Pyrazines

41270-66-0, 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. 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, A new synthetic method of this compound is introduced below.

2-chloro-5,6-diphenylpyrazine (10 gm), 4-(isopropylamino)-1 -butanol (44 gm) and N-methylpyrrolidine (50 mL) were charged into a 250 mL round bottom flask at 30C. The reaction mass was heated to 190C and stirred for 10 hours. The reaction mass was cooled to 30C and poured into cold water, extracted with ethylacetate, dried over anhydrous magnesium sulphate and then concentrated to get 9 gm of the title compound.

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; DR. REDDY’S LABORATORIES LIMITED; ORUGANTI, Srinivas; KANDAGATLA, Bhaskar; DAHANUKAR, Vilas Hareshwar; CHINTADA, Krishnarao; SHAIKH, Latif Jafar; YARRAGUNTLA, Sesha Reddy; PEDDIREDDY, Subba Reddy; KOTTUR, Mohan Kumar; (33 pag.)WO2017/29594; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

5049-61-6, 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 5049-61-6 as follows.

3,5-Dibromo-2-aminopyrazine N-Bromosuccinimide (5.1 g, 28.7 mmol) was added slowly and portion wise to a mixture of aminopyrazine (1.3 g, 13.6 mmol) in dimethylsulfoxide (11 ml) and water (17 ml). During the addition of N-bromosuccinimide, the temperature of the reaction mixture was maintained below 15 C. After the addition, the reaction mixture was stirred for 16 h at RT. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with 10 % Na2C03 solution followed by washing with water and brine. The organic layer was collected, dried over sodium sulfate and concentrated in vacuo to obtain crude product. The product was purified using column chromatography. Yield: 1.51 g 1H NMR (CDC13): 5.04 (2H, s), 8.03 (1H, s)

According to the analysis of related databases, 5049-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDEIA THERAPEUTICS LTD; GOLDSTEINS, Gundars; KOISTINAHO, Jari; KOISTINAHO, Milla; RATILAINEN, Jari; PYSTYNEN, Jarmo; WO2014/68171; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 19745-07-4, name is 2,5-Dichloropyrazine, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 19745-07-4

Step G: To a solution of (3S)-l-(3,3-dimethylpiperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one (0.010 g, 0.026 mmol) in DMF (1 mL) was added 2,5-dichloropyrazine (0.0078 g, 0.052 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.018 mL, 0.10 mmol) and the reaction was stirred for 3 hours at 100 ¡ãC. The reaction was cooled, poured into brine and extracted into EtOAc. The organic layer was washed with water and brine, dried over MgS04, filtered and concentrated under vacuum. Reverse phase HPLC purification of the crude material gave (3S)-l-(l-(5-chloropyrazin-2-yl)-3,3- dimethylpiperidin-4-yl)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one (0.0023 g, 0.0046 mmol, 18percent yield) as a white solid. XH NMR (CDC13, 400 MHz) delta 1.02 (s, 3H), 1.03 (s, 3H), 1.81 – 1.91 (m 1H), 2.12 – 2.21 (m, 1H), 2.71 – 2.81 (m, 2H), 2.95 – 3.05 (m, 2H), 3.03 (m, 3H), 3.52 (dd, 2H), 3.97 (d, 1H), 4.15 – 4.23 (m, 2H), 4.47 – 4.51 (m, 1H), 5.12 (bs, 1H), 6.80 (t, 1H), 7.55 (d, 1H), 7.61 (d, 1H), 7.90 (s, 1H), 8.05 (s, 1H).

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, 19745-07-4, other downstream synthetic routes, hurry up and to see.

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

5900-13-0, 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. 5900-13-0, name is 5-Bromo-3-methoxypyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

3-Methoxy-5-vinylpyrazin-2-amine A mixture of 5-bromo-3-methoxypyrazin-2-amine (800 mg, 3.92 mmol, 1 eq.; Jiang, B. et al. Bioorg. Med. Chem (2001 ), 9, 1149-1 154.), trivinylboroxine pyri- dine-complex (944 mg, 3.92 mmol, 1.0 eq), tetrakis(triphenylphosphin)palladium(0) (45 mg, 0.04 mmol, 0.01 eq) and potassium carbonate (542 mg, 3.92 mmol, 1.0 eq) in 40 ml_ dimethoxyethane/water (3/1) was stirred at room temperature for 10 min and then heated to reflux temperature for 3 hours. The reaction mixture was hydrolysed with 100 ml_ of water and extracted with ethyl acetate. The resulting organic phase was washed with brine, dried with sodium sulphate and concentrated in vacuo. The crude mixture was purified via MPLC (column: Snap cartridge, eluent: hexane -> hexane/ethyl acetate 1/1) to deliver 495 mg (78%) of the title compound. UPLC-MS (Method 2): RT = 0.87 min; m/z = 152 (M+H) +.

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; BAYER INTELLECTUAL PROPERTY GMBH; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SCOTT, William; HAeGEBARTH, Andrea; INCE, Stuart; REHWINKEL, Hartmut; POLITZ, Oliver; NEUHAUS, Roland; BOeMER, Ulf; WO2013/104610; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 486460-20-2, name is 3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 486460-20-2

3-(Trifluoromethyl)-l,2,4-triazolo[4,3-a] pyrazine (540 mg, 2.87 mmol, from Step A)was hydrogenated under atmospheric hydrogen with 10% Pd/C (200 mg) as a catalyst in ethanol (10 mL)at ambient temperature for 18 h. Filtration through Celite followed by concentration gave a dark coloredoil. Dichloromethane was added to the above oil and the insoluble black precipitate was filtered off.Concentration of the filtrate gave the title compound as an oil.’H NMR (500 MHz, CDC13) 5 2.21 (br, 1H), 3.29 (t, 2H, J = 5.5 Hz), 4.09 (t, 2H, J = 5.5 Hz), 4.24 (s,2H); LC-MS 193 (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, 486460-20-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2006/23750; (2006); A2;,
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. 6705-33-5, name is Pyrazin-2-ylmethanol, A new synthetic method of this compound is introduced below., 6705-33-5

Step 1: Intermediate 40-a [0220] To a solution of intermediate 29-g (4.62 g, 19.1 mmol) and pyrazin-2-ylmethanol (2.10 g, 19.1 mmol) in THF (38 mL) were sequentially added triphenylphosphine (7.50 g, 28.6 mmol) and DIAD (5.19 ml, 26.7 mmol) at room temperature and the reaction was then stirred at room temperature overnight. Volatiles were removed under reduced pressure. Purification by silica gel chromatography provided intermediate 40-a as a colorless oil.

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; Pharmascience, Inc.; Laurent, Alain; Rose, Yannick; Jaquith, James B.; US2015/191473; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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. 24241-18-7

2-chloroacetaldehyde (0.79 g, 4 mmol) was slowly added to a freshly prepared solution of 3,5-dibromopyrazin-2-amine (1) (0.51 g, 2 mmol) in 2-propanol (20 mL). The mixture was stirred at reflux under a nitrogen atmosphere for 24 h. After cooling, CH2Cl2 (25 mL) and Et3N (1 mL) were added to the reaction solution. Thereafter, the solvent was evaporated under reduced pressure, and then the residue was washed with 11 mL mixed solution (water: 2-propanol = 10:1) for 2 times, filtered and dried under vacuum to give 6,8-dibromoimidazo[1,2-a]pyrazine (2) as a brown solid, which was pure enough to be used in the next step without further purification.

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 24241-18-7.

Reference:
Article; Huang, Boshi; Liang, Xin; Li, Cuicui; Chen, Wenmin; Liu, Tao; Li, Xiao; Sun, Yueyue; Fu, Lu; Liu, Huiqing; De Clercq, Erik; Pannecouque, Christophe; Zhan, Peng; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 330 – 337;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

24241-18-7, 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 24241-18-7 as follows.

Step 1 A 500 ml three necked round bottom flask was charged with 3,5-dibromopyrazine-2- amine (25.0 g, 0.0988 mole) which was dissolved in acetonitrile (250 ml). The reaction mixture was cooled to 0 C and triethylamine (50.0 g, 0.4941 mole), copper (1) iodide (2.26 g, 0.0119 mole), and Pd (PPh3)4 (5.7 g, 0.0049 mole) were added under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0 C followed by slow addition of trimethylsilylacetylene (10.7g, 0.1089 mole) over 15 min at the same temperature. After completion of the addition, the reaction mixture was warmed up to RT and stirred for 90 min. The reaction mixture was diluted by ethyl acetate and filtered. The filtrate was collected and washed with water. Layers were separated and aqueous layer was re-extracted by ethyl acetate. Combined organic layer was dried over Na2S04, filtered and concentrated to afford crude product which was purified using column purification to afford 20.0 g of 5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine.

According to the analysis of related databases, 2-Amino-3,5-dibromopyrazine, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David, Michael; BRAMELD, Kenneth, Albert; OWENS, Tim; WO2014/81732; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

122-05-4,Some common heterocyclic compound, 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, molecular formula is C6H4N2O4, 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.

Pyrazine-2,5-dicarboxylic acid (900 mg, 5.35 mmol) was dissolved in MeOH (9 mL) and Hydrogen chloride ~1.25M solution in Methanol (9 mL) was added. Then the mixture was heated to 50 C and stirred at that temperature for 8 hrs. Then it was left stirring at RT overnight. The day after 2 mL more of HCI ~1.25 M in MeOH was added and the mixture heated to 50 C and stirred at that temperaure for further 1 h. The mixture was cooled down to RT and concentrated under reduced pressure affording 2,5-dimethyl pyrazine-2,5- dicarboxylate (p139, 949 mg, y= 90%). MS (m/z): 197.1 [MH]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Pyrazine-2,5-dicarboxylic acid, its application will become more common.

Reference:
Patent; INDIVIOR UK LIMITED; CREMONESI, Susanna; MICHELI, Fabrizio; SEMERARO, Teresa; TARSI, Luca; (364 pag.)WO2016/67043; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 23688-89-3

General procedure: The compounds were prepared following a literature procedure.57 To a solution of carboxylic acid (1.0 equiv.) in anhydrous CH2Cl2(0.1 M) was added oxalyl chloride (1.5 equiv.) and DMF (0.1 equiv.) at0 C, and the resulting mixture was allowed to warm to RT for 2 h. Thenthe volatiles were concentrated under reduced pressure, and the residuewas dissolved in anhydrous CH2Cl2 (0.1 M), followed by the addition ofaniline (1.0 equiv.) and triethylamine (1.1 equiv.), and the resultingmixture was stirred at RT for another 2 h. After completion monitoredby TLC, the reaction mixture was quenched with H2O and extractedwith CH2Cl2 (3¡Á20 mL), and washed with 1% HCl solution, and thensat. Na2CO3 (aq.). The combined organic layers were dried over MgSO4and concentrated in vacuo.

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, 23688-89-3, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhou, Qingqing; Reekie, Tristan A.; Abbassi, Ramzi H.; Indurthi Venkata, Dinesh; Font, Josep S.; Ryan, Renae M.; Munoz, Lenka; Kassiou, Michael; Bioorganic and Medicinal Chemistry; vol. 26; 22; (2018); p. 5852 – 5869;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem