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
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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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