Category: 55557-52-3

Synthetic Route 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: 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.

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; Fresneau, Nathalie; Cailly, Thomas; Fabis, Frederic; Bouillon, Jean-Philippe; Tetrahedron; vol. 69; 26; (2013); p. 5393 – 5400;,
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

55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 55557-52-3

EXAMPLE 5.1 (+-)-3-[(6R,8aS)-6-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]pyrazine-2-carbonitrile (+-)-(6R,8aS)-6-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]octahydropyrrolo[1,2-a]pyrazine (40 mg, 0.131 mmol) was mixed with 3-chloropyrazine-2-carbonitrile (23.8 mg, 0.17 mmol) and Et3N (0.1 mL) in THF (1 mL) in a sealed vial and heated at 90 C. for 30 min. The reaction mixture was quenched with water and extracted with DCM. The product was purified by column chromatography with 20% ethyl acetate in hexanes to give the title compound (23.8 mg, 44.5%, yellow foam). 1H NMR (CDCl3), delta (ppm): 8.27 (s, 1H), 8.26 (s, 1H), 8.08 (d, 1H), 8.03 (s, 1H), 7.49 (m, 2H), 4.69 (d, 1H), 4.52 (d, 1H), 3.86 (t, 1H), 3.30 (d, 1H), 3.22 (d, 1H), 3.11 (dd, 1H), 2.32-2.60 (m, 4H), 2.04 (m, 1H), 1.84 (m, 1H).

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

Reference:
Patent; AstraZeneca AB; NPS Pharmaceuticals; US2007/37816; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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.

At room temperature,(3-(Aminomethyl)cyclobutyl)methyl benzoate (0.3 g, 5 mmol)And triethylamine (0.2 mL, 12 mmol)Add to 3-chloropyrazine-2-carbonitrile (0.5 g, 6 mmol) in THF (10 mL)The reaction solution was reacted at 25 C for two hours.After the reaction is completed,Concentrated under reduced pressure,The residue was purified by silica gel column chromatography (eluent: EtOAc (V/V) = 5/1)The title compound (0.32 g, 54%)

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Liu Xinchang; Tang Changhua; Zhang Jiancun; Zhang Yingjun; (30 pag.)CN104402833; (2016); B;,
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.

EXAMPLE 13.1 (+-)-3-[(6R,8aS)[[(3-chlorophenyl)ethynyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl] pyrazine-2-carbonitrile A mixture of (+-)-(6R,8aS)-6-[(3-chlorophenyl)ethynyl]octahydropyrrolo[1,2-a]pyrazine (40 mg, 0.15 mmol), 2-chloro-3-cyanopyrazine(30 mg, 0.22 mmol), Et3N (0.1 mL) and THF (1.5 mL) was stirred at 80 C. for 4 h. The resulting mixture was concentrated and purified on silica gel column to provide product (44 mg, 81%). 1H NMR (300 MHz, CDCl3): delta (ppm) 1.62 (m, 1H), 1.85-2.25 (m, 5H), 3.02 (dd, 1H), 3.24-3.48 (m, 3H), 4.61 (dt, 2H), 7.29 (m, 3H), 7.45 (s, 1H), 8.02 (d, 1H), 8.27 (d, 1H).

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; AstraZeneca AB; NPS PHARMACEUTICALS; US2007/37817; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products 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.

To a solution of (1 r,4r)-4-( 1 -(3-(2-fluoropropan-2-yl)- 1 ,2,4-oxadiazol-5-yl)piperidin-4- yloxy)cyclohexanol (154 mg, 0.470 mmol) and 3-chloropyrazine-2-carbonitrile (83.8 mg, 0.601 mmol) in 2 mL THF, 1 M potassium tert-butoxide in THF (0.6 mL, 0.600 mmol) was added slowly. After stirring at rt for 0.5 h, the dark brown solution was extracted with water and CH2C12. Organic phases were dried over MgSO4, filtered, and concentrated. Residue was purified by Biotage column chromatography (Si02, hexane/AcOEt gradient). Fractions containing product were concentrated and re-purified by HPLC (CH3CN/H20 gradient + 0.1% TFA). Fractions containing product were partly concentrated and residue was extracted with 1 M NaHCO3 and CH2C12. Organic phases were dried over MgSO4, filtered, and concentrated to afford the title compound (125 mg, 0.290 mmol, 6 1.7%) as a white solid. Exact mass calculated for C2,H27FN603: 430.21, found: LC/MS m/z = 431.2 (M+H); ?H NMR (400 MHz, CDC13) oe ppm 1.51-1.60 (m, 2H), 1.66-1.76 (m, 1OH), 1.86-1.93 (m, 2H), 1.99-2.06 (m, 2H), 2.10-2.17 (m, 2H), 3.47-3.53 (m, 2H), 3.56-3.62 (m, 1H), 3.66-3.72 (m, 1H), 3.82-3.89 (m, 2H), 5.20-5.27 (m, 1H), 8.23 (d, J = 2.5 Hz, 1H), 8.30 (d, J = 2.5 Hz, 1H).

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.

Related Products of 55557-52-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 55557-52-3 name is 3-Chloropyrazine-2-carbonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-Cyano-3-chloropyrazine (1.5 g, 10.8 mmol) and Raney-Ni (50% slurry in water, 0.5 g) were added to 15 mL of glacial acetic acid under nitrogen for three times.Stir at 50 C overnight under a hydrogen atmosphere of 3 atm. After the reaction is complete, it is filtered.The filtrate was concentrated and the residue dissolved in ethyl acetate.Dry over anhydrous sodium sulfate, concentrate,The pale yellow oil was separated by a silica gel column (0.82 g).The yield was 53%.

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.

55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C5H2ClN3

iv) (+-)-3-[(6R,9aS)-6-(hydroxymethyl)octahydro-2H-pyrido[1,2-a]pyrazin-2-yl]pyrazine-2-carbonitrile (+-)-(6R,9aS)-Octahydro-2H-pyrido[1,2-a]pyrazin-6-ylmethanol (500 mg, 2.93 mmol) was dissolved in THF (7 mL) and Et3N (2.03 mL, 14.7 mmol). 3-Chloropyrazine-2-carbonitrile (573 mg, 4.11 mmol) was added with stirring, and the reaction was stirred overnight at 35 C. The reaction mixture was then diluted with DCM and washed with water. The organic phase was purified by column chromatography to yield the desired product (650 mg, 81%). 1H NMR (300 MHz, CDCl3): delta (ppm) 1.40 (m, 1H); 1.69 (m, 4H); 1.82 (m, 1H); 2.21-2.32 (m, 4H); 2.93 (dd, 1H); 3.28 (m, 2H); 3.35 (d, 1H); 3.96 (dd, 1H); 4.34 (d, 1H); 4.48 (d, 1H); 8.02 (d, 1H); 8.26 (d, 1H).

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

Reference of 55557-52-3, 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.

A.5 Synthesis of pyrazine-2-carboxylic acid derivativesA.5.1 Synthesis of pyrazine-2-carbonitrile derivativesA mixture of the respective boronic acid derivative (B-B(OH)2) (21.5 mmol), 3-chloro- pyrazine-2-carbonitrile (21.5 mmol), a solution of K2CO3 (59.4 mmol) in water (30 ml_), PPh3 (3. 2 mmol), Pd(OAc)2 (1.05 mmol) in dry DME was stirred at reflux under inert atmosphere for 16 h. After cooling to rt, the reaction mixture was diluted with EtOAc, filtered over celite, the filtrate was dried over MgSO4, filtered and concentrated in vacuo to yield the desired pyrazine-2-carbonitrile derivative which was used for the next step without further purification3-m-Tolyl -pyrazine-2-carbonitrile prepared by reaction with commercially available 3-m-tolyl-boronic acid LC-MS: tR = 0.88 min; [M+H+MeCN]+ = 243.63

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; BROTSCHI, Christine; GABILLET, Jerome; SIEGRIST, Romain; SIFFERLEN, Thierry; WILLIAMS, Jodi T.; WO2010/38200; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 55557-52-3, 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.

(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 %).

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