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A kind of synthetic method of imidazolone compound

A synthetic method and compound technology, applied in the direction of organic chemistry, etc., can solve the problems of difficulty in obtaining synthetic starting materials and the need to improve the reaction yield, and achieve the effect of broad market prospects

Inactive Publication Date: 2018-08-31
JIANGSU ZHIJIANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] As mentioned above, a variety of methods for the synthesis of imidazolone compounds have been disclosed in the prior art, but these methods still have certain defects, such as synthetic starting materials are often difficult to obtain, and the reaction yield still needs to be improved

Method used

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  • A kind of synthetic method of imidazolone compound
  • A kind of synthetic method of imidazolone compound
  • A kind of synthetic method of imidazolone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]

[0038] At room temperature, in an appropriate amount of organic solvent (a mixture of diethylene glycol monobutyl ether and acetonitrile at a volume ratio of 1:3), add 100 mmol of the above formula (I) compound, 150 mmol of the above formula (II) compound, 10 mmol of catalyst ( It is a mixture of 2.5mmol tris(acetylacetonate)ruthenium and 7.5mmol cerium trifluoromethanesulfonate), 100mmol oxidant cerium ammonium nitrate, 100mmol base tetramethylethylenediamine (TMEDA) and 20mmol auxiliary agent tetraphenylporphyrin; Then the temperature was raised to 70° C., and the reaction was stirred at this temperature for 9 hours;

[0039] After the reaction is over, filter the reaction liquid while it is hot, adjust the pH value of the filtrate to neutral, then fully wash with aqueous sodium carbonate, then add acetone to extract 2-3 times, combine the organic phases, concentrate under reduced pressure, and pass the residue over 200 - 300-mesh silica gel column chromatography...

Embodiment 2

[0042]

[0043] At room temperature, in an appropriate amount of organic solvent (a mixture of diethylene glycol monobutyl ether and acetonitrile at a volume ratio of 1:3), add 100 mmol of the above formula (I) compound, 200 mmol of the above formula (II) compound, 15 mmol of catalyst ( It is a mixture of 3.4mmol tris(acetylacetonate)ruthenium and 11.6mmol cerium trifluoromethanesulfonate), 130mmol oxidant cerium ammonium nitrate, 150mmol alkali tetramethylethylenediamine (TMEDA) and 25mmol auxiliary agent tetraphenylporphyrin; Then the temperature was raised to 80° C., and the reaction was stirred at this temperature for 8 hours;

[0044] After the reaction is over, filter the reaction liquid while it is hot, adjust the pH value of the filtrate to neutral, then fully wash with aqueous sodium carbonate, then add acetone to extract 2-3 times, combine the organic phases, concentrate under reduced pressure, and pass the residue over 200 - 300-mesh silica gel column chromatogra...

Embodiment 3

[0047]

[0048] At room temperature, in an appropriate amount of organic solvent (a mixture of diethylene glycol monobutyl ether and acetonitrile at a volume ratio of 1:3), add 100 mmol of the above formula (I) compound, 250 mmol of the above formula (II) compound, 20 mmol of catalyst ( A mixture of 4mmol tris(acetylacetonate) ruthenium and 16mmol cerium trifluoromethanesulfonate), 160mmol oxidant cerium ammonium nitrate, 200mmol base tetramethylethylenediamine (TMEDA) and 30mmol auxiliary agent tetraphenylporphyrin; to 90°C, and stirred and reacted at this temperature for 6 hours;

[0049] After the reaction is over, filter the reaction liquid while it is hot, adjust the pH value of the filtrate to neutral, then fully wash with aqueous sodium carbonate, then add acetone to extract 2-3 times, combine the organic phases, concentrate under reduced pressure, and pass the residue over 200 - 300-mesh silica gel column chromatography, eluting with a mixture of chloroform and petr...

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Abstract

The invention relates to a synthesis method for an imidazolone compound shown in the formula (III). The synthesis method includes the steps that a compound of the formula (I) is reacted with a compound of the formula (II) in an organic solvent when a catalyst, an oxidizing agent, alkali and an assistant exist, aftertreatment is carried out after the reaction, and therefore the compound in formula (III) (please see the specification) is obtained, wherein R1 is selected from H or C1-C6 alkyl; R2 is selected from C1-C6 alkyl; R3 is selected from H or C1-C6 alkyl or halogen; X is halogen. According to the synthesis method, specific reaction substrates and the unique reaction system are adopted, the imidazolone compound is efficiently converted under the synthetic action of multiple reagent combinations accordingly, the high-yield technical effect is obtained, and quite-broad market prospects are achieved.

Description

technical field [0001] The invention relates to a synthesis method of imidazolone compounds, belonging to the technical field of organic chemical synthesis. Background technique [0002] The imidazolone structure is a fragment of various biologically active molecules, which usually have a variety of pharmaceutical activities, such as RSV inhibitors, non-nucleoside reverse transcriptase, etc., so it is very important in organic chemical synthesis, especially in the design of drug molecules. important. [0003] According to existing reports, some methods for synthesizing imidazolone structures have been developed in the prior art, such as: [0004] Darin J.Gustin et al. ("Discovery and SAR studies of a novel series of noncovalent cathepsin S inhibitors", Bioorganic & Medicinal Chemistry Letters, 2005,15,1687-1691) reported a synthetic method of imidazolone compounds, the reaction formula is as follows: [0005] [0006] Philip H. Elsinga et al. (“Synthesis and Evaluation ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/26
CPCC07D235/26
Inventor 付正云黄程
Owner JIANGSU ZHIJIANG CHEM
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