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A kind of synthetic method of quinazolinone compound

A synthesis method and quinazolinone technology are applied in the field of organic chemical intermediate synthesis, and can solve the problems of limited means of source of reaction materials, and the synthesis yield needs to be further improved.

Active Publication Date: 2016-12-14
上海凌富药物研究有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, there are certain defects in these methods, for example, the substrate needs to be pre-functionalized or materials with specific functional groups need to be selected, which leads to the limitation of the source of reaction materials; in addition, the synthesis yield needs to be further improved

Method used

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  • A kind of synthetic method of quinazolinone compound
  • A kind of synthetic method of quinazolinone compound
  • A kind of synthetic method of quinazolinone compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] In the appropriate amount of solvent DMF in the synthesis kettle, add 100mmol of the above formula (I) compound and 120mmol of the above formula (II) compound, stir and mix for 10 minutes, then add 5mmol tetraacetonitrile palladium tetrafluoroborate, 20mmol scandium trifluoromethanesulfonate and 6mmol of 1-benzyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide salt, then stirred and heated to 60°C for 10 hours;

[0036] After the reaction, the reaction system was naturally cooled to room temperature, filtered, deionized water was added to the filtrate, and then sodium bicarbonate was added to neutralize the system until the pH of the system was 6.5-7.5, then extracted three times with dichloromethane, the organic phases were combined, and vacuum Concentrate, recrystallize the resultant with ethanol, filter the solid, and dry in vacuo to obtain the compound of formula (III) with a yield of 95.8%.

[0037] 1 H-NMR (400MHz, DMSO) δ: 12.41(s, 1H), 8.18(d...

Embodiment 2

[0039]

[0040]In the appropriate amount of solvent DMF in the synthesis kettle, add 100mmol of the above formula (I) compound and 140mmol of the above formula (II) compound, stir and mix for 15 minutes, then add 8mmol tetraacetonitrile palladium tetrafluoroborate, 30mmol scandium trifluoromethanesulfonate and 9mmol of 1-benzyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide salt, then stirred and heated to 70°C for 9 hours;

[0041] After the reaction, the reaction system was naturally cooled to room temperature, filtered, deionized water was added to the filtrate, and then sodium bicarbonate was added to neutralize the system until the pH of the system was 6.5-7.5, then extracted three times with dichloromethane, the organic phases were combined, and vacuum Concentrate, recrystallize the resultant with ethanol, filter the solid, and dry in vacuo to obtain the compound of formula (III) with a yield of 96.2%.

[0042] 1 H-NMR (400MHz, DMSO) δ: 12.54 (s, 1H), 8.26-8....

Embodiment 3

[0044]

[0045] In the appropriate amount of solvent DMF in the synthesis kettle, add 100mmol of the above formula (I) compound and 150mmol of the above formula (II) compound, stir and mix for 12 minutes, then add 10mmol tetraacetonitrile palladium tetrafluoroborate, 50mmol scandium trifluoromethanesulfonate and 12mmol of 1-benzyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide salt, then stirred and heated to 65°C for 9 hours;

[0046] After the reaction, the reaction system was naturally cooled to room temperature, filtered, deionized water was added to the filtrate, and then sodium bicarbonate was added to neutralize the system until the pH of the system was 6.5-7.5, then extracted three times with dichloromethane, the organic phases were combined, and vacuum Concentrate, recrystallize the resultant with ethanol, filter the solid, and dry in vacuo to obtain the compound of formula (III) with a yield of 95.4%.

[0047] 1 H-NMR (400MHz, DMSO) δ: 12.43 (s, 1H), 8.17...

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Abstract

The invention provides a synthesis method for a quinazolinone compound shown as a formula (III). The synthesis method includes adding compounds shown as a formula (I) and a formula (II) into solvents in a reactor; stirring and mixing the compounds and the solvents with one another for 10-15 minutes; then adding catalysts, auxiliaries and accelerators into the reactor; stirring and heating the catalysts, the auxiliaries, the accelerators, the compounds and the solvents until the temperatures of the catalysts, the auxiliaries, the accelerators, the compounds and the solvents reach 60-70 DEG C, carrying out reaction on the catalysts, the auxiliaries, the accelerators, the compounds and the solvents for 8-10 hours to obtain the compound shown as the formula (III). R1 and R2 respectively independently represent alkyl groups or halogen or nitro groups or cyano groups of H, C1, C<2>, C<3>, C<4>, C<5> and C<6>. The synthesis method has the advantages that target products with high yields can be obtained under the mutual synergistic effects of the catalysts, the auxiliaries, the accelerators and the solvents, accordingly, the purpose of developing novel substrate reaction sources for synthesizing the quinazolinone compound can be achieved, and the synthesis method has a broad market prospect.

Description

technical field [0001] The invention relates to a method for synthesizing nitrogen-containing heterocyclic compounds, more particularly to a method for synthesizing quinazolinone compounds, and belongs to the field of synthesis of organic chemical intermediates. Background technique [0002] As an important pharmacological module, the quinazolinone structure widely exists in natural products and drugs, for example, camelline A in the traditional Chinese medicine Evodia rutaecarpa for the treatment of headache and cholera showed an effect on mouse leukemia P388 cells Inhibitory effect, and raltitrexed, which also contains the quinazolinone parent structure, has also played a great role in clinical treatment. [0003] In addition, the quinazolinone structure also has a variety of other biopharmaceutical activities, such as anti-virus, anti-inflammatory, anti-microbial, anti-malarial and so on. [0004] It is precisely because of the important role and application potential of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/91
CPCC07D239/91
Inventor 王文明
Owner 上海凌富药物研究有限公司