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Synthesis method of pyrimido-indazole compound

A synthetic method and compound technology, applied in the direction of organic chemistry, can solve the problems of harsh reaction conditions, expensive catalysts, cumbersome post-treatment, etc., and achieve the effect of simple process, easy operation, avoiding waste of resources and environmental pollution

Active Publication Date: 2019-06-21
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These literature methods have the disadvantages of using corrosive and toxic reagents and expensive catalysts, harsh reaction conditions, tedious post-processing and low yields, which largely limit the application of this type of synthetic method in practical production.

Method used

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  • Synthesis method of pyrimido-indazole compound
  • Synthesis method of pyrimido-indazole compound
  • Synthesis method of pyrimido-indazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018]

[0019] Add benzaldehyde 1a (53mg, 0.5mmol), 3-aminoindazole 2a (66.5mg, 0.5mmol), triethylamine (126mg, 1.25mmol), ammonium iodide (108.8mg, 0.75mmol) into a 35mL reaction flask and chlorobenzene (2mL), then placed in an oil bath at 120°C and stirred for 12h. Add 50mL of water to quench the reaction, extract with ethyl acetate (50mL×3), and then the organic phase is treated with 10% Na 2 S 2 o 3 The solution was washed successively with saturated brine, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=15 / 1) to obtain the yellow solid product 3aa (112.7 mg, 92%). The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 8.68 (d, J = 4.4Hz, 1H), 8.36 (d, J = 8.4Hz, 1H), 8.25–8.16 (m, 2H), 7.87 (d, J = 8.8Hz, 1H) ,7.67–7.57(m,4H),7.34(d,J=7.2Hz,1H),7.31–7.27(m,1H); 13 C NMR (100MHz, CDCl 3 )δ (ppm) 151.0, 145.2, 145.0 (4), 144.9 (8), 131.3...

Embodiment 2

[0021] Add 1a (53mg, 0.5mmol), 2a (66.5mg, 0.5mmol), triethylamine (126mg, 1.25mmol), ammonium iodide (72.5mg, 0.5mmol) and chlorobenzene (2mL) into a 35mL reaction flask, Then placed in an oil bath at 120°C and stirred for 12h. Add 50mL of water to quench the reaction, extract with ethyl acetate (50mL×3), and then the organic phase is treated with 10% Na 2 S 2 o 3 The solution was washed successively with saturated brine, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=15 / 1) to obtain the yellow solid product 3aa (100.4 mg, 82%).

Embodiment 3

[0023] Add 1a (53mg, 0.5mmol), 2a (66.5mg, 0.5mmol), triethylamine (126mg, 1.25mmol), ammonium iodide (72.5mg, 0.5mmol) and chlorobenzene (2mL) into a 35mL reaction flask, Then placed in an oil bath at 110°C and stirred for 12h. Add 50mL of water to quench the reaction, extract with ethyl acetate (50mL×3), and then the organic phase is treated with 10% Na 2 S 2 o 3 The solution was washed successively with saturated brine, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=15 / 1) to obtain the yellow solid product 3aa (75.9 mg, 62%).

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Abstract

The invention discloses a synthesis method of a pyrimido-indazole compound and belongs to the technical field of organic synthesis. The key point of the technical scheme is as follows: the synthesis method of the pyrimido-indazole compound particularly comprises the following steps: dissolving an aromatic aldehyde compound, a 3-amnioindazole derivative and triethylamine into a solvent, adding NH4Iand an oxidizing agent, and reacting at 110 to 150 DEG C to prepare a target product pyrimido-indazole compound. The synthesis process is simple and efficient, the pyrimido-indazole compound is directly prepared at one step through one-pot cascade reaction without transition metal catalysis, resource waste and environmental pollution caused by the use of various reagents in multi-step reaction aswell as purification treatment on a reaction intermediate at each step are avoided, the synthesis process is convenient to operate, the raw materials are simple, the reaction condition is mile, and the application range of substrates is wide; meanwhile the triethylamine serves as the raw materials, so that the production cost is greatly reduced.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of pyrimidoindazole compounds. Background technique [0002] Studies have shown that pyrimidazole derivatives have significant biological activity and are potential protein kinase inhibitors and Alzheimer's disease, viral infection, autoimmune diseases, neurodegenerative diseases and anti-tumor drugs. They have great potential in the fields of biology and medicine. important application value. However, the synthetic methods of pyrimidindazole compounds reported in relevant literatures are mainly the condensation reaction of 3-aminoindazole and 1,3-dicarbonyl compound or propiolate and the synthesis of 3-aminoindazole, aromatic aldehyde and alkene. Or the Grieco condensation reaction of alkyne and the addition and cyclization of 3-aminoindazole and Michael acceptor. These literature methods have the disadvantages of using corrosive and to...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 高庆贺邱培勇刘兆敏杨利敏吴曼曼
Owner XINXIANG MEDICAL UNIV
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