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Preparation method of triazoie compound

A compound, triazole technology, applied in the field of preparation of triazole compounds, can solve the problems of complex operation, high cost, low product yield, etc.

Active Publication Date: 2015-04-29
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the preparation process of Suvorexant, the intermediate compound (1) needs to be prepared first, and in the prior art, the methods disclosed in the patent application WO2013169610 are complex and cumbersome to operate, and its isomer impurity compound (2) is easily generated, resulting in The yield of product is low, and cost is high, is unfavorable for industrialized production,

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  • Preparation method of triazoie compound
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  • Preparation method of triazoie compound

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specific Embodiment approach

[0027] In order to enable those skilled in the art to better understand the technical solutions of the present invention, some non-limiting examples are further disclosed below to further describe the present invention in detail.

[0028] The reagents used in the present invention can be purchased from the market or can be prepared by the methods described in the present invention.

[0029] In the present invention, g means gram, mL means milliliter, rpm means revolution / minute, and mol / L means mole / liter.

Embodiment 1

[0031] In the reactor, add 250mL of acetone, stir, add 26.2g of compound (01), then add 35.0g of potassium carbonate, 0.38g of cuprous iodide (CuI), 7.6g of 1,2,3-triazole and 200mL of acetone. The external temperature was raised to 70° C., during which a large amount of gas was generated, and the reaction solution was refluxed for 5 hours. Then the reaction solution was distilled under reduced pressure. When the reaction system was relatively viscous, 30 mL of water was added, and the distillation was continued until there was no acetone in the distillate (gas phase detection without acetone). 300 mL of water was added to the residue after distillation, and 6 mol / L hydrochloric acid was added dropwise at room temperature to adjust the pH of the system to 1-2 to obtain a khaki suspension. Stir for 15 minutes, filter, and wash the solid with water 3 times, 50 mL each time. The obtained solid was vacuum-dried to dryness at 70°C to obtain 19.45 g of a light green solid, which wa...

Embodiment 2

[0033] In the reactor, add 350mL butanone, stir, add 26.2g of compound (01), then add 44.15g of potassium carbonate trihydrate, 0.38g of cuprous iodide (CuI), and 7.6g of 1,2,3-triazole. The external temperature was raised to 85° C., during which a large amount of gas was generated, and the reaction solution was refluxed for 5 hours. Then the reaction solution was distilled under reduced pressure at 40°C. When the reaction system was relatively viscous, 50 mL of water was added, and the distillation was continued until the distillate was free of butanone (gas phase detection without butanone). 300 mL of water was added to the residue after distillation, and concentrated hydrochloric acid was added dropwise at room temperature to adjust the pH of the system to 1-2 to obtain a yellow suspension. Stir for 30 minutes, filter, and wash the solid with water 3 times, 60 mL each time. The obtained solid was vacuum-dried to dryness at 60° C. to obtain 19.29 g of a light green solid, w...

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Abstract

The invention provides a preparation method of a triazoie compound and belongs to the technical field of pharmaceutical manufacturing. The preparation method comprises the following steps: a raw material reacts in a ketone reaction solvent at a solvent reflow temperature in the presence of alkali and cuprous iodide, and after reaction, through post-processing, an objective product is obtained; the ketone reaction solvent is acetone, butanone, 3-pentanone or the combination thereof. Through selecting and controlling conditions such as reaction temperature and the like, a product with low content of isomere impurities can be obtained, the method is simple and convenient to operate and is suitable for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of a triazole compound, which belongs to the technical field of pharmacy. Background technique [0002] Suvorexant (trade name Belsomra) is an orexin (orexin) receptor antagonist that can affect the signal transduction of the orexin pathway and is clinically used to treat diseases such as insomnia; its structure is shown in the following formula: [0003] [0004] In the preparation process of Suvorexant, the intermediate compound (1) needs to be prepared first, but in the prior art, the methods disclosed in the patent application WO2013169610 are complicated and cumbersome to operate, and its isomer impurity compound (2) is easily generated, resulting in The yield of product is low, and cost is high, is unfavorable for industrialized production, [0005] [0006] In order to solve the above problems, the present inventor has developed a new method for preparing compound (1) after research, which can...

Claims

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Application Information

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IPC IPC(8): C07D249/06
CPCC07D249/06
Inventor 何必飞刘光元樊玉平
Owner SUNSHINE LAKE PHARM CO LTD
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