Sugar label reagent based on triazine structure as well as synthesis method and application thereof
A labeling reagent, labeling technology, applied in organic chemistry methods, chemical instruments and methods, introduction of isotopes into organic compounds, etc., can solve problems such as restricting development
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Embodiment 1
[0087] 2-Chloro-4,6-dimethoxy-s-triazine was dissolved in tetrahydrofuran, and hydrazine hydrate was added, n(reactant):n(hydrazine hydrate)=1:5, and heated to reflux for 8h. The reaction solution was poured into a sufficient amount of crushed ice, extracted three times with dichloromethane, and concentrated. (The results are reported in Table 1).
Embodiment 2
[0089] 2-Chloro-4,6-dimethoxy-s-triazine was dissolved in acetonitrile, hydrazine hydrate was added, n(reactant):n(hydrazine hydrate)=1:3, and heated to reflux for 12h. The reaction solution was poured into a sufficient amount of crushed ice, extracted three times with ethyl acetate, and concentrated. (The results are reported in Table 1).
[0090] Example 1 of T2 synthesis
[0091] Dissolve cyanuric chloride in methanol, add sodium bicarbonate, n (cyanuric chloride): n (sodium bicarbonate) = 1: 1.5, stir and react under ice bath conditions for 12 hours, monitor by chromatography until the reaction is complete . After the reaction was complete, the reaction solution was poured into an ice-water mixture, stirred, filtered, washed with water until there was no chloride ion, and dried in vacuum to obtain a white powder.
[0092] Dissolve the product from the previous step in dichloromethane, add N,N-diisopropylethylamine (DIPEA), n(reactant):n(DIPEA)=1:2, add diethylamine at r...
Embodiment 3
[0105] Dissolve cyanuric chloride in acetonitrile, add imidazole, n (reactant): n (imidazole) = 1: 3, add diethylamine at room temperature, n (reactant): n (diethylamine) = 1: 3. Stir at room temperature to continue the reaction for 18h. Reaction completion was monitored via thin layer chromatography. After the reaction is completed, wash with a large amount of hydrochloric acid solution and water three times respectively, collect the organic phase, and concentrate.
[0106] The product from the previous step was dissolved in chloroform, added with hydrazine hydrate, n(reactant):n(hydrazine hydrate)=1:7, and heated under reflux for 6h. The reaction solution was poured into a sufficient amount of crushed ice, extracted three times with ether, and concentrated. (The results are reported in Table 1)
[0107] Example 1 of the synthesis of deuterium-labeled T3
[0108]Dissolve cyanuric chloride in dichloromethane, add DIPEA, n (reactant): n (DIPEA) = 1: 2.2, add deuterated diet...
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