Author: Jessica.F

Application 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

Reference of 55557-52-3,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.

To a solution of 5-(methylthio)-1,3,4-thiadiazole-2-thiol (821 mg, 5.0 mmol) in DMF and benzene (10 ml, 1/1) was added NaH (60% dispersion in mineral oil, 220 mg, 5.5 mmol) slowly at 0 C. under nitrogen atmosphere. The resulting suspension was stirred at 0 C. for 15 minutes and then to the mixture was added 3-chloropyrazine-2-carbonitrile (698 mg, 5.0 mmol). The reaction was stirred at 80 C. for 4 hr. The reaction was then cooled to room temperature and quenched with saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with water, brine and dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel to give the title compound as a white solid. 1H-NMR (CDCl3) delta 2.83 (s, 3H), 8.54 (d, J=1.8 Hz, 1H), 8.58 (d, J=1.8 Hz, 1H). Mass Spectrum (ESI) m/e=268 (M++1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloropyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; Amgen Inc.; US2008/96900; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 1458-18-0, The chemical industry reduces the impact on the environment during synthesis 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (1.0 eq.) in 2-propanol (5 mL/mmol), an appropriate primary or secondary amine(3-6 eq.) was added, and the reaction mixture wasrefluxed for 2 h.10) The solution was cooled to roomtemperature, concentrated under reduced pressure, andthe residue was purified by silica-gel column chromatography(Wako gel C-200, 30-40% ethyl acetate/n-hexane) to afford the series 1 intermediate (yield:32-95%). The regioselectivity of the nucleophilicsubstitution at the 5-position of the pyrazine ring wasconfirmed by an X-ray structural analysis (Fig. S1).

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, Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Murai, Masatoshi; Habu, Sayako; Murakami, Sonomi; Ito, Takeshi; Miyoshi, Hideto; Bioscience, Biotechnology and Biochemistry; vol. 79; 7; (2015); p. 1061 – 1066;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 63744-22-9,Some common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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.

General procedure: 6,8-dibromoimidazo[1,2-a]pyrazine (6, 1.86 g, 6.72 mmol) was added to asolution of 3a-3c, 5a-5e (5.6 mmol), DIPEA (1.4 mL, 8.4 mmol) inisopropanol (60 mL), stirred at 85 C for 8 h, and then the solvent wasevaporated to dryness. The crude product was purified by columnchromatography to obtain the desired intermediates 7a, 11a-11 g.

The synthetic route of 63744-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fan, Yan; Huang, Zhi; Li, Yao; Qin, Zhongxiang; Wang, Cheng; Wang, Tianqi; Wang, Xin; Xiang, Rong; Yang, Shengyong; Bioorganic Chemistry; vol. 95; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 27825-20-3, 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 27825-20-3 as follows.

3-Hydroxypyrazine-2-carboxylic acid methyl ester (1 g, 6.49 mmol, 1 eq.) Was added to a suspension of sodium hydride (60%, 259 mg, 6.49 mmol, 1 eq.DMF (50 mL). The reaction solution was stirred at room temperature for 1 h and then (3,3-dimethoxycyclobutyl) methylmethanesulfonate(1.46 g, 6.49 mmol, 1 eq.) Was added and the mixture was stirred at 130 & lt; 0 & gt; C for 18 h. After completion of the reaction, the mixture was diluted with 50 mL of waterThe mixture was extracted with EtOAc (60 mL x 2) and the organic phase was washed with saturated sodium chloride solution (60 mL x 2), dried over anhydrous sodium sulfate,Filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: PE / EtOAc (v / v) = 3/1) to give the title compound as a white solid(220 mg, 54%).

According to the analysis of related databases, 27825-20-3, the application of this compound in the production field has become more and more popular.

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

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. 17890-77-6, name is 3-Amino-6-bromopyrazine-2-carboxamide belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 17890-77-6

10 g of 3-amino-6-bromopyrazine-2-carboxamide was added to 120 ml of tetrahydrofuran, 0.1 g of tetrakis(triphenylphosphine)palladium and 12.6 g of sodium carbonate were added, and then 14 g of 3-chloro-5-methyl was added. The phenylboronic acid was heated to reflux for 5 hours and concentrated. Water and ethyl acetate were added to extract and the mixture was separated. The organic phase was collected and concentrated. The residue was separated on a silica gel column to give 7 g of 3-amino-6-(3-chloro-5-methylphenyl)pyrazine-2-carboxamide

The synthetic route of 17890-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changsha Shencheng Biological Technology Co., Ltd.; Bu Gonggaofamingren; (5 pag.)CN107513041; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, 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. Application In Synthesis of 3-Chloropyrazine-2-carbonitrile

To a solution of 3-chloropyrazine-2-carbonitrile (Compound 101) (6.00 g, 43.0 mmol, 1.0 equiv.) In acetic acid (50 mL) was added Raney nickel (4.00 g) In the hydrogen ball under the room temperature reaction for 1.5 days. The reaction solution was filtered and the filtrate was taken dry and the residue was spin-fed with toluene (40 mL), 1 N HCl (15 mL) and toluene (40 mL) The residue was dissolved in tetrahydrofuran (30 mL), filtered, the cake was spin dried, To give (3-chloropyrazin-2-yl) methanamine hydrochloride (8.75 g, yield: 100%). Black solid;

The synthetic route of 55557-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dongguan Zhen Xing Beite Pharmaceutical Co., Ltd.; Cai Xiong; Zhong Xianbin; Ye Chunqiang; He Qijie; Tan Shifeng; Qian Changgeng; (44 pag.)CN106588937; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, 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. Product Details of 16298-03-6

Step 1: synthesis of methyl 3-bromopyrazine-2-carboxylate (99)[0305]To a solution of methyl 3-amino-2-pyrazinecarboxylate (13.06 mmol, 2 g) in hydrobromic acid (13.06 mmol, 7.4 ml, 1.057 g) at 0 C. was added bromine (38.9 mmol, 2 mL, 6.22 g) drop wise and then a solution of sodium nitrite (33.3 mmol, 2.3 g) in water (4 mL). The reaction was stirred for 2 h at 0 C. and the reaction mixture was extracted with CH2Cl2. Organic layer was dried and evaporated to give crude methyl 3-bromopyrazine-2-carboxylate 101 (1.2 gr, 43%). (m/z)=217 and 219 (M+H)+.

The synthetic route of 16298-03-6 has been constantly updated, and we look forward to future research findings.

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

Adding a certain compound to certain chemical reactions, such as: 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, 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 486460-21-3, Product Details of 486460-21-3

3S-t-butoxycarbonylamino-4-(5-methyl-2-oxo-oxazolidin-3-yl)-butyric acid benzyl ester 120 mg (0.31 mmol) of obtained in PREPARATION 19 was dissolved in methanol, then 12 mg of palladium/carcol (Pd/C) was added thereto, followed by stirring under hydrogen atmosphere for 3 hours, 40 minutes. After completion of a reaction, the reaction solution was filtered by Cellite, then washed with methanol, followed by concentration. 9 mg (0.31 mmol) of amine was added immediately thereto, then the resulting solution was dissolved in dichloromethane. The reaction was cooled to 0C, then 50 mg (0.37 mmol) of HOBT was added there. After stirring for 10 minutes, 88 mg (0.47 mmol) of EDC was added to thereto. After removal of an icebath, the reaction solution was stirred for abour 17 hours, then the concentrated residue was purified by prep-TLC (10:1 CH Cl :MeOH) to give 88 mg of the title compound in a total yield of 60%.[560] 1K NMR (CDCl3) delta 5.6-5.9(1H, m), 4.9-5.1(2H, m), 4.6-4.8 (IH, m), 3.9-4.3 (5H, m), 3.6-3.8 (IH, m), 3.1-3.5 (3H, m), 2.5-2.9 (2H, m), 1.40(12H, m)[561] Mass (m/e) 477 (M+l)

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-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LG LIFE SCIENCES, LTD.; WO2006/104356; (2006); 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. 486460-21-3, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H7F3N4

A mixture of (3S,4S)-i -(6-chloro-3-cyanoquinolin-4-yl)-3 -methoxypiperidine-4-carboxylic acid (65 mg, 0.187 mmol), 3-(trifluoromethyl)-5,6,7,8-tetrahydro- [1,2,4jtriazolo[4,3-ajpyrazine (40 mg, 0.206 mmol), HATU (142 mg, 0.375 mmol) and DIPEA (131 1iL, 0.749 mmol) in DMF (3 mL) was stirred at 16 C for 1.5 h. Water (20 mL)was added and the mixture was extracted with EtOAc (3 x 8 mL). The combined organic layers were dried with Na2504, filtered and concentrated. The residue was purified by prepHPLC then dried by lyophilization to 6-chloro-4- [(3S,48)-3 -methoxy-4- { [3 -(trifluoromethyl)5 ,6-dihydro [1 ,2,4jtriazolo [4,3-al pyrazin-7(8H)-ylj carbonyl } piperidin- 1 -ylj quinoline-3- carbonitrile (Human CYP8B 1 150 (nM) 22) and 6-chloro-4- [(3S,4R)-3-methoxy-4- { [3-(trifluoromethyl)-5 ,6-dihydro [1 ,2,4jtriazolo[4,3 -ajpyrazin-7(8B)-ylj carbonyl } piperidin- 1- yljquinoline-3-carbonitrile (Human CYP8B1 1C50 (nM) 441). MS: 556 (M + 1).

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 486460-21-3.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CUMMING, Jared, N.; DYKSTRA, Kevin, D.; HRUZA, Alan; LI, Derun; LIU, Hong; TANG, Haiqun; TAOKA, Brandon, M.; VERRAS, Andreas; WALSH, Shawn, P.; WU, Wen-Lian; (170 pag.)WO2018/34918; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem