Month: June 2021

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. 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 6-Chloropyrazine-2-carbonitrile

Reference Example 104 2-Cyano-6-methylthiopyrazine A mixture of 2-chloro-6-cyanopyrazine (1.40 g, 10.0 mmol), sodium thiomethoxide (0.78 g, 11.0 mmol) and THF (100 ml) was refluxed for 2 hrs.. The reaction mixture was combined with ethyl acetate and water.. The organic layer was washed with saturated brine and dried over magnesium sulfate.. The solvent was evaporated to give the titled compound (1.25 g, 83 %) as pale yellow crystals.1H-NMR (CDCl3) delta: 2.61 (3H, s), 8.49 (1H, s), 8.60 (1H, s). IR(KBr): 2241, 1670, 1521, 1390, 1190, 1167, 1138, 1108, 887, 734 cm-1.

According to the analysis of related databases, 6863-74-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1424336; (2004); 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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Amino-6-bromopyrazine-2-carboxylic acid

-Amino-6-bromopyrazine-2-carboxylic acid (53.59 g, 0.229 mol) and 4-hydroxy-3-aminopyridine (33.64 g, 0.275 mol) were mixed in THF (500 mL) and triethyl amine (115.86 g, 1.145 mol) was added. The mixture was stirred at 25 for 10 min. The temperature was raised to 55 C. and T3P (218.90 g, 0.344 mol) was added. The mixture was stirred at 55 C. for 30 min. Water (150 mL) was added at 55 C. and the mixture was stirred for 2 h at 55 C. Solvents were distilled of until fractions at 55-80 C. was removed.Acetonitrile (500 mL) was added followed by water (350 mL) while maintaining the temperature at 75 C. The mixture was stirred for 2 h at 75 C. The solid was isolated by filtration. The solid was washed with water (250 mL) followed by acetonitrile (250 mL). The solid was dried under vacuum at 80 C. for 5 h to give the title compound (84.5%)1HNMR (400 MHz, DMSO-d6): 11.64 (s, 1H) 10.26 (s, 1H) 8.78 (s, 1H) 8.45 (s, 1H) 7.78 (s, 2H) 7.72 (d, 1H) 6.31 (d, 1H).MS (ESI+) m/z 310 [M+H]+

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 486424-37-7.

Reference:
Patent; ASTRAZENECA AB; US2011/118275; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 14508-49-7, The chemical industry reduces the impact on the environment during synthesis 14508-49-7, name is 2-Chloropyrazine, I believe this compound will play a more active role in future production and life.

[Referential Example 33] 2-Hydrazinopyrazine; [Show Image] Hydrazine monohydrate (21.80 g) was added to a solution of 2-chloropyrazine (10.44 g) in ethanol (65 ml) at room temperature, and the mixture was heated under reflux for 17 hours. After cooling with air, the reaction solvent was evaporated under reduced pressure, and benzene was added to the residue, then the insoluble content was’ removed by decantation. After evaporation of the benzene solution under reduced pressure, hexane was added to the resulting solid, and the product was collected by filtration to give the title compound (4.67 g, 47%). 1H-NMR (400 MHz, CDCl3)delta: 7.89 (1H, d, J = 2.7 Hz), 7.99-8.05 (1H, m), 8.20 (1H, d, J = 1.5 Hz). ESI-MSm/z: 111 (M+H)+.

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, 2-Chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1698626; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 87486-33-7, name is 3,5-Dichloro-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Cl2N2O, 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. Safety of 3,5-Dichloro-1-methylpyrazin-2(1H)-one

EXAMPLE 2 3-Amino-5-chloro-1-methyl-2(1H)-pyrazinone A solution of 3,5-dichloro-1-methyl-2(1H)-pyrazinone (7.16 g, 0.040 mol) in dioxane (120 mL) was treated with a concentrated aqueous solution of ammonia (28%, 16 mL, 0.24 mol). After stirring at room temperature for three days a suspension of solid had formed. The solid was collected, rinsed with a little water, ether, and hexanes and air dried. The product, 3-amino-5-chloro-1-methyl-2(1H)-pyrazinone, was obtained as a white crystalline powder (4.81 g) melting above 250 C. PMR (DMSO-d6, 200 MHz): delta 7.16 (broad s, 2H, NH2); 6.99 (s, 1H, Het-H); 3.34 (s, 3H, N–CH3). IR (Nujol mull): 3310 (w, NH); 3170 (w, NH); 1660 (s, C=O) cm-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87486-33-7, its application will become more common.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4802908; (1989); A;,
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

Reference of 126069-70-3,Some common heterocyclic compound, 126069-70-3, name is 2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine, molecular formula is C7H8F3N3, 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.

2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1 ,2-a]pyrazine (I4) (287 mg, 1.5 mmol) and DIPEA (0.314 ml_, 1.800 mmol) were dissolved at 0 0C in dichloromethane (DCM) (15 ml_). 2-chloro-4-fluorobenzoyl chloride (290 mg, 1.500 mmol, commercially available from e.g. Sigma-Aldrich, Maybridge or Apollo ) dissolved in DCM (5 ml.) was added dropwise and the solution stirred to room temperature over 4 h. Solvents were removed in vacuo and the residue was partitioned between dichloromethane (50 ml.) and saturated sodium bicarbonate solution (25 ml_). The aqueous phase was extracted with dichloromethane (3 x 50 ml.) and the combined extracts were washed with water (50 ml_), brine (50 ml_), dried over anhydrous sodium sulfate and concentrated in vacuo to afford a crude oil (759 mg). The crude product was purified by flash chromatography (Isolera, 25 g, 0-100% 2M ammonia in methanokdichloromethane (1 :9)/dichloromethane) to afford crude product. Concentration of the waste afforded material which was also identified as product. Samples were combined to afford crude product. This was purified by MDAP, product containing fractions concentrated and loaded directly on to an SCX cartridge (Varian, 10 g). The column was washed with methanol and the product eluted with 2M ammonia methanol. The solvents were evaporated in vacuo to afford the desired product in 318 mg. LC/MS = 348/350 (M+H)+, retention time = 0.94 minutes (2 minute method)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine, its application will become more common.

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

Electric Literature of 4774-14-5, A common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

107241 2,6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heatedto 90 C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90 C in portions (1 g)20-3 0 second intervals. An exotherm was observed and the color of the mixture turned from yellowto dark red/brown. The mixture was stirred at 90 C for 2 h and then cooled to room temperature.The mixture was diluted with water (500 mL) and filtered. The filtrate layers were separated. Theaqueous layer was extracted with IPAchloroform (1/3, 3 x 750 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil. The oil was purified by silica gel chromatography (0 to 100% EtOAc in hexanes) to provide the title product as a colorless solid (25 g, 36% yield). ?HNMR (400 IVIHz, DMSO-d6): ppm 8.87 (s, 1H), 8.18 (br. s.,1H), 8.01 (br. s., 1H).

The synthetic route of 4774-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLX BIO, INC.; BECK, Hilary, Plake; BIANNIC, Berenger; BUI, Minna Hue, Thanh; HU, Dennis, X.; KETCHAM, John, Michael; POWERS, Jay, Patrick; REILLY, Maureen, Kay; ROBLES-RESENDIZ, Omar; SHUNATONA, Hunter, Paul; WALKER, James, Ross; WUSTROW, David, Juergen; YOUNAI, Ashkaan; ZIBINSKY, Mikhail; (396 pag.)WO2018/22992; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1196152-38-1, 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

1 ,1 -dimethylethyl (1 S,4S,6S)-4-(aminomethyl)-3-azabicyclo[4.1.0]heptane-3- carboxylate D29 (400 mg) and 2-bromo-5-(trifluoromethyl)pyrazine (401 mg, 1.767 mmol) were dissolved in DMF (2 ml) then sodium carbonate (375 mg, 3.53 mmol) was added and the mixture was heated to 50 0C for 2 hours. DMF was concentrated under vacuum and the residue was taken up with DCM (3 ml) and washed with NaHCO3 saturated solution (4 ml). The organic phase was filtered through a phase separator tube, concentrated under vacuum and purified by silica gel chromatography (Biotage SP- column size 25 g SNAP using Cy:EtOAc = 8:2 to 2:8 as eluent). It was recovered the title compound D30 (300 mg)

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-(trifluoromethyl)pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; ALVARO, Giuseppe; AMANTINI, David; CASTIGLIONI, Emiliano; DI FABIO, Romano; PAVONE, Francesca; WO2010/63662; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 4949-13-7, A common heterocyclic compound, 4949-13-7, name is 2-Fluoropyrazine, molecular formula is C4H3FN2, 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.

10264] To a 2.5 M solution of n-butyllithium (40 mE, 0.1 mol) in anhydrous THF (250 mE) cooled to -78 C. under N2 protection was added TMP (2,2,6,6-tetramethylpiperidine, 15 g, 0.106 mol) dropwise over a period of 20 minutes. The mixture was warmed to 0 C. by replacing the dry ice/acetone bath with an ice bath and stirred for 1.5 h. The mixture was cooled back to -78C. and a solution of 9a (3 g, 0.03 mol) and tributyltin chloride (10 g, 0.03 mol) in SOmE of dry THF was added over 10 mm. The mixture was stirred at -78 C. for 6 h, then warmed to -40 C. by replacing the dry ice/acetone bath with an dry ice/acetonitrile bath. A solution of 35% HC1, ethanol and THF (1:4:5) was added. The mixture was warmed to room temperature and washed with saturated NaHCO3 solution (100 mE) and extracted with EtOAc (3×100 mE). The combined organic layers were dried over anhydrous Na2504 and concentrated under reduced pressure. The residue was purified by column chromatography (silica, EtOAc:petroleum ether=1:15) to provide 9b (3.4 g, 29% yield) as light yellow oil. ?H-NMR (CDC13, 300 MHz): oe=8.41 (d, 1H), 8.17 (d, 1H), 1.8-0.53 (m, 27H).

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; Helsinn Healthcare SA; Giuliano, Claudio; Garcia Rubio, Silvina; Daina, Antoine; Guainazzi, Angelo; Pietra, Claudio; US2015/252021; (2015); 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. 59489-71-3, name is 2-Amino-5-bromopyrazine, A new synthetic method of this compound is introduced below., name: 2-Amino-5-bromopyrazine

Step 1: 2-amino-5-cyanopyrazine. To a stirred solution of 5-bromo-2-aminopyrazine (1.0 g) 5.8 mmol), CuI (2.76 g, 14.5 mmol), 18-crown-6 (121 mg; 0.46 mmol), potassium cyanide (943 mg; 14.5 mmol) in dimethylformamide (20 mL) was added Pd(PPh3)4 (196 mg; 0.17 mmol). After stirring at room temperature for 20 minutes the reaction was placed in an oil bath at 155 C. for 2 hours. The reaction was allowed to cool to room temperature and then poured into chloroform (300 mL). A precipitate formed that was filtered and triturated with hexanes to yield an off white solid (60% yield).

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; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem