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Practical method for synthesizing novel bioactive molecule with N-methoxy-amide as nitrogen source

A bioactive molecule, methoxyamide technology, applied in the field of synthesizing new bioactive molecules, can solve the problems of dangerous azide nitrogen sources, cumbersome synthesis routes, inconvenient storage, etc., and achieves reaction conditions that are simple, easy to operate, abundant The effect of reducing structure and by-products

Active Publication Date: 2019-06-21
SUZHOU UNIV
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  • 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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  • Practical method for synthesizing novel bioactive molecule with N-methoxy-amide as nitrogen source
  • Practical method for synthesizing novel bioactive molecule with N-methoxy-amide as nitrogen source
  • Practical method for synthesizing novel bioactive molecule with N-methoxy-amide as nitrogen source

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] This implementation case shows a practical method for synthesizing new biologically active molecules using N-methoxyamide as a nitrogen source: using 3-methyl-2-phenylpyridine and N-methoxybenzamide as raw materials , The reaction formula is as follows:

[0047]

[0048] (1) Add 0.0338 g (0.2 mmol) of 3-methyl-2-phenylpyridine, 0.0040 g (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, reacted at 120°C for 12 hours in an air atmosphere;

[0049] (2) TLC follows the reaction until it is completely over;

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

[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),7.55 –7.47(m,3H),7.47–7.40(m,1...

Embodiment 2

[0053] This example shows a practical method for synthesizing new biologically active molecules using N-methoxyamide as a nitrogen source according to the following steps: nitrogen heterocyclic compounds substituted with aryl groups and 2-chloro-4-methylsulfonyl-N- Methoxybenzamide is the raw material, and the reaction formula is as follows:

[0054]

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

[0056] ⑵ TLC ​​follows the reaction until it is completely over;

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

[0058] 1 H NMR(400MHz, CDCl 3 )δ9.9...

Embodiment 3

[0060] This example shows a practical method for the synthesis of new bioactive molecules using N-methoxyamide as a nitrogen source according to 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 silver hexafluoroantimonate 0.0069 in the reaction tube G (0.02 mmol), 0.0867 g (0.3 mmol) of N-(benzyloxy)undec-10-enamide, and 1.00 mL of 1,2-dichloroethane, reacted at 120°C for 12 hours in an air atmosphere ;

[0063] ⑵ TLC ​​follows the reaction until it is completely over;

[0064] (3) The crude product obtained after the reaction is 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,1H)...

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Abstract

The invention discloses a practical method for synthesizing a novel bioactive molecule with N-methoxy-amide as a nitrogen source. The practical method comprises the following steps: sequentially adding an aryl-substituted nitrogen heterocyclic compound, a dichloro-(pentamethyl cyclopentadienyl) iridium (III) dimer, silver hexafluoroantimonate and N-methoxybenzamide into a glass reaction tube and performing a reaction at the temperature of 120-140 DEG C by taking 1,2-dichloroethane as a solvent to obtain the novel bioactive molecule synthesized by taking N-methoxy-amide as the nitrogen source.With adoption of the method disclosed by the invention, obtained products are diversified in type, can be directly applied to synthesis and decoration of pharmaceutical molecules and can also be usedfor other further reactions; meanwhile, the method is safe and easy in synthesis route, low in cost, simple in reaction operation and aftertreatment process and good in selectivity; methanol is an only by-product, therefore, the practical method conforms to the concept of green chemistry.

Description

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

Claims

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Application Information

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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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