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Asymmetric heterocyclic ring substituent urea compound and preparation method and application thereof

A substituted urea, asymmetric technology, applied in the field of asymmetric heterocyclic substituted urea compounds, can solve problems such as unsafe production, and achieve the effect of a safe and non-toxic preparation method

Active Publication Date: 2014-04-16
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Another object of the present invention is to overcome the shortcomings of unsafe production in the existing synthetic method of asymmetric substituted urea, and provide a safe and stable synthetic method of asymmetric substituted urea

Method used

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  • Asymmetric heterocyclic ring substituent urea compound and preparation method and application thereof
  • Asymmetric heterocyclic ring substituent urea compound and preparation method and application thereof
  • Asymmetric heterocyclic ring substituent urea compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] This example illustrates the preparation of (5-trifluoromethyl-1,3,4-thiadiazol-2-yl)phenylcarbamate

[0079]

[0080] 6g (0.355mol) NaH was added into a 250mL round-bottomed flask containing 25mL THF, and 5-trifluoromethyl-1,3,4-thiadiazol-2-amine (20g , 0.118mol) into a 100mL constant-pressure dropping funnel, and added dropwise under an ice bath. After the dropwise addition was completed, the reaction was continued for 15 min under ice bath, and then diphenyl carbonate (25.33 g, 0.118 mol) was added, and the reaction was continued for 5 hours under ice bath, overnight at 20°C. After the reaction was completed, 100 mL of ethyl acetate was added to the reaction solution, the organic phase was separated, and then washed 3 times with saturated brine (50 mL each time), the organic phase was dried with anhydrous sodium sulfate, spin-dried the solvent, and washed with petroleum Ether / ethyl acetate=1:1 (volume ratio) was separated through a silica gel column to obtain (5...

Embodiment 2

[0082] This example illustrates the preparation of 1-(pyridin-2-yl)-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)urea (compound 1)

[0083] (5-trifluoromethyl-1,3,4-thiadiazol-2-yl)carbamate phenyl ester (500mg, 1.73mmol) and 2-pyridinamine (195.3mg , 2.075mmol) and 2mL THF were added into a microwave reaction bottle, and the microwave reaction bottle was placed in an Initiator Biotage microwave reactor with a reaction temperature of 150°C and a reaction time of 25 minutes. After the reaction, a large amount of white solid precipitated, filtered, washed with tetrahydrofuran, and dried at room temperature to obtain compound 1, a total of 280.2 mg, yield 56.4%, white solid, m.p.225-227 ° C, 1 H NMR [DMSO, 400MHz]: δ=12.859(s, 1H, NH), 10.123(s, 1H, NH), 8.35(d, J=4Hz, 1H), 7.861-7.817(m, 1H), 7.528( d, J=8.4Hz, 1H), 7.149-7.118 (t, J=6.2Hz, 1H); ESI-MS: (M - )m / z(%)=287(100); theoretical value: C 9 h 6 f 3 N 5 OS (289.2): C, 37.37; H, 2.09; N, 24.21, actual value: C, 37.27; ...

Embodiment 3

[0085] This example illustrates the preparation of 1-(6-methylpyridin-2-yl)-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)urea (compound 2)

[0086] (5-trifluoromethyl-1,3,4-thiadiazol-2-yl)carbamate phenyl ester (500mg, 1.73mmol) and 6-picoline-2 prepared according to the method of Example 1 - Amine (187mg, 1.73mmol) and 2mL THF were added to a microwave reaction vial, and the microwave reaction vial was placed in an Initiator Biotage microwave reactor with a reaction temperature of 150°C and a reaction time of 25 minutes. After the reaction, a large amount of white solid precipitated, filtered, washed with tetrahydrofuran, and dried at room temperature to obtain compound 2, 240.2mg, yield 55.0%, white solid, m.p.238-240°C, 1 H NMR [DMSO, 300MHz] δ=13.056(s, 1H, NH), 10.130(s, 1H, NH), 7.746(t, J=10.6Hz, 1H), 7.330(d, J=11.2Hz, 1H) , 7.016 (d, J=10.0Hz, 1H), 2.476 (s, 3H, CH3); ESI-MS: (M - )m / z(%)=302(100); theoretical value: C 10 h 8 f 3 N 5 OS.(303.3): C, 39.6; H, 2.66;...

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Abstract

The invention relates to an asymmetric heterocyclic ring substituent urea compound and a preparation method and application thereof. The compound is a compound or a non-toxic salt thereof with a structure shown in the formula I, wherein R1 is selected from halogen, nitryl, cyan, hydroxyl, ester group, carboxyl, trifluoromethyl, alkyl, alkoxyl, aryl, heteroaryl, aryloxy, acyl, acyloxy or heterocyclic radical; and R2 is selected from alkyl, aryl, heteroaryl or cluste aryl. The asymmetric heterocyclic ring substituent urea compound has the characteristics of weeding activity, sterilizing activity and plant growth adjusting activity; and the preparation method is safe and non-toxic.

Description

technical field [0001] The invention relates to an unsymmetrical heterocyclic substituted urea compound, its preparation method and application. Background technique [0002] Unsymmetrical heterocyclic substituted urea compounds are extremely useful and important fine chemicals and chemical raw materials, and can be widely used as herbicides, insecticides, plant growth regulators and pharmaceutical intermediates. Due to the differently substituted peptide bonds (-CO-NH-) in the structure, most of them are biologically active, and the asymmetric urea unit is a common structural feature of many enzyme inhibitors and biomimetic peptides. The traditional method for the synthesis of unsymmetrically substituted ureas is the phosgene or phosgene-based isocyanate method. Because isocyanate is unstable, it is not easy to store, and highly toxic phosgene is used, so the production is extremely unsafe. Therefore, it is of great significance to study the synthesis of urea compounds, e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12C07D285/135A01N47/36A01P13/00A01P3/00A01P21/00
Inventor 席真陈文彬李克建王勇
Owner NANKAI UNIV
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