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Preparation method of 3-chloro-4-amino maleimide compound

A technology of maleimide and chlorosuccinimide, applied in the field of organic compound synthesis, to achieve the effects of simple post-processing, high yield and purity, and high reaction efficiency

Active Publication Date: 2021-04-16
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the discovery of amine halogenation reagents in 1953, they have been widely used in the amine halogenation reaction of alkenes to synthesize β-halogenated organic amine compounds. Such reactions often use relatively stable sulfonamide chloride or amide chloride reagents. In 2019, Fu The Junkai research group reported for the first time that terminal olefins and amine halogenation reagents containing 8-aminoquinoline as a directing group realized the amine chlorination and amine bromination of olefins under the action of copper catalysis (Directed Copper-Catalyzed Intermolecular Aminative Difunctionalization of UnactivatedAlkenes, J.Am.Chem.Soc.2019, 141, 46, 18475-18485); so far, the use of amine halogenation reagents as substrates to realize the amine oxide halogenation of alkenes has not been reported

Method used

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  • Preparation method of 3-chloro-4-amino maleimide compound
  • Preparation method of 3-chloro-4-amino maleimide compound
  • Preparation method of 3-chloro-4-amino maleimide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 3-chloro-4-morpholino-1-phenylmaleimide

[0031]

[0032] At room temperature, N-phenylmaleimide (0.2mmol, 1.0equiv), N-chlorosuccinimide (0.6mmol, 3.0equiv), cuprous chloride (0.02mmol, 0.1equiv) and 2mL of toluene were added to the reaction tube, then morpholine (0.6mmol, 3.0equiv) was added, gas pumped and replaced with oxygen three times, stirred at room temperature for 1h, and then stirred at a reaction temperature of 100°C for 23h. The reaction mixture was cooled, then diluted with ethyl acetate, the organic phase was filtered into a heart bottle, the organic solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ethyl acetate was 9:1), The product was a yellow solid with a melting point of 145-146° C., a yield of 90%, and a product weight of 52 mg.

[0033] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0034] 1 H NMR (500MHz, CDCl 3 ): δ7.43(t, J=7...

Embodiment 2

[0040] Synthesis of 3-chloro-4-hexahydropyridyl-1-phenylmaleimide

[0041]

[0042]At room temperature, N-phenylmaleimide (0.2mmol, 1.0equiv), N-chlorosuccinimide (0.6mmol, 3.0equiv), cuprous chloride (0.02mmol, 0.1equiv) and 2mL of toluene were added to the reaction tube, then hexahydropyridine (0.6mmol, 3.0equiv) was added, pumped and replaced with oxygen three times, stirred at room temperature for 1h, and then stirred at a reaction temperature of 100°C for 23h. The reaction mixture was cooled, then diluted with ethyl acetate, the organic phase was filtered into a heart bottle, the organic solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ethyl acetate was 9:1), The product is a yellow liquid, the yield is 82%, and the product weight is 47mg.

[0043] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0044] 1 H NMR (500MHz, CDCl 3 ): δ7.49-7.45(m, 2H), 7.39-7.35(m, 3H), ...

Embodiment 3

[0050] Synthesis of 3-chloro-4-tetrahydropyrrolyl-1-phenylmaleimide

[0051]

[0052] At room temperature, N-phenylmaleimide (0.2mmol, 1.0equiv), N-chlorosuccinimide (0.6mmol, 3.0equiv), cuprous chloride (0.02mmol, 0.1equiv) and 2mL of toluene were added to the reaction tube, then tetrahydropyrrole (0.6mmol, 3.0equiv) was added, pumped and replaced with oxygen three times, stirred at room temperature for 1h, and then stirred at 100°C for 23h. The reaction mixture was cooled, then diluted with ethyl acetate, the organic phase was filtered into a heart bottle, the organic solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ethyl acetate was 9:1), The product was a yellow solid with a melting point of 117-118°C, a yield of 92%, and a product weight of 51 mg.

[0053] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0054] 1 H NMR (500MHz, CDCl 3 ): δ7.49-7.45(m, 2H), 7.38-7.34(...

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Abstract

The invention relates to a preparation method of a 3-chloro-4-amino maleimide compound, which comprises the following steps: in an organic solvent and under the condition of oxygen, using N-chloro succinimide, secondary amine and N-substituted maleimide as reaction raw materials; under the catalytic action of transition metal copper, using an in-situ generated chloramidation reagent, and carrying out free radical cascade reaction to obtain the 3-chloro-4-amino maleimide compound. The method is simple in reaction condition and high in product yield and purity, opens up a synthetic route and method for preparation of the 3-chloro-4-amino maleimide compound, and has good application potential and research value.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, in particular to a preparation method of 3-chloro-4-aminomaleimide compound. Background technique [0002] 3,4-Difunctionalized maleimide as the core skeleton widely exists in marine natural alkaloids and anti-tumor active molecules with important biological activities, candidate drug molecules and AIE fluorescent materials, such as: G2 cell cycle checkpoint kinase Isogranulatimide, LPS-induced macrophage inhibitor Himanimide A, anti-breast cancer drug Camphorataimide B, specific porcupine inhibitor, marine alkaloid aqabamycin G, and liver X receptor agonist GSK3987. In addition, maleimide can also undergo a variety of functional group transformations to synthesize derivatives such as succinimide, tetrahydropyrrole and 2-pyrrolone. Therefore, exploring the efficient construction of 3,4-difunctionalized maleimides from cheap and readily available raw materials has become one of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/456
Inventor 吴戈周雪莹张文亮
Owner WENZHOU MEDICAL UNIV
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