 hours and then poured into ice water, the water layer was extracted with dichloromethane, the combined organic phases were washed with water, dried with anhydrous magnesium sulfate, suction filtered, and washed with petroleum ether and ethyl acetate The ester was recrystallized to obtain the product.

[0052] The different reaction parameters are shown in Table 1. The amount of DCM (ml) is 6-10 times the amount of 2-fluoroanisole mass (g) respectively (other reaction parameters are the same as in Example 1),...

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Abstract

The invention discloses a preparation method of Deracoxib, and belongs to the field of Deracoxib preparation. The preparation method of Deracoxib disclosed by the invention comprises the following steps: (1) taking methane chloride as a reaction solvent, and reacting 2-fluoroanisole with acetylchloride under the effect of acid so as to obtain 3-fluoro-4-methoxyacetophenone; (2) taking methane chloride as a reaction solvent, and reacting 3-fluoro-4-methoxyacetophenone with ethyl difluoroacetate under the effect of alkaline so as to obtain 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-1,3-butanedione; and (3) under the existence of an ethyl alcohol solvent, reacting 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-1,3-butanedione with para-sulfamine phenylhydrazine or salt thereof so as to obtain Deracoxib. According to the preparation method of Deracoxib disclosed by the invention, dichloromethane is used as a solvent, the toxicity of the solvent is low, the cost of the solvent is lower than thatof methyl tertiary butyl ether, and the production cost is obviously reduced on the premise of guaranteeing the yield.

Description

technical field [0001] The invention relates to a preparation method of deracoxib, which belongs to the field of preparation of deracoxib. Background technique [0002] Deracoxib is a new type of non-steroidal anti-inflammatory drug, which belongs to the cyclooxygenase-2 (COX-2) inhibitor, and is used to relieve pain and anti-inflammation caused by dog ​​surgery and osteoarthritis. It is currently the first A non-steroidal anti-inflammatory drug of the COX-2 inhibitor class for use in animals. At present, there are no relevant patents on the preparation of deracoxib in China, and only the US patent US5760068 is the first to disclose its structure and anti-inflammatory effect. [0003] Deracoxib, the chemical name is: 4-(3-difluoromethyl-5-(3-fluoro-4-methoxyphenyl)-1H-pyrazol-1-yl)benzenesulfonamide, the structure is as follows : [0004] [0005] Prepared by: [0006] [0007] As described in the patent US5760068, the first step is to dissolve aluminum trichloride...

Claims

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Application Information

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IPC IPC(8): C07D231/12
CPCC07D231/12
Inventor 张秀英杨洪亮
Owner NORTHEAST AGRICULTURAL UNIVERSITY
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