Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, 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 4744-50-7, category: Pyrazines

General procedure: Pyrazine-2,3-dicarboxylic anhydride (1.0 g, 6.7 mmol) was dissolved in tetrahydrofuran (40 mL)in an Erlenmeyer flask and the corresponding substituted aniline (6.7 mmol, 1 equiv.) was added in one dose. The reaction mixture was stirred for 1 hour at laboratory temperature. Water (30 mL) was added into the mixture followed by the saturated aqueous solution of NaHCO3 until pH 6 to form thecorresponding 3-(phenylcarbamoyl)pyrazine-2-carboxylic acid 1-18. Obtained crystals were filtered off and washed with water. The progress of the procedure was monitored by TLC eluted with thesystem water/butanol/acetic acid 5:4:1.

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

Reference:
Article; Semelkova, Lucia; Jano?cova, Petra; Fernandes, Carlos; Bouz, Ghada; Jand?Ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; Molecules; vol. 22; 9; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 912773-21-8, name is 2-Bromo-5-chloropyrazine, 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 912773-21-8, Application In Synthesis of 2-Bromo-5-chloropyrazine

A mixture of 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-2-[l-(trifluoromethyl)cyclobutoxy]pyridine (2.1 g, 6.12 mmol), 2-bromo-5-chloro- pyrazine (1.18 g, 6.12 mmol), Pd(dppf)Cl2(671.68 mg, 0.92 mmol) and CS2CO3(3.99 g, 12.24 mmol) in l,4-Dioxane (20 mL) and Water (2 mL)was stirred at 60 C for 6 hours under N2. After cooling to room temperature, the mixture was concentrated to give the residue. The residue was diluted with H2O (20 mL), and the mixture was extracted with EtOAc (20 mL x 2). The combined organic phase was washed with water (20 mL) and brine (40 mL), dried over Na2S04, filtered and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 1% to 10%) to give the product (1.5 g, 4.263mmol, 70% yield) as an oil. ‘H NMR (CDCI3, 400MHz) 5H = 8.80 – 8.72 (m, 2H), 8.63 (d, 1H), 8.25 (dd, 1H), 6.91 (d, 1H), 3.01 – 2.83 (m, 2H), 2.78 – 2.62 (m, 2H), 2.18 – 1.84 (m, 2H).

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-Bromo-5-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; MARTINEZ BOTELLA, Gabriel; REDDY, Kiran; WITTMANN, Marion; (0 pag.)WO2019/232209; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 109838-85-9, 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. 109838-85-9 name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, 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.

[0562] A solution of compound 4-01-5 (8.9 g, 48 mmol) in tetrahydrofuran (100 mL) was cooled to -70C and n-butyl lithium (2.5 M, 19.5 mL, 49 mmol) was added under nitrogen while the temperature was kept below -70C. A solution of compound 7- bromohept-l-ene (8.0 g, 45 mmol) in tetrahydrofuran (15 mL) was added at -70C. The reaction mixture was stirred at -70C for 2 hours, then slowly heated to 20C and stirred for 1 hour. The reaction mixture was poured into saturated ammonium chloride solution (50 mL) and extracted with ethyl acetate (200 mL *2). The combined organic phase was washed with brine (100 mL*2), dried over anhydrous sodium sulfate, and concentrated in reduced pressure. The residue was purified by column chromatography (petroleum ether to petroleum ether: ethyl acetate = 50: 1) to afford compound 4-01-6 (7 g, 55% yield) as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, and friends who are interested can also refer to it.

Reference:
Patent; CORNELL UNIVERSITY; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE; LIN, Gang; NATHAN, Carl; KIRKMAN, Laura; ZHAN, Wenhu; MORGAN, Trevor; SATO, Kenjiro; HARA, Ryoma; KAWASAKI, Masanori; IMAEDA, Toshihiro; TOITA, Akinori; OKAMOTO, Rei; YUKAWA, Takafumi; ASO, Kazuyoshi; WONG, Tzu-Tshin; GINN, John, D.; FOLEY, Michael, A.; (296 pag.)WO2019/75259; (2019); 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., COA of Formula: C4H4BrN3

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

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. 25911-65-3, name is 3-Aminopyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Aminopyrazine-2-carbonitrile

c) 4-Amino-2-[(4-methoxyphenoxy)methyl]pteridine Obtained using the procedure described in section c of Example 2, starting with 9.8 g (0.082 mole) of 3-amino-2-pyrazinecarbonitrile and the above solution of 2-(3-methoxyphenoxy)acetamidine in absolute ethanol. Refluxing time: 2 hours. Yld: 5.5 g (24%), m.p. 238-240 C. (ethanol/N,N-dimethylformamide). NMR (DMSO-d6): delta=3.7 (3H, s); 5.0 (2H, s); 6.9 (4H, s); 8.3 (2H, peak exchangeable with CF3 COOD); 8.8 (1H, d); 9.0 (1H, d).

The synthetic route of 25911-65-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lipha, Lyonnaise Industrielle Pharmaceutique; US5167949; (1992); A;,
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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H4BrN3

A method for preparing methyl (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate, comprising the steps of: (1) using 5-bromo-4,7-diazaindene as raw material,Reacting with the prepared 20% ammonia water at a temperature of 140 C and a pressure of 3 MPa,The molar ratio of 5-bromo-4,7-diazaindene to ammonia water is 1:12. A cuprous chloride/ferrous chloride composite catalyst is added to the reaction system, and the molar ratio of cuprous chloride to ferrous chloride is 1:1, and the total amount of the catalyst is2% by mass of 5-bromo-4,7-diazepine, the reaction gives compound 1;

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; Nanjing Xin Meihe Pharmaceutical Technology Co., Ltd.; Zhou Wenbin; Yang Yuanming; Wang Zhengxi; (6 pag.)CN110105363; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

5521-58-4, name is 5-Methylpyrazin-2-amine, 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 C5H7N3

Palladium (II) acetate (lOmg) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene(40mg) were added to a mixture of S-4-chloro-6-methyl-2-{2-[3-(pyrid-2-yl)isoxazol-5- yl]pyrrolidin-l-yl}pyrimidine (272mg, 0.80mmol), 2-amino-5-methylpyrazine (85mg, 0.78mmol) and cesium carbonate in 1,4-dioxane (5ml) under nitrogen. The mixture was heated at 100C in a sealed vessel under microwave irradiation for 18 hours. The solution was allowed to cool, the insolubles were removed by filtration and the solvent was removed from the filtrate by evaporation. The residue was purified by column chromatography on silica gel eluting with EtOAc / hexane (25:75 increasing in polarity to 0:100). The purified product was triturated with ether and hexane and the solid collected by filtration to give the title compound (174mg, 53%); NMR (398K) 2.03-2.15 (2H, m), 2.15-2.20 (IH, m), 2.15 (3H, s), 2.35-2.45 (IH, m), 2.38 (3H, s), 3.70-3.75 (IH, m), 3.76-3.84 (IH, m), 5.45-5.55 (IH, m), 6.48 (IH, s), 6.65 (IH, s), 7.40-7.46 (IH, m), 7.85-7.90 (IH, m), 7.90-7.95 (IH, d), 8.10 (IH, s), 8.61-8.65 (IH, d), 9.10 (IH, s), 9.30-9.35 (IH, br s); m/z 415 [MH]+ .

The synthetic route of 5521-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/31745; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 160252-31-3, 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. 160252-31-3 name is 1-(5-Chloropyrazin-2-yl)ethanone, 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.

Step 1: 1-(5-(4-fluoro-1H-pyrazol-1-yl)pyrazin-2-yl)ethan-1-one Sodium hydride (60 wt %, 276 mg, 6.90 mmol) was added to a mixture of 1-(5-chloropyrazin-2-yl)ethanone (800 mg, 5.11 mmol) and 4-Fluoro-1H-pyrazole (484 mg, 5.62 mmol) in N,N-dimethylformamide (6.0 mL) at ambient temperature for 10 minutes. The reaction mixture was then poured into water (70 mL) and was sonicated and stirred for 20 minutes. A dark red solid was isolated by filtration, washed with small amounts of water, and dried to 1-(5-(4-fluoro-1H-pyrazol-1-yl)pyrazin-2-yl)ethan-1-one (919 mg, 95% yield). MS: M+1=207.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(5-Chloropyrazin-2-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Kim, Joseph L.; Kevin, Douglas J.; Brubaker, Jason D.; (57 pag.)US2017/267661; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 113305-94-5, 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. 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 298a (4-{5-[(5-Cyanopyrazin-2-yl)amino]-1-methyl-6-oxo-1,6-dihydropyridin-3-yl}-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl)methyl aAcetate 298a A 50-mL round-bottomed flask equipped with a reflux condenser was charged with [4-(5-bromo-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-{4,4-dimethyl-9-oxo-1,10-diazatricy-clo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl]methyl acetate 273a (269 mg, 0.50 mmol), 5-aminopyrazine-2-carbonitrile (60 mg, 0.50 mmol), XantPhos (29 mg, 0.050 mmol), Pd2(dba)3 (45 mg, 0.050 mmol), Cs2CO3 (326 mg, 1.0 mmol), and 1,4-dioxane (10 mL). The reaction mixture was heated at 100C under microwave irradiation for 1h after three times atmosphere/argon flush. The mixture was filtered off and the solid was washed with methanol (50 mL). The combined filtrate was evaporated under reduced pressure and the residue was purified with silica-gel column chromatography eluting with 50:1 dichloromethane/methanol to afford 298a (200 mg, 69%) as yellow solid. MS-ESI: [M+H]+ 579.3.

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

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 63286-28-2,Some common heterocyclic compound, 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, molecular formula is C4H5ClN4, 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.

Reference Example 141-2 Preparation of N’-(3-chloropyrazin-2-yl)cyclohexanecarbohydrazide To a mixture of 2-chloro-3-hydrazinylpyrazine (1.10 g), triethylamine (1.27 mL), and chloroform (38 mL) in a 200 mL eggplant flask was added cyclohexanecarbonyl chloride (1.13 mL) under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture were added a saturated aqueous solution of sodium hydrogen carbonate (40 mL), saturated brine (40 mL), and ethyl acetate (120 mL), and the resulting mixture was stirred for a while. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the insoluble matters were removed by filtration. The resulting filtrate was concentrated under reduced pressure to give the title compound (1.53 g) (yield 79%) as a pale yellow solid. MS(ESI) m/z: 255/257 [M+H]+

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

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; UBE INDUSTRIES, LTD.; NAKAJIMA, Tatsuo; HAYASHI, Norimitsu; ISHIZAWA, Kouhei; TSUZAKI, Yasunori; IWAMURA, Ryo; TSUBOIKE, Kazunari; US2019/185479; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem