Xanthine derivatives
A compound, selected from the technology, applied in the field of dipeptidyl peptidase IV inhibitors
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Embodiment 1
[0052]
[0053] Synthesis of the first step compound 1a
[0054] Using known methods, 8-bromo-3-methylxanthine (5g, 20.4mmol) was dissolved in N,N-dimethylformamide (30ml), N,N diisopropylethylamine (2.633 g, 20.4mmol), 1-bromo-2-butyne (2.714g, 20.4mmol), react overnight at room temperature, follow the reaction process by thin-layer chromatography, after the reaction is complete, pour the reaction solution into water, filter with suction, and wash the solid with water for 3 times, dried to obtain 1a (5.15g, pale yellow solid), yield: 85%.
[0055] MS m / z(ES):297,299[M+1]
[0056] Synthesis of the second step compound 1b
[0057] Using a known method, 1a (156 mg, 0.53 mmol) was dissolved in N,N dimethylformamide (3 ml), and 2-bromomethyl-5-fluoro-1,3-benzothiazole (140 mg, 0.57 mmol), potassium carbonate (118mg, 0.79mmol), reacted overnight at room temperature, after the reaction was completed by thin-layer chromatography, poured into water, filtered with suction, washed...
Embodiment 2
[0070]
[0071] The first step is the same as the first step in implementation example 1;
[0072] The second step is the same as the implementation example 1 second step;
[0073] The third step is the same as the third step of implementation example 1;
[0074] The fourth step is the same as the fourth step of implementation example 1;
[0075] Synthesis of the fifth step compound 2
[0076] Using a known method, compound 1d (140mg, 0.29mmol) and triethylamine (44mg, 0.44mmol) were dissolved in dichloromethane (4ml), and diethyl chlorophosphate (50mg, 0.29mmol) was added dropwise in an ice-water bath ). After dropping, react overnight at room temperature, and track the reaction by thin-layer chromatography, which shows that the raw materials are completely consumed. The reaction solution was washed with saturated brine, separated, dried, concentrated and purified by preparative thin-layer chromatography (dichloromethane:methanol=10:1) to obtain the product compound 2 ...
Embodiment 3
[0080]
[0081] The first step is the same as the first step in implementation example 1;
[0082] The second step is the same as the implementation example 1 second step;
[0083] The third step is the same as the third step of implementation example 1;
[0084] The fourth step is the same as the fourth step of implementation example 1;
[0085] Synthesis of the fifth step compound 3e
[0086] Using a known method, compound 1d (2.4g, 4.99mmol) was dissolved in dichloromethane (50ml), and N-Boc-L-alanine (940mg, 4.97mmol), dicyclohexylcarbodiimide, and (1.23g, 5.97mmol), 1-hydroxybenzotriazole (800mg, 5.93mmol), sodium carbonate (1.1g, 10.38mmol), react overnight at room temperature, follow the reaction by thin layer chromatography, showing that the raw materials are completely consumed, filter, di The filter cake was washed with methyl chloride (30ml*3), the filtrate was concentrated and purified by column chromatography to obtain the product compound 3e (2.4g, yellow s...
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