Category: 179543-88-5

Synthetic Route of 179543-88-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 179543-88-5, name is 5-Hydrazinyl-2-methoxypyridine hydrochloride. A new synthetic method of this compound is introduced below.

[Referential Example 17] 5-(4-Dimethylaminophenyl)-1-(6-methoxy-3-pyridyl)-1H-pyrazole-3-carboxylic acid; [Show Image] 1) Ethyl 5-(4-dimethylaminophenyl)-1-(6-methoxy-3-pyridyl)-1H-pyrazole-3-carboxylate; To a solution of sodium ethoxide (1.36 g) in ethanol (50 ml) was added a solution of diethyl oxalate (2.72 ml) and 4′-dimethylaminoacetophenone (1.632 g) in ethanol (50 ml), and the mixture was heated under reflux for 16 hours. After cooling with air, 5-hydrazino-2-methoxypyridine hydrochloride (2.102 g) of Referential Example 1 was added to the solution and the mixture was heated under reflux for 3 hours. After cooling with air, the reaction solvent was evaporated under reduced pressure. Water and ethyl acetate were added to the residue and the phases were separated, and the organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate-hexane) to give ethyl 5-(4-dimethylaminophenyl)-1-(6-methoxy-3-pyridyl)-1H-pyrazole-3-c arboxylate (2.134 g, 58%) as an oily product. 1H-NMR (400 MHz, CDCl3)delta: 1.42 (3H, t, J = 7.1 Hz), 2.97 (6H, s), 3.94 (3H, s), 4.45 (2H, q, J = 7.1 Hz), 6.62 (2H, d, J= 8.8 Hz), 6.73 (1H, d, J = 8.8 Hz), 6.94 (1H, s), 7.06 (2H, d, J = 8.8 Hz), 7.58 (1H, dd, J = 8.8, 2.7 Hz), 8.16 (1H, d, J = 2.7 Hz). ESI-MSm/z: 367 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,179543-88-5, 5-Hydrazinyl-2-methoxypyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1698626; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 179543-88-5 ,Some common heterocyclic compound, 179543-88-5, molecular formula is C6H10ClN3O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

[0489] Scheme 3: synthesis of 2-(5-methoxy-lH-indol-3-yl)-N,N-dimethylethanamine (KD19) and 2-(5-methoxy-lH-pyrrolo[3,2-b]pyridin-3-yl)-N,N-dimethylethanamine (KD20)[0490] A reported procedure was followed to prepare the compounds(i).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 179543-88-5, 5-Hydrazinyl-2-methoxypyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; OZPOLAT, Bulent; LOPEZ-BERESTEIN, Gabriel; DALBY, Kevin N.; JOSE, Jiney; WO2013/63492; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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