Benzimidazole derivatives, preparation method and medical use thereof
A kind of use, pharmaceutical technology, applied in the field of benzimidazole derivatives and preparation thereof
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Embodiment 1
[0088] (Isopropyloxycarbonyloxy)methyl-2-ethoxy-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazole)- Synthesis of 3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate
[0089]
[0090] Dissolve QR01000-IN-01 (2.2 mmol, 1.0 equivalent) and QR01002-IN-01 (3.3 mmol, 1.5 equivalent) in 20 mL of N-methylpyrrolidone, add triethylamine (4.4 mmol, 2.0 equivalent), and heat to 65 °C, the reaction was monitored by TLC, and the reaction was complete. Water and ethyl acetate were added to the reaction liquid, extraction and separation were carried out, and the organic layer was washed with water and saturated brine. The organic layer was dried and concentrated, and purified by column chromatography to obtain the target compound QR01002, whose structure was double-confirmed by LCMS spectrum and H NMR spectrum.
Embodiment 2
[0092] 1-(isopropyloxycarbonyloxy)ethyl-2-ethoxy-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazole Synthesis of )-3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate
[0093]
[0094] Dissolve QR01000-IN-01 (2.2 mmol, 1.0 equivalent) and QR01003-IN-01 (3.3 mmol, 1.5 equivalent) in 20 mL of N-methylpyrrolidone, add triethylamine (4.4 mmol, 2.0 equivalent), and heat to 65 °C, the reaction was monitored by TLC, and the reaction was complete. Water and ethyl acetate were added to the reaction liquid, extraction and separation were carried out, and the organic layer was washed with water and saturated brine. The organic layer was dried and concentrated, and purified by column chromatography to obtain the target compound QR01003, whose structure was double confirmed by LCMS spectrum and H NMR spectrum.
Embodiment 3
[0096] Acetoxyethyl-2-ethoxy-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol)-3-yl)biphenyl- Synthesis of 4-yl]methyl}-1H-benzimidazole-7-carboxylate
[0097]
[0098] Dissolve QR01000-IN-01 (2.2 mmol, 1.0 equivalent) and QR01004-IN-03 (3.3 mmol, 1.5 equivalent) in 20 mL of N-methylpyrrolidone, add triethylamine (4.4 mmol, 2.0 equivalent), and heat to 65 °C, the reaction was monitored by TLC, and the reaction was complete. Water and ethyl acetate were added to the reaction liquid, extraction and separation were carried out, and the organic layer was washed with water and saturated brine. The organic layer was dried and concentrated, and purified by column chromatography to obtain the target compound QR01004, whose structure was double-confirmed by LCMS spectrum and H NMR spectrum.
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