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Synthetic method and application of 3-cyanoimidazo[1,2-a]pyridine compound

A cyanoimidazole and synthesis method technology, applied in the field of synthesis of 3-cyanoimidazo[1,2-a]pyridine compounds, can solve the problems of lengthy reaction steps and low reaction yield, and achieve simple operation, The effect of easy to obtain and simple raw materials

Inactive Publication Date: 2016-06-08
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of these synthetic methods have the disadvantages of lengthy reaction steps and low reaction yields.

Method used

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  • Synthetic method and application of 3-cyanoimidazo[1,2-a]pyridine compound
  • Synthetic method and application of 3-cyanoimidazo[1,2-a]pyridine compound
  • Synthetic method and application of 3-cyanoimidazo[1,2-a]pyridine compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] The following steps were adopted: 2-aminopyridine (56 mg, 0.6 mmol), acetophenone (60 mg, 0.5 mmol), CuI (95 mg, 0.5 mmol) were added to a 25 mL reaction tube, NMP (1 mL) was added, and finally phenylacetonitrile was added. (70 mg, 0.6 mmol). The reaction solution was placed in an oil bath at 120° C. and reacted under air conditions for 17 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, 10 mL of ethyl acetate was added to it, filtered through celite, the filtrate was poured into 15 mL of water, and extracted three times with ethyl acetate (3×5 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, the solvent ethyl acetate was removed by a rotary evaporator, and then separated by column chromatography to obtain 80 mg of the product with a yield of 73%. 1 HNMR (400MHz, CDCl 3 ): δ8.38(dt,J=6.8,1.2Hz,1H),8.24-8.15(m,2H),7.79(d,J=9.2Hz,1H),7.58-7.43(m,4H),7.11( td,J=6.8,0.8Hz,1H). ...

Embodiment 2

[0023]

[0024] The following steps were adopted: 2-aminopyridine (56mg, 0.6mmol), 4-methylacetophenone (67mg, 0.5mmol), CuI (95mg, 0.5mmol) were added to a 25mL reaction tube, and the solvent NMP (1mL) was added, Finally phenylacetonitrile (70 mg, 0.6 mmol) was added. The reaction solution was placed in an oil bath at 120° C. and reacted under air conditions for 17 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, 10 mL of ethyl acetate was added to it, filtered through celite, the filtrate was poured into 15 mL of water, and extracted three times with ethyl acetate (3×5 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, the solvent ethyl acetate was removed by a rotary evaporator, and then separated by column chromatography to obtain 93 mg of the product with a yield of 80%. 1 HNMR (400MHz, CDCl 3 ): δ8.36(d,J=6.8Hz,1H),8.10(d,J=8.0Hz,2H),7.77(d,J=9.2Hz,1H),7.51–7.43(m,1H),7.33 (d, J=8.0Hz, ...

Embodiment 3

[0026]

[0027]The following steps were adopted: 2-aminopyridine (56mg, 0.6mmol), 2-methylacetophenone (67mg, 0.5mmol), CuI (95mg, 0.5mmol) were added to a 25mL reaction tube, and the solvent NMP (1mL) was added, Finally phenylacetonitrile (70 mg, 0.6 mmol) was added. The reaction solution was placed in an oil bath at 100° C., and reacted under air conditions for 15 hours. After the reaction, the reaction mixture was cooled to room temperature, 10 mL of ethyl acetate was added thereto, and filtered with diatomaceous earth, the filtrate was poured into 15 mL of water, and extracted three times with ethyl acetate (3×5 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered, and the solvent ethyl acetate was removed with a rotary evaporator, and then separated by column chromatography to obtain 65 mg of the product with a yield of 56%. 1 HNMR (400MHz, CDCl 3 ):δ8.41(d,J=6.8Hz,1H),7.83(d,J=8.8Hz,1H),7.59(d,J=7.6Hz,1H),7.55–7.48(m,1H),7.42 –7.29(m...

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Abstract

The invention discloses a synthetic method for 3-cyano group imidazo [1, 2-a] pyridine compounds and an application thereof. Materials such as 2-aminopyridine compounds, methyl ketone compounds and benzyl cyanide are used to be reacted with N-heteroaryl nitrile through cheap and efficient cuprous iodide in catalyzing, oxidizing and cyclizing modes, and a series of the 3-cyano group imidazo [1, 2-a] pyridine compounds are constructed. The synthetic method has the advantages that the materials are easy to obtain, the operation is simple and convenient, the condition is gentle, the substrate is good in universality, the economic benefit is obtained, and the efficiency is achieved, and the method can be applied to efficient and simple and convenient composition of medicine molecules such as saripidem and necopidem.

Description

technical field [0001] The invention relates to a method for synthesizing a 3-cyanoimidazo[1,2-a]pyridine compound and its application. Background technique [0002] Imidazo[1,2-a]pyridine derivatives widely exist in many important drug molecules. These drug molecules have antiviral, antibacterial, and anti-inflammatory effects. Although there are many reports on the synthesis of this series of backbone molecules, the synthesis of 3-cyanoimidazo[1,2-a]pyridine compounds is rare (Synthesis 2011, 15, 2445–2453). Moreover, the existing literature methods have disadvantages such as poor substrate universality, complex synthesis of raw materials, and low reaction yields. As an important functional group, the cyano group can be converted into a variety of other functional groups, so it is of great significance for the development of new routes for the synthesis of 3-cyanoimidazo[1,2-a]pyridine compounds. [0003] Both salipide and necopidem are drug molecules with aminomethyl-s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 吕萍王彦广温俏冬
Owner ZHEJIANG UNIV