Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of 3-morpholinyl-4-arylseleno maleimide compound

A technology of methylmaleimide and maleimide, which is applied in the field of organic compound synthesis, can solve the problems of reducing the discovery opportunities of innovative drug molecules and the inability to effectively apply late-stage modification of drug molecules, and achieve high yields , high yield and purity, and easy post-treatment

Active Publication Date: 2020-11-24
WENZHOU MEDICAL UNIV
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Baidya's group reported the transition metal ruthenium-catalyzed oxidative selenylation reaction of maleimide and diaryldiselenide. However, the pre-preparation of diaryldiselenide and the use of noble metal ruthenium catalysts make this reaction difficult. It can be effectively applied to the late modification of drug molecules, reducing the chance of discovery of innovative drug molecules

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
  • Preparation method of 3-morpholinyl-4-arylseleno maleimide compound
  • Preparation method of 3-morpholinyl-4-arylseleno maleimide compound
  • Preparation method of 3-morpholinyl-4-arylseleno maleimide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of N-methyl-3-morpholino-4-(4-methylphenylselenyl)maleimide

[0036]

[0037] At room temperature, 4-methylphenylboronic acid (0.6mmol, 3.0equiv), selenium powder (0.6mmol, 3.0equiv), morpholine (0.6mmol, 3.0equiv), N-methylmaleimide (0.2 mmol, 1.0equiv), cuprous iodide (0.04mmol, 0.2equiv), 1,10-phenanthroline (0.04mmol, 0.2equiv), silver carbonate (0.4mmol, 2.0equiv), cesium carbonate (0.6mmol, 3.0equiv), and 2mL N,N-dimethylformamide were added to the reaction tube, then filled with oxygen, and replaced three times, and stirred at a reaction temperature of 140°C for 36h. The reaction mixture was cooled, then diluted with ethyl acetate, extracted with brine, the organic phase was separated, dried with anhydrous sodium sulfate, filtered to a chicken heart bottle, then the solvent was spun off, and the product was obtained by column chromatography (elution Agent: petroleum ether: ethyl acetate is 9: 1), the product is a yellow liquid, the yield is 87%, and...

Embodiment 2

[0045] Synthesis of N-methyl-3-morpholino-4-(4-methoxyphenylselenyl)maleimide

[0046]

[0047] At room temperature, 4-methoxyphenylboronic acid (0.6mmol, 3.0equiv), selenium powder (0.6mmol, 3.0equiv), morpholine (0.6mmol, 3.0equiv), N-methylmaleimide ( 0.2mmol, 1.0equiv), cuprous iodide (0.04mmol, 0.2equiv), 1,10-phenanthroline (0.04mmol, 0.2equiv), silver carbonate (0.4mmol, 2.0equiv), cesium carbonate (0.6mmol , 3.0equiv), and 2mL N,N-dimethylformamide were added to the reaction tube, then filled with oxygen, and replaced three times, and stirred at a reaction temperature of 140°C for 36h. The reaction mixture was cooled, then diluted with ethyl acetate, extracted with brine, the organic phase was separated, dried with anhydrous sodium sulfate, filtered to a chicken heart bottle, then the solvent was spun off, and the product was obtained by column chromatography (elution Agent: petroleum ether: ethyl acetate is 9: 1), the product is a yellow liquid, the yield is 88%, an...

Embodiment 3

[0055] Synthesis of N-methyl-3-morpholino-4-(4-fluorophenylselenyl)maleimide

[0056]

[0057] At room temperature, 4-fluorophenylboronic acid (0.6mmol, 3.0equiv), selenium powder (0.6mmol, 3.0equiv), morpholine (0.6mmol, 3.0equiv), N-methylmaleimide (0.2mmol , 1.0equiv), cuprous iodide (0.04mmol, 0.2equiv), 1,10-phenanthroline (0.04mmol, 0.2equiv), silver carbonate (0.4mmol, 2.0equiv), cesium carbonate (0.6mmol, 3.0 equiv), and 2mL N,N-dimethylformamide were added to the reaction tube, then filled with oxygen, and replaced three times, and stirred at a reaction temperature of 140°C for 36h. The reaction mixture was cooled, then diluted with ethyl acetate, extracted with brine, the organic phase was separated, dried with anhydrous sodium sulfate, filtered to a chicken heart bottle, then the solvent was spun off, and the product was obtained by column chromatography (elution Agent: petroleum ether: ethyl acetate is 9: 1), the product is a yellow liquid, the yield is 65%, an...

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 relates to a preparation method of a 3-morpholinyl-4-arylseleno maleimide compound. The preparation method comprises the following steps: in an organic solvent, under the condition of oxygen, by using arylboronic acid, selenium powder, morpholine and N-methylmaleimide as reaction raw materials, and carrying out a four-component cascade reaction under the common synergistic catalyticaction of a transition metal copper catalyst, a silver salt, a ligand and alkali, so as to obtain the 3-morpholinyl-4-arylseleno maleimide compound. The method is simple in reaction condition and highin product yield and purity, opens up a synthetic route and method for preparation of the 3-morpholinyl-4-arylseleno maleimide compound, and has good application potential and research values.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a preparation method of a 3-morpholino-4-arylselenomaleimide 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 mate...

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): C07D207/456
CPCC07D207/456
Inventor 吴戈马云飞
Owner WENZHOU MEDICAL UNIV