Supercharge Your Innovation With Domain-Expert AI Agents!

A method for synthesizing 2-aminothiazole derivatives

An aminothiazole and derivative technology, which is applied in the field of synthesizing 2-aminothiazole derivatives, can solve the problems of high catalyst cost, heating under reaction conditions, complicated preparation of raw materials, etc., and achieves the effects of easy availability of reaction reagents, widening scope and simple operation.

Active Publication Date: 2020-12-22
河北诺加生物科技有限公司
View PDF13 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The disadvantage of this method is that the preparation of raw materials is complicated, not easy to obtain, the cost of the catalyst is high, and the reaction conditions need to be heated, which is not conducive to operation.

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
  • A method for synthesizing 2-aminothiazole derivatives
  • A method for synthesizing 2-aminothiazole derivatives
  • A method for synthesizing 2-aminothiazole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The method for synthesizing 2-amino-4-phenyl-5-cyanothiazole (III-a), comprises the steps:

[0035] Add 3-carbonyl-3-phenylpropionitrile (I-a) (145 mg) and thiourea (II) (152 mg) to methanol (5 mL) at room temperature, then add tert-butanol peroxide (288 μL) and azobis Isobutyronitrile (33 mg), stirred at room temperature for 2 hours. Add saturated aqueous sodium bicarbonate solution (50mL) after the reaction, extract with ethyl acetate, the organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product, and the crude product is subjected to column chromatography (ethyl acetate:petroleum ether (v / v)=3:7) separation and purification to obtain 175 mg of white solid 2-amino-4-phenyl-5-cyanothiazole (III-a), yield: 87%.

[0036] 1 H NMR (600MHz, DMSO-d 6 )δ8.25(s,2H),7.93(d,J=7.2Hz,2H),7.56–7.39(m,3H). 13 C NMR (150MHz, DMSO-d 6 )δ170.6, 161.0, 132.5, 130.0, 128.8, 127.4, 115.3, 83.6.

Embodiment 2

[0038] The method for synthesizing 2-amino-4-(4-methoxyphenyl)-5-cyanothiazole (III-b), comprises the steps:

[0039] 3-Carbonyl-3-(4-methoxyphenyl)propionitrile (I-b) (175 mg) and thiourea (II) (152 mg) were added to methanol (5 mL) at room temperature, and peroxygen was added to the reaction tert-butanol (288 μL) and azobisisobutyronitrile (33 mg), stirred at room temperature for 2 hours. Add saturated aqueous sodium bicarbonate solution (50mL) after the reaction, extract with ethyl acetate, the organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product, and the crude product is subjected to column chromatography (ethyl acetate:petroleum ether (v / v)=3:7) separation and purification to obtain 213 mg of white solid 2-amino-4-(4-methoxyphenyl)-5-cyanothiazole (III-b), yield: 92%.

[0040] 1 H NMR (600MHz, DMSO-d 6 )δ8.19(s,2H),7.90(d,J=9.0Hz,2H),7.07(d,J=8.4Hz,2H),3.82(s,3H). 13 C NMR (150MHz, DMSO-d 6 )δ170.3,...

Embodiment 3

[0042] A method for synthesizing 2-amino-4-(4-chlorophenyl)-5-cyanothiazole (III-c), comprising the steps of:

[0043] 3-Carbonyl-3-(4-chlorophenyl)propionitrile (I-c) (180 mg) and thiourea (II) (152 mg) were added to methanol (5 mL) at room temperature, and tert-butyl peroxide was added to the reaction Alcohol (288 μL) and azobisisobutyronitrile (33 mg) were stirred at room temperature for 2 hours. Add saturated aqueous sodium bicarbonate solution (50mL) after the reaction, extract with ethyl acetate, the organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product, and the crude product is subjected to column chromatography (ethyl acetate:petroleum ether (v / v)=3:7) separation and purification to obtain 191 mg of white solid 2-amino-4-(4-chlorophenyl)-5-cyanothiazole (III-c), yield: 81%.

[0044] 1 H NMR (600MHz, DMSO-d 6 )δ8.27(s,2H),7.93(d,J=9.0Hz,2H),7.60(d,J=8.4Hz,2H). 13 C NMR (150MHz, DMSO-d 6 )δ170.7, 15...

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 discloses a method for synthesizing a 2-aminothiazole derivative. The method comprises the following steps: by taking a ketone derivative (I) with an electron withdrawing group at the alpha position and thiourea (II) as raw materials, t-butylhydroperoxide as an oxidizing agent and azodiisobutyronitrile as a free radical initiator, performing free radial coupling reaction and dehydration reaction in a solvent methanol under the condition of room temperature to reflux, so as to generate the 2-aminothiazole derivative (III), wherein the reaction formula is as shown in the description. According to the method, a non-metal azodiisobutyronitrile and t-butylhydroperoxide free radical oxidation system is utilized, the use of an expensive transition metal catalyst is avoided, the range of a substrate is enlarged, a substrate with carbonyl alpha position being electron withdrawing group is used, and an easy leaving group is not necessary. The method has the advantages of simplicityin operation, easily available reaction raw materials and reaction reagents, high yield and the like.

Description

technical field [0001] The invention relates to a method for synthesizing 2-aminothiazole derivatives. Background technique [0002] The 2-aminothiazole structure exists in a variety of pharmaceutical molecules or important intermediates in the synthesis of some natural products, such as the antiprotozoal agent Nitazoxanide (Nitazoxanide, A) [1] , non-ergot dopamine agonist pramipexole hydrochloride hydrate (Pramipexole Dihydrochloride Hydrate, B) [2] , voltage-gated sodium channel blocker and glutamate release inhibitor Riluzole (Riluzole, C) [3] , cyclooxygenase (COX) inhibitor meloxicam (Meloxicam, D) [4] Wait. Therefore, pharmaceutical molecules or natural products containing such structures can be prepared from such 2-aminothiazole compounds. [0003] [0004] In the literature and published patents, a series of 2-aminothiazole derivatives have been reported to inhibit the formation of advanced glycation end products, thereby inhibiting glucose oxidase [5] . An...

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 Patents(China)
IPC IPC(8): C07D277/56C07D417/04C07D277/40
CPCC07D277/40C07D277/56C07D417/04
Inventor 杜云飞孙纪云赵康
Owner 河北诺加生物科技有限公司
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com