1-oxygen-2-hydroxylmethyl-3-(1-ethoxyl)-quinoxaline, as well as preparation method and application of 1-oxygen-2-hydroxylmethyl-3-(1-ethoxyl)-quinoxaline
A technology of ethoxycarbonyloxyethyl and quinoxaline, which is applied in the field of 1-oxo-2-hydroxymethyl-3-quinoxaline and its preparation, can solve rough detection and cannot accurately reflect the metabolism of acemethaquine , unfavorable problems such as the pharmacokinetics of acemethaquine and its residue elimination rules, and achieve the effects of cheap and easy-to-obtain raw materials, mild reaction conditions, and high reaction yields
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Embodiment 1
[0055] Dissolve 25 grams of acetylmethaquine in 200 ml of methanol, add 3 grams of sodium borohydride (completely added within 20 minutes) at 0°C under stirring, then control the reaction temperature and continue the reaction at 30°C for 8 hours, TLC spotting End of follow-up reaction. Then the solid precipitate was collected by filtration to obtain the product 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline, the filtrate was concentrated to 50 ml, placed at 0°C, and the precipitate was collected by filtration 14 grams of 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline product were obtained after merging, with a yield of 56%;
[0056] Mix 3.1 g of 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline, 50 ml of pyridine, and 1.6 g of acetic anhydride at 0°C, and then continue to stir at room temperature for 5 hours , concentrated under reduced pressure to 5-10 ml, then added 50 ml of ice water, then extracted three times with 50 ml of ethyl acetate, combined the organic phases...
Embodiment 2
[0062] Dissolve 25 grams of acemethaquine in 100 milliliters of 95% by volume ethanol aqueous solution, add 5 grams of potassium borohydride at 10°C under stirring (completely added within 20 minutes), then control the reaction temperature and continue the reaction at 20°C for 1 hour , TLC spot plate tracking reaction ended. Then the solid precipitate was collected by filtration to obtain the product 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline, the filtrate was concentrated to 50 ml, placed at 0°C, and the precipitate was collected by filtration 15.75 grams of 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline product were obtained after merging, with a yield of 63%;
[0063] Mix 3.1 g of 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline, 10 ml of pyridine, and 5 g of acetic anhydride at 0°C, then continue to stir at 30°C for 1 hour , concentrated under reduced pressure to 5-10 ml, then added 50 ml of water, then extracted three times with 50 ml of ethyl acetate, combine...
Embodiment 3
[0073] After 12 hours of oral administration of acemetquine, the healthy pigs were slaughtered, and the lung tissue was collected, mechanically crushed, extracted with organic solvents for 3 times, blown dry with nitrogen, and added mobile phase to make a sample solution; Methods to make a blank control; take compound (I) and add mobile phase to make a 1mg / mL reference solution.
[0074] High performance liquid chromatograph, Diana Corporation, USA; chromatographic conditions: Hypersil BDS C 18 Chromatographic column, 250 mm×4.6 mm×5 μm, column temperature: 30 ℃; mobile phase: methanol (B) / water (containing 0.01% formic acid) (A), gradient elution: 0-40 min, 20%-35 % B; 40-45 min, 35%-60% B; 45-57 min, 60% B; 57-60 min, 60%-20% B; 60-65 min, 20% B; flow rate: 1 mL / min, detection wavelength: 241 nm.
[0075] The retention time of compound (I) was 32.15min, the peak appeared in the sample solution at 32.09min, and the blank sample did not appear at 30min-35min.
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