Category: 55557-52-3

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.

The starting compound 3-chloropyrazine-2-carboxamide was prepared via partial hydrolysis of the nitrile group of 3-chloropyrazine-2-carbonitrile (Fluorochem, Co., Hadfield, Derbyshire, UK). A mixture of concentrated (30%) hydrogen peroxide (29 mL) and water (195 mL) was prepared and alkalinized with an 8% (w/v) solution of sodium hydroxide to obtain a solution with pH 9. The carbonitrile (104 mmol) was then added portionwise into the heated (50 C) mixture over a period of 30 min. The whole mass was stirred for an additional 2.5 h at 55 C while the pH was periodically monitored and alternatively adjusted to the value of 9 by adding a few drops of 8% NaOH solution. The reaction mixture was cooled in a fridge to initiate crystallization. The crude product was recrystallized from ethanol [27]. The yield of this reaction was approximately 80%.

The chemical industry reduces the impact on the environment during synthesis 3-Chloropyrazine-2-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Jandourek, Ondrej; Tauchman, Marek; Paterova, Pavla; Konecna, Klara; Navratilova, Lucie; Kubicek, Vladimir; Holas, Ondrej; Zitko, Jan; Dolezal, Martin; Molecules; vol. 22; 2; (2017);,
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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., 55557-52-3

To a solution of 3-chloropyrazine-2-carbonitrile (15.0 g, 108 mmol) in AcOH (200 mL) was added Raney Ni (3 g, in water), and the mixture was stirred for 48 h under an atmosphere of hydrogen with a balloon at rt. The mixture was filtered and the filtrate was concentrated in vacuo to give a crude product, which was dissolved in 250 mL of aqueous HC1 (2M) and extracted with EtOAc (200 mL x 2). The aqueous layer was concentrated under vacuo to give 14.5 g of (3-chloropyrazin-2-yl)methanamine hydrochloride as a brown solid which was used in the next step without further purification.

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; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David; OWENS, Timothy D.; (121 pag.)WO2016/210165; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

55557-52-3, 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below.

Preparation 228N-(3-Cyanopyrazin-2-yl)-N-methylbenzenesulfonamide10721] To a solution of 2-chloro-3-cyanopyrazine (5 g,35.94 mmol) and Cs2CO3 (16.27 g, 50 mmol) in acetonitrile(75 mE) was added N-methylbenzenesulfonamide (7.37 g, 43mmol) and the reaction heated to 80 C. for 3 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between water and EtOAc. The organic layer was collected, dried, concentrated in vacuo and purified by silica gel column chromatography eluting with 50% EtOAc in hexanes to afford the title compound (7.2 g, 73%). ?H NMR (400 MHz, DMSO-d5): oe ppm 3.12 (s, 3H), 7.64 (m, 4H), 7.76 (m, 1H), 8.80 (d, 1H), 8.85 (d, 1H).

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; Pfizer Inc.; Coe, Jotham Wadsworth; Dehnhardt, Christoph Martin; Jones, Peter; Sabnis, Yogesh Anil; Strohbach, Joseph Walter; Wakenhut, Florian Michel; Whitlock, Gavin Alistair; (180 pag.)US2015/329542; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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. 55557-52-3

General procedure: alpha,beta-unsaturated tosylhydrazones 1 (0.11 mmol, 1.1 equiv), heteroaryl chlorides 2 (0.1 mmol, 1 equiv), Cs2CO3 (0.25 mmol, 2.5 equiv) and MeCN (1 mL) were added to a tube. The mixture was stirred at 60 C until the heteroaryl chlorides was completely disappeared for 4-8h. After cooling to room temperature, the mixture was quenched with NH4Cl (2 mL, saturated aqueous solution) and extracted with CH2Cl2 (3 ¡Á 2 mL). The combined organic phases were dried over Na2SO4 and solvents removed in vacuo. The residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:10-1:4, V/V) as the eluent, affording the desired product 3 and 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 55557-52-3, its application will become more common.

Reference:
Article; Zeng, Lin; Guo, Xiao-Qiang; Yang, Zai-Jun; Gan, Ya; Chen, Lian-Mei; Kang, Tai-Ran; Tetrahedron Letters; vol. 60; 33; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 55557-52-3

Step 7: synthesis of Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate (7) A mixture of 3-chloropyrazine-2-carbonitrile (17.9 g, 128 mmol), sodium carbonate (17.7 g, 167 mmol) and ethyl-2-mercaptoacetate (18.4 mL, 167 mmol) in ethanol (120 mL) was heated to reflux for 4.5 h. Quenched with water (1.5 L) and stirred for 30 min. The resulting precipitate was collected and washed with water. The residue was dissolved in diethyl ether and a black precipitate was filtrated off. Ether was evaporated to give pure compound ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate 7 (19.6 g, 68.5%). 1H-NMR (400 MHz, CDCl3) 1.42 (t, J=7.2 Hz, 3H), 4.40 (q, J=7.2 Hz, 2H), 6.19 (br s, 1H), 8.58 (d, J=2.2 Hz, 1H), 8.63 (d, J=2.2 Hz, 1H).

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, 55557-52-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Folmer, Brigitte Johanna Bernita; Man, de Adrianus Petrus Antonius; Gernette, Elisabeth Sophia; Corte Real Goncalves Azevedo, Rita; Ibrahim, Hemen; US2013/79341; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

55557-52-3, 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 55557-52-3 as follows.

Step-1: (0930) Preparation of (3-chloropyrazin-2-yl)methanamine hydrochloride: (0931) [00352] To a solution of 3-chloropyrazine-2-carbonitrile (10 g) in acetic acid (100 mL) was added Raney Nickel (50% slurry in water, 10 g). The resulting mixture was stirred under 4 bar hydrogen pressure at room temperature for 15 h. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure and co-evaporated with toluene. The remaining brown solid was dissolved in ethyl acetate at 50 C and cooled on an ice-bath. 4M hydrochloric acid in dioxane (50 mL) was added and the reaction mixture was allowed to stir at room temperature for 18 h. The precipitate formed was collected by filtration, washed with diethyl ether and dried under reduced pressure. The product brown solid obtained was dissolved in methanol at 60 C and filtered. The filtrate was partially concentrated, cooled to room temperature and diethyl ether (500 mL) was added. The mixture was allowed to stir at room temperature 18 h. The solids formed were collected by filtration, washed with diethyl ether and dried under reduced pressure to afford the title compound (3-chloropyrazin-2- yl)methanamine hydrochloride (7.67 g, crude) as a brown solid. Calculated (M+H): 144.03; Found (M+H): 144.0

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 55557-52-3, and friends who are interested can also refer to it.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

55557-52-3, 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step 7: synthesis of Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate (7)A mixture of 3-chloropyrazine-2-carbonitrile (17.9 g, 128 mmol), sodium carbonate (17.7 g, 167 mmol) and ethyl-2-mercaptoacetate (18.4 mL, 167 mmol) in ethanol (120 mL) was heated to reflux for 4.5h. Quenched with water (1.5 L) and stirred for 30 min. The resulting precipitate was collected and washed with water. The residue was dissolved in diethyl ether and a black precipitate was filtrated off. Ether was evaporated to give pure compound ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate 7 (19.6 g, 68.5 %). 1H-NMR (400 MHz, CDC13) 1.42 (t, J= 7.2 Hz, 3H), 4.40 (q, J= 7.2 Hz, 2H), 6.19 (br s, 1H), 8.58 (d, J= 2.2 Hz, 1H), 8.63 (d, J= 2.2 Hz, 1H).

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; N.V. ORGANON; FOLMER, Brigitte, Johanna, Bernita; MAN, de, Adrianus, Petrus, Antonius; GERNETTE, Elisabeth, Sophia; CORTE REAL GONCALVES AZEVEDO, Rita; IBRAHIM, Hemen; WO2011/147764; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

55557-52-3,Some common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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 A: 3-[(4-Methoxybenzyl)amino]pyrazine-2-carbonitrile To a solution of 3-chloropyrazine-2-carbonitrile (500 mg, 3.6 mmol) in dichloromethane (DCM) (4.0 mL) was added, 4-methoxy-benzenemethanamine (470 muL, 0.0036 mol), N,N-diisopropylethylamine (620 muL, 0.0036 mol) and the resulting mixture was stirred at room temperature (25 C.) for 5 h. The crude residue was purified by flash column chromatography to yield the desired product (650 mg, 75%). MF=C13H12N4O; LCMS calculated for C13H13N4O(M+H)+: m/z=241.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloropyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; US2008/119491; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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. 55557-52-3

A.1.11. Synthesis of 3-aryl-pyrazine-2-carboxylic acids:; A.1.11.1 3-p-Tolyl-pyrazine-2-carboxylic acid; 3-Chloropyrazine-2-carbonitrile (3.0 g; 21.5 mmol) was dissolved in dimethoxyethane (65 ml) and 4-tolylboronic acid (3.2 g; 23.65 mmol) was added, followed by the addition of K2CO3 (8.2 g; 59 mmol) and water (30 ml). The reaction mixture was deoxygenized with N2 (g) for 3 minutes followed by the addition of triphenylphosphine (842 mg; 3.2 mmol) and palladium(II)acetate (237 mg; 1.06 mmol). The reaction mixture was heated to 900C for 14 h, cooled to rt, diluted with EtOAc, filtered over a plug of celite and dried with magnesiumsulfate. The organic solvent was evaporated under reduced pressure to give 5.3 g of S-p-tolyl-pyrazine-l-carbonitrile. The intermediate nitrile was dissolved in MeOH (110 ml) followed by the addition of 4M aq NaOH (180 ml). The resulting mixture was heated to 85C for 14 h, cooled to rt and the MeOH was evaporated under reduced pressure. The residual aq. phase was acidified to pH=2 by the addition of cone. HCl and the precipitated product was filtered off, dissolved in DCM / EtOAc and dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 2.30 g of 3-p- tolyl-pyrazine-2-carboxylic acid. LC-MS: tR = 0.40 min; [M-H]+ = 213.14.

The chemical industry reduces the impact on the environment during synthesis 3-Chloropyrazine-2-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/104155; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, 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. 55557-52-3

1-[3-(3-Chloro-phenyl)-acryloyl]-piperazine-2-carboxylic acid methyl ester (1.6 g, 5.18 mmol) was mixed with 3-chloro-pyrazine-2-carbonitrile (0.868 g, 6.22 mmol) and triethylamine (1.05 g, 10.36 mmol) in acetonitrile at 90 C. overnight. The reaction mixture was quenched water and extracted with dichloromethane. The product was purified by column chromatography with 50% ethyl acetate in hexanes to give 4-[3-(3-chloro-phenyl)-acryloyl]-3′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3-carboxylic acid methyl ester (white solid, 1.5 g, 70.3%).

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 55557-52-3.

Reference:
Patent; AstraZeneca AB; NPS PHARMACEUTICALS; US2007/49578; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem