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Synthetic method for 3-cyano group imidazo [1, 2-a] pyridine compounds and application thereof

The technology of a cyanoimidazole and a synthesis method is applied in the field of synthesis of 3-cyanoimidazo[1,2-a]pyridine compounds, can solve the problems of long reaction steps, low reaction yield and the like, and achieves easy operation, The effect of easy availability of raw materials and mild conditions

Inactive Publication Date: 2015-09-23
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 for 3-cyano group imidazo [1, 2-a] pyridine compounds and application thereof
  • Synthetic method for 3-cyano group imidazo [1, 2-a] pyridine compounds and application thereof
  • Synthetic method for 3-cyano group imidazo [1, 2-a] pyridine compounds and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] Use the following steps: add 2-aminopyridine (56mg, 0.6mmol), acetophenone (60mg, 0.5mmol), CuI (95mg, 0.5mmol) to a 25mL reaction tube, add solvent NMP (1mL), and finally add phenylacetonitrile (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, 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 80 mg of the product with a yield of 73%. 1 H NMR (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). 13 C NMR (100MHz, CDC...

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, 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, 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 93 mg of the product with a yield of 80%. 1 H NMR (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=8.0H...

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 H NMR (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(...

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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 synthesis method and application of 3-cyanoimidazo[1,2-a]pyridine compounds. Background technique [0002] Imidazo[1,2-a]pyridine derivatives widely exist in many important drug molecules. These drug molecules have antiviral, antibacterial, anti-inflammatory and other medicinal effects. Although there are many reports on the synthesis of this series of backbone molecules, there are few reports on the synthesis of 3-cyanoimidazo[1,2-a]pyridine compounds (Synthesis 2011, 15, 2445–2453). Moreover, the existing literature methods have disadvantages such as poor substrate universality, complex raw material synthesis, and low reaction yield. Since the cyano group, as an important functional group, can be converted into other various functional groups, it is of great significance to develop new routes for the synthesis of 3-cyanoimidazo[1,2-a]pyridine compounds. [0003] Both saripidem and necopiridan are drug molecules with an a...

Claims

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Application Information

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