Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, 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 5521-55-1, HPLC of Formula: C6H6N2O2

[Referential Example 36] 5-(5-Methyl-2-pyrazinyl)-1-(3-pyridyl)-1H-pyrazole-3-carboxylic acid; [Show Image] 1) 5-Methylpyrazine-2-carboxylic acid N-methoxy-N-methylamide; Triethylamine (28.9 ml) was added to a solution of 5-methylpyrazine-2-carboxylic acid (13.0 g), N,O-dimethyl hydroxylamine hydrochloride (10.1 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (19.8 g), and 1-hydroxybenzotriazole (14.0 g) in N, N-dimethylformamide (130 ml) at room temperature, and the mixture was stirred for 63 hours. Water and ethyl acetate were added to the reaction liquid and the phases were separated, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane-ethyl acetate) to give 5-methylpyrazine-2-carboxylic acid N-methoxy-N-methylamide (12.3 g, 72%) as an oily product. 1H-NMR (400 MHz, CDCl3)delta: 2.63 (3H, s), 3.41 (3H, s), 3.74 (3H, s), 8.46 (1H, s), 8.82 (1H, s). FAB-MSm/z: 182 (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, 5-Methylpyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1698626; (2006); A1;,
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, category: Pyrazines

Ste -1: (0958) Preparation of (3-chloropyrazin-2-yl)methanamine: (0959) [00361] To a solution of 3-chloropyrazine-2-carbonitrile (2 g) in acetic acid (20 mL) was added Raney nickel (50% slurry in water, 1.6 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 to afford the title compound (3-chloropyrazin-2-yl)methanamine acetate (2.9 g, crude) as brown solid. Calculated (M+H): 144.03; Found (M+H): 144.0

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; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); 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. 153800-11-4, name is 2-Ethynylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 153800-11-4

A reaction flask was charged with (2R,4S,4aS)-9,10-difluoro-8-iodo-2,4-dimethyl-2,4,4a,6- tetrahydro-lH,leta-spiro[[l,4]oxazino[4,3-a]quinoline-5,5′-pyrimidine]-2′,4′,6′(3eta)-trione(Intermediate 89(b), 350 mg, 0.71 mmol), copper(I) iodide (6.78 mg, 0.04 mmol) and dichlorobis(triphenylphosphne)palladium (II) (25.01 mg, 0.04 mmol) in acetonitrile (3 ml) underN2. The flask was degassed and backfilled 3 times with a balloon containing a 50:50 mixture ofArgon/H2. TEA (0.794 ml, 5.70 mmol), which had been degassed by bubbling Ar through for 20 minutes, was added. A solution of 2-ethynylpyrazine (119 mg, 1.14 mmol) in 1 ml CH3CN that had been degassed by bubbling Ar through for 5 minutes, was added. The reaction mixture was heated to 90 0C (external temperature) under the N2/H2 balloon atmosphere for 45 minutes. The mixture was diluted with EtOAc and washed with water and brine. The combined aqueous layers were twice more extracted with EtOAc, which was washed with brine. The combined EtOAc extracts were dried and concentrated, and the residue was chromatographed on silica gel (100%CH2Cl2, followed by gradient elution to 100% EtOAc), to afford the title product as a yellow solid.MS (MH+): 468 for C23Hi9F2N5O41H NMR (300MHz, DMSO-d6) delta: 0.9 (d, 3H), 1.1 (d, 3H), 2.9 (d, IH), 3.1 (m, IH), 3.5 (d, IH),3.7-3.8 (m, IH), 3.9 (m, IH), 4.1 (d, IH), 7.1 (d, IH), 8.6 (s, IH), 8.7 (s, IH), 8.8 (s, IH), 11.6 (s,IH), 11.9 (s, IH).

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 153800-11-4.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/4382; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-29-5, These common heterocyclic compound, 33332-29-5, name is 2-Amino-5-chloropyrazine, 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.

Description 5 2,5-Dichloropyrazine (D5); 5-Chloro-2-pyrazinamine (D4) (753 mg, 5.81 mmol) was dissolved in concentrated hydrochloric acid (8 ml), cooled in an ice-acetone bath and treated with a solution of sodium nitrite (822 mg, 11.9 mmol) in water (6 ml) dropwise over a period of 1 hour. The mixture was transferred to an ice-water bath and left to stir for 1 hour. The mixture was allowed to warm to room temperature over 2 hours, neutralised by addition of an aqueous 50percent sodium hydroxide solution and extracted with dichloromethane (x 4). The dichloromethane layers were combined, dried under magnesium sulfate and evaporated. The resulting residue was purified by Biotage column chromatography eluting with 10percent ethyl acetate in pentane to afford the title compound (112 mg). 1H NMR (CDCI3) 8.40 (2H, s).

The synthetic route of 33332-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/123723; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 59489-71-3,Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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.

Concentrated H2SO4 (55 mL) was cooled to approximately 0 C. in a round-bottomed flask. NaNO2 (8.23 g, 119.3 mmol) was added portion-wise to the flask over approximately 5 min. After the addition was complete, the solution was allowed to mix and warm to ambient temperature over 30 min. The solution was cooled again in an ice bath, and a separate solution of the product from Part A (18.33 g, 105.3 mmol) in concentrated H2SO4 (90 mL) was added dropwise while maintaining a temperature of less than 10 C. After addition was complete, the solution was mixed in the ice bath for 15 min and then warmed to 40 C. for 15 min. The resulting mixture was allowed to cool to ambient temperature and then slowly poured into 500 g of ice. The resulting aqueous mixture was extracted with diethyl ether (3?500 mL). The organic extracts were dried over MgSO4, filtered, and concentrated in vacuo to solids. The solids were slurried in hexanes (100 mL) at ambient temperature for approximately 1 hr, filtered, and desiccated to produce 9.55 g (51.8%) of solids.

The synthetic route of 59489-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C6H7F3N4, 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-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

At room temperature, a 50 ml three-necked flask was charged with F (2.6 g) prepared by the oxidation reaction ,J (1.9 g), DMF (20 ml), HOBT (0.22 g), N, N-diisopropylethylamine (2.6 ml). After the reaction solution was reduced to -15-15 C, EDC (3.0 g) was added and stirring was continued at -10-5 C for 30 minutes to 120 minutes. After the reaction solution was warmed to room temperature, the reaction was continued for 1 to 5 hours. Then, 50ml of ethyl acetate and water were added, stirred well, and separated. The aqueous layer was extracted once with 30ml of ethyl acetate. The organic layers were combined, washed with 30ml of water and concentrated to obtain G4.41g as an off white solid with a molar yield of 84.2%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 486460-21-3, its application will become more common.

Reference:
Patent; Chengdu Qianxilai Pharmaceutical Technology Co., Ltd.; Chen Shaowu; Yang Renming; (14 pag.)CN105017099; (2017); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 6705-33-5, name is Pyrazin-2-ylmethanol belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Formula: C5H6N2O

Example 264; 4-[3,5-dimethyl-1-(pyrazin-2-ylmethyl)-1H-pyrazol-4-yl]benzonitrile A solution (0.090 mol/L, 2.2 mL) of 4-(3,5-dimethyl-1H-pyrazol-4-yl)benzonitrile obtained in Reference Example 5 in THF was added to pyrazin-2-ylmethanol (37.1 mg) and the mixture was stirred. Cyanomethylene tri-N-butylphosphorane (about 250 mg) was added, and the mixture was stirred with heating at 60 C. for 31 hr. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (50-100% ethyl acetate/hexane, 0-30% methanol/ethyl acetate), and further by reversed-phase preparative HPLC (Gilson, UniPoint system, YMC ODS column 30×75 mm, 0.1% TFA containing acetonitrile-water (5:95-100:0)), and the eluted fraction was passed through ion-exchange resin, whereby the TFA salt was converted to a free form to give the title compound (23.1 mg).MS (ESI+, m/e) 290 (M+1)1H-NMR (DMSO-d6) delta: 2.16 (3H, s), 2.33 (3H, s), 5.47 (2H, s), 7.51 (2H, d), 7.87 (2H, d), 8.52 (1H, d), 5.89-8.63 (2H, m).

The synthetic route of 6705-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/270359; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 59489-71-3, 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 59489-71-3 as follows.

General procedure: To a dioxane solution (6.0ml) of 2-amino-3,5-dibromopyrazine 7 (304mg, 1.20mmol) was successively added tetrakis(triphenylphosphine)palladium (112mg, 9.6×10-5mol, 8mol%), 4-trifluoromethylphenylboronic acid 8a (230mg, 1.21mmol), and 1ml of 2-moldm-3 sodium carbonate under argon atmosphere. The mixture was then refluxed for 4h under argon atmosphere. After cooling to room temperature, water (10ml) was added, and organic materials were extracted using chloroform (15ml×3). The combined organic layer was then dried over sodium sulfate. The removal of the solvent afforded brown solid, which was purified by preparative thin-layered chromatography on Merck silica gel (particle size, 5-40mum; 200×200×1.75mm, 5 plates) with a mixed solvent system (ethylacetate:hexane=8:3) as a mobile phase to give 9a (293mg, 77%) in the form of a pale yellow solid and 10a (17mg, 4%) in the form of a pale yellow solid.

According to the analysis of related databases, 59489-71-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Saito, Ryota; Hirano, Takashi; Maki, Shojiro; Niwa, Haruki; Journal of Photochemistry and Photobiology A: Chemistry; vol. 293; (2014); p. 12 – 25;,
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. 98-97-5, name is Pyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 98-97-5

Example 1; Methyl pyrazine-2-carboxylate (Formula 3). 20.0 g (805.8 mmole) of pyrazine-2-carboxylic acid was added to 160 mL of methanol, and 1.0 mL of a concentrated sulfuric acid was gradually dropwise added thereto with stirring. A reaction solution was refluxed at a temperature of 80 to 85C for 5 hours. The reaction solution was cooled to a temperature of 20 to 22 C and concentrated to a volume of 25mL. Then, 80 mL of methylenechloride and 40 mL of water were added to the resultant concentrate. The resultant solution was then neutralized by gradual addition of 40 mL of a saturated sodium hydrogen carbonate solution to get a pH of 8.5. An organic layer was separated and a water layer was extracted again with 40 mL of methylenechloride. The combined organic layer was dried over anhydrous magnesium sulfate, filtered, and washed with 20 mL of methylenechloride. A filtrate was concentrated to give 21.1 g of the titled compound as a pale brown solid (yield 94.8%). Melting point: 60-61 C

According to the analysis of related databases, 98-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CJ CORPORATION; WO2004/48369; (2004); 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. 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 63286-28-2

STEP2 Preparation of Compound 8-chloro-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)-[1,2,4]triazolo[4, 3-a]pyrazine To a solution of (3aR,4R,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole-4-carbaldehyde (1.75 g, 9.3 mmol) in DCM (55 mL) was added 2-chloro-3-hydrazinylpyrazine (1.34 g, 9.3 mmol)(red suspension). The mixture was stirred at room temperature and monitored by TLC until disappearance of starting material (3 h). After cooled in ice-bath, the mixture was treated PhI(OAc)2 (4.49 g, 13.94 mmol) and stirred for 4 h at room temperature. The reaction mixture was washed with sat. aMeOH:DCM. NaHCO3 solution and brine, dried over Na2SO4 and filtered. The organic layer was concentrated in vacuo to purified by MPLC on SiO2 (Hexanes:EtOAc=9:1 to 1:1) to give 8-chloro-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)-[1,2,4]triazolo[4, 3-a]pyrazine (28.6 g, 89%) as a yellow oil. 1H-NMR (CDCl3, 400 MHz): delta 7.85 (d, J=4.4 Hz, 1H), 7.75 (d, J=4.8 Hz, 1H), 6.55 (brs, 1H), 5.67 (d, J=5.6 Hz, 1H), 5.28 (m, 1H), 4.82 (t, J=4.4 Hz, 1H), 4.56 (s, 1H), 2.98 (d, J=2.8 Hz, 2H), 1.59 (s, 3H), 1.41 (s, 3H).

The synthetic route of 63286-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANDOK INC.; Lee, Jin-Hwa; Kim, Seung-Yong; Kim, Do-Ran; Ahn, Koo-Hyeon; Lee, Gwi-Bin; Kim, Doo-Seop; Hwang, Hyun-Sook; (74 pag.)US2017/204101; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem