Azide and preparation method thereof

An azide compound and azidation technology, applied in the direction of organic chemistry, to achieve the effects of high product yield and chiral purity, mild and easy-to-control reaction conditions, and simple preparation methods

Active Publication Date: 2013-09-18
徐州飞云泡沫制品有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] So far, there is no method for constructing 1,2,3-triazole first, and then constructing [4,5]pyrimidine ring to prepare ticagrelor

Method used

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  • Azide and preparation method thereof
  • Azide and preparation method thereof
  • Azide and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add [3aR-(3aα, 4α, 6α, 6aα)]-6-amino-2,2-dimethyl-tetrahydro-4H-cyclopentadiene-1,3-dioxane in the reaction flask Pentan-4-ol (II) (1.73g, 10mmol), potassium carbonate (2.76g, 20mmol), copper sulfate (32mg, 2%eq) and anhydrous methanol 25mL, add imidazolesulfonyl azide at 0°C under nitrogen atmosphere Nitrogen (III) (2.1 g, 12 mmol) in methanol was stirred at room temperature and reacted for 5 hours. TLC detected that the reaction was complete. Concentrate under reduced pressure, and recrystallize the residue with n-hexane and ethyl acetate to obtain [3aR-(3aα, 4α, 6α, 6aα)]-6-azido-2,2-dimethyl-tetrahydro-4H - Cyclopenta-1,3-dioxol-4-ol (I) 1.8 g, yield 90.4%.

Embodiment 2

[0028] Add [3aR-(3aα, 4α, 6α, 6aα)]-[6-amino-2,2-dimethyl-tetrahydro-4H-cyclopentadiene-1,3-dioxa to the reaction flask Cyclopent-4-oxyl]ethanol (II) (2.17g, 10mmol), potassium carbonate (2.76g, 20mmol), copper sulfate (32mg, 2%eq) and acetonitrile 25mL, added trifluoro A solution of methanesulfonyl azide (III) (2.1 g, 12 mmol) in acetonitrile was stirred at room temperature and reacted for 3 hours. TLC detected that the reaction was complete. Concentrate under reduced pressure, and recrystallize the residue with n-hexane and ethyl acetate to obtain [3aR-(3aα, 4α, 6α, 6aα)]-[6-azido-2,2-dimethyl-tetrahydro- 4H-Cyclopenta-1,3-dioxol-4-oxyl]ethanol (I) 2.25 g, yield 92.6%.

Embodiment 3

[0030] Add [3aR-(3aα, 4α, 6α, 6aα)]-[6-amino-2,2-dimethyl-tetrahydro-4H-cyclopentadiene-1,3-dioxa to the reaction flask Cyclopent-4-oxyl]methyl acetate (II) (2.45g, 10mmol) and dry tetrahydrofuran 30mL, cooled to 0°C and added dropwise sodium hydride (6g, 60% mineral oil) in tetrahydrofuran under nitrogen atmosphere solution and p-toluenesulfonyl azide (III) (3.0 g, 15 mmol) in tetrahydrofuran. After the dropwise addition was completed, the temperature was raised to room temperature, and the reaction was stirred for 30 hours, and TLC detected that the reaction was complete. The reaction was quenched with methanol in an ice bath, poured into water, adjusted to weakly acidic pH with hydrochloric acid, extracted three times with ethyl acetate, and dried over anhydrous sodium sulfate. Concentrate to dryness under reduced pressure, recrystallize from n-hexane / ethyl acetate to obtain off-white solid [3aR-(3aα, 4α, 6α, 6aα)]-[6-azido-2,2-dimethyl-tetra Hydrogen-4H-cyclopentadieno-1...

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Abstract

The invention discloses an azide and a preparation method thereof. The azide (I) can be used as a key raw material for preparing medicines with a 1,2,3-triazole structure, such as ticagrelor. The preparation method for the azide comprises the following step of: performing azidation reaction on an amino compound (II) and an azidation reagent (III) to obtain the azide (I). The preparation method is moderate in conditions, safe and environmentally-friendly, high in chemical yield, and especially capable of keeping the original absolute configuration and chiral purity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis route design and preparation of raw materials and intermediates, and in particular relates to a new azide compound and a preparation method thereof. Background technique [0002] 1,2,3-Triazole is an important triazine aromatic heterocycle, because it is easy to form hydrogen bonds, coordination bonds, etc., and can play a variety of non-covalent interactions, so it is widely used in the construction of high molecular Various types of functional molecules such as catalysts, drugs and their supramolecular drugs. In recent years, especially in the field of medicine, 1,2,3-triazole parent rings have been widely used to design new drug molecules. So far, many compounds containing 1,2,3-triazole parent rings have entered clinical trials or It has been used clinically, involving many therapeutic fields such as anti-bacteria, anti-fungal, anti-tuberculosis, anti-virus, anti-tumor, anti-coagula...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/44
Inventor 许学农
Owner 徐州飞云泡沫制品有限责任公司
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