Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

4-aminopyridazinone compound and preparation method thereof

A technology of aminopyridazinone and compounds, which is applied in the field of organic chemical synthesis, can solve problems such as harsh reaction conditions, potential safety hazards, and equipment corrosion, and achieve the effects of mild reaction conditions, avoiding high-temperature reflux, and high yields

Active Publication Date: 2020-08-14
CHENGDU UNIV
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But, the method for synthesizing the pyridazinone skeleton by the above-mentioned method has obvious shortcoming, as: (1) needs to use the bigger and expensive hydrazine reagent of toxicity; (3) It is often necessary to use a large amount of strong acid such as concentrated hydrochloric acid, resulting in serious corrosion of equipment and potential safety hazards

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 4-aminopyridazinone compound and preparation method thereof
  • 4-aminopyridazinone compound and preparation method thereof
  • 4-aminopyridazinone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] Synthesis of compound 4a: Take a dry hard reaction tube, add α-bromohydrazone 1a (36.6 mg, 0.1 mmol) into the reaction tube, add azlactone 2a (35.6 mg, 0.15 mmol), and then add anhydrous carbonic acid Sodium (10.6 mg, 0.1 mmol), and finally anhydrous toluene (2 mL) was added to replace the nitrogen, and the reaction was carried out at room temperature for 24 h under the protection of nitrogen. After the reaction was completed, the solvent was concentrated under reduced pressure, separated and purified by column chromatography (volume ratio: petroleum ether / ethyl acetate=10 / 1-3 / 1) to obtain compound 4a as a white solid, the purity of which was detected by HPLC was 99%, and the yield was 98%.

[0042] Scale-up reaction: Scale up the reaction until the feed amount of α-halohydrazone 1a is 1.0 g. After the reaction is completed, concentrate under reduced pressure and recover the reaction solvent toluene. After concentrating to dryness, add CH to the system 2 C...

Embodiment 2

[0044]

[0045]Synthesis of compound 4b: Take a dry hard reaction tube, add α-bromohydrazone 1b (35.2 mg, 0.1 mmol) into the reaction tube, add azlactone 2a (35.6 mg, 0.15 mmol), and then add anhydrous carbonic acid Potassium (13.8mg, 0.1mmol), finally added anhydrous chloroform (2mL), replaced nitrogen, reacted at room temperature for 24h under the protection of nitrogen. After the reaction was completed, the solvent was concentrated under reduced pressure, separated and purified by column chromatography (petroleum ether / ethyl acetate=10 / 1-3 / 1) to obtain compound 4b. White solid, yield 81%; m.p.:221.8-222.0℃. 1 H NMR (300MHz, CDCl 3 )δ7.95(d, J=7.9Hz, 2H), 7.88(d, J=6.5Hz, 2H), 7.75-7.71(m, 3H), 7.64(t, J=7.9Hz, 1H), 7.53- 7.38(m, 8H), 7.22-7.18(m, 1H), 7.11-7.09(m, 4H), 4.94(d, J=17.5Hz, 1H), 3.47(d, J=17.4Hz, 1H). 13 C NMR (75MHz, CDCl 3 )δ166.1, 166.0, 152.8, 136.9, 134.5, 134.2, 133.5, 132.1, 131.1, 129.1, 128.90, 128.87, 128.65, 128.64, 127.0, 126.6, 126.0, 58.8, ...

Embodiment 3

[0047]

[0048] Synthesis of compound 4c: Take a dry hard reaction tube, add α-chlorohydrazone 1c (35.2 mg, 0.1 mmol) into the reaction tube, add azlactone 2a (35.6 mg, 0.15 mmol), and then add anhydrous carbonic acid Potassium hydrogen (10.0 mg, 0.1 mmol), and finally anhydrous toluene (2 mL) was added to replace the nitrogen, and the reaction was carried out at room temperature under the protection of nitrogen for 24 h. After the reaction was completed, the solvent was concentrated under reduced pressure, separated and purified by column chromatography (petroleum ether / ethyl acetate=10 / 1-3 / 1) to obtain compound 4c. White solid, yield 84%. m.p.:189.0-191.5℃. 1 H NMR (300MHz, CDCl 3 )δ7.88-7.85 (m, 2H), 7.80-7.77 (m, 2H), 7.56-7.42 (m, 9H), 7.34-7.32 (m, 3H), 4.70 (d, J=17.4Hz, 1H) , 3.79(d, J=17.5Hz, 1H), 3.39(s, 3H). 13 C NMR (75MHz, CDCl 3 )δ166.6, 166.5, 153.1, 134.9, 134.2, 133.5, 132.2, 131.1, 129.6, 129.4, 128.9, 128.7, 127.0, 126.5, 126.2, 59.2, 41.3, 32.7. HRM...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a 4-aminopyridazinone compound and a preparation method thereof. The invention belongs to the technical field of organic chemical synthesis, and the invention also discloses apreparation method of the compound. According to the invention, the alpha-halogenated hydrazone compound and actone or an actone precursor are used for [4+2] cyclization reaction for the first time toconstruct the 4-aminopyridazinone compound. According to the method, the blank of synthesis of the 4-aminopyridazinone compound is filled up, and the variety of pyridazinone alkaloids is enriched, sothat more selectable compound sources are provided for screening of drug activity, and a chemical combination library for drug screening is enriched. The method has the advantages of mild reaction conditions, easily available raw materials, simple operation and high yield.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to 4-aminopyridazinone compounds and a preparation method thereof. Background technique [0002] The structure of pyridazinone is the core skeleton of many natural products and drugs, some of which have been approved for marketing as drugs, such as Zardaverine, Imazodan, Pimobendan, etc. 4-aminopyridazinone is a member of the pyridazinone skeleton, and the existing reported molecular structure containing the 4-aminopyridazinone skeleton is as follows: [0003] [0004] According to existing reports, the above-mentioned compounds containing 4-aminopyridazinone skeleton have a wide range of biological activities, many of which have been proved to have antibacterial, anti-inflammatory, anti-cancer, anti-tumor activities, and have great potential application value . Therefore, it is of great significance to provide novel 4-aminopyridazinone compounds and to devel...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/04
CPCC07D237/04
Inventor 赵建强全保学游勇王振华袁伟成
Owner CHENGDU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com