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Preparation method of imidazole [1, 2-a] pyridine-containing secondary amine and tertiary amine derivatives

A technology of pyridine secondary amine and 2-a, which is applied in the field of medicinal chemistry, can solve problems such as drug development and marketing obstacles, high requirements for reaction conditions, and limited types of derivatives, and achieves wide application range, environmental friendliness, and high product yield Effect

Active Publication Date: 2021-09-03
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 1. Complex preparation and high cost
It needs to go through multi-step reaction and has high requirements on reaction conditions, which hinders the development and marketing of drugs;
[0008] 2. The types of derivatives that can be prepared are limited and need to be further expanded
There is no research on the synthesis of amine derivatives specifically targeting imidazo[1,2-a]pyridine, an excellent structural motif, and there is a big gap in this market

Method used

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  • Preparation method of imidazole [1, 2-a] pyridine-containing secondary amine and tertiary amine derivatives
  • Preparation method of imidazole [1, 2-a] pyridine-containing secondary amine and tertiary amine derivatives
  • Preparation method of imidazole [1, 2-a] pyridine-containing secondary amine and tertiary amine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Add 35.4 mg (0.3 mmol) of imidazo[1,2-a]pyridine shown below, 142 mg (0.45 mmol) of hexahydrotriphenyltricyanide substrate into a reaction tube with a stirring bar, followed by 8.5 mg ( 0.06mmol) Catalyst BF3·OEt 2 , and then added MeCN (2ml) solvent to dissolve it, stirred at room temperature for 10 hours, spin-dried and separated by silica gel chromatography to obtain the target product with a yield of 91%.

[0044] Concrete reaction formula is as follows:

[0045]

[0046] The specific hydrogen spectrum, carbon spectrum and mass spectrum data are as follows:

[0047] 1 H NMR (400MHz, CDCl 3 )δ8.16(d, J=6.8Hz, 1H), 7.68(d, J=9.1Hz, 1H), 7.62(s, 1H), 7.26–7.19(m, 3H), 6.83(dt, J=17.3 ,7.1Hz,2H),6.75(d,J=8.0Hz,2H),4.60(s,2H),3.81(s,1H).

[0048] 13 C NMR (100MHz, CDCl 3 )δ142.8, 127.4, 124.8, 120.2, 119.6, 116.4, 113.8, 113.0, 108.6, 108.0, 72.6, 72.6, 72.4, 72.0, 33.8.

[0049] HRMS MALDI m / z calcd for C 14 h 14 N 3 [M+H] + :224.1188,found:224.1188.

[...

Embodiment 2

[0052] Add 58.2 mg (0.3 mmol) of imidazo[1,2-a]pyridine shown below, 188 mg (0.45 mmol) of hexahydrotriphenyltricyanide substrate into a reaction tube with a stirring bar, followed by 8.5 mg ( 0.06mmol) Catalyst BF3·OEt 2 , and then added MeCN (2ml) solvent to dissolve it, stirred at room temperature for 10 hours, spin-dried and separated by silica gel chromatography to obtain the target product with a yield of 90%.

[0053] Concrete reaction formula is as follows:

[0054]

[0055] The specific hydrogen spectrum, carbon spectrum and mass spectrum data are as follows:

[0056] 1 H NMR (400MHz, DMSO-d 6 )δ8.37(d, J=7.0Hz, 1H), 7.79(d, J=7.6Hz, 2H), 7.66(d, J=9.0Hz, 1H), 7.49(t, J=7.5Hz, 2H) ,7.38(dt,J=15.7,7.8Hz,2H),7.10(d,J=8.5Hz,2H),7.01(t,J=6.8Hz,1H),6.66(d,J=8.5Hz,2H) ,6.35(t,J=4.7Hz,1H),4.62(d,J=4.1Hz,2H).

[0057] 13 C NMR (101MHz, DMSO-d 6 )δ147.4, 144.2, 143.4, 134.4, 128.8, 128.6, 128.2, 127.8, 125.2, 125.2, 119.8, 117.2, 116.8, 113.8, 112.4, 37.0.

[0058]...

Embodiment 3

[0061] Add 68.4 mg (0.3 mmol) of imidazo[1,2-a]pyridine shown below, 142 mg (0.45 mmol) of hexahydrotriphenyltricyanide substrate into a reaction tube with a stir bar, followed by 8.5 mg ( 0.06mmol) Catalyst BF3·OEt 2 , and then added MeCN (2ml) solvent to dissolve it, stirred at room temperature for 10 hours, spin-dried and separated by silica gel chromatography to obtain the target product with 88% yield.

[0062] Concrete reaction formula is as follows:

[0063]

[0064] The specific hydrogen spectrum, carbon spectrum and mass spectrum data are as follows:

[0065] 1 H NMR (400MHz, DMSO-d 6 )δ8.33(d, J=6.9Hz, 1H), 7.80(d, J=7.6Hz, 2H), 7.63(d, J=9.0Hz, 1H), 7.48(t, J=7.5Hz, 2H) ,7.38(t,J=7.3Hz,1H),7.33–7.28(m,1H),6.96(t,J=6.8Hz,1H),6.89(d,J=7.9Hz,2H),6.57(d, J=8.0Hz, 2H), 5.92(t, J=5.0Hz, 1H), 4.61(d, J=4.5Hz, 2H), 2.15(s, 3H).

[0066] 13 C NMR (101MHz, DMSO-d 6 )δ146.2, 144.0, 143.2, 134.4, 129.4, 128.6, 128.0, 127.6, 125.2, 124.8, 124.8, 117.6, 116.8, 112.6, 1...

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Abstract

The invention provides a preparation method of imidazo [1, 2-a] pyridine-containing secondary amine and tertiary amine derivatives from triazine compounds and imidazo [1, 2-a] pyridine, and relates to the field of medicinal chemistry. According to the present invention, the triazine compound is reacted with the imidazo [1, 2-a] pyridine compound, the Lewis acid catalysis is performed, the reaction conditions such as the reaction temperature and the reaction time are controlled, and the controllable cracking and the fixed-point selectivity of the triazine compound are utilized to synthesize different imidazo [1, 2-a] pyridine-containing secondary amine and tertiary amine derivatives, such that the synthesis method is simple, the multi-step reaction is not required, the product purity and yield are high, selectable substrate range is wide, and the preparation method can be well applied to the field of pharmacy.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a method for preparing secondary and tertiary amine derivatives containing imidazo[1,2-a]pyridine, in particular to a method for preparing triazine compounds and imidazo[1,2-a] A new method for preparing secondary and tertiary amine derivatives containing imidazo[1,2-a]pyridine from ]pyridine compounds. Background technique [0002] Amines are widely found in natural products and synthetic drugs, and some amines are essential for maintaining life activities and displaying extremely important physiological functions, and play vital roles in many fields such as biology, pharmaceuticals, agrochemicals and materials . Therefore, the synthesis of amine compounds has always been the focus of research in the field of medicine. Furthermore, imidazo[1,2-a]pyridine is known to be one of the most preferential structural motifs with diverse biological and pharmaceutical properties, such as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 曹华刘想汪裕涵
Owner GUANGDONG PHARMA UNIV
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