Pyrazines

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-Dichloropyrazine, 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 19745-07-4, category: Pyrazines

To a stirred solution of 2,5-dichloro-pyrazine (0.5 g, 3.37 mmol) in toluene (10 ml_) was added 6-(tert-butyl- dimethyl-silanyloxy)-naphthalen-2-yl-boronic acid (1.02 g, 3.37 mmol), EtOH (10 ml_), water (2 ml_) and NaHCO3 (0.42 g, 5.0 mmol). Argon was bubbled through the reaction mixture for 30 min. Then Pd(PPh3)4 (0.19 g, 0.16 mmol) was added and the mixture was heated at 45¡ãC for 2 hours. The EtOH was evaporated under vacuum and the mixture was diluted with ethyl acetate (35 ml_). The reaction mixture was then filtered through celite. The organic layer was washed with water (1 x 10 ml_), and brine (1 x 10 ml_), then dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silica gel (ethyl acetate: hexane, 1 :19) to afford the title compound as a white solid (450 mg). 1H NMR (400 MHz, DMSO-d6): delta= 0.28 (6H, s), 1.00 (9H, s), 7.20 (1 H, d), 7.38 (1 H, s), 7.99 (2H, m), 8.17 (1 H, m), 8.70 (1 H, s), 8.75 (1 H, s), 9.40 (1 H, s). LCMS (System 1 ) (run time = 5 min): Rt = 3.45 min, 371 [M+H]+

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Reference:
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; PRYDE, David Cameron; TRAN, Thien Duc; WO2011/4276; (2011); 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H2ClN3

Step 1: [6-(3-Cyano-pyrazin-2-yloxy)-l-hydroxy-4-methyl-l,3-dihydro- benzo[c] [ 1 ,2] oxaborol-3-yl] -acetic acid ethyl ester I *- CCfeEt[0598] To a solution of ethyl 2-(l ,6-dihydroxy-4-methyl- 1 ,3-dihydrobenzo[c] [ 1 ,2] oxaborol-3-yl)acetate (1.0 g, 4.0 mmol) and S-chloro-pyrazine^-carbonitrile (0.84 g, 6.0 mmol) in DMF (24 mL) was added cesium carbonate (2.68 g, 8.8 mmol). The mixture was heated to 8O0C for 2 hrs. The reaction was cooled down, diluted withH2O, acidified to pH 3 with aqueous HCl (IN). The mixture was extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by column chromatography (silica, Hexanes/Ethyl acetate = 1 : 4) affording the title compound (1.30 g, 92%) as a white solid. 1H NMR (CDCl3) delta 8.40 (d, IH), 8.29 (d, IH), 7.36 (d, IH), 7.11 (d, IH), 5.69 (dd, IH), 4.81 (s, IH), 4.20 (q, 2H), 3.11 (dd, IH), 2.44 (dd, IH), 2.39 (s, 3H), 1.26 (t, 3H). MS found: (M+H)+ = 354.

The synthetic route of 55557-52-3 has been constantly updated, and we look forward to future research findings.

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;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 13515-06-5,Some common heterocyclic compound, 13515-06-5, name is 5,6-Dimethylpyrazine-2-carboxylic acid, molecular formula is C7H8N2O2, 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.

5,6-dimethylpyrazine acid (about 0.27 mmol, prepared as Example 2), EDCI (0.35mmol) and DMAP (0.027mmol) were dissolved in dry methylene chloride (20mL), the chlorinated hederagenin(152 mg, 0.27 mmol, prepared as Example 4) was then dissolved in dichloromethane (20 ml). It was dropped into 5,6-dimethylpyrazine acid solution within 20 minutes, and stirred at room temperature for 12 hours. It was then diluted with dichloromethane (20 mL), washed with saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to obtain a white powder, H-23. Yield: 36% (afterchromatograph with DCM / MeOH, 1% -2%) as a white powder, m.p .: 123.6 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dimethylpyrazine-2-carboxylic acid, its application will become more common.

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

Adding a certain compound to certain chemical reactions, such as: 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, 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 117719-17-2, name: 5-Bromo-3-morpholinopyrazin-2-amine

Three batches of 5-bromo-3-morpholin-4-yl-pyrazin-2-ylamine (I-02, 2 g, 7.7 mmol), ethyl-3-bromo-4-oxo-piperidine-1-carboxylate (2.4 g, 10 mmol) and small amount of DME (~ 0.3 mL) were heated in parallel at 120 C for 4 h, until the reactants were consumed as determined by LCMS analysis. The three reaction mixtures were mixed and diluted with DCM (100 mL), washed with saturated aqueous solution of NaHC03 (2 x 200 mL) and brine (250 mL), dried over Na2S04 and concentrated in vacuo rendering a dark residue. The black residue was purified in two portions by Biotage flash column chromatography (cartridge 40M) eluting with a solvent system of EtOAc/cyclohexane (30%-75% of EtOAc), yielding the required intermediate I-03 (2 g, 21%) as cream solid

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONC&Oacgr;LOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ ARISTEGUI, Sonsoles; GONZALES CANTALAPIEDRA, Esther; HERNANDEZ HIGUERAS, Ana Isabel; VARELA BUSTO, Carmen; WO2011/36461; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4774-14-5, name is 2,6-Dichloropyrazine, 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 4774-14-5, SDS of cas: 4774-14-5

In a 250 mL flame dried RBF equipped with a temperature probe was added nBuLi (2.46 M, 2.2 mL, 5.39 mmol) and THF (49 mL) under nitrogen. The solution was cooled at -20 oC and 2,2,6,6-tetramethylpiperidine (0.95 mL, 5.64 mmol) was added dropwise. The solution was stirred at 0 oC for 30 min. before cooling at -105 oC with a nitrogen/Et2O bath. A – 78 C solution of 2,6-dichloropyrazine (730 mg, 4.90 mmol) in THF (16 mL) was then cannulated over 10 min. to the -105 C LiTMP solution. The mixture was allowed to stir an additional 30 min. at -100/-105 C and a -78 C solution of 2-chlorobenzaldehyde (0.83 mL, 7.35 mmol) in THF (7 mL) was added. The resulting solution was allowed to stir at -95 C for an additional 1h15. An aqueous saturated solution of NH4Cl (10 mL) was then added and the mixture was allowed to warm at room temperature. Water (200 mL) was added and the mixture was extracted with Et2O (3 x 50 mL). Combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtrated and the volatiles were removed under reduced pressure. The resulting residue was purified by silica gel chromatography (5 to 18% gradient of EtOAc/hexanes) to give (2-chlorophenyl)(3,5-dichloropyrazin-2-yl)methanol (1.10 g, 78% yield) as a yellow oil.1H NMR (500 MHz, CDCl3) delta ppm 8.56- 8.56 (m, 1H), 7.41 (dd, J = 7.7, 1.5 Hz, 1H), 7.27 (td, J = 7.4, 1.8 Hz, 1H), 7.23 (td, J = 7.5, 1.4 Hz, 1H), 7.12 (dd, J = 7.6, 1.8 Hz, 1H), 6.47 (d, J = 7.2 Hz, 1H), 4.07 (d, J = 7.2 Hz, 1H). MS (ES+) m/z 271/273/275 (MH-H2O)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichloropyrazine, and friends who are interested can also refer to it.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; ALBRECHT, Brian K.; GIORDANETTO, Fabrizio; GREISMAN, Jack, Benjamin; MARAGAKIS, Paul; TAYLOR, Alexander M.; WALTERS, W. Patrick; (117 pag.)WO2018/57884; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 87885-43-6, name is 2-Chloro-3-nitropyrazine, 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 87885-43-6, COA of Formula: C4H2ClN3O2

EXAMPLE 2 1-(3-Nitro-2-pyrazinyl)hexahydro-1H-1,4-diazepin-5-one To a solution of hexahydro-1H-1,4-diazepin-5-one (1.14 g, 10 mmol) and triethylamine (1.01 g, 10 mmol) in isopropanol (30 ml) cooled in an ice bath, was added over 30 minutes a solution of 2-chloro-3-nitropyrazine (1.59 g, 10 mmol) in chloroform (20 ml). After addition was complete, the reaction mixture was allowed to warm to 20-25 and was stirred at this temperature for 20 hours. Solvents were removed under reduced pressure and the residue was partitioned between a saturated aqueous solution of sodium chloride and ethyl acetate. The ethyl acetate extract was dried over anhydrous sodium sulfate, filtered and concentrated to an oil. Flash chromatography over silica gel and elution with 2% methanol -98% chloroform gave pure 1-(3-nitro-2-pyrazinyl)hexahydro-1H-1,4-diazepin-5-one. STR3

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Merck & Co., Inc.; US4619927; (1986); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5049-61-6,Some common heterocyclic compound, 5049-61-6, name is Pyrazin-2-amine, molecular formula is C4H5N3, 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.

[0383] A solution of 2-aminopyrazine (23.86 g, 0.2509 mol) in methylene chloride (420 mL) was cooled to 0 C. and then treated with N-chlorosuccinimide (33.50 g, 0.2509 mol). The reaction mixture was stirred at 0 C. for 24 h. The resulting dark reaction mixture was diluted with water (500 mL) and then concentrated in vacuo to remove methylene chloride. The aqueous layer was continuously extracted with ethyl acetate until product was absence from the aqueous layer as determined by thin layer chromatography. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 25% ethyl acetate/hexanes) afforded 2-amino-5-chloropyrazine (2.66 g, 8.2%) as a yellow solid: mp 126-128 C.; EI-HRMS m/e calcd for C4H4ClN3 (M+) 129.0094, found 129.0090. [0384] A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acid (prepared as in Example 60, 200 mg, 0.56 mmol) and triphenylphosphine (192 mg, 0.73 mmol) in methylene chloride (4.0 mL) cooled to 0 C. was treated with N-bromosuccinimide (128 mg, 0.73 mmol) in small portions. After the complete addition of N-bromosuccinimide, the reaction mixture was allowed to warm to 25 C. over 30 min. The bright orange reaction mixture was then treated with 2-amino-5-chloropyrazine (145 mg, 1.12 mmol) and 2,6-lutidine (0.28 mL, 2.24 mmol). The resulting reaction mixture was stirred at 25 C. for 4 h. The reaction mixture was then diluted with methylene chloride (25 mL) and was successively washed with a 10% aqueous hydrochloric acid solution (1¡Á20 mL), a saturated aqueous sodium bicarbonate solution (1¡Á20 mL) and water (1¡Á20 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 13/7 hexanes/ethyl acetate to 2/3 hexanes/ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-N-(5-chloro-pyrazin-2-yl)-3-(4-oxo-cyclohexyl)-propionamide (137 mg, 52%) as a light yellow foam: [alpha]23589=-27.35 (c=0.49, chloroform); EI-HRMS m/e calcd for C20H21Cl2N3O4S (M+H)+ 470.0703, found 470.0705.

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

Reference:
Patent; Corbett, Wendy Lea; Grimsby, Joseph Samuel; Haynes, Nancy-Ellen; Kester, Robert Francis; Mahaney, Paige Erin; Racha, Jagdish Kumar; Sarabu, Ramakanth; Wang, Ka; US2003/225283; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H3Br2N3

Intermediate Example 10-1 : Preparation of 6,8-dibromo-3-iodo-imidazo[1 ,2- ajpyrazineTo a stirred solution of intermediate example 9-1 (8.7 g g, 31.4 mmol) in DMF (210 mL) was added NIS (7.42 g, 33 mmol, 1 .05 eq) in one portion at rt. After 18 h stirring at 60C, the solvent was removed in vaccuo and the residue was taken up in DCM and washed with water and saturated sodium thiosulfate solution. The organic phase was dried over sodium sulphate, filtered and the solvent was evaporated to yield 9.46 g (74.8 %) 6,8-Dibromo-3-iodo-imidazo[1 ,2-a]pyrazine: 1H- NMR (300 MHz, CDCb): delta = 8.22 (1 H, s), 7.91 (1 H, s) ppm.

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 63744-22-9.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80229; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 63286-28-2, 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 63286-28-2 as follows.

Step 3. N’-(3-chloropyrazin-2-yl)-l-(5-ethylpyrimidin-2-yl)piperidine-4- carbohydrazide[0323] To a solution of l-(5-ethylpyrimidin-2-yl)piperidine-4-carboxylic acid (3.0 g, 13 mmol) in DMF (50 niL), was added 0-(7-Azabenzotriazol-l-yl)- N,N,N’,N’-tetramethyluronium hexafluorophosphate (5.2 g, 14 mmol), diisopropylethylamine (2.5 mL, 14 mmol), and 2-chloro-3-hydrazinylpyrazine (2.0 g, 14 mmol). After 1 h at rt, the solution is diluted with DCM (200 mL), and washed with brine (100 mL) and water (100 mL), concentrated to residue, and taken up in ethyl acetate (50 mL). The resulting precipitate is isolated by filtration to give Nu’-(3-chloropyrazin-2-yl)-l-(5-ethylpyrimidin-2-yl)piperidine-4- carbohydrazide as off-white solid (3.3 g, 71%). 1H NMR (400 MHz, DMSOd6) delta 9.89 (s, IH), 8.93 (s, IH), 8.22 (s, 2H), 8.06 (d, IH), 7.73 (d, IH), 4.60 (d, 2H), 2.92 (t, 2H), 2.56 (m, IH), 2.40 (q, 2H), 1.78 (m, 2H), 1.49 (m, 2H), 1.10 (t, 3H). LCMS: 362.2 (M+H)+.

According to the analysis of related databases, 63286-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KALYPSYS, INC.; KAHRAMAN, Mehmet; SMITH, Nicholas, D.; BONNEFOUS, Celine; NOBLE, Stewart, A.; PAYNE, Joseph, E.; WO2010/88518; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H9N3

5,6,7,8-Tetrahydroimidazo[1 ,2-a]pyrazine(l17) (4.53 g, 36.8 mmol) and triethylamine (6.16 mL, 44.2 mmol) were dissolved in dichloromethane (DCM) (200 mL) and treated with di-tert-butyl dicarbonate (10.25 mL, 44.2 mmol). The solution was stirred at RT for 48 h and concentrated in vacuo to afford a crude oil. The crude product was purified by flash chromatography (Isolera, 340 g, 0-100% 2M ammonia in methanokdichloromethane (1 :9)/dichloromethane) to afford 3 fractions. Fraction 2 was identified by LC/MS as containing desired product. The residue was dissolved in ethyl acetate (300 ml), washed with saturated sodium bicarbonate solution (50 ml_), water (2 x 50 ml_), brine (50 ml_), dried over anhydrous sodium sulfate and concentrated to afford product in 6.77g. LC/MS = 224 (M+H)+, retention time = 0.71 minutes (2 minute method (high pH)).

According to the analysis of related databases, 91476-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem