Category: 5521-55-1

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. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C6H6N2O2

5-methylpyrazine acid (0.27 mmol, prepared as Example 2), EDCI (0.35mmol) And DMAP (0.027 mmol) were dissolved in dry methylene chloride (20 mL). The compound hederagenin alcohol (140 mg, 0.27 mmol, prepared as Example 3) was dissolved in dichloromethane (20 mL). This solution was dropped into the 5-methylpyrazine acid solution within 20 minutes, and stirred at room temperature for 12 hours. The reaction mixture was then diluted with dichloromethane (20 mL), washed with saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain a white powder, H-09. Yield: 55% (after chromatograph with DCM / MeOH, 1% -2%) as a white powder, m.p .: 192.6 C.

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xinhuo Zhiyao (Beijing) Technology Co., Ltd.; Fang Kang; Guo Wenbo; Wang Penglong; Cheng Gang; (26 pag.)CN110964078; (2020); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5521-55-1,Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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.

The reaction is carried out, under nitrogen, in a 1 L×4 neck flask equipped with a mechanical stirrer, water condenser (with gas inlet), and a thermocouple. The reactor is charged with 5-methylpyrazinecarboxylic acid (100 g), ethanol (300 g) and sulfuric acid (2 g). The contents are refluxed for eight hours at 78 C. The reaction mixture is cooled to ambient temperature and sodium bicarbonate (4 g) is added. About 75% of the solvent is removed under reduced pressure and the resulting suspension is allowed to stand overnight. The solids are filtered and washed with cold methanol (2×80 g). Drying under oven (25 inches of Hg) yielded 101.25 g (84%) of 5-methyl-2-pyrazonecarboxylic acid, ethyl ester.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methylpyrazine-2-carboxylic acid, its application will become more common.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Methylpyrazine-2-carboxylic acid

HATU (109 mg, 0.0.29 mmol) was added to a solution of 6-(2-(trifluoromethyl)phenyl)imidazo[1,2-b]pyridazin-3-amine (50.0 mg, 0.18 mmol), 5-methylpyrazine-2-carboxylic acid (37.0 mg, 0.27 mmol), and DIEA (78 mul, 0.44 mmol) in DMAC (7 mL) The mixture was stirred at 60 C for 3 h. H2O (45 mL) was added and the resulting ppt was collected by filtration, rinsed with H2O, and dried under vacuum. The crude residue was purified by MPLC eluting with CH2Cl2/MeOH (0-5%). The product was further purified by recrystallization from CH3CN to give 5-methyl-N-(6-(2-(trifluoromethyl)phenyl)imidazo[1,2-b]pyridazin-3-yl)pyrazine-2-carboxamide (55.0 mg, 77% yield). MS (ESI) calcd for C19H13F3N6O (m/z): 398.11; found: 399 [M+H].

According to the analysis of related databases, 5521-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GlaxoSmithKline LLC; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; (583 pag.)EP2768509; (2017); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 5521-55-1,Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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.

A boron trifluoride-diethyl ether complex (91.7 muL) was added dropwise to a suspension of 2-methylpyrazine-5-carboxylic acid (1 g) and tert-butyl 2,2,2-trichloroacetimidate (4.75 g) in THF (20 mL) under ice-cooling. The reaction solution was warmed to RT, followed by stirring for 2 h. A saturated NaCl solution and EtOAc were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous MgSO4, and the insoluble matter was separated by filtration. The filtrate was concentrated and purified by silica gel column chromatography to obtain the title compound (1.4 g). 1H-NMR (CDCl3) delta (ppm): 1.65 (s, 9H), 2.65 (s, 3H), 8.57 (d, J=1.2 Hz, 1H), 9.10 (d, J=1.6 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 5-Methylpyrazine-2-carboxylic acid, its application will become more common.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; HALL, Adrian; FARTHING, Christopher Neil; CASTRO PINEIRO, Jose, Luis; WO2012/98213; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 5521-55-1, A common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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.

Step 1. tert-butyl 5-methylpyrazin-2-ylcarbamate To solution 5-methylpyrazine-2-carboxylic acid (2.5 g, 18.1 mmol), tert-butanol (6.92 mL, 72.4 mmol), Et3N (3.78 mL, 27.1 mmol) in 1,4-dioxane (12.5 mL) at 95 C. was dropwise added diphenylphosphoryl azide (DPPA, 3.23 mL, 18.1 mmol), and the reaction was heated at 95 C. for 1.5 h, followed by a 2nd portion of DPPA (1 mL, 5.6 mmol) and heated for additional 1.5 h. The reaction mixture was cooled down, concentrated and the residue was diluted with EtOAc (50 mL), washed with water (30 mL), 3 M NaOH (30 mL), sat. NaHCO3 (30 mL) and brine (30 mL), dried over Na2SO4, and concentrated. The residue was purified by flashed chromatography on silica gel eluting with gradient EtOAc/CH2Cl2 (0-20%) to afford tert-butyl 5-methylpyrazin-2-ylcarbamate as white solid. LCMS (m/z): 210.1 (MH+), 0.69 min; 1H NMR (400 MHz, CDCl3) delta ppm 9.17 (s, 1H), 8.09 (s, 1H), 7.75 (br. s., 1H), 2.51 (s, 3H), 1.56 (s, 9H).

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5521-55-1,Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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.

To a flask fitted with overhead stirrer, condenser, thermometer and nitrogen line was added 5-methylpyrazine-2-carboxylic acid (1.0 eq), tert-butanol (3.5 vols) and di-isopropylethylamine (1.5 eq) under a nitrogen atmosphere. The mixture was heated to 82 C., then diphenylphosphorylazide (1.0 eq) was added over a time period of 5-14 hours, maintaining the temperature of the reaction mixture at approximately 82 C. The reaction mixture was stirred for at least 1.5 hours, and then cooled to approximately 60 C. A solution of 4% w/w sodium hydroxide (1.75 eq) was added over a period of 2 hours. The mixture was cooled to 15 C. over at least 5 hours then held at 15 C. for 3 hours. The batch was then filtered, and the solid slurry washed with water (2 vols). The batch was again slurry washed with water (2 vols). After drying at 55-60 C. overnight, the desired product was obtained as a solid (corrected yield 56-63%). 1H NMR delta (400 MHz CDCl3): 9.18 (s, 1H), 8.17 (bs, 1H), 8.11 (s, 1H), 2.51 (s, 3H), 1.56 (s, 9H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methylpyrazine-2-carboxylic acid, its application will become more common.

Reference:
Patent; AstraZeneca AB; US2010/210841; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5521-55-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of the corresponding acid (1.0 to 2.0 equiv) and amine (1.0 equiv) in CH2CI2 was added DIPEA (3.0 equiv). HBTU (2.0 equiv) was added at 0 C. The resulting mixture was stirred at r.t. for 24 h. The reaction mixture was diluted with CH2CI2 and washed with water. The organic layer was separated and dried over anhydrous Na2SO4. The solution was concentrated to give a crude product, which was purified with a silica gel column (EtOAc/hexane) to obtain the desired product.

The synthetic route of 5-Methylpyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; NEAMATI, Nouri; ZHOU, Jia; KUANG, Yuting; YE, Na; (130 pag.)WO2016/187544; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Methylpyrazine-2-carboxylic acid

5-methyl-2-pyrazinecarboxylic acid (122 mg, 0.88 mmol),CDI (143 mg, 0.88 mmol),DMAP (108 mg, 0.88 mmol)Was dissolved in anhydrous dichloromethane (10 mL)Nitrogen protection, the reaction at room temperature for 2 hours.Betulin amine (200 mg, 0.44 mmol) was added to the above reaction solution to continue the reaction for 8 hours.After completion of the TLC detection reaction, the solvent was removed under reduced pressure,The mixture was extracted with H2O (30 mL) and extracted with ethyl acetate (20 mL ¡Á 3). The combined organic phases were dried over anhydrous Na2SO4, concentrated and purified by silica gel column chromatography(DCM: MeOH = 20: 1) to give a white solid (205 mg, 81%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; East China Normal University; Qiu Wenwei; Yi Zhengfang; Liu Mingyao; Cui Haiwei; He Yuan; Wang Jinhua; Yang Lianfang; Gao Cheng; (22 pag.)CN104744549; (2017); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5521-55-1, These common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, 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.

Example B5Preparation of compound 6: rac-5-methyl-pyrazine-2-carboxylic acid [3-(6-amino-2,4- dimethy 1-3 -oxo -2,3,4,5 -tetrahydro -pyrazin-2-y l)-pheny 1] -amide5-Methylpyrazine-2-carboxylic acid (0.014 g, 0.104 mmol) was added to a suspension of intermediate 18 (0.021 g, 0.09 mmol) in DCM (1.5 mL) at room temperature. Then, pyridine (0.01 mL, 0.118 mmol) was added and after stirring at room temperature for 5 minutes HATU (0.038 g, 0.099 mmol) was added. The mixture was stirred at room temperature for 16 hours. The mixture was diluted with water and extracted with DCM. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; MeOH in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo. The residue was purified again by flash column chromatography (silica gel; solid injection; 7 M solution of ammonia in methanol in DCM 0/100 to 2/98). The desired fractions were collected and concentrated in vacuo to yield compound 6(0.009 g, 28% yield).

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary, John; MACDONALD, Gregor, James; VEGA RAMIRO, Juan, Antonio; WO2011/154374; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, belongs to Pyrazines compound, 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 5521-55-1, Formula: C6H6N2O2

To a flask fitted with overhead stirrer, condenser, thermometer and nitrogen line was added 5-methylpyrazine-2-carboxylic acid (1.0 eq), toluene (2.5 vols) and di-isopropylethylamine (1.50 eq) under a nitrogen atmosphere. The mixture was vacuum distilled at a batch temperature of 50 C., distilling to a final volume of 2 vols. The batch was sampled to ensure the water content was <0.1% w/w, then cooled to 15+-2 C., and diphenylphosphorylazide (1.00 eq) was added over a time period of 5-6 hours, maintaining the temperature of the reaction mixture at 15+-2 C. The mixture was stirred for a further 1.5 hours. Meanwhile to a second flask was added benzyl alcohol (3.00 eq) and toluene (11 vols). The mixture was azeotropically dried to a volume of 10 vols. The contents of the second flask were sampled to ensure the water content was <0.1% w/w, then heated to 85-90 C. The contents of the first flask were added slowly to the contents of the second flask over approximately 2 hours, maintaining the reaction temperature at approximately 85 C. The reaction mixture was stirred for 1 hour at 85 C., then cooled to 20 C. 5% w/w Sodium hydroxide solution (1.75 eq) was added slowly over 1 hour, the mixture cooled to 5 C., agitated at 5 C. for 1 hour, then filtered. The isolated solid was washed sequentially with water (2 vols), then methanol (2 vols). After drying in the vacuum oven at 40 C. overnight, the desired product was obtained as a solid (corrected yield 78-85%). 1H NMR (400 MHz, CDCl3): 9.41 bs (1H), 9.24 s (1H), 7.87 s (1H), 7.39-7.41 m (5H), 5.22 s (2H), 2.31 s (3H) 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, 5-Methylpyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see. Reference:
Patent; AstraZeneca AB; US2010/210841; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem