Preparation method of condensed benzimidazole azetidinone derivative and application of derivative in anti-tumor drug
A technology of azetidinone and anti-tumor drugs, which is applied in the field of benzimidazole azetidinone derivatives and their application in anti-tumor drugs, can solve the problems that new structural compounds have not been reported, and achieve cost Low cost, short synthetic route, and simple operation process
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Embodiment 1
[0042] where R 1 is an alkyl group, R 2 For a hydrogen atom, namely ethyl 2-(1 H -Synthesis of ethyl benzimidazol-2-yl)-1-(2-bromobenzyl)-4-oxoazetidine-2-carboxylate, the specific steps are as follows:
[0043] In a 10-mL microwave reaction tube, ethyl glyoxylate (1.5 mmol) and 2-bromobenzylamine (1.0 mmol) were first dissolved in 2.0 mL of methanol solution, followed by bromoacetic acid (1.0 mol) and isocyanide (1.0 mmol) were added to the solution in turn, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanide raw material, the solution was dried with nitrogen, and then Dissolve it with 5.0 ml of dimethylformamide (DMF), then add diisopropylamine (DIPA) (2.0 mmol), and place in a microwave oven at 90 o C for 10 minutes. The solution was diluted with ethyl acetate (15 ml), and washed three times with 20 ml of saturated brine. After the organic phase was drie...
Embodiment 2
[0046] where R 1 is an alkyl group, R 2 For a hydrogen atom, namely ethyl 2-(1 H -Benzimidazol-2-yl)-1-benzyl-4-oxoazetidine-2-carboxylic acid ethyl ester, the specific steps are as follows:
[0047] In a 10 mL microwave reaction tube, ethyl glyoxylate (1.5 mmol) and benzylamine (1.0 mmol) were first dissolved in 2.0 mL of methanol solution, followed by bromoacetic acid (1.0 mmol) and Isocyanides (1.0 mmol) were added to the solution in turn, the reaction solution was stirred overnight at room temperature, and then the isocyanides were detected by thin-layer chromatography. If there were no remaining isocyanides, the solution was dried with nitrogen, and then 5.0 mL of dimethylformamide (DMF) was dissolved, then diisopropylamine (DIPA) (2.0 mmol) was added, and the microwave oven was heated at 90 o C for 10 minutes. The solution was diluted with ethyl acetate (15 ml), and washed three times with 20 ml of saturated brine. After the organic phase was dried with magnesium su...
Embodiment 3
[0050] where R 1 is an alkyl group, R 2 For a hydrogen atom, namely ethyl 2-(1 H - Synthesis of ethyl benzimidazol-2-yl)-1-(3-fluorobenzyl)-4-oxoazetidine-2-carboxylate, the specific steps are as follows:
[0051] In a 10-mL microwave reaction tube, ethyl glyoxylate (1.5 mmol) and 3-fluorobenzylamine (1.0 mmol) were first dissolved in 2.0 mL of methanol solution, and then bromoacetic acid (1.0 mol) and isocyanide (1.0 mmol) were added to the solution in turn, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanide raw material, the solution was dried with nitrogen, and then Dissolve it with 5.0 ml of dimethylformamide (DMF), then add diisopropylamine (DIPA) (2.0 mmol), and place in a microwave oven at 90 o C for 10 minutes. The solution was diluted with ethyl acetate (15 ml), and washed three times with 20 ml of saturated brine. After the organic phase was drie...
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