5-amino-1,4-disubstituent-1,2,3-triazole and preparation method thereof

A technology of disubstituted and triazoles, which is applied in the design of organic synthesis routes and the preparation of raw materials and intermediates, achieves the effects of cheap and easy-to-obtain raw materials, mild and easily controllable reaction conditions, and high product yields

Active Publication Date: 2013-09-18
鄄城县人民医院
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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 ring

Method used

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  • 5-amino-1,4-disubstituent-1,2,3-triazole and preparation method thereof
  • 5-amino-1,4-disubstituent-1,2,3-triazole and preparation method thereof
  • 5-amino-1,4-disubstituent-1,2,3-triazole and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 0-5°C under a nitrogen atmosphere, add 2-cyanoacetamide (IIIa) (1.0g, 12mmol), sodium ethoxide (1.0g, 15mmol) and 20mL of absolute ethanol into the reaction flask, react for 30 minutes, add dropwise [3aR-(3aα, 4α, 6α, 6aα)]-6-azido-2,2-dimethyl-tetrahydro-4H-cyclopentadiene-1,3-dioxol-4 - Alcohol (II) (2.0 g, 10 mmol) in 20 mL ethanol. Slowly raise the temperature to co-flow, and keep the reflux reaction for 5 hours, and TLC detects that the reaction is complete. Cool to room temperature and filter to remove solids. The residue precipitated after adding water, filtered, and the solid was recrystallized with ethanol and ethyl acetate to obtain 1-[3aR-(3aα, 4α, 6α, 6aα)-[2,2-dimethyl-tetrahydro-4H- Cyclopenta-1,3-dioxol-4-ol]-6-yl]-5-amino-4-carboxamido-1,2,3-triazole (I) 2.4g , yield 84.8%.

Embodiment 2

[0030] 0-5°C under a nitrogen atmosphere, add 2-cyanoacetamide (IIIa) (1.0g, 12mmol), sodium methoxide (0.8g, 15mmol) and 20mL of anhydrous methanol into the reaction flask, react for 30 minutes, drop Add [3aR-(3aα, 4α, 6α, 6aα)]-[6-azido-2,2-dimethyl-tetrahydro-4H-cyclopentadiene-1,3-dioxol - 4-Oxy]ethanol (II) (2.4 g, 10 mmol) in 20 mL of methanol. Slowly rise to choke temperature, and keep at room temperature for 24 hours, and TLC detects that the reaction is complete. The solid was removed by filtration, and the residue was precipitated after adding water. After filtration, the product was recrystallized with isopropanol and ethyl acetate to obtain 1-[3aR-(3aα, 4α, 6α, 6aα)-[[2,2-dimethyl Base-tetrahydro-4H-cyclopentadiene-1,3-dioxol-4-oxyl]ethanol]-6-yl]-5-amino-4-carboxamido-1,2, 2.6 g of 3-triazole (I), yield 79.5%.

Embodiment 3

[0032] Add malononitrile (IIIc) (0.8g, 12mmol), potassium tert-butoxide (1.8g, 15mmol) and dry tetrahydrofuran solvent 25mL into the reaction flask under nitrogen atmosphere at 0-5°C, react for 30 minutes, drop Add [3aR-(3aα, 4α, 6α, 6aα)]-[6-azido-2,2-dimethyl-tetrahydro-4H-cyclopentadiene-1,3-dioxol -4-Oxy]methyl acetate (II) (2.7g, 10mmol) was dissolved in 30mL of tetrahydrofuran. Slowly rise to co-current, and maintain the reflux reaction for 6 hours, TLC detection of the completion of the reaction. The solid was removed by filtration, and the residue was precipitated after adding water. After filtration, the crude product was recrystallized with ethanol and ethyl acetate to obtain 1-[3aR-(3aα, 4α, 6α, 6aα)-[[2,2-dimethyl- Tetrahydro-4H-cyclopentadieno-1,3-dioxol-4-oxy]methyl acetate]-6-yl]-5-amino-4-cyano-1,2,3 - Triazole (I) 2.9g, yield 86.1%.

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Abstract

The invention discloses a 5-amino-1,4-disubstituent-1,2,3-triazole and a preparation method thereof. The compound (I) is a key intermediate for preparing medicines with a 1,2,3-triazole structure, such as ticagrelor. The preparation method for 5-amino-1,4-disubstituent-1,2,3-triazole comprises the following step of: performing cyclization reaction on an azide (II) with a cyano derivative (III) to obtain 5-amino-1,4-disubstituent-1,2,3-triazole. The preparation method is easily-available in raw materials, moderate in conditions, and high in yield.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis route design and preparation of raw materials and intermediates, in particular to a novel intermediate 5-amino-1,4-disubstituent-1,2,3-triazole and its preparation method. 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, ...

Claims

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Application Information

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IPC IPC(8): C07D405/04
Inventor 许学农
Owner 鄄城县人民医院
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