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A kind of synthetic method of intermediate thiosuccinimide compound in pharmaceutical field

A technology of thiosuccinimide and synthesis method, applied in directions such as organic chemistry, can solve the problems of low product yield, increased reaction flow and the like, and achieve the effects of low price and good industrial production potential

Inactive Publication Date: 2016-09-21
庞凤
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] As mentioned above, the synthetic method of multiple N-thioether succinimides is disclosed in the prior art, but these methods still have certain defectives, for example use the sulfur phenolic compound that has malodorous smell and toxicity, or need Firstly, disulfide is synthesized, which leads to increased reaction process and low product yield

Method used

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  • A kind of synthetic method of intermediate thiosuccinimide compound in pharmaceutical field
  • A kind of synthetic method of intermediate thiosuccinimide compound in pharmaceutical field
  • A kind of synthetic method of intermediate thiosuccinimide compound in pharmaceutical field

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Experimental program
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Effect test

Embodiment 1

[0048]

[0049] At room temperature, in an appropriate amount of organic solvent dimethylsulfoxide (DMSO), add 100mmol formula (II) compound bromobenzene, 100mmol formula (III) compound N-bromosuccinimide, 150mmol formula (IV) compound vulcanization Ammonium, 200mmol base 2-methylpiperidine, 4mmol catalyst (as 3mmol copper trifluoromethanesulfonate (Cu(OTf) 2 ) and 1 mmol of tetrakis(triphenylphosphine) palladium), the temperature was raised to 70° C., and the reaction was stirred at this temperature for 15 hours, and the whole reaction process was carried out under nitrogen atmosphere.

[0050] After the reaction is finished, place it, let it cool naturally to room temperature, fully wash with deionized water, separate layers, get the upper layer with a camera, remove the solvent under reduced pressure, and the residue is subjected to flash column chromatography (the eluent used in flash column chromatography is dichloro The mixture of methane and petroleum ether, wherein ...

Embodiment 2

[0054]

[0055] At room temperature, in an appropriate amount of organic solvent dimethylsulfoxide (DMSO), add 100mmol formula (II) compound p-bromotoluene, 150mmol formula (III) compound N-bromosuccinimide, 200mmol formula (IV) compound Ammonium sulfide, 300mmol base 2-methylpiperidine, 7mmol catalyst (as 5mmol copper trifluoromethanesulfonate (Cu(OTf) 2 ) and 2 mmol of tetrakis(triphenylphosphine) palladium), the temperature was raised to 90° C., and the reaction was stirred at this temperature for 12 hours, and the whole reaction process was carried out under nitrogen atmosphere.

[0056] After the reaction is finished, place it, let it cool naturally to room temperature, fully wash with deionized water, separate layers, get the upper layer with a camera, remove the solvent under reduced pressure, and the residue is subjected to flash column chromatography (the eluent used in flash column chromatography is dichloro The mixture of methane and petroleum ether, wherein the ...

Embodiment 3

[0060]

[0061] At room temperature, in an appropriate amount of organic solvent dimethylsulfoxide (DMSO), add 100mmol formula (II) compound o-bromonitrobenzene, 200mmol formula (III) compound N-bromosuccinimide, 250mmol formula (IV ) compound ammonium sulfide, 400mmol base 2-methylpiperidine, 10mmol catalyst (7.5mmol copper trifluoromethanesulfonate (Cu(OTf) 2 ) and 2.5 mmol of tetrakis(triphenylphosphine) palladium), the temperature was raised to 110° C., and the reaction was stirred at this temperature for 8 hours, and the whole reaction process was carried out under nitrogen atmosphere.

[0062] After the reaction is finished, place it, let it cool naturally to room temperature, fully wash with deionized water, separate layers, get the upper layer with a camera, remove the solvent under reduced pressure, and the residue is subjected to flash column chromatography (the eluent used in flash column chromatography is dichloro The mixture of methane and petroleum ether, wher...

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Abstract

The invention relates to a synthesis method of a sulfo-succinimide compound as shown in a formula (I) as an intermediate in a pharmaceutical field. The method comprises the following step: reacting a compound in a formula (II), a compound in a formula (III) and a compound in a formula (IV) in an organic solvent in presence of alkali and a solvent, so as to obtain the compound in the formula (I), wherein R is H, halogen, nitro, C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkyl or halogenated C1-C6 alkoxy; X1 and X2 are independently halogen; and m is an integer from 0 to 3. According to the method, a target product with high yield can be obtained through combined synergistic effect of a proper catalyst, alkali and the solvent; and the method has good application prospect and industrialization potential.

Description

technical field [0001] The invention relates to a synthesis method of a sulfur-containing compound, more particularly to a synthesis method of an intermediate thiosuccinimide compound in the pharmaceutical field, and belongs to the field of medicinal chemical intermediates. Background technique [0002] In the field of medicinal chemistry, sulfur is an important component, and sulfur-containing compounds are important building blocks and / or intermediates of many drugs, such as penicillin, sulfonamides, various cephalosporins, and VB1. elements or contain sulfur-containing heterocycles. [0003] In addition, due to the relatively active nature of sulfur, the groups connected to it can be introduced into the parent structure of the drug, or the peripheral groups of the parent structure of the drug can be modified and improved. [0004] Therefore, in the field of medicinal chemistry, sulfur-containing compounds are a class of important structural units and / or intermediates, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/48
CPCC07D207/48
Inventor 庞凤
Owner 庞凤
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