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A Practical Method for the Synthesis of Novel Bioactive Molecules Using N-Methoxyamides as Nitrogen Sources

A bioactive molecule, the technology of methoxyamide, applied in the field of synthesizing new bioactive molecules, can solve the problems of inconvenient storage, danger of azide nitrogen source, cumbersome synthesis route, etc., and achieve less by-products and simple post-processing process , the effect of rich structure

Active Publication Date: 2021-08-03
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the above technical scheme, the azide nitrogen source has certain dangers when used, and it is inconvenient to store
The synthetic route of 1,4,2-dioxazol-5-one amidation test is cumbersome, and the substrate has certain limitations

Method used

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  • A Practical Method for the Synthesis of Novel Bioactive Molecules Using N-Methoxyamides as Nitrogen Sources
  • A Practical Method for the Synthesis of Novel Bioactive Molecules Using N-Methoxyamides as Nitrogen Sources
  • A Practical Method for the Synthesis of Novel Bioactive Molecules Using N-Methoxyamides as Nitrogen Sources

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] This example demonstrates a practical method for the synthesis of novel bioactive molecules using N-methoxyamide as a nitrogen source in the following steps: 3-methyl-2-phenylpyridine and N-methoxybenzamide as raw materials , and its reaction formula is as follows:

[0047]

[0048] (1) Add 0.0338 grams (0.2 mmol) of 3-methyl-2-phenylpyridine, 0.0040 grams (0.005 mmol) of dichloro(pentamethylcyclopentadienyl) iridium (III) dimer, and six 0.0069 g (0.02 mmol) of silver fluoroantimonate, 0.045 g (0.3 mmol) of N-methoxybenzamide and 1.00 mL of 1,2-dichloroethane were reacted at 120°C for 12 hours in an air atmosphere;

[0049] ⑵ TLC ​​tracking reaction until the complete end;

[0050] (3) The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 15:1) to obtain the target product (96% yield).

[0051] 1 H NMR (400MHz, CDCl 3 )δ13.45(s,1H),8.94–8.63(m,1H),8.44(s,1H),8.05(dd,J=7.6,1.8Hz,2H),7.69–7.56(m,3H),7.5...

Embodiment 2

[0053] This example demonstrates a practical method for the synthesis of novel bioactive molecules using N-methoxyamides as nitrogen sources in the following steps: aryl-substituted nitrogen heterocycles and 2-chloro-4-thiamphenyl-N- Methoxybenzamide is a raw material, and its reaction formula is as follows:

[0054]

[0055] (1) Add 0.0379 grams (0.2 mmol) of 2-(2-chlorophenyl) pyridine, 0.0040 grams (0.005 mmol) of dichloro(pentamethylcyclopentadienyl) iridium (III) dimer, and six 0.0069 g (0.02 mmol) of silver fluoroantimonate, 0.0789 g (0.3 mmol) of 2-chloro-4-thiamphenyl-N-methoxybenzamide and 1.00 mL of 1,2-dichloroethane, in an air atmosphere Under 120°C for 12 hours;

[0056] ⑵ TLC ​​tracking reaction until the complete end;

[0057] (3) The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 15:1) to obtain the target product (yield 70%).

[0058] 1 H NMR (400MHz, CDCl 3 )δ9.98(s,1H),8.51(d,J=4.0Hz...

Embodiment 3

[0060] This example demonstrates a practical method for the synthesis of novel bioactive molecules using N-methoxyamide as a nitrogen source in the following steps: 2-phenylpyridine and N-(benzyloxy)undec-10-ene Amide is a raw material, and its reaction formula is as follows:

[0061]

[0062] (1) Add 0.0310 g (0.2 mmol) of 2-phenylpyridine, 0.0040 g (0.005 mmol) of dichloro(pentamethylcyclopentadienyl) iridium (III) dimer, and 0.0069 g of silver hexafluoroantimonate into the reaction tube gram (0.02 mmol), N-(benzyloxy) undec-10-enamide 0.0867 gram (0.3 mmol) and 1.00 mL 1,2-dichloroethane, under air atmosphere, 120 ℃ for 12 hours ;

[0063] ⑵ TLC ​​tracking reaction until the complete end;

[0064] (3) The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 15:1) to obtain the target product (yield 48%).

[0065] 1 H NMR (400MHz, CDCl 3 )δ12.09(s,1H),8.64–8.63(m,1H),8.56(d,J=8.2Hz,1H),7.84(td,J=7.9,1.8Hz,...

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Abstract

The invention discloses a practical method for synthesizing novel biologically active molecules using N-methoxyamide as a nitrogen source. In a glass reaction tube, aryl-substituted nitrogen heterocyclic compounds, dichloro(pentamethylcyclopentadiene) Alkenyl) iridium (III) dimer, silver hexafluoroantimonate, and N-methoxybenzamide, using 1,2-dichloroethane as a solvent, reacting at 120-140°C to obtain use N‑methoxyamides as nitrogen sources for the synthesis of novel bioactive molecules. There are various types of products obtained by the method of the present invention, which can be directly applied to the synthesis and modification of drug molecules and can be used in other further reactions; meanwhile, the synthetic route is safe and easy, the cost is low, and the reaction operation and post-treatment process are simple , Good selectivity, methanol is the only by-product, in line with the concept of green chemistry.

Description

technical field [0001] The present invention relates to a practical method for the synthesis of novel biologically active molecules using N-methoxyamides as nitrogen sources. Background technique [0002] The construction of C-N bonds is one of the most basic operations in nature and organic synthesis, and the resulting amino compounds are widely found in natural products, pharmaceuticals and functional materials. Traditional synthetic methods use functionalized compounds, such as alkenyl or aryl halides, reacted with nitrogen sources, etc. [0003] In the prior art, there are a large number of documents reporting the amidation reaction of C-H bond, which realizes the construction of C-N bond. For example, literature (1). Yoonsu Park, Kyung Tae Park, Jeung Gon Kim, and SukbokChang. Mechanistic Studies on the Rh(III)-Mediated Amido Transfer Process Leading to Robust C-H Amination with a New Type of Amidating. J.Am.Chem.Soc .2015,137, 4534–4542.(2).Ruhuai Mei,Joachim Loup,an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C07D213/40C07D271/06C07D231/12C07D405/12C07D231/22C07D277/66C07D263/10
Inventor 赵应声鞠国栋
Owner SUZHOU UNIV
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