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N-((2-heteroarylimidazoheteroaryl-3-yl)methyl)benzenesulfonamide compound and its synthesis method

A technology of heteroaryl imidazole and benzenesulfonamide, which is applied in the field of preparation of N-methyl)benzenesulfonamide compounds, can solve few problems and achieve the effect of wide applicability of substrates

Active Publication Date: 2020-07-17
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of methanol as the methylene synthesis moiety for C–H aminomethylation has been rarely reported

Method used

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  • N-((2-heteroarylimidazoheteroaryl-3-yl)methyl)benzenesulfonamide compound and its synthesis method
  • N-((2-heteroarylimidazoheteroaryl-3-yl)methyl)benzenesulfonamide compound and its synthesis method
  • N-((2-heteroarylimidazoheteroaryl-3-yl)methyl)benzenesulfonamide compound and its synthesis method

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Experimental program
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Effect test

Embodiment 1

[0025] The structural formula of the compound N-((2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamide of this embodiment is:

[0026]

[0027] The preparation method is: in an air environment, add 0.1mmol of 2-(thiophen-2-yl)imidazo[1,2-a]pyridine compound, 0.2mmol of benzenesulfonamide, 0.2mmol of di tert-butyl peroxide, 0.1 mmol of potassium permanganate, 0.1 mmol of sodium tert-butoxide, 2 mL of hexafluoroisopropanol and methanol (volume ratio 1:9), reacted at 130 ° C for 8 hours; after the reaction, chromatographic separation (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0 / 100 to 100 / 0), and dried to obtain a light yellow solid with a yield of 73%. mp 222-223°C; 1 H NMR (600MHz, DMSO) δ8.36–8.17(m,2H),7.76(d,J=7.2Hz,2H),7.66–7.46(m,5H),7.31(s,2H),7.09(s, 1H), 6.97(t, J=5.8Hz, 1H), 4.56(d, J=3.4Hz, 2H); 13 C NMR (101MHz, DMSO) δ144.0, 139.7, 138.2, 137.0, 132.5, 129.0, 127.9, 126.5, 126.3, 125.5, 124.8, ...

Embodiment 2

[0029] The structural formula of the compound N-((2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamide of this embodiment is:

[0030]

[0031] The preparation method is: in an air environment, add 0.1mmol of 2-(thiophen-2-yl)imidazo[1,2-a]pyridine compound, 0.3mmol of benzenesulfonamide, 0.1mmol of di tert-butyl peroxide, 0.2 mmol of potassium permanganate, 0.1 mmol of sodium tert-butoxide, 2 mL of hexafluoroisopropanol and methanol (volume ratio 1:9), reacted at 140 ° C for 10 hours; after the reaction, chromatographic separation (silica gel 200-300 mesh, eluent: gradient elution with ethyl acetate / petroleum ether, the ratio is from 0 / 100 to 100 / 0), and dried to obtain a light yellow solid with a yield of 74%. mp 222-223°C; 1 H NMR (600MHz, DMSO) δ8.36–8.17(m,2H),7.76(d,J=7.2Hz,2H),7.66–7.46(m,5H),7.31(s,2H),7.09(s, 1H), 6.97(t, J=5.8Hz, 1H), 4.56(d, J=3.4Hz, 2H); 13 C NMR (101MHz, DMSO) δ144.0, 139.7, 138.2, 137.0, 132.5, 129.0, 127.9, 126.5, 126.3, 1...

Embodiment 3

[0033] The structural formula of the compound N-((2-(furan-2-yl)imidazo[1,2-a]pyridin-3-yl)methyl)benzenesulfonamide of this embodiment is:

[0034]

[0035]The preparation method is: in an air environment, add 0.1mmol of 2-(furan-2-yl)imidazo[1,2-a]pyridine compound, 0.2mmol of benzenesulfonamide, 0.2mmol of tert-butyl peroxide, 0.1 mmol of potassium permanganate, 0.2 mmol of sodium tert-butoxide, 2 mL of hexafluoroisopropanol and methanol (volume ratio 1:9), reacted at 100 ° C for 12 hours; after the reaction, chromatographic separation (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether gradient elution, ratio from 0 / 100 to 100 / 0), and dried to obtain a white solid with a yield of 48%. mp 236-237°C; 1 H NMR (600MHz, DMSO) δ8.31–8.16(m,2H),7.75(d,J=7.1Hz,2H),7.70–7.58(m,2H),7.54(t,J=8.4Hz,3H) ,7.32(t,J=7.3Hz,1H),6.98(s,1H),6.81(s,1H),6.59(s,1H),4.67(s,2H); 13 C NMR (101MHz, DMSO) δ149.4, 144.5, 142.9, 139.8, 135.0, 132.4, 129.0, 126.3, 125.5, 124.6, 116.5, ...

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Abstract

The invention discloses an N-((2-heteroarylimidazoheteroaryl-3-yl)methyl)benzenesulfonamide type compound and a synthesis method thereof. The synthesis method comprises the following steps: in an airenvironment, adding a 2-heteroarylimidazoheteroaryl type compound and benzenesulfonamide into a reaction tube; adding di-tert-butyl peroxide, potassium permanganate and sodium tert-butoxide; then adding solvents; reacting at 100 to 140 DEG C for 8 to 12 hours; after reaction is finished, carrying out chromatographic separation and drying to obtain a target product. The reaction takes methanol andhexafluoroisopropanol as reaction solvents and aminomethylation reaction between the 2-heteroarylimidazoheteroaryl type compound and the benzenesulfonamide is realized; the method is simple and efficient, low in cost, liable to purify and wide in substrate applicability; functionalized reaction types of an imidazo[1,2-a]pyridine compound are enriched, and the method has significant meaning on researches and application of the aminomethylation reaction of the 2-heteroarylimidazoheteroaryl type compound.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis and application, and in particular relates to a preparation method of N-((2-heteroarylimidazoheteroaryl-3-yl)methyl)benzenesulfonamide compounds. Background technique [0002] As a special N-heterocycle, imidazoheteroaryl has various biological activities (Med. Chem. 2007, 7, 888-899; Med. Chem. 2016, 16, 2963-2994.). Various commercialized drugs such as albatide, zolpidem, GSK812397, minodronic acid, nedopiperidine, and thalidomide have been prepared by appropriately inserting amidomethyl, hydroxymethyl, or other groups at the C3 position Degree, for the treatment of insomnia, anxiety, HIV infection and osteoporosis. In recent years, the research on the functionalization of pyridoimidazoles has become more and more mature, but there are few reports on the sulfonamide methylation of imidazoheteroaryls. Considering the importance of methylene-containing imidazopyridines, it is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07D513/04
Inventor 宋冰黄恩玲刘子琳朱钰深刘炳慧赵雪梅朱新举郝新奇
Owner ZHENGZHOU UNIV
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