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A synthetic method and use of more than 2-amino pyridine derivatives

A technology of aminopyridine and synthesis method, which is applied in the field of synthesis of multi-substituted 2-aminopyridine derivatives, can solve the problems of cumbersome synthesis process, high storage and transportation requirements, and achieve environmental friendliness, high yield, and easy control of reaction conditions Effect

Active Publication Date: 2022-08-05
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this direction, Boger (Boger, D.L.Chem.Rev.1986,86,781), Okatani (Okatani, T.; Koyama, J.; Tagahara, K.Heterocycles 1989,29,1809), Igeta (Igeta, H.Chem . Pharm. Bull. 1985, 33, 3050.) and Neunhoeffer (Neunhoeffer, H.; Clausen, M.; Voetter, H.; Ohl, H.; Krueger, C.; Angermund, K. Liebigs Ann. Chem. 1985 , 1732.) etc. have made pioneering contributions, but unfortunately, in their research work, they all need to use highly active molecules, such as enamines, alkyneamines, etc., and these active components require tedious synthesis processes , coupled with the high requirements for storage and transportation, make their reaction methods have certain limitations

Method used

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  • A synthetic method and use of more than 2-amino pyridine derivatives
  • A synthetic method and use of more than 2-amino pyridine derivatives
  • A synthetic method and use of more than 2-amino pyridine derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035]

[0036]

[0037] In the above reaction, the amount of the substrate 1,2,3-triazine compound a, the cyanomethyl compound b and the amount of the base reagent is in a molar ratio: under a nitrogen environment, 1a:1b:base=1.0:1.0:1.5, and the bottom The concentration of compound 1,2,3-triazine a was 1M.

[0038] The operation steps of the reaction are as follows: in a dry sealed reaction tube, 5-bromo-1,2,3-triazine 1a, alkali and cyanomethyl diethyl phosphate 1b are sequentially added. After nitrogen replacement for three times, solvent was added, and the sealed reaction tube was placed under constant temperature for reaction. The reaction was monitored by TLC. After the reaction was completed, the mixture was extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated in vacuo, and the target product 1c was obtained after column chromatography.

[0039]For label 16, other conditions remain unchanged, and the...

Embodiment 2-3

[0047] Embodiment 2-3 is the synthesis of C3 substituted 2-aminopyridine

Embodiment 2

[0048] Example 2: Synthesis of 2-aminonicotinic acid ethyl ester (compound 2c)

[0049]

[0050] In a 10 mL dry sealed reaction tube, 1,2,3-triazine 2a (8.1 mg, 0.10 mmol), ethyl cyanoacetate 2b (24.9 mg, 0.22 mmol) and triethylenediamine (22.4 mg, 0.22 mmol) were added sequentially 0.20 mmol). After three times of nitrogen replacement, ethyl acetate (1.0 ml) was added as a solvent, and the sealed reaction tube was placed at room temperature for 3 h. The reaction was monitored by TLC. After the reaction was complete, it was extracted with dichloromethane (3*10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. After column chromatography, the target product 2c (11.1 mg, 67%) was obtained. NMR is characterized as: 1 H NMR (500MHz, CDCl 3 )δ8.13(dd,J=5.0,2.0Hz,1H),8.06(dd,J=8.0,2.5Hz,1H),6.53(dd,J=7.5,5.0Hz,1H),4.26(q,J =7.0Hz,2H),1.30(t,J=7.0Hz,3H). 13 C NMR (125MHz, CDCl3) δ166.9, 159.4, 153.3, 140.0, 112.5, 106.4, 60.8, 14.2.

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Abstract

The invention belongs to the field of organic synthetic chemistry, and relates to a method for synthesizing polysubstituted 2-aminopyridine derivatives, namely uses. The method uses 1,2,3-triazine compounds and cyanomethyl compounds as substrates, The multi-substituted 2-aminopyridine derivatives are synthesized only by one-step cycloaddition reaction under natural conditions, and the use of dangerous and controlled reagents and drugs is not involved in the reaction, which provides a simple method for the synthesis of multi-substituted 2-aminopyridine derivatives. , safe, efficient and environmentally friendly strategies. After further derivatization of the obtained product of the present invention, active molecules or drug molecules containing 2-aminopyridine structure can be synthesized, such as active molecule SC-53606, drug molecules Apatinib and Nevirapine.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, in particular to a synthetic method and application of a polysubstituted 2-aminopyridine derivative. Background technique [0002] 2-Aminopyridine is an important class of nitrogen-containing aromatic heterocyclic compounds. The structural units of this type of aromatic heterocyclic ring are not only Apatinib, Nevirapine, Vemurafenib, Ruibo, etc. Ribociclib and Palbociclib are the main skeletons of many drugs, and are also widely used in many natural products and organic catalysts, and are often used as synthetic precursors for active molecules and ligands. [0003] There are many methods for synthesizing 2-aminopyridine, such as Chichibabin reaction, Kaiser-Johnson-Middleton dinitrile cyclization reaction, etc. However, there are few methods for the efficient synthesis of polysubstituted 2-aminopyridines due to the disadvantages of poor chemoselectivity and low reactivity when directl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/80C07D213/803C07D213/85C07D213/73C07D213/82C07D471/04C07D519/00C07D401/12C07D471/14
CPCC07F9/58C07D213/80C07D213/803C07D213/85C07D213/73C07D213/82C07D471/04C07D519/00C07D401/12C07D471/14C07B2200/13C07B2200/07
Inventor 李葆生罗翰张远安峤宇徐鸣川卢棋星唐宗元李珊珊
Owner CHONGQING UNIV
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