Category: 58539-65-4

Application of 58539-65-4 ,Some common heterocyclic compound, 58539-65-4, molecular formula is C7H8N2O, 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.

30) 2-methyl-nicotinonitrileCyanuric acid (418 mg, 2.2 mmol) was added in one portion to a suspension of 2-methylnicotinamide (intermediate 29) (613 mg, 4.5 mmol) in 2.5 ml of DMF cooled in ice. The 0 reaction was stirred for 2.5 hours then poured into ice. The reaction was extracted with ethyl acetate until the organic layer no longer contained product. The combined organic layers, were dried over Na2SO4, filtered and concentrated. Purified on normal phase chromatography with ethyl acetate/heptane 0 to 50 gradient then 50/50 EA/heptane. Yield (216 mg, 41 %). IH NMR (400 MHz, CHLOROFORM-D) delta ppm 2.78 (s, 3 H), 7.25 (dd, s J=7.71, 4.98 Hz, 1 H), 7.89 (dd, J=7.81, 1.56 Hz5 1 H), 8.68 (s, 1 H)

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. 58539-65-4, 2-Methylnicotinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2007/73303; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58539-65-4 , The common heterocyclic compound, 58539-65-4, name is 2-Methylnicotinamide, molecular formula is C7H8N2O, 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.

[0621] A mixture of XI-2 (13 g, 95.6 mmol, 1 eq) and 18.2 mL of N,N-dimethylformamide dimethyl acetal was heated at 50 C. for 2 hrs. During the second hour, all the volatiles was removed. The residue was cooled to rt., diluted with 100 mL of anhydrous N,N-dimethylformamide, and then treated carefully with batch wise portions of sodium hydride (5 g, 124.3 mmol, 1.3 eq, 60% oil dispersion; caution: vigorous evolution of hydrogen). The mixture was heated at 80 C. for 2.5 hrs, and then ice-cooled, treated cautiously with 25 mL of 2-propanol, and then maintained at 0-5 C. overnight. The solid were collected, and then dissolved in 10 mL of hot water. The solution was filtered, the filtrate was ice-cooled and then treated dropwise with concentrated hydrochloric acid to pH=7.0. After storage at 0-5 C. for 3 hrs, the precipitated solids were collected, washed with ice-cold water, and dried in vacuum to give XI-3 (3 g, 32% yield). 1H NMR (DMSO-d6, 300 MHz): delta 8.90 (s, 1H), 8.49 (d, J=7.6 Hz, 1H), 7.51-7.43 (m, 2H), 6.61 (d, J=7.6 Hz, 1H).

The synthetic route of 58539-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58539-65-4, 2-Methylnicotinamide, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Product Details of 58539-65-4, blongs to pyridine-derivatives compound. Product Details of 58539-65-4

The 2 – methyl nicotinic acid amide (200 mg, 1 . 47 mmol) dissolved in anhydrous tetrahydrofuran (5 ml) in, 0 C under argon conditions, dropping borane tetrahydrofuran solution (1 M, 7.4 ml, 7.4 mmol), the reaction 30 minutes, up to 60 C reaction 8 hours. Saturated ammonium chloride aqueous solution quenching, ethyl acetate extraction, anhydrous sodium sulfate drying, filtering of evaporation to dryness to obtain colourless oil of 200 mg, crude product is directly used for the next step reaction

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58539-65-4, 2-Methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Seth Ming Qiang Pharmaceutical Technology Co., Ltd.; Zhang Qiang; Liu Yansheng; Li Xingfu; Hu Chenming; (96 pag.)CN109535132; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 58539-65-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 58539-65-4 as follows.

A mixture of X-2 (13 g, 95.6 mmol, 1 eq) and 18.2 mL of N,Ndimethylformamide dimethyl acetal was heated at 50C for 2 hrs. During the second hour, all the volatiles was removed. The residue was cooled to rt., diluted with 100 mL of anhydrous N,Ndimethylformamide, and then treated carefully with batch wise portions of sodium hydride (5 g, 124.3 mmol, 1.3 eq, 60% oil dispersion; caution: vigorous evolution of hydrogen). The mixture was heated at 80C for 2.5 hrs, and then ice-cooled, treated cautiously with 25 mL of 2-propanol, and then maintained at 0-5C overnight. The solid were collected, and then dissolved in 10 mL of hot water. The solution was filtered, the filtrate was ice-cooled and then treated dropwise with concentrated hydrochloric acid to pH=-7.0. After storage at 0-5C for 3 hrs, the precipitated solids were collected, washed with ice-cold water, and dried in vacuum to give X-3 (3 g, 32% yield). ?H NMR (DMSO-d6, 300 MHz): oe 8.90 (s, 1H), 8.49 (d, J=7.6 Hz, 1H), 7.51-7.43 (m, 2H), 6.61 (d, J =7.6 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58539-65-4, its application will become more common.

Reference:
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem