Category: 55557-52-3

Adding a certain compound to certain chemical reactions, such as: 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, 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 55557-52-3, Safety of 3-Chloropyrazine-2-carbonitrile

(a). (3-Chloropyrazin-2-yl)methanamine hydrochloride was prepared as follows. 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 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloropyrazine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (732 pag.)WO2016/24230; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

General procedure: Compounds 5-10 (Supplemental Figure 6A, Scheme 1), 12-15 (Supplemental Figure 6B, Scheme 2), and 17, 18 (Supplemental Figure 6C, Scheme 3) were prepared by a modified procedure as reported by Kayser F. et al. (ref 1) and Chen Z. et al. (ref. 2). To a solution of the corresponding thiol, or phenol 4 (0.85 g, 5.0 mmol) in 15 ml DMF (N, N-Dimethylformamide) 3-chloropyrazine-2-carbonitrile (0.66 g, 4.76 mmol) and Na2CO3 (1.01 g, 9.52 mmol), or substituted chrolopyridines, or chlorobenzenes, were added respectively and the resulting mixture was refluxed at 80 C for 12 h. The DMF was evaporated at reduced pressure and the compound A residue was recrystallized from ethyl acetate. The rest of the compounds were purified by flash chromatography on silica gel with ethyl acetate:hexanes (5-100% gradient).

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; Freeman, Lita A.; Demosky, Stephen J.; Konaklieva, Monika; Kuskovsky, Rostislav; Aponte, Angel; Ossoli, Alice F.; Gordon, Scott M.; Koby, Ross F.; Manthei, Kelly A.; Shen, Min; Vaisman, Boris L.; Shamburek, Robert D.; Jadhav, Ajit; Calabresi, Laura; Gucek, Marjan; Tesmer, John J. G.; Levine, Rodney L.; Remaley, Alan T.; Journal of Pharmacology and Experimental Therapeutics; vol. 362; 2; (2017); p. 306 – 318;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, 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 55557-52-3, Recommanded Product: 55557-52-3

Step 6: synthesis of N-(3-(7-aminothieno[2,3-b]pyrazine-6-carbonyl)-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide (116) A solution of 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetyl)-4-methylphenyl)benzamide 115 (0.094 mmol, 33 mg), 3-chloropyrazine-2-carbonitrile (0.094 mmol, 13 mg) and sodium carbonate (0.112 mmol, 12 mg) in ethanol (1 mL) was stirred 2 h at 50 C. Quenched in 1N HCl solution and extracted with CH2Cl2. Organic layer was dried and evaporated. Purification by HPLC gave N-(3-(7-aminothieno[2,3-b]pyrazine-6-carbonyl)-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 116 (9 mg, 21%). NMR (400 MHz, DMSO-d6) 1.74 (s, 6H), 2.27 (s, 3H), 7.37 (d, J=8.6 Hz, 1H), 7.60 (t, J=7.8 Hz, 1H), 7.76 (d, J=7.8 Hz, 1H), 7.81 (dd, J=8.2 Hz and 2.3 Hz), 7.95 (m, 2H), 8.04 (m, 3H), 8.82 (s, 2H), 10.44 (s, 1H).(m/z)=457 (M+H)+.

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; 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

Reference of 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.

General procedure: Compounds 5-10 (Supplemental Figure 6A, Scheme 1), 12-15 (Supplemental Figure 6B, Scheme 2), and 17, 18 (Supplemental Figure 6C, Scheme 3) were prepared by a modified procedure as reported by Kayser F. et al. (ref 1) and Chen Z. et al. (ref. 2). To a solution of the corresponding thiol, or phenol 4 (0.85 g, 5.0 mmol) in 15 ml DMF (N, N-Dimethylformamide) 3-chloropyrazine-2-carbonitrile (0.66 g, 4.76 mmol) and Na2CO3 (1.01 g, 9.52 mmol), or substituted chrolopyridines, or chlorobenzenes, were added respectively and the resulting mixture was refluxed at 80 C for 12 h. The DMF was evaporated at reduced pressure and the compound A residue was recrystallized from ethyl acetate. The rest of the compounds were purified by flash chromatography on silica gel with ethyl acetate:hexanes (5-100% gradient).

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:
Article; Freeman, Lita A.; Demosky, Stephen J.; Konaklieva, Monika; Kuskovsky, Rostislav; Aponte, Angel; Ossoli, Alice F.; Gordon, Scott M.; Koby, Ross F.; Manthei, Kelly A.; Shen, Min; Vaisman, Boris L.; Shamburek, Robert D.; Jadhav, Ajit; Calabresi, Laura; Gucek, Marjan; Tesmer, John J. G.; Levine, Rodney L.; Remaley, Alan T.; Journal of Pharmacology and Experimental Therapeutics; vol. 362; 2; (2017); p. 306 – 318;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 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.

2-cyano-3-chloropyrazine (0.8 g, 5.8 mmol) and Raney-Ni (0.3 g) were added to 10 mL glacial acetic acid, the atmosphere was replaced with hydrogen gas for three times, the mixture was stirred under 3 atmospheric pressure of hydrogen gas at 50 C overnight. The reaction was filtered after the reaction was complete, filtrate was concentrated, the residue was dissolved in ethyl acetate, washed with saturated solution of sodium bicarbonate, dried over anhydrous sodium sulfate, concentrated, and separated by silica gel column to afford 0.5 g of a light yellow oil, yield was 60%. LC-MS(APCI): m/z = 144(M+1)+.

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; Shenzhen Targetrx, Inc.; WANG, Yihan; XING, Qingfeng; (51 pag.)EP3492471; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 55557-52-3, A common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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.

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 %).

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; MSD Oss B.V.; Man, de, Adrianus, Petrus, Antonius; Sterrenburg, Jan-Gerard; Raaijmakers, Hans C.A.; Kaptein, Allard; Oubrie, Arthur A.; Rewinkel, Johannes, Bernardus, Maria; Jans, Christiaan, Gerardus, Johannes, Maria; Wijkmans, Jacobus C.H.M.; Barf, Tjeerd A.; Gao, Xiaolei; Boga, Sobhana Babu; Yao, Xin; Zhu, Hugh Y.; Cooper, Allen B.; Kim, Ronald M.; EP2548877; (2013); 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloropyrazine-2-carbonitrile

The starting compound 3-chloropyrazine-2-carbonitrile (35.8 mmol) was dispersed in a 10percentsolution of sodium hydroxide (125 mmol, 3.5 equiv.) in a round bottom flask. The reaction mixturewas stirred and heated under reflux in an oil bath for 7 h. The progress of the reaction was monitoredby TLC in the system butanol/acetic acid/water (4:1:5). The reaction mixture was acidified by 10percentsolution of hydrochloric acid to pH 3. Resulting crystals of 3-chloropyrazine-2-carboxylic acid weresuctioned. The melting point and 1H-NMR corresponded with the literature [17].

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; Semelkova, Lucia; Jand’ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Franti?ek; Kubi?ek, Vladimir; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; McPhee, Derek J.; Molecules; vol. 22; 3; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 55557-52-3, 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.

General procedure: In a degassed solution of DME/H2O (2:1) (12mL/mmol of diazine), were successively introduced S-Phos (10mol%) and Pd(OAc)2 (5mol%). The solution was heated at 80C for 10min then sodium carbonate (4.0equiv), appropriate boronic acid (1.05 or 1.5equiv) and appropriate diazine (1.0equiv) were added. The solution was then refluxed (15min or overnight) under Ar. The resulting mixture was filtered on Celite and washed with ethyl acetate and water. The aqueous phase was then extracted three times with ethyl acetate. The combined organic phase was dried over MgSO4 and evaporated to dryness. The residue was purified by column chromatography (eluent: PE/EtOAc) to give the desired product.

The synthetic route of 3-Chloropyrazine-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fresneau, Nathalie; Cailly, Thomas; Fabis, Frederic; Bouillon, Jean-Philippe; Tetrahedron; vol. 69; 26; (2013); p. 5393 – 5400;,
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. Recommanded Product: 55557-52-3

(a). (3-Chloropyrazin-2-yl)methanamine hydrochloride was prepared as follows. 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 %).

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:
Patent; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (268 pag.)WO2016/24227; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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.

3-Chloro-2-cyanopyrazine (2.24 g, 1.6 eq), 4-amino-2-pyrimidinecarboxylic acid(1.39g, 1eq) and potassium carbonate(4.1g, 3eq) solution in 20mL DMF, stirred and heated to 60 C, reaction for 5h,Cool to room temperature, filter, and refine the solution with (DCM / MeOH = 20:1).Obtained a yellowish solid product 1.73g(Yield: 71%).

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; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Hu Xiande; Zhou Liming; Sui Guilan; (22 pag.)CN109568256; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem