Tag: M.W=100-200

These common heterocyclic compound, 1209459-10-8, name is 2-Bromo-5-fluoropyrazine, 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. Formula: C4H2BrFN2

Zinc dust (Aldrich, 325 mesh, 263 mg, 4.05 mmol) was stirred and heated in tetrahydrofuran (5 mL) with 1,2-dibromoethane (Aldrich, 68 mg, 0.364 mmol) at 65 C. under N2 for approximately 5 min. The mixture was cooled to ambient temperature. Chlorotrimethylsilane (Aldrich, 39 mg, 0.364 mmol) was then added. This mixture was allowed to stir under N2 at ambient temperature for approximately 30 min. The iodide from Part E (1.36 g, 3.0 mmol) was added, and the resulting mixture was stirred at 40 C. under N2 for approximately 3 hr. The product from Part C (0.7 g, 2.28 mmol), N,N-Dimethylacetamide (14 mL), and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (Aldrich, 93 mg, 0.114 mmol) were added to the mixture. It was stirred overnight at 80 C. under N2. The mixture was cooled to ambient temperature. Saturated aqueous NH4Cl (10 mL) was then added. The resulting mixture was diluted further with dH2O (50 mL) and ethyl acetate (100 mL), and then filtered through a bed of Celite . The layers were separated, and the aqueous layer was back-extracted with ethyl acetate (50 mL). The combined organic layers were washed with 1/1 dH2O/saturated aqueous NaCl and saturated aqueous NaCl (50 mL each), dried over MgSO4, filtered, and concentrated in vacuo to produce an oil that was purified by chromatography (silica, ethyl acetate/hexanes) to produce 90 mg (7%) of product.

The synthetic route of 2-Bromo-5-fluoropyrazine 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

Synthetic Route of 312736-49-5, 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. 312736-49-5, name is 3,5-Dichloropyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

a) Synthesis of 3,5-dichloro-pyrazine-2-carboxylic acid methyl ester To a solution of 3,5-dichloro-pyrazine-2-carboxylic acid (0.50 g, 2.60 mmol) in dimethylformamide (8 ml) is added potassium carbonate (0.54 g, 3.90 mmol) at RT followed by the addition of methyl iodide (0.8 ml, 13.0 mmol). The resulting mixture is stirred at RT for 1 h. After completion of the reaction, the mixture is diluted with water (15 ml) and extracted with EtOAc (3*20 ml). The combined organic layers are washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get 3,5-dichloro-pyrazine-2-carboxylic acid methyl ester (0.45 g, 2.18 mmol, 84%), which is used in the next step without further purification.

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, 3,5-Dichloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; LUCAS, Simon; Kuehnert, Sven; Bahrenberg, Gregor; Schroeder, Wolfgang; US2014/148454; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 912773-24-1, name is 6-Bromoimidazo[1,2-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 912773-24-1, SDS of cas: 912773-24-1

To a solution of 6-bromoimidazo[1,2-a]pyrimidine (2.4 g, 12.1 mmol) in DMF, were sequentially added (4-methylpiperazin-1-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanone (80% of 4.1 g, 12.1 mmol), a solution of NaHCO3 (3.1 g, 36.3 mmol) in water (30 mL), water (3 mL) and (A-Phos)2PdCl2 (400 mg, 0.60 mmol). The reaction mixture was heated at 90 C. for 4 h, then was diluted with water (100 mL) and extracted with EtOAc (3*100 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, eluent CHCl3/MeOH 95:5 to 85:15) to afford of (4-(imidazo[1,2-a]pyrazin-6-yl)phenyl)(4-methylpiperazin-1-yl)methanone (1.5 g, 65%). 1H NMR (400 MHz, CDCl3) delta 8.60 (d, J=2.0 Hz, 1H), 8.10 (d, J=4.0, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.58 (m, 4H) 7.39 (d, J=8.0, 1 H), 3.84 (br s, 2H), 3.50 (br s, 2H), 2.40 (br s, 4H), 2.35 (s, 3H); MS (ESI) m/z 322 [M+1]

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, 6-Bromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); 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. 33332-29-5, name is 2-Amino-5-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 33332-29-5

General procedure: To a solution of amines 12a-f in dichloromethane (20 mL) at 0 C was added triethylamine dropwise and the solution was stirred for 10 min. Methyl 2-(chlorosulfonyl)acetate in dichloromethane (10 mL) was added slowly at the same temperature. The reaction mixture was allowed to warm to room temperature and stirred for overnight after the addition completed. Water was added once the completion of reaction, and the mixture was stirred for 15 min. The organic layer was separated and dried over anhydrous sodium sulphate. Dried residue was evaporated under reduced pressure and was purified by flash column chromatography (silica gel, petroleum ether ramping to ethyl acetate:petroleum ether = 1:1) to give 13a-f.

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 33332-29-5.

Reference:
Article; Long, Yi; Yu, Mingfeng; Li, Peng; Islam, Saiful; Goh, Aik Wye; Kumarasiri, Malika; Wang, Shudong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5674 – 5678;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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-Chloro-3-aminomethylpyrazine HCl (2 g; 11.1 minol), (5)-(-)-l-(carbobenzyloxy)-2- piperidine carboxylic acid (3.2 g; 12.2 minol) and N,N-diisopropylethylamine (7.7 mL; 44.4 minol) were dissolved in dichloromethane (100 mL). N-[(dimethylamino)-lH-l,2,3-triazolo- [4,5-6]pyridin-l -ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HATU) (6.3 g; 16.7 minol) was added and the resulting mixture was stirred overnight at room temperature. The mixture was washed with aqueous sodium bicarbonate solution and water. The organic layer was then dried over sodium sulfate, filtered and evaporated to dryness. The crude material was chromatographed over S1O2 using a gradient of 20 -80% ethyl acetate in heptane to give 4.4 g; 11.3 minol of benzyl (2Patent; ACERTA PHARMA B.V.; BARF, Tjeerd; KAPTEIN, Allard; VERKAIK, Saskia; DEMONT, Dennis; COVEY, Todd; VAN DE KAR, Bas; VAN LITH, Bart; GULRAJANI, Michael; (166 pag.)WO2018/134786; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 19847-12-2, These common heterocyclic compound, 19847-12-2, name is Pyrazinecarbonitrile, 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.

General procedure: Cu(II)-NaY (0.1 g) was added to a mixture of benzonitrile (0.206 g, 2.0 mmol) and sodium azide (0.169 g, 2.6 mmol) in DMF (5 mL) and mixture was stirred at 120 C for 3 h. After completion of reaction (as monitored by TLC), the catalyst was centrifuged, washed with ethyl acetate and the centrifugate was treated with ethyl acetate (30 mL) and 5 N HCl (20 mL) and stirred vigorously. The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (20 mL). The combined organic layers were washed with water and concentrated to give the crude solid crystalline 5-phenyltetrazole. The product was characterizedby 1H NMR , 13C NMR and mass spectroscopic analysis.

Statistics shows that Pyrazinecarbonitrile is playing an increasingly important role. we look forward to future research findings about 19847-12-2.

Reference:
Article; Sudhakar; Purna Chandra Rao; Prem Kumar; Suresh; Ravi; Asian Journal of Chemistry; vol. 29; 4; (2017); p. 864 – 866;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 6164-79-0, A common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, molecular formula is C6H6N2O2, 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.

To a stirred solution of sodium methoxide (25% in MeOH, 27.54 mL, 72.4 mmol, 1 eq) in 90 mL of toluene at 110 C. in a 3-neck flask attached with a mechanical stirrer, condenser and dropping funnel was added a solution of methylpyrazine-2-carboxylate (10 g, 72.4 mmol, 1 eq) in 115 mL of methyl acetate, dropwise, over a period of ?35-40 min. A yellow precipitate was formed. Stirring was continued at 110 C. for 3 hrs. The reaction was cooled and the yellow precipitate was filtered and washed with a small quantity of toluene. This solid was taken into 200 mL of saturated ammonium chloride and 400 mL of EtOAc. The aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 6.52 g (50%) of methyl 3-oxo-3-(pyrazin-2-yl)propanoate as a yellow solid.

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; Hoffmann-La Roche Inc.; Alam, Muzaffar; Du Bois, Daisy Jo; Hawley, Ronald Charles; Minatti, Ana Elena; Kennedy-Smith, Joshua; Thakkar, Kshitij Chhabilbhai; Wilhelm, Robert Stephen; US2013/158066; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 41110-33-2, name is Methyl 5-methylpyrazine-2-carboxylate, 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 41110-33-2, name: Methyl 5-methylpyrazine-2-carboxylate

A mixture of methyl 5-methylpyrazine-2-carboxylate (3.000 g, 19.7 17 mmol),1 -bromopyrrolidine-2,5-dione (NB S, 3.685 g, 20.703 mmol) and Azobisisobutyronitrile (AIBN, 1.295 g, 7.887 mmol) in carbon tetrachioride (20 mL) prepared at theroom temperature was heated at reflux for 10 hr, and cooled down to the ambient temperature. Then, water was added to the reaction mixture, followed by extraction withethyl acetate. The organic layer was washed with aqueous saturated sodium chloridesolution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residuewas chromatographed (Si02, 40 g cartridge; ethyl acetate / hexane = 0 % to 15 %) togive methyl 5-(bromomethyl)pyrazine-2-carboxylate as gray solid (1.500 g, 32.9 %).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6924-68-1, A common heterocyclic compound, 6924-68-1, name is Ethyl pyrazine-2-carboxylate, molecular formula is C7H8N2O2, 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.

General procedure: A mixture of the ester derivative 8a or 8b (5.5 mmol) and hydrazine hydrate (11 mmol) in 50 mL of ethanol was heated under reflux for 6 h. The reaction mixture was left overnight at room temperature, and the solid which separated was collected by filtration. The solid was then washed with ethanol, dried, and recrystallized from ethanol (Yoshino et al., 2006; Vlaovic et al., 1990).

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:
Article; Abu Khalaf, Reema; Abdula, Ahmed Mutanabbi; Mubarak, Mohammad S.; Taha, Mutasem O.; Medicinal Chemistry Research; vol. 24; 6; (2015); p. 2529 – 2550;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4774-14-5, These common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, 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.

To a solution of tert-butyl azetidin-3-ylcarbamate hydrochloride (LXIII) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXIV) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous Na2504, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes-*hexanes:EtOAc 1:1) to yield tert-butyl (1-(6- chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXV) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17C1N402 mlz 285.1 (M+H).

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

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (271 pag.)WO2017/24026; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem