Author: Jessica.F

Synthetic Route of 186534-02-1,Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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.

5.5 g (36.7 mmol) of compound 1a-4The sample was dissolved in 30 ml of formic acid.Weigh 3.2g (45.9mmol)Hydroxylamine hydrochloride was added, followed by 3.13 g (45.9 mmol)Sodium formate, miscible, 120 C oil bath reaction reflux overnight.The pH of the reaction mixture was adjusted to 10 with a saturated aqueous sodium hydroxide solution and extracted with dichloromethane (30 ml*5 times). 100-200 mesh silica gel sample, dry sample column chromatography:Mobile phase EA: PE (1:5), TLC monitors the fraction of the effluent fraction,The compound 1a-5 fraction was collected. Combine the same fraction and distill dry,White solidCompound 1a-5, yield 65%.

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Xique Pharmaceutical Co., Ltd.; Wang Yuqiang; Yao Hui; Wu Chuanbin; Tao Liang; Sun Yewei; (27 pag.)CN103804309; (2019); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 36070-75-4, 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. 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-1H-pyrazole (170 mg, 2.0 mmol), and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at the 100C for 4 hours. The reaction mixture was cooled to 20C, poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and purified by column chromatography (hexane: ethyl acetate = 5:1) to give 5-(4-fluoro-1H-pyrazol-1- yl)pyrazine-2-carbonitrile (310 mg, Yield 82%). The structure was confirmed by LC-MS.

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

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; DIPIETRO, Lucian, V.; (105 pag.)WO2018/22761; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 19745-07-4, 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 19745-07-4 as follows.

Step C: A flask was charged with (S)-3-(2,6-difluoro-4-(methylsulfonyl)phenylamino)-l,4′-bipiperidin-2-one hydrochloride (0.250 g, 0.590 mmol), 2,5-dichloropyrazine (0.105 g, 0.708 mmol), Hunig’s base (0.309 mL, 1.77 mmol), and DMF (5 mL). The reaction mixture was stirred at 100 ¡ãC overnight. The organic solvents were removed under reduced pressure. The residue was purified using silica gel column chromatography eluting with ethyl acetate to provide (S)-l’-(5-chloropyrazin-2-yl)-3-(2,6- difluoro-4-(methylsulfonyl)phenylamino)-[l,4′-bipiperidin]-2-one (0.102 g, 0.204 mmol, 34.6percent yield) as light yellow solid. Mass spectrum (apci) m/z = 500.1 (M+H).

According to the analysis of related databases, 19745-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; AICHER, Thomas Daniel; BENCSIK, Josef Roland; BOYD, Steven Armen; CONDROSKI, Kevin Ronald; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald Jay; PRATT, Scott Alan; SINGH, Ajay; TURNER, Timothy M.; WO2011/146335; (2011); A1;,
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. 120984-76-1, name is 2-Bromo-3-methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Bromo-3-methylpyrazine

4-[3-Methyl-4-(4,4,5,5-tetramethyl-1 ,3 ,2-dioxaborolan-2-yl)phenoxy]furo[3 ,2-c]pyridine (C2) (250 mg, 0.712 mmol), 5-bromo-4,6-dimethylpyrimidine (160 mg, 0.855 mmcl), tris(dibenzylideneacetone)dipalladium(0) (95%, 26.9 mg, 0.142 mmol), tricyclohexyiphosphine (79.9 mg, 0.285 mmcl) and potassium phosphate (302 mg, 1.42 mmol) were combined in a 3:1mixture of 1 ,4-dioxane and water (12 mL), and subjected to irradiation in a microwave reactor at120 00 for 5 hours. The reaction mixture was filtered through Celite; the filtrate was concentrated under reduced pressure, taken up in ethyl acetate, filtered through silica gel (1 g), and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) afforded the product as a colorless oil. Yield: 123 mg, 0.371 mmol,52%. LCMS m/z 332.1 (M+H). 1H NMR (500 MHz, ODd3) oe 8.98 (s, 1H), 8.07 (d, J5.9 Hz, 1H),7.67 (d, J=2.2 Hz, 1H), 7.25-7.27 (m, 1H, assumed; partially obscured by solvent peak), 7.24(br d, J=2.4 Hz, 1H), 7.19 (brdd, J=8.3, 2.4 Hz, 1H), 7.08 (d, J=8.3 Hz, 1H), 6.90 (dd, J=2.2, 1.0 Hz, 1H), 2.27 (s, 6H), 2.04 (s, 3H).

The synthetic route of 120984-76-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1379338-74-5, A common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, molecular formula is C7H3Cl2N3, 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.

Intermediate 20: 1,1-Dimethylethyl (2S)-2-{[(7-chloropyrido[3,4-b]pyrazin-5-yl)oxy]methyl}-4-morpholinecarboxylate 1,1-Dimethylethyl (2S)-2-(hydroxymethyl)-4-morpholinecarboxylate (Preparation reference: WO 2009/071658) (586 mg, 2.70 mmol) was dissolved in N,N-Dimethylformamide (7 mL) and cooled in an ice bath to 5 C. under a nitrogen atmosphere. Sodium hydride 60% in mineral oil (162 mg, 4.05 mmol) was added portionwise over 15 min. 5,7-dichloropyrido[3,4-b]pyrazine (647 mg, 3.24 mmol) was then added portionwise and the mixture stirred at 5 C. for 35 min and quenched by addition of saturated aqueous ammonium chloride solution (20 mL). The solution was partitioned between ethyl acetate and water. The aqueous was re-extracted with ethyl acetate and the combined organic layers were washed with water, separated using a phase separation cartridge and the solvent removed to give a brown solid. The crude residue was dissolved in DCM and purified by silica chromatography eluting with a 12-62% ethyl acetate in petroleum ether gradient. The appropriate fractions were combined and the solvent was evaporated to give the title compound as a brown solid (917 mg). LCMS (Method B): Rt=1.12 min, MH+=380.9

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; GLAXO GROUP LIMITED; Atkinson, Francis Louis; Atkinson, Stephen John; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander G.; Shipley, Tracy Jane; Wilson, David Matthew; Watson, Robert J.; US2014/5188; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

110223-15-9, name is 2-Amino-3-benzyloxypyrazine, 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. Computed Properties of C11H11N3O

General procedure: 2-Amino-3-benzyloxypyridine or pyrazine derivative(2.5 mmol) was dissolved in dry THF (10 mL), isocyanate derivative(3.0 mmol) was added to the reaction mixture. The reaction wasrefluxed for 3-6 h. After cooling, the reaction mixture was evaporated and the residue was purified by solidification with cold methanol and filtered to give the target compounds.

The synthetic route of 110223-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elkamhawy, Ahmed; Park, Jung-eun; Hassan, Ahmed H.E.; Pae, Ae Nim; Lee, Jiyoun; Park, Beoung-Geon; Roh, Eun Joo; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 529 – 543;,
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. 912773-21-8, name is 2-Bromo-5-chloropyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C4H2BrClN2

Example 19 1-(5-Chloropyrazin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-tetrazol-1-yl)propan-2-ol (49) To a stirred suspension of copper powder (3.0 g, 46.51 mmol) in DMSO (10 mL) was added ethyl 2-bromo-2,2-difluoroacetate (4.7 g, 23.15 mmol) at RT, and the mixture was stirred at RT for 1 h under inert atmosphere. A solution of 2-bromo-5-chloropyrazine (3.0 g, 15.54 mmol) in DMSO (20 mL) was added to the reaction mixture, and stirring was continued for another 16 h at RT. After the consumption of starting material (by TLC), the reaction mixture was diluted with aq NH4Cl solution (40 mL), filtered through a Celite pad and washed with CH2Cl2 (3*25 mL). The collected filtrate was washed with H2O (30 mL) and brine (30 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by column chromatography (eluting with 20% EtOAc/hexane) afforded ester AS (1.12 g, 4.73 mmol, 31%) as a liquid. 1H NMR (500 MHz, CDCl3): delta 8.78 (s, 1H), 8.62 (s, 1H), 4.38 (q, J=7.0 Hz, 2H), 1.37 (t, J=7.0 Hz, 3H).

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; VIAMET PHARMACEUTICALS, INC.; US2012/329802; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5049-61-6, name is Pyrazin-2-amine, 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 5049-61-6, Product Details of 5049-61-6

At room temperature,2-aminopyrazine (8.00 g, 84.12 mmol) was dissolved in dimethylsulfoxide (160 mL)Add water (4 mL),Ice bath,N-bromosuccinimide (31.50 g, 177.00 mmol) was added portionwise to the reaction solution over 30 min,Feeding is completed,Stirred at room temperature overnight,Add water (500mL) quenching,Ethyl acetate (500 mL x 3)Dried over anhydrous Na2SO4,The solvent was removed and the residue was subjected to column chromatography (eluent: PE / EtOAc (v / v) = 6/1) to give 16.40 g of light yellow Color solid, yield: 76.6%.

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

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd; Liu, Bing; Huang, Jiuzhong; Zhang, Yingjun; Xue, Yaping; Xing, Wei; Xu, Juan; Wu, Zuping; Yu, Tianxi; (106 pag.)CN106432246; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 69816-38-2, These common heterocyclic compound, 69816-38-2, name is 5-(Trifluoromethyl)pyrazin-2-amine, 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.

Step 2: 3-{4-Trifluoromethyl-2-[3-(5-tri-fluoromethyl-pyrazin-2-yl)-ureido]-phenoxymethyl}-piper-idine-1-carboxylic acid tert-butyl ester. 3-[2-(4-Nitro-phenoxycarbonylamino) -4-trifluoromethyl-phenoxymethyl] -piperidine-1-carboxylic acid tert-butyl ester (217 mg, 0.4 mmol) and 5-trifluoromethyl-pyrazin-2-ylamine (66 mg, 0.4 mmol) (prepared according to the method of U.S. 4,293,552) were mixed as solids in a 5 mL reaction vial, diluted with 400 uL NMP, capped and stirred as a darkyellow solution that then was immersed in an oil bath at 85C and stirred for six hours. The reaction mixture was cooled to room temperature and stirred overnight. NMP then was removed by Kugelrohr distillation at 0.5 mm and 80C. The brown residue was diluted to 30 mL with CH2C12 then washed 3 x 30 mL with 1M Na2C03 to remove p-nitro-phenol. The organics were dried (MgS04) , filtered, and concentrated to a crude solid that was triturated with EtOAc and filtered to give the desired product as a white solid.

Statistics shows that 5-(Trifluoromethyl)pyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 69816-38-2.

Reference:
Patent; ICOS CORPORATION; WO2006/21002; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 313339-92-3, name is 3,5-Dichloropyrazine-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 313339-92-3, HPLC of Formula: C5HCl2N3

A solution of compound C1-4 (1.90 g, 4.67 mmol) and TFA (6.00 mL) in DCM (20 mL) was stirred for 1H at RT. The resulting mixture was concentrated under reduced pressure. 3,5-dichloropyrazine-2-carbonitrile (818 mg, 4.70 mmol) , DMSO (8 mL) and DIPEA (6.56 g, 50.76 mmol) was added and stirred for 1H at 70 . The reaction mixture was diluted with water (50 mL) and extracted with EA (2 ¡Á 50 mL) . The combined organic layers were dried over anhydrous Na 2SO 4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting with EA : Hex = 1 : 2, v/v) to give compound 50-1 (1.81 g) . MS: 444 [M+1] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichloropyrazine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; HAN, Huifeng; GAO, Panliang; MA, Cunbo; KANG, Di; (214 pag.)WO2020/63760; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem