Category: 55557-52-3

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: Into a 2000 mL 4 necked round bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of 3-chloropyrazine-2-carbonitrile (100 g, 716 mmol) in ethanol (660 mL), ethyl 2-sulfanylacetate (112 g, 932 mmol) and sodium carbonate (99 g, 930 mmol). The resulting solution was stirred for 4.5 h at 100 C in an oil bath. The reaction mixture was cooled to room temperature and poured into 7.5 L of water. The solid was collected by filtration. The solid was dissolved in 1500 mL of ethyl ether and filtered. The filtrate was concentrated under reduced pressure. This resulted in ethyl 7-aminothieno[2,3-Z>]pyrazine-6- carboxylate as a solid.

According to the analysis of related databases, 3-Chloropyrazine-2-carbonitrile, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; GIBEAU, Craig, R.; (84 pag.)WO2016/144849; (2016); 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., 55557-52-3

The starting compound 3-chloropyrazine-2-carboxamide was synthesized using two published procedures. The first method was classified as less effective and was based on the homolytic amidation of 2-chloropyrazine. Thus, 2-chloropyrazine (0.17 mol) was dissolved in formamide (3.7 mol), heated to 90 C and ammonium peroxodisulphate (0.18 mol) was added portionwise over one hour period. This mixture reacted for another one hour at 90 C and then it was left to stand for 24 h at laboratory temperature. Dilution with 100 mL of water was followed by filtration and this filtrate was extracted continuously with chloroform for 16 h [34,42]. The mixture of three positional isomers was separated by flash chromatography using silica gel as stationary phase. The second process used 3-chloropyrazine-2-carbonitrile, which was submitted to partial hydrolysis of the nitrile group. The powdered carbonitrile (0.104 mol) was added little by little into the reaction mixture of concentrated hydrogen peroxide (0.95 mol) and water (195 mL) heated to 50 C. The pH was adjusted and regulated around a value of 9 using an 8% solution of sodium hydroxide and the temperature of the reaction was regulated between 55 and 60 C. The reaction was stopped after 2.5 h and was cooled to 5 C. Newly-emerged crystals were removed by suction and recrystallized from ethanol [42].

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; Jandourek, Ondrej; Dolezal, Martin; Kunes, Jiri; Kubicek, Vladimir; Paterova, Pavla; Pesko, Matus; Buchta, Vladimir; Kralova, Katarina; Zitko, Jan; Molecules; vol. 19; 7; (2014); p. 9318 – 9338;,
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

General procedure: In a degassed solution of DME/water 2:1 (12mLmmol-1 of diazine), was introduced S-Phos (10mol%) and Pd(OAc)2 (5mol%). The solution was heated at 80C for 10min and sodium carbonate (4equiv), the arylboronic species (1.05 or 1.50equiv) and 3-chloropyrazine-2-carbonitrile (1equiv) were added. The solution was then refluxed (15min or overnight) under argon. The resulting solution was filtrated on celite and washed with ethyl acetate and water. The aqueous phase was then extracted 3 times with ethyl acetate. The combined organic phases were washed with water, dried over MgSO4 and evaporated to dryness. The residue was purified by silica gel chromatography to give the desired product.

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:
Article; Fresneau, Nathalie; Dumas, Noe; Tournier, Benjamin B.; Fossey, Christine; Ballandonne, Celine; Lesnard, Aurelien; Millet, Philippe; Charnay, Yves; Cailly, Thomas; Bouillon, Jean-Philippe; Fabis, Frederic; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 386 – 396;,
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.

The 3 – chloro -2 – cyanopyrazine (2.24 g 1.6 eq), 4 – amino -2 – pyrimidine formic acid (1.39 g 1 eq) and potassium carbonate (4.1 g 3 eq) solution 20 mLDMF in, stirring and heating to 60 C, reaction 5 h, cooling to room temperature, filter, solution (DCM/MeOH=20:1) for refining, yellow solid product to be 1.73 g (yield: 71%).

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; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Zou Mingming; Hu Xiande; Sui Rongchun; Xu Man; (14 pag.)CN108689997; (2018); A;,
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

(90 g, 645 mmol), CH3COOH (1 L) and Raney Ni (20 g) were added to a 2 Lautoclave successively. A reaction was carried out in the autoclave while the reaction solution was stirred under ahydrogen pressure of 1 MPa for 48 hours at atmospheric temperature. After the reaction was completed, the reactionsolution was filtered through diatomite, and a solution of HCl in MeOH (200mL, 6.0N) was used to wash diatomite The filtrate after being concentrated was poured into toluene and the obtained system was stirred, and was thenconcentrated again. The obtained mixture was stirred in MTBE (methyl tert-butyl ether) and was filtered. The filtercake was stirred in MTBE and MeOH and was then filtered to obtain intermediate 2 (40g, yield: 35%) as a brownsolid. LCMS showed a molecular ion peak (M+1) 144.0.

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; Hangzhou Sanyintai Pharmaceutical Technology Co., Ltd.; Yin, Jianming; YIN, Jianming; LV, Yubin; LI, Bangliang; (36 pag.)EP3480199; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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.

(3-hydroxy-cyclobutyl) methyl benzoate (1.48g, 7.18mmol, 1.05eq.) In anhydrous THF (2mL) was added to sodium hydride(60%, 274mg, 6.84mmol, 1eq.) In anhydrous THF (30mL) suspension, and the mixture was stirred for 1h at room temperature, and then added 3-Chloro-pyrazine-2-carbonitrile (909mg, 6.84mmol, 1eq.), The reaction mixture was stirred at room temperature for 15h. The mixture was diluted with 50mL of water was added,Then EtOAc (30mL x 2) and extracted. The organic solution was washed with saturated sodium chloride combined (30mL x 2), dried over anhydrous sodium sulfate,Then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: PE / EtOAc (V / V) = 2.7 / 1) to give the title compound as a white solid (1g, 28%).

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; East Sunshine Pharmaceutical Co., Ltd. of Guangdong; Ren, Qingyun; Luo, Huichao; Tang, Changhua; Zhang, Jiancun; Zhang, Yingjun; (30 pag.)CN104447583; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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.

Into a vessel containing 50 mL ethanol was added 1.0 g of 3-chloropyrazine-2- carbonitrile (Exp-5-g22, 7.2 mmol), 1.1 g PMBNHNH2 (7.3 mmol) and 1.9 g K2C03 (14.2 mmol). The reaction mixture thus provided was heated to reflux and refluxing was continued for 6 hours, then the mixture was cooled to ambient temperature, filtered and the solid was washed sequentially with 10 mL H20 and 10 mL of methanol and dried yielding 1.0 g Exp-5-g23 (calculated yield 56%).

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; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; JONES, Philip; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/63100; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 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).

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; 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

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

Step 1. Preparation of N-(3-cyano-pyrazin-2-yl)-N-methyl-methane sulfonamide (B2-1): A solution of chloropyrazine-2-carbonitrile (4.2 g, 30.21 mmol) in acetonitrile (200 mL) at 25 C. was treated sequentially with Cs2CO3 (13.7831 g, 42.293 mmol) and N-methyl-methane sulfonamide (3.957 g, 36.25 mmol). The mixture was then heated to 80 C. After about 20 hours the mixture was cooled to 25 and filtered. The solids were washed with EtOAc (3*25 mL) and the combined filtrates were concentrated. The resultant residue was treated with water (50 mL) and extracted with EtOAc (3*75 mL). The combined organic layers were washed with water (50 mL), brine, dried over anhydrous sodium sulfate and concentrated. The resultant residue was purified by column chromatography (100-200 mesh silica gel; 40% EtOAc in petroleum ether as eluding solvent) to provide B2-1 as a pale brown liquid. Yield: 4.7 g, 73.43%). 1H NMR (CDCl3) delta: 8.92 (d, 2H), 3.4 (s, 3H) and 3.25 (s, 3H). Mass: (M+1) 213 calculated for C7H8N4O2S. (Note: The product contained unreacted N-methanesulfonamide as an impurity.

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; Pfizer Inc.; US2009/54395; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 rert-hutyl 4-(ir,4-4-hydroxycyclohexyioxy)piperidine-i -carboxylate (W0201 1127051) (4 g, 13.36 mmol) in THF (10 mL) was added 1 M potassium tert-butoxide solution in THF (16.03 mL, 16.03 mmol) at 0 E/ under nitroger. After stirring for 10 mm, asolution of 3-chioropyrazine-2–earbonitrile (2.051 g, 14.70 mmoi) in THF (6 mL) was added. The reaction mixture was slowly warmed to room temperatuw and stirred for I Ii. The mixture was quenched with water and 1 N HC1 (aq) and extracted with EtOAc. The organic layer was washed with brine, dried with anhydrousMgSO,, fihered, and concentrated under reducedpressure. The residue was purified by silica gel column chromatography to afford the titlecompound (4.80 g, 11.9 mmoi, 89,3%), Exact mass calculated for C21H30N404: 402.2, fOundLCMS m/z =403.2 [M¡ÀHf; ?H NMR (CDCI1, 400 MHz) S ppm 1.46 (s, 9H), 1.46-1.58 (m,4Fl). 1.65-1.72 (m, 2H), 1.75-1.82 (in, 21-1). 1.96-2.05 (in. 2H). 2.10-2.18 (m, 2H), 3.05-3.12(m, ZR), 3.52-3.58 (m, 21-i). 3.73-3.82 (m. 21-1), 5.18-5.25 (m, Hi), 8.22 (d, J= 2.5 Hz, 11-i).8.29 (d, .J= 2,5 Hz. 11-I).

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; ARENA PHARMACEUTICALS, INC.; THE UNIVERSITY OF COPENHAGEN; JONES, Robert M.; SCHWARTZ, Thue Walter; KRISTENSEN, Line Vildbrad; MADSEN, Torben Andreas Nygaard; WO2014/74700; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem