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Synthetic method of quinoline-4-formamides compound

A technology of formamides and synthesis methods, which is applied in the field of synthesis of quinoline-4-carboxamides, can solve problems such as application limitations, and achieve the effects of simple operation, simple process, and avoiding environmental pollution

Active Publication Date: 2017-12-22
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In particular, 2-aryl-4-carboxamide-quinoline compounds can also be used as prolyl-tRNA synthetase inhibitors and calcium-dependent proteolytic enzyme inhibitors and GABA A Regulators, etc., and its preparation method is mainly based on the Pfitzinger reaction through multiple steps, while generating a large amount of waste, so that the application of the classic synthesis method in actual production is greatly limited

Method used

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  • Synthetic method of quinoline-4-formamides compound
  • Synthetic method of quinoline-4-formamides compound
  • Synthetic method of quinoline-4-formamides compound

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Embodiment 1

[0016]

[0017] Add 1a (0.5mmol, 88.6mg), 2a (0.5mmol, 73.6mg), iodine (0.25mmol, 63.5mg), triethylamine (0.25mmol, 25.3mg) and chlorobenzene (2mL) into a 25mL sealed tube , and then placed in an oil bath at 130 °C and stirred for 10 h. Add 50mL of water to quench the reaction, extract with ethyl acetate (50mL×3), and then the organic phase is treated with 10% Na 2 S 2 o 3 The solution was washed successively with saturated brine, and dried over anhydrous sodium sulfate. Filtration, spin-drying, and silica gel column separation (petroleum ether / ethyl acetate=5 / 1) gave white solid product 2-phenylquinoline-4-carboxamide 3a (106.7 mg, 86%). The characterization data of this compound are as follows: 1 H NMR (600MHz, DMSO-d 6 ):δ(ppm)8.36(s,1H),8.35–8.30(m,2H),8.29(d,J=7.8Hz,1H),8.18(s,1H),8.14(d,J=7.8Hz, 1H),7.99(s,1H),7.85–7.79(m,1H),7.68–7.62(m,1H),7.62–7.55(m,2H),7.55–7.50(m,1H); 13 C NMR (150MHz, DMSO-d 6 )δ(ppm)168.7,155.8,148.0,143.1,138.3,130.1,129.9,129.5,128.9...

Embodiment 2

[0019] Add 1a (0.5mmol, 88.6mg), 2a (0.5mmol, 73.6mg), iodine (0.25mmol, 63.5mg), triethylamine (0.25mmol, 25.3mg) and chlorobenzene (2mL) into a 25mL sealed tube , and then placed in an oil bath at 120°C and stirred for 10 h. Add 50mL of water to quench the reaction, extract with ethyl acetate (50mL×3), and then the organic phase is treated with 10% Na 2 S 2 o 3 The solution was washed successively with saturated brine, and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=5 / 1) to obtain the target product 3a (104.2 mg, 84%).

Embodiment 3

[0021] Add 1a (0.5mmol, 88.6mg), 2a (0.5mmol, 73.6mg), iodine (0.25mmol, 63.5mg), diethylamine (0.25mmol, 18.3mg) and chlorobenzene (2mL) into a 25mL sealed tube , and then placed in an oil bath at 120°C and stirred for 10 h. Add 50mL of water to quench the reaction, extract with ethyl acetate (50mL×3), and then the organic phase is treated with 10% Na 2 S 2 o 3 The solution was washed successively with saturated brine, and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=5 / 1) to obtain the target product 3a (83.1 mg, 67%).

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Abstract

The invention discloses a synthetic method of a quinoline-4-formamides compound, and belongs to the technical field of organic synthesis. The the invention is characterized in that the synthetic method of the quinoline-4-formamides compound comprises the following steps: dissolving an oxime ester acetate compound and isatin or a derivative of the oxime ester acetate compound and the isatin in a solvent; then adding a catalyst and alkali to carry out reaction at 100 to 130 DEG C in a sealing tube to prepare the quinoline-4-formamides compound. A synthetic process of the synthetic method disclosed by the invention is simple and high-efficient; through one-pot series connection reaction, the quinoline-4-formamides compound is directly prepared in one step, so that resource waste and environment pollution caused by the use of a plurality of reagents in multi-step reaction, purification treatment on intermediates obtained in all reaction steps and the like are avoided, raw materials are cheap and easy to get or the raw materials are easy to prepare; reaction conditions are mild, and a substrate has a wide application range.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of quinoline-4-carboxamide compounds. Background technique [0002] Studies have shown that quinoline-4-carboxamide derivatives are a dominant drug molecular structure, which covers a wide range of drug activities. For example, as antagonists of peptide GPCRs and inhibitors of NK3, CCR3, CCR5, NPY5, VCAM. In particular, 2-aryl-4-carboxamide-quinoline compounds can also be used as prolyl-tRNA synthetase inhibitors and calcium-dependent proteolytic enzyme inhibitors and GABA A Regulators, etc., and its preparation method is mainly based on the Pfitzinger reaction through multiple steps, while generating a large amount of waste, so that the application of the classic synthesis method in actual production is greatly limited. Therefore, researching and developing the synthesis of quinoline-4-carboxamide compounds with cheap and safe reagents ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18C07D215/52C07D405/04C07D409/04
CPCC07D215/52C07D221/18C07D405/04C07D409/04
Inventor 高庆贺刘兴霞刘兆敏杨利敏原焕贺爽
Owner XINXIANG MEDICAL UNIV
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