Synthetic Route of 179543-88-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.179543-88-5, name is 5-Hydrazinyl-2-methoxypyridine hydrochloride, molecular formula is C6H10ClN3O, molecular weight is 175.62, as common compound, the synthetic route is as follows.
[Reference Example 5] 1-(6-Methoxy-3-pyridyl)-5-(1H-pyrrol-2-yl)pyrazole-3-carboxylic acid [Show Image] Diethyl oxalate (3.10 mL) and 1-[1-(phenylsulfonyl)-1H-pyrrol-2-yl]-1-ethanone (2.49 g) were added to a solution of sodium ethoxide (1.63 g) in ethanol (20 mL) under ice cooling, and the resultant mixture was stirred for 5 hours at room temperature. To this reaction solution, 5-hydrazino-2-methoxypyridine hydrochloride (2.52 g) of Reference Example 1 and ethanol (20 mL) were added, and the mixture was heated to reflux for 14.5 hours. After air cooling, ethyl acetate and a saturated aqueous solution of sodium hydrogen carbonate were added to a residue obtained by evaporating the reaction solvent under reduced pressure, and the mixture was partitioned. The aqueous layer was further extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. After separation by filtration, a residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (ethyl acetate-hexane), to obtain 1-(6-methoxy-3-pyridyl)-5-[1-(phenylsulfonyl)-1H-pyrrol-2-yl]pyrazole-3-carboxylic acid ethyl ester (3.28 g, 72%) as an oily product. To a solution of this ethyl ester product (3.28 g) in ethanol (22 mL), an aqueous 1 N sodium hydroxide solution (22 mL) was added, and the mixture was stirred for 2 days at room temperature. An aqueous 1 N hydrochloric acid solution was added to the reaction solution, and the precipitated solid was filtered, to obtain the title compound (1.40 g, 68%) as a solid. 1H-NMR(400MHz, DMSO-d6)delta: 3.94(3H, s), 5.49-5.51(1H, m), 5.98-6.00(1H, m), 6.87-6.89(1H, m), 6.98(1H, dd, J=8.8, 0.5Hz), 7.08(1H, s), 7.80(1H, dd, J=8.8, 2.7Hz), 8.25(1H, dd, J=2.7, 0.5Hz), 11.39(1H, br s). ESI-MSm/z: 285(M+H)+.
Statistics shows that 179543-88-5 is playing an increasingly important role. we look forward to future research findings about 5-Hydrazinyl-2-methoxypyridine hydrochloride.
Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1785418; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem