Category: Pyrazines

Related Products of 87486-34-8, A common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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.

A 100-mL three-neck round-bottomed flask equipped with a mechanical stirrer and reflux condenser was charged with Ik (780 mg, 3.56 mmol), 11 (998 mg, 3.73 mmol), cesium carbonate (2.36 g, 7.26 mmol) and 1,4-dioxane (40 mL). After bubbling nitrogen through the resulting solution for 30 minutes, Xantphos (.162 g, 0.281 mmol) and tris(dibenzylideneacetone)dipalladium(0) (.15 g, .165 mmol) were added, and the reaction mixture was heated at reflux for 16 h. After this time the reaction was cooled to room temperature and concentrated under reduced pressure. The resulting residue was absorbed onto silica gel and purified by flash chromatography to afford a 57percent yield (818 mg) of Im as an orange solid: mp 206- 207 0C; 1U NMR (500 MHz, CDCl3) delta 8.27 (bs, IH), 7.72 (dd, IH, J = 2.0, 8.5 Hz), 7.36 (dd, 2H, J = 2.0, 8.5 Hz), 6.73 (s, IH), 3.71 (m, IH), 3.69 (s, IH), 3.52 (s, 3H), 3.21 (m, IH), 3.01 (m, IH), 2.97 (s, 3H), 2.67 (m, IH), 2.19 (s, 3H); MS (ESI+) m/z 406 (M+H).

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CGI PHARMACEUTICALS, INC.; GENENTECH, INC.; WO2009/137596; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5780-66-5, The chemical industry reduces the impact on the environment during synthesis 5780-66-5, name is Pyrazine-2-carbaldehyde, I believe this compound will play a more active role in future production and life.

The compound (99 mg) obtained in Example 47-3 and the compound (51.0 mg) obtained in Example 84-1 were dissolved in anhydrous methanol (5.0 ml). The solution was added with sodium cyanoborohydride (35.6 mg) and further added with acetic acid (1.0 ml) to adjust the solution to pH 5, followed by stirring for 5 minutes and then stirring at room temperature for 17 hours. After completion of the reaction, methanol was distilled off and the solution was then added with 1 mol/l sodium hydroxide to adjust the solution to pH 11, followed by extraction with chloroform. The organic layer was washed with saturated saline solution and dried with anhydrous magnesium sulfate. After that, the solvent was distilled off. Then, the residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (16.8 mg) of the subject compound as a white solid. MS(FAB,Pos.):m/z=512[M+H]+1H-NMR(500MHz,DMSO-d6+D2O):delta=0.82(6H,t,J=7.3Hz),1.42(4H,sext.,J=7.3Hz),2.32(4H,t ,J=7.5Hz),3.48(2H,s),3.71(2H,s),3.73(2H,s),3.77(2H,s),6.85(1 H,s),7.11(1H,s),7.27(2H,d,J=8.5Hz),7.56(2H,d,J=8.3Hz),7.67(2 H,J=8.5Hz),7.89(2H,d,J=8.3Hz),8.51(1H,s),8.55(1H,s),8.84(1H, s).

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, Pyrazine-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 98-97-5, 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. 98-97-5, name is Pyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A catalytic amount of concentrated H2SO4 wasadded to a solution of carboxylic acids 16(a-j) (1.0 mmol)in 50 mL of methanol, and the mixture was refluxed for 6 h. It was allowed to cool. The saturated solution ofNaHCO3 was added to the reaction mixture, and it wasextracted with EtOAc (2 X 50 mL). The combined organiclayer was dried Na2SO4 and concentrated to obtain puremethyl esters 17(a-j).

The chemical industry reduces the impact on the environment during synthesis Pyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Murty; Penthala, Raju; Polepalli, Sowjanya; Jain; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 627 – 643;,
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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Product Details of 63744-22-9

A mixture of known compound 6 (4.0g, 14.44mmol) (25mL), cyclopropylamine (1.5mL, 21.67mmol) and N, N-diisopropylethylamine (3.8mL, 21.67mL) in 1,4-dioxane was stirred at 80C for 5h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated aqueous NaHCO3. The organic phase was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (Hexanes: EtOAc=1:1) to afford the title compound 8 (3.43g, 94%). 1H NMR (300MHz, DMSO-d6) delta 8.08 (s, 1H), 8.02 (s, 1H), 7.80 (s, 1H), 7.46 (s, 1H), 2.88 (m, 1H), 0.67 (m, 4H).

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:
Article; Kang, Seok Jong; Lee, Jung Wuk; Chung, Shin Hyuck; Jang, Sun Young; Choi, Jaeyul; Suh, Kwee Hyun; Kim, Young Hoon; Ham, Young Jin; Min, Kyung Hoon; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 660 – 670;,
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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. 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6863-74-7

Step 1: [6-(6-Cyano-pyrazin-2-yloxy)-l-hydroxy-4-methyl-l,3-dihydro- benzo[c] [ 1 ,2] oxaborol-3-yl)-acetic acid ethyl ester[0592] To a solution of (1 ,6-dihydroxy-4-methyl-l ,3-dihydro- benzo[c][l,2]oxaborol-3-yl)-acetic acid ethyl ester (1.6 g, 6.4 mmol) in anhydrous DMF (15 mL) was added cesium carbonate (5.2 g, 16.0 mmol) and 6-chloro-pyrazine- 2-carbonitrile (0.89 g, 6.4 mmol). The resulting mixture was stirred at room temperature overnight then quenched with crushed ice. The pH was adjusted to 2 with 6M HCl and the mixture extracted with EtOAc (2 x 200 mL). The organic extracts were washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (0-75% EtOAc in hexane) to give 6-(6-cyano-pyrazin-2-yloxy)-l-hydroxy-4-methyl-l,3- dihydro-benzo[c][l,2]oxaborol-3-yl)-acetic acid ethyl ester (1.6 g, 71%). 1H NMR 400 MHz (DMSO-J6) delta 9.30 (s, IH), 8.93 (s, IH), 8.90 (s, IH), 7.33 (s, IH), 7.18 (s, IH), 5.58(m, IH), 4.05 (q, J = 7.2, 2H), 3.17 (m, IH), 2.40 (m, IH), 2.33 (s, 3H), 1.13 (t, J = 6.8 Hz, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6863-74-7.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; GLAXOSMITHKINE LLC; XIA, Yi; ALLEY, Michael, Richard Kevin; ZHOU, Yasheen; SINGH, Rajeshwar; DING, Charles; CAO, Kathy; PLATTNER, Jacob, J.; OU, Ligong; JIA, Guofeng; SARASWAT, Neerja; RAMACHANDRAN, Sreekanth; ZHOU, Ding; WO2011/17125; (2011); A1;,
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Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5521-55-1, 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.

N,N-Dimethylformamide (5.0 mL), pyridine (1.0 mL, 12.36 mmol), and 1- [bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (945 mg, 2.48 mmol, HATU) were added to a mixture of 5- methylpyrazine-2-carboxylic acid (Alfa, 277 mg, 2.0 mmol) and tert-butyl (3- aminobicyclo[1.1.1]pentan-1-yl)carbamate (Pharmablock, 379 mg, 1.91 mmol) in sequential order. The reaction mixture was then stirred at ambient temperature for 1 hour and was then partitioned between dichloromethane (2 × 50 mL) and aqueous sodium carbonate (1.0 M, 100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Trifluoroacetic acid (10 mL, 130 mmol) was added to the residue, and the resulting solution was stirred at ambient temperature for 1 hour and concentrated in vacuo. The residue was directly purified by preparative HPLC [Waters XBridge C185 mum OBD column, 50 × 100 mm, flow rate 90 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1% trifluoroacetic acid)] to give the title compound ( (0.71 g, 1.59 mmol, 83% yield). MS (ESI+) m/z 219 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 5-Methylpyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
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Pyrazine | C4H4N2 – PubChem

Application of 153800-11-4, These common heterocyclic compound, 153800-11-4, name is 2-Ethynylpyrazine, 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.

To a solution of 235(100mg, 0.272mrno1) and 10(56.6mg, 0.543mrno1) in 2OmL of Et3N was added Pd(PPh3)2C12 (9.53mg, 0.Oi4mmol) and Cul (5.17mg, C.O27mmol). The mixture was protected with N2 atmosphere, then was heated at 70C for 4 hours. TLC analysis showed complete conversion of starting material to major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep-1-IPLC to give the target product Compound 134(3mg, yield: 24.59%).LCMS: m/z 345 (M+H?H M?IR (400 MHz cDCI.) oe 8 78 (s 1H), 8 58 (s 1H) 8 O (s IH) 7 53 (d, 1= 8 8 Hz, 2H),7.35 (d, J:= 8.0 Hz, 2K), 6.51 (s, 1K), 2.38 (s, 3H).

The synthetic route of 153800-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 98-97-5, name is Pyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Product Details of 98-97-5

(1) Pyrazine-2-carboxylic acid is fully dissolved in anhydrous methanol,Then add an appropriate amount of concentrated sulfuric acid and heat to reflux for 5 h.After the reaction is cooled, adjust the pH to neutral with saturated NaHCO3,Extract with dichloromethane and keep the dichloromethane layer,The solvent was removed by rotary evaporation to obtain an oily pyrazine-2-carboxylic acid methyl ester;After dissolving it in anhydrous methanol, hydrazine hydrate was added dropwise, and after heating under reflux for 21 h,Cool to room temperature, remove methanol by rotary evaporation to obtain pyrazine-2-hydrazide as a red solid product;The ratio of the amount of pyrazine-2-carboxylic acid methyl ester to the amount of hydrazine hydrate is 1: 2.

The synthetic route of 98-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin Medical University; Xu Jingyuan; Wang Zhigang; Xie Chengzhi; (13 pag.)CN110372681; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 55557-52-3, The chemical industry reduces the impact on the environment during synthesis 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, I believe this compound will play a more active role in future production and life.

To a solution of 3-chloropyrazine-2-carbonitrile (160 g, 1.147 mol) in acetic acid (1.5 L) was added Raney Nickel (50% slurry in water, 70 g, 409 mmol). The resulting mixture was stirred under 4 bar hydrogen at room temperature overnight. Raney Nickel was removed by filtration over decalite and the filtrate was concentrated under reduced pressure and co-evaporated with toluene. The remaining brown solid was dissolved in ethyl acetate at 50C and cooled on an ice-bath. 2M hydrogen chloride solution in diethyl ether (1.14 L) was added in 30 min. The mixture was allowed to stir at room temperature over weekend. The crystals were collected by filtration, washed with diethyl ether and dried under reduced pressure at 40C. The product brown solid obtained was dissolved in methanol at 60C. The mixture was filtered and partially concentrated, cooled to room temperature and diethyl ether (1000 ml) was added. The mixture was allowed to stir at room temperature overnight. The solids formed were collected by filtration, washed with diethyl ether and dried under reduced pressure at 40C to give 153.5 g of (3-chloropyrazin-2-yl)methanamine. hydrochloride as a brown solid (74.4 %, content 77 %).

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, 3-Chloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MSD OSS B.V.; MAN, de Adrianus, Petrus, Antonius; WIJKMANS, Jacobus C.H.M.; STERRENBURG, Jan-Gerard; RAAIJMAKERS, Hans C.A.; BARF, Tjeerd A.; BUIJSMAN, Rogier, Christian; OUBRIE, Arthur A.; REWINKEL, Johannes, Bernardus, Maria; JANS, Christiaan, Gerardus, Johannes, Maria; STOCK, Herman, Thijs; WO2013/10869; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 312736-49-5, name is 3,5-Dichloropyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Product Details of 312736-49-5

To a solution of 2,6-dichloropyrazine-3-carboxylic acid (9 g, 46.6 mmol) in dichloromethane (250 mL) at room temperature (RT) was added oxalyl chloride (5.2 mL, 61.5 mmol) dropwise followed by careful addition of DMF (3 drops) and then the reaction mixture was stirred at RT for 3 hr. Then it was concentrated in a rotavap and the residue was taken in toluene (150 mL) and added dropwise to a mixture of 3-dimethylaminoacrylic acid ethyl ester (8.5 g, 59.4 mmol) and triethylamine (9.7 mL, 69.5 mmol) and the resulting reaction mixture was stirred at 90 C. for 16 hr. Then the reaction mixture was cooled, filtered, and the filtrate was concentrated. The residue obtained was purified by column chromatography (silica gel 60-120 mesh) eluting with 0-40% EtOAc in petroleum ether to obtain the product as pale yellow solid.Yield: 6.7 g (45%).1H NMR (300 MHz, DMSO-d6): 8.8 (s, 1H), 8.0 (s, 1H), 3.8 (q, 5 Hz, 2H), 3.4 (s, 3H), 3.0 (s, 3H), 0.9 (t, 5 Hz, 3H). LC/MS (M+H)+ 318, 320

The synthetic route of 312736-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sudhakar, Anantha; US2011/105497; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem