Month: November 2020

Adding some certain compound to certain chemical reactions, such as: 4858-85-9, name is 2,3-Dichloropyrazine, 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 4858-85-9. 4858-85-9

2,3-Dichloropyrazine (448 mg, 3 mmol) and 1 -[2-(4-fluorophenoxy)ethyl] piperazine (CAS 77602-92-7, 2.9 mmol) were dissolved in DMSO (0.4 ml). Subsequently, NaOH pellets (1 g, 25 mmol) were added. The reaction was stirred at 150 0C under microwave irradiation for 0.5 hours. Then, 0.4 ml of NaOH (4M) and 0.4 ml of DMSO were added, heating at 150 0C in microwave for 0.5 hours more. The mixture was dissolved in AcOEt, washed with H2O and brine, dried with MgSO4 and evaporated under vacuum. The product was used without any further purification, yielding 710 mg of the desired final compound 13-1 (77 %).

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 2,3-Dichloropyrazine.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/135131; (2007); 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. 19745-07-4, name is 2,5-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., 19745-07-4

To a solution of l-(2,5-difluoro-4-(methylsulfonyl)benzyl)-3-(piperidin-4- yl)imidazolidin-2-one 2,2,2-trifluoroacetate (Intermediate 10; 0.2 g, 0.410 mmol) in DMF (2 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.300 mL, 1.641 mmol) and 2,5- dichloropyrazine (0.0917 g, 0.615 mmol) and the reaction was heated to 100 ¡ãC for 8 hours. The reaction was diluted with EtOAc (100 mL), washed with water (50 mL) and brine (50 mL), dried over MgS04, filtered and concentrated in vacuo. The crude material was chromatographed eluting with 7:3 EtOAc/Hexane to yield a solid, which was further purified by reverse phase preparative HPLC to give l-(l-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(2,5- difluoro-4-(methylsulfonyl)benzyl)imidazolidin-2-one (0.0071 g, 0.0146 mmol, 3.6percent yield). Mass spectrum 485.7, 487.7 (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; ARRAY BIOPHARMA INC.; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald J.; WO2013/74641; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

122-05-4, The chemical industry reduces the impact on the environment during synthesis 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, I believe this compound will play a more active role in future production and life.

A solution of ScCl3¡¤6H2O (30 mg, 0.116 mmol) in distilled water(1.0 ml) was mixed with a solution of H2pzc dihydrate (35 mg, 0.171 mmol) in N,N-dimethylacetamide (1.0 ml). Acetonitrile(2.0 ml) and 0.25 ml of concentrated hydrochloric acid were added to the mixture. The prepared reaction mixture was placedinto a sealed glass tube and kept at 100 C for 48 h. The obtained colorless needle-like crystals were filtered off, washed bytwo portions (2 ml) of acetonitrile and dried in air. The product yield was 18 mg (43%). Elemental analysis: found (%)C 37.2, H 2.8, N 15.2. Calculated for C22H18N8O15Sc2 (%): C 36.8, H 2.5, N 15.5. IR spectrum (KBr), v, cm-1: 417 (w),489 (m), 509 (m), 532 (m), 510 (w), 773 (s), 845 (s), 949 (w), 1016 (w), 1051 (s), 1180 (s), 1200 (w), 1298 (s), 1385 (s),1479 (s), 1666 (s), 2250 (w), 2816 (w), 3100 (w), 3375 (w), 3470 (w).

The chemical industry reduces the impact on the environment during synthesis Pyrazine-2,5-dicarboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Barsukova; Sapianik; Samsonenko; Fedin; Journal of Structural Chemistry; vol. 60; 5; (2019); p. 823 – 829; Zh. Strukt. Kim.; vol. 60; 5; (2019); p. 857 – 863,7;,
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. 5521-58-4, name is 5-Methylpyrazin-2-amine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 5521-58-4

l-Chloro-N,N,2-trimethyl-l-propenylamine (2.67 mL, 20 mmol) was added to a solution of 3-{[6-(azetidin-l-ylcarbonyl)pyridin-3-yl]oxy}-5-[(phenylmethyl)oxy]benzoic acid (6.18 g, 15.3 mmol) in DCM (100 mL) and the reaction stirred at RT for 50mins. 2-Amino-5- methylpyrazine (3.34 g, 30.6 mmol) and pyridine (2.5 mL, 30.6 mmol) were added and the reaction stirred overnight. The solvent was removed in vacuo, and the residue taken up in ethyl acetate(350 mL). The organic phase was washed with water (2 x 100 mL), brine (100 mL), dried (MgSO4), filtered, and evaporated in vacuo. The residue was chromatographed on silica, eluting with a gradient of 50-75% ethyl acetate in isohexane, to give the desired material (4.01 g). 1H NuMR delta (CDCl3): 2.28 (quin, 2H), 2.49 (s, 3H), 4.18 (t, 2H), 4.63 (t, 2H), 5.05 (s, 2H), 6.78 (s, IH), 7.10 (s, IH), 7.25 – 7.37 (m, 7H), 8.04 (d, IH), 8.07 (s, IH), 8.25 (s, 2H), 9.46 (s, IH); m/z 496 (M+H)+

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; WO2007/7041; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

38557-72-1, 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. 38557-72-1, name is 2-Chloro-3,5-dimethylpyrazine, A new synthetic method of this compound is introduced below.

Step 1: Synthesis of 3,5-Dimethyl-2-(dibenzofuran-4-yl)pyrazine (abbreviation: Hdm4 dbfpr) First, into a recovery flask equipped with a reflux pipe were placed 1.51 g of 2-chloro-3,5-dimethylpyrazine, 2.25 g of 4-dibenzofuranylboronic acid, 1.12 g of sodium carbonate, 0.048 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile, and the air inside the flask was replaced with argon. Heating was performed by microwave irradiation (2.45 GHz, 100 W) of this reaction container for 10 minutes, so that reaction occurred. After that, water was added to this reaction solution, and extraction with dichloromethane was carried out. A solution of the obtained extract was washed with water and dried over magnesium sulfate. After the drying, the solution was filtered. After the solvent of this solution was distilled, the obtained residue was washed with methanol, so that the pyrazine derivative which was the object of the synthesis, Hdm4 dbfpr, was obtained (a pale orange powder in a yield of 65%). Note that a microwave synthesis system (Discover, produced by CEM Corporation) was used for the microwave irradiation. The synthesis scheme of Step 1 is illustrated in the following scheme (x-1).

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; Semiconductor Energy Laboratory Co., Ltd.; US2012/104373; (2012); 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. 19745-07-4, name is 2,5-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., 19745-07-4

Dissolved 2,5-dichloropyrazine (50 mg, 0.336 mmol), dicaesium(l+) carbonate (436 mg, 1.34 mmol), and (3S)-l,3-dihydrospiro[indene-2,4′-piperidin]-3-amine dihydrochloride (92.3 mg, 0.336 mmol, Intermediate I) in DMF (2 mL). The reaction mixture was stirred at 80 C for 3 h. The reaction mixture was then partitioned between EtOAc and water, and the aqueous layer was extracted 3 x with EtOAc. The organic layers were combined, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by column chromatography (0-10% MeOH in DCM w/ 1% NH4OH) to give (3S)-T- (5-chloropyrazin-2-yl)-l,3-dihydrospiro[indene-2,4′-piperidin]-3-amine (52.0 mg, 49% yield). LCMS m/z [M+H]+ = 315.4.

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; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-25-1, A common compound: 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, 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.

Methyl 5-chloropyrazine-2-carboxylate (CAS no. 33332-25-1)(345.1 g) was dissolved in DMF (1.73 l). Lithium chloride (423.9 g) was added and the mixture heated to 140 C. over one hour. The mixture was evaporated, and the residue dissolved in water (3.4 l) by continued stirring. The solution was acidified by addition of 2N HCl (900 ml) and extracted into ethyl acetate (5¡Á1.73 l). The combined organic extracts were washed with water (2¡Á900 ml), brine (900 ml), dried (MgSO4), and evaporated to give the title compound (298.1 g). 1H NMR 6 (400.132 MHz, DMSO) 8.92 (d, 1H), 9.02 (d, 1H), 13.87 (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, Methyl 5-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; US2008/153800; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6863-74-7, 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. 6863-74-7 name is 6-Chloropyrazine-2-carbonitrile, 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.

Example 1F (60 mg), 6-cyano-2-chloropyrazine (26 mg), KF (1 mg) and TEA (0.07 mL) were combined in a microwave tube and dissolved in ACN (2 mL). The reaction mixture was stirred in the micro wave oven at 130 C. for 1 h. The reaction mixture was filtrated and purified by preparative HPLC to yield an off-white solid (9 mg; 12%). MS: m/z=462.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Chloropyrazine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Banner, David; Grether, Uwe; Haap, Wolfgang; Kuehne, Holger; Mauser, Harald; Plancher, Jean-Marc; US2012/115843; (2012); 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.

Step 3b: NBS Bromide Formation (Aryl) (Int-118) 2-Aminopyrazine (4 g, 42 mmol) was dissolved in water (2 mL) and DMSO (70 mL), and NBS (7.5 g, 42 mmol) was added over 1 hour at 0 C. The reaction was warmed to room temperature and stirred overnight. The mixture was poured onto ice and extracted 4 times with EtOAc. The combined organic layers were washed with 5% Na2CO3, water, and brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel to give the desired product.

According to the analysis of related databases, Pyrazin-2-amine, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amira Pharmaceuticals, Inc.; US2007/105866; (2007); 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. 120984-76-1

A solution of C39 (2.35 g, 5.78 mmol), 2-bromo-3-methylpyrazine (1.0 g, 5.8mmol), [1 ,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (634 mg, 0.866mmol), and potassium carbonate (3.2 g, 23 mmol) in a mixture of 1,4-dioxane (30 mL) and water (8 mL) was stirred at 100 C for 2 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified via silica gel chromatography (Eluent: ethyl acetate) to afford the product as a yellow solid. Yield:0.90 g, 2.4 mmol, 42%. 1H NMR (400 MHz, CDCI3) oe 8.46(brd, J=2 Hz, 1H), 8.41 (d, J=2.6 Hz, 1H), 7.15 (d, J=8.2 Hz, 1H), 6.60 (dd, J=8.3, 2.3 Hz, 1H), 6.54 (d, J=2.3 Hz, 1H), 3.76 (5, 3H), 2.43 (5, 3H), 1.24-1.37 (m, 3H), 1.08-1.18 (m, 18H).

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

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; ZHANG, Lei; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/162515; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem