Acethydrazide derivatives containing thieno[3.2-c]pyridine, preparation method and use thereof
A technology of acetyl hydrazide and pyridine, applied in the field of medicine, can solve problems such as weak alkalinity and difficult purification, and achieve the effect of inhibiting platelet aggregation
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[0059] Example 1:
[0060] α,α-[(4-Fluorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]acethydrazine (Compound 1)
[0061] In a reaction flask equipped with a stirrer, a condenser and a thermometer, add α,α-[(4-fluorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridine- 5-yl)] methyl acetate 19g, anhydrous ethanol 30ml, slowly heated under stirring to dissolve the reaction materials, add 23.3g hydrazine hydrate (80%), continue to heat to reflux, keep the temperature for 6 hours (the plate shows the reaction complete). Then, the solvent was evaporated under reduced pressure. After the evaporation, 50ml of distilled water and 30ml of dichloromethane were added to the residue, stirred well, and the organic layer was separated. The aqueous layer was extracted with 3×30ml of dichloromethane. The organic layers were combined and used anhydrous sulfuric acid. Sodium is fully dried. Dichloromethane was evaporated under reduced pressure to obtain 13.11g of white solid, yield 69%, HPLC:...
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[0062] Example 2:
[0063] α,α-[(4-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]-N′-(dimethylmethylene Base) Acetylhydrazine (Compound 2)
[0064] Add α,α-[(4-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridine- into a reaction flask equipped with a stirrer, a condenser and a thermometer. 5-yl)] Acetylhydrazine 4g, anhydrous methanol 40ml, start stirring, heat to dissolve. Continue to heat to 40°C, add 0.8 g of acetone dropwise, after the addition, keep the temperature and react for 3 hours. The reaction was stopped and cooled, and a light yellow solid was formed. Filter, wash 3×2ml with anhydrous methanol, and dry to obtain 3.8g of light yellow solid. HPLC: 99.3%, m.p. 169.5-171.1°C, Rf=0.3 (developing solvent: petroleum ether (60-90°C): ethyl acetate=1:1). 1 HNMR (400MHz, DMSO-d6, δppm): 1.64 (s, 3H), 1.86 (s, 3H), 3.30-3.34 (t, 2H), 3.58-3.62 (t, 2H), 4.36 (s, 2H), 5.61 (s, 1H), 7.13-7.77 (m, 6H), 9.99 (br s, 1H).
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[0065] Example 3:
[0066] α,α-[(3-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]-N′-[(2-chlorobenzene Yl)methylidene) acetylhydrazine (compound 3)
[0067] The compound was prepared according to the preparation process provided in Example 2, and was composed of α,α-[(3-chlorophenyl)-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl )] Acetylhydrazine reacts with o-chlorobenzaldehyde. HPLC: 99.7%, m.p. 182.6-183.6°C, Rf=0.84 (developing solvent: petroleum ether (60-90°C): ethyl acetate=1:1). 1 H NMR (400MHz, DMSO-d6, δppm): 3.17-3.22 (t, 2H), 3.40-3.51 (t, 2H), 4.72 (s, 2H), 5.46 (s, 1H), 6.88-7.94 (m, 10H), 8.46 (s, 1H), 11.99 (br s, 1H).
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