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A kind of method for preparing parecoxib intermediate

A technology of parecoxib and intermediates, applied in the field of drug synthesis, can solve the problems of complex reaction steps, high equipment requirements, fluoride environmental pollution, etc., and achieve the effect of increased reaction yield, simple reaction steps and mild conditions

Inactive Publication Date: 2018-07-03
姚美艳 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In the above method, the intermediate 5-methyl-3,4-diphenylisoxazole has complicated reaction steps, which can be obtained through the cyclization step first, and then dehydration, and in the cyclization step, the acetyl oxygen is also It will participate in the hydroxylamine reaction to generate by-products; in addition, the elimination step uses trifluoroacetic acid system for dehydration, which requires high equipment, and fluoride will also cause environmental pollution

Method used

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  • A kind of method for preparing parecoxib intermediate
  • A kind of method for preparing parecoxib intermediate
  • A kind of method for preparing parecoxib intermediate

Examples

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Embodiment 1

[0021] A method for preparing parecoxib intermediate, the method comprising: 1,2-diphenyl-2-acetyl ethyl ketone 29.1g (100mmol), ammonium acetate 23.1g (300mmol), iodobenzene diacetate 16.1 g (50mmol), potassium iodide 8.3g (50mmol) were added in the flask that 120ml dichloromethane was housed, 60 ℃ carried out contact reaction for 1 hour, after reaction finished, the organic phase was concentrated, washed with water, washed with saturated saline, anhydrous sodium sulfate Dry, then recrystallize from ethanol, and dry to obtain 21.1 g of 5-methyl-3,4-diphenylisoxazole, an intermediate of parecoxib, with a yield of 89.7% and a purity of 99.45%.

Embodiment 2

[0023] A method for preparing parecoxib intermediate, the method comprising: 1,2-diphenyl-2-acetyl ethyl ketone 29.1g (100mmol), ammonium acetate 38.5g (500mmol), iodobenzene diacetate 12.9 g (40mmol), potassium iodide 9.9g (60mmol) were added in the flask that 120ml dichloromethane was housed, 50 ℃ carried out contact reaction for 1 hour, after the reaction finished, the organic phase was concentrated, washed with water, washed with saturated saline, anhydrous sodium sulfate Dry, then recrystallize from ethanol, and dry to obtain 21.2 g of 5-methyl-3,4-diphenylisoxazole, an intermediate of parecoxib, with a yield of 90.1% and a purity of 99.39%.

Embodiment 3

[0025] A method for preparing parecoxib intermediate, the method comprising: 1,2-diphenyl-2-acetyl ethyl ketone 29.1g (100mmol), ammonium acetate 30.8g (400mmol), iodobenzene diacetate 12.9 g (40mmol) and potassium iodide 8.3g (50mmol) were added to a flask containing 120ml of dichloromethane, and the contact reaction was carried out at 55°C for 1 hour. After the reaction, the organic phase was concentrated, washed with water, washed with saturated brine, anhydrous sodium sulfate Dry, then recrystallize from ethanol, and dry to obtain 20.8 g of 5-methyl-3,4-diphenylisoxazole, an intermediate of parecoxib, with a yield of 88.6% and a purity of 99.41%.

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Abstract

The invention discloses a method for preparing a parecoxib intermediate. The method includes subjecting 1, 2-diphenyl-2-acetyl ethyl ketone and ammonium acetate to contact reaction with the presence of iodobenzene diacetate and potassium iodide, performing organic-phase concentration and washing after reaction, performing ethyl alcohol recrystallization, and drying to obtain 5-methyl-3, 4-diphenyl isoxazole. The method for preparing the parecoxib intermediate has the advantages of simplicity in procedure and high yield.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a method for preparing a parecoxib intermediate. Background technique [0002] Parecoxib Sodium (Parecoxib Sodium) is a specific cyclooxygenase-2 inhibitor that can be given intravenously and intramuscularly. . The chemical name of parecoxib sodium is N-[[4-(5-methyl-3-phenyl-4-isoxazolyl)phenyl]sulfonyl]propionamide sodium salt, and the specific structure is as follows: [0003] [0004] At present, there are many studies on the synthesis method of parecoxib (sodium), but basically all of them use 5-methyl-3,4-diphenylisoxazole as the key intermediate to prepare parecoxib. For example, WO2005123701A1 discloses a preparation method of parecoxib, which uses diacetophenone as a starting material, first reacts with tetrahydropyrrole, and then undergoes acetylation, ring-closure reaction with hydroxylamine hydrochloride, elimination and dehydration to obtain an intermed...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D261/08
CPCC07D261/08
Inventor 姚美艳肖波王晓岳
Owner 姚美艳
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