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Chiral amino quinazoline compound as well as preparation method and application thereof

A technology of aminoquinazoline and phenylquinazoline, which is applied in the field of chiral aminoquinazoline compounds and their preparation, can solve the problems of reduced drug efficacy, aggravated pollution, different biological activities and the like, and achieves a simple synthesis route Effect

Active Publication Date: 2022-06-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the multiple enantiomers of pharmaceutical and pesticide molecules, isomers with different configurations generally have different biological activities, and enantiomers with low or ineffective or toxic side effects may lead to reduced drug efficacy , pollution intensified, and it is very likely to lead to drug damage or drug resistance

Method used

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  • Chiral amino quinazoline compound as well as preparation method and application thereof
  • Chiral amino quinazoline compound as well as preparation method and application thereof
  • Chiral amino quinazoline compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] The preparation of embodiment 1 chiral amine

[0081] Dissolve 600g of S-mandelic acid in 1800ml of ethanol, then add 600g of 2-amino-5-diethylaminopentane, stir to release heat to room temperature, precipitate a large amount of solid, filter with suction, and retain the filtrate to obtain a white solid, 75 It was dried at °C to obtain 520 g of S-mandelate. The above mandelate was dissolved in 1200 mL of water, neutralized with 15% (w / v) sodium hydroxide solution to pH=11, stirred and extracted twice with 1000 mL of dichloromethane, and the filtrates were combined after separation, and the solution was mixed with waterNa 2 SO 4 Dry, filter and spin to dry to obtain (S)-2-amino-5-diethylaminopentane (ie (S)-N',N'-diethyl-1,4-pentanediamine), weighed 260g.

[0082] The filtrate obtained in the previous step was spin-dried and added with 1200 mL of water, neutralized to pH=11 with a 15% (w / v) sodium hydroxide solution, stirred and extracted with 1200 mL of dichlorometh...

Embodiment 2

[0083] The preparation of embodiment 2 (S)-4-amino-2-phenylquinazoline

[0084] (1) Synthesis of 2-phenylquinazolin-4(3H)-one:

[0085] Take 50.0g anthranilamide, 40.0g benzaldehyde, 85g CuCl 2 , add 600 mL of ethanol, stir and react at 80 ° C for 16 h, TLC detection (developing solvent is ethyl acetate and petroleum ether mixed in a volume ratio of 1:1) After the anthranilamide reaction, add 500 mL of water to continue heating and stirring 1 h, filtered, and the filter cake was dried at 90° C. to obtain 67.2 g of a white solid. The solid was 2-phenylquinazolin-4(3H)-one, and the yield was 82.3%.

[0086] (2) Synthesis of 4-chloro-2-phenylquinazoline:

[0087] The solid obtained in step (1) was added to 200 mL of chloroform, 115.0 g of SOCl 2 , the reaction was carried out at 70°C for 12h, and the tail gas was absorbed by 30% (w / w) NaOH solution. TLC detection (developing solvent is obtained by mixing dichloromethane and petroleum ether in a volume ratio of 1:1) After the ...

Embodiment 3

[0094] Example 3 Preparation of (S)-4-amino-2-(4-chlorophenyl)-quinazoline

[0095] (1) Synthesis of 2-(4-chlorophenyl)-quinazolin-4(3H)-one:

[0096] Take 45.0g anthranilamide, 48.0g 4-chlorobenzaldehyde, 80.0g CuCl respectively 2 , add 500 mL of isopropanol, stir at 82 ° C for 16 h, TLC detection (developing solvent is ethyl acetate and petroleum ether mixed by volume 1:1) After the anthranilamide reaction, add 400 mL of water to continue heating Stir for 1 h, filter, and dry the filter cake at 90° C. to obtain 66.8 g of 2-(4-chlorophenyl)-quinazolin-4(3H)-one as a light yellow solid, with a yield of 81.5%.

[0097] (2) Synthesis of 4-chloro-2-(4-chlorophenyl)-quinazoline:

[0098] The solid obtained in step (1) was added to 200 mL of chloroform, 105 g of SOCl 2 , the reaction was carried out at 80°C for 12h, and the tail gas was absorbed by 30% (w / w) NaOH solution. TLC detection (developing solvent is obtained by mixing dichloromethane and petroleum ether in a volume ra...

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Abstract

The invention discloses a chiral amino quinazoline compound as well as a preparation method and application thereof. The structural formula of the chiral amino quinazoline compound is shown as a formula I or II. The preparation method comprises the following steps: reacting anthranilamide, substituted benzaldehyde and CuCl2 to obtain a product, reacting the product with a chlorination reagent, and reacting the product with chiral amine and an acid-binding agent to obtain a chiral amino quinazoline compound crude product; and dissolving by using a salt-forming solvent, and purifying to obtain the chiral amino quinazoline compound. The preparation method is simple, the obtained chiral amino quinazoline compound can be easily separated from acid salt-forming crystals, and chiral acid with high optical purity can be efficiently separated by using the chiral amino quinazoline compound as a resolving agent. And the resolving agent and the remaining chiral acid after resolution can be recycled for racemization, so that the purposes of energy conservation, emission reduction and consumption reduction are achieved.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a chiral aminoquinazoline compound and its preparation method and application. Background technique [0002] Optically active chemical substances have a wide range of applications in medicine, pesticides and other fields. Among the multiple enantiomers of pharmaceutical and pesticide molecules, isomers with different configurations generally have different biological activities, and enantiomers with low or ineffective or toxic side effects may lead to reduced drug efficacy , Pollution intensifies, and it is very likely to lead to drug damage or drug resistance. Therefore, it is of great significance to efficiently obtain optically active chiral compounds. [0003] Most of the products of common chemical synthesis are inactive racemates, which must be resolved to obtain a single enantiomer. The current resolution methods include biological enzyme resolution method, c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/94C07B57/00C07C51/41C07C51/02C07C51/48C07C53/19
CPCC07D239/94C07B57/00C07C51/412C07C51/02C07C51/48C07B2200/07C07C53/19Y02P20/55
Inventor 张逸伟代晨廖能王湘丽林东恩
Owner SOUTH CHINA UNIV OF TECH
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