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Preparation method of pyrrolidine-2, 5-dione derivatives

A technology of alkyl and compound, applied in the field of medicine, can solve problems to be developed and so on

Inactive Publication Date: 2017-06-27
WWHS BIOTECH INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, current methods for preparing pyrrolidinyl compounds remain to be developed

Method used

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  • Preparation method of pyrrolidine-2, 5-dione derivatives
  • Preparation method of pyrrolidine-2, 5-dione derivatives
  • Preparation method of pyrrolidine-2, 5-dione derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] In this example, the influence of the type of reaction solvent, the combination of silver salt, the reaction temperature and the amount of aliphatic silver salt was studied.

[0113] Carry out the reaction according to the following reaction formula, wherein the whole reaction system is carried out under nitrogen atmosphere, the concentration of substrate 5a is 0.1mmol, the concentration of aliphatic silver salt is 0.22mmol, the volume of reaction solvent is 10mL, and the reaction time is 24 hours.

[0114]

[0115] The influence of the combination of table 1 reaction solvent type, silver salt, temperature of reaction and the amount of aliphatic silver salt

[0116] sequence silver source temperature(°C) solvent 6a yield (%) 1 a

AgOAc 120 toluene 50 2 b

AgOAc 120 toluene 80 3 c

AgOAc 120 toluene 80 4 b

AgOAc 120 DMF 72 5 b

AgOAc 120 wxya 70 6 b

AgOAc 120 1,2-DCB 70 7 b ...

Embodiment 2

[0120] In this example, the study substrate R 1 The effect of the type of group.

[0121] The reaction was carried out according to the following reaction formula, wherein the concentration of substrate 5 was 0.1 mmol, the concentration of AgOAc was 0.22 mmol, the volume of toluene was 10 mL, the reaction temperature was 120° C., and the time was 24 hours.

[0122]

[0123] It can be seen that the electronic properties of the substituents on the aromatic ring do not affect the transformation, such as N-Fused imidazoles with electroneutral (6a) and halogen atom groups (6b), electron donating groups (6c and 6d) and absorbing Electron groups (6e and 6f) also succeeded in giving the desired products in moderate to good yields (71-80%). In addition, substituents on the aromatic ring system also gave the desired results (6g, 75%; 6h, 80%; 6i, 65%; 6j, 68%). N-Fused imidazole with 2-furyl (6k), N-methyl-2-pyrrolyl (6l), 2-thiazolyl (6m), 3-indolyl (6n) and ethyl carboxylate ( 6...

Embodiment 3

[0125] In this example, the effect of heterocycles in the substrate was investigated.

[0126] The reaction was carried out according to the following reaction formula, wherein the concentration of substrate 7 was 0.1 mmol, the concentration of AgOAc was 0.22 mmol, the volume of toluene was 10 mL, the reaction temperature was 120° C., and the time was 24 hours.

[0127]

[0128] Heterocyclic compounds pyrazine, pyrimidine, benzothiazole and adenine were used instead of the pyridine ring (the pyridine ring of substrate 5 in Example 1) as substrates. found regardless of R 1 Regardless of group differences, pyrazine, pyrimidine, benzothiazole, and adenine as heterocyclic substituents reacted smoothly, and the products were obtained in good to excellent yields (8a, 78%; 8b, 60%; 8c, 65%; 8d, 70%, 8e, 50%).

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PUM

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Abstract

The invention provides a method for preparing compounds shown as a formula 1, the compounds and reactants. The method comprises the step of performing an oxidation rearrangement reaction on compounds shown as a formula 2 and compounds shown as a formula 3 to obtain the compounds shown as the formula 1. By the method, synthesis of a series of biologically-active and diversely-functionalized 3-aminopyrrolidine-2,5-dione derivatives (compounds shown as the formula 1) is achieved, the yield is high, and operation is easy.

Description

technical field [0001] The present invention relates to the field of medicine. Specifically, the present invention relates to a method for preparing pyrrolidine-2,5-dione derivatives. More specifically, the present invention relates to methods, compounds and reactants for the preparation of compounds represented by Formula 1. Background technique [0002] The pyrrolidinyl fragment (formula below) is a pharmacodynamic backbone structure with important biological activities for many different active targets, and widely exists in various drugs and their clinical research compounds. Aminoxopyrrolidine is an important structure, and it exists in a wide range of drug molecules, such as analgesics, antiviral agents, antidepressants, antibacterial agents, anti-inflammatory drugs or anti-ischemic, anti-tumor or central nervous system ligand. [0003] [0004] However, current methods for preparing pyrrolidinyl compounds remain to be developed. Contents of the invention [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C07D417/12C07D473/34C07D401/12C07D417/14C07D471/04C07D513/04
CPCC07D403/12C07D401/12C07D417/12C07D417/14C07D471/04C07D473/34C07D513/04
Inventor 王国新廖滔唐梅杰
Owner WWHS BIOTECH INC
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