Month: April 2021

Reference of 41110-28-5, These common heterocyclic compound, 41110-28-5, name is 3-Methylpyrazine-2-carboxylic acid, 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.

A solution of 3-methylpyrazine-2-carboxylic acid (10 g, 72.4 mmol) in MeOH (80 mL) and sulfuric acid, 95% (5 mL, 90 mmol) was heated to 60 C. for 4 hours. The solution was concentrated to remove MeOH, the residue dissolved in 50 mL of water and neutralized with 10% aq Na2CO3 solution to pH 12. The resulting solution was extracted with ethyl acetate (2¡Á). The combine organic was dried and concentrated to give crude product methyl 3-methylpyrazine-2-carboxylate (9.1 g, 59.8 mmol, 83% yield). It was used for next step without further purification. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 8.63 (1H, s), 8.53 (1H, s), 4.02 (3H, s), 2.87 (3H, s). MS m/z=153 [M+H]+. Calculated for C7H8N2O2: 152.0.

Statistics shows that 3-Methylpyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 41110-28-5.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
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

Synthetic Route of 24241-18-7, 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. 24241-18-7 name is 2-Amino-3,5-dibromopyrazine, 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.

(Trimethylsilyl)acetylene (1.845 g, 2.655 mL, 18.78 mmol) was added dropwise to a solution of 3,5-dibromopyrazin-2-amine 1 (5 g, 19.77 mmol) in DMF (25 mL)Triethylamine (10.00 g, 13.77 mL, 98.85 mmol), copper(I) iodide (451.7 mg, 2.372 mmol) and Pd(PPh3)4 (1.142 g, 0.9885 mmol) were then added and the resulting solution stirred at RT for 30 minutes. The reaction mixture was diluted with EtOAc and water and the layers separated. The aqueous layer was extracted further with EtOAc and the combined organic layers washed with water, dried (MgS04) and concentrated in vacuo. The residue was purified by column chromatography eluting with 15% EtO Ac/Petroleum ether to give the product as a yellow solid (3.99g, 75% Yield). XH NMR (400.0 MHz, DMSO) ? 0.30 (9H, s), 8.06 (IH, s); MS (ES+) 271.82

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-3,5-dibromopyrazine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; STORCK, Pierre-Henri; STUDLEY, John; PIERARD, Francoise Yvonne, Theodora Marie; DURRANT, Steven, John; LITTLER, Benjamin, Joseph; ANGELL, Paul; HUGHES, Robert, Michael; SIESEL, David, Andrew; URBINA, Armando; ZWICKER, Carl; LOCONTE, Nicholas; BARDER, Timothy; WO2013/49722; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 939412-86-9, 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. 939412-86-9 name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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.

A suspension of 3-(trifluoromethyl)-1 ,2,4-triazolo[4,3-a]piperazine hydrochloride (10.94 mmol, 2.5 g) in a mixture of tetrahydrofuran (50 ml) and N,N-diisopropylethylamine (32.8 mmol, 5.42 ml) was added to trichloromethyl chloroformate (13.12 mmol, 1.583 ml) in tetrahydrofuran (50 ml) at 0 C. After one hour at 0 C the reaction mixture was filtered over decalite and the filter washed with tetrahydrofuran. Then the filtrate was concentrated in vacuo. The residue (4.52 g, crude) was added to 2-aminomethyl-3- chloropyrazine hydrochloride (content 77%; 8.43 mmol, 1.97 g) in a mixture of dichloromethane (50 ml) and triethylamine (25.3 mmol, 3.52 ml) and the reaction mixture was stirred over night at room temperature. Then the reaction mixture was filtered over decalite and the filter washed with dichloromethane. The filtrate was washed with water. The aqueous layer was extracted three times with dichloromethane. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. The crude product was purification by column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol) to give N-((3-chloropyrazin-2-yl)methyl)-3- (trifluoromethyl)-5,6-dihydro-[1 ,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxamide (2.707g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (3-Chloropyrazin-2-yl)methanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1053656-22-6, The chemical industry reduces the impact on the environment during synthesis 1053656-22-6, name is 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, I believe this compound will play a more active role in future production and life.

A solution of 7-tert-butyl 2-ethyl-5,6-dihydroimidazo[1,2-a]pyrazin-2,7(8H)-dicarboxylate (300 mg, 1.02 mmole) in THF (15 ml) was cooled to -78 C. and DIBAL-H (1 M in hexane, 2.0 ml, 2.0 mmole) was slowly added under a N2 atmosphere. The reaction mixture was stirred for 1 hour at this temperature and Na2SO4¡Á10 H2O was then added until the evolution of gas was no longer observed. Further Na2SO4¡Á10 H2O was added, filtered, and the residue was washed with DCM (25 ml). The filtrate was concentrated and the crude product obtained (450 mg) was used without further purification in the next stage

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, 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUENENTHAL GmbH; US2009/186899; (2009); 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. 1209646-17-2, name is 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

Method 19: Synthesis of 5-(5-{(R)-l-Cvclopropyl-l-r5-(3,4,5,6-tetrahvdro-2H- ri,2nbipyrazinyl-5′-yl)-ri,2,41oxadiazol-3-yll-ethyl}-pyridin-2-yl)-pyrimidin-2- ylamine (Example 134) Step 1: Synthesis of 1-25A suspension of 1- 18.3 (209 mg, 0.657 mmol) and CDI (102 mgs, 06328 mmol) in 1,4- dioxane (3 mL) in a sealed tube is stirred at 55 C for one hour. A solution of 1-8.10 (225 mg, 0.598 mmol) in dioxane (3ml) is added and the reaction mixture is stirred at 120 C for 18 hours. After cooling to room temperature, the reaction mixture is poured into brine and extracted with EtOAc (4x20ml). The combined organic fractions are dried with sodium sulfate, filtered, and is concentrated in vacuo. The resdiue is purified by flash chromatography (Si02, Biotage SNAP lOOg, 0-5 MeOH/DCM) to yield 1-25 (298 mg), m/z 649 [M+H]

The synthetic route of 1209646-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John, D.; LIU, Weimin; LO, Ho Yin; LOKE, Pui Leng; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee, M.; WO2012/40137; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, molecular formula is C6H6N2O, 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. category: Pyrazines

General procedure: A 100 mL round-bottom flask charged with 2-acetylpyrazine (1.47 g, 2 mmol) was added MeOH (30 mL), KOH pellets (0.675 g,2 mmol) and water (2 mL). The resulting mixture was stirred for10 min and then added corresponding n,n?-dimethoxybenzaldehydes (1.0 g, 1 mmol) and ammonium solution (6 mL) was added slowly stirring at room temperature for 4 h, a white precipitate obtained was filtered, washed with MeOH and diethyl ether. The crude products on recrystallization in a mixture of CHCl3:MeOH (1:1) gave white crystals of desired compounds, 1-4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22047-25-2, its application will become more common.

Reference:
Article; Golla, Ramesh; Kumar, P. Raghavendra; Suchethan; Foro, Sabine; Nagaraju; Journal of Molecular Structure; vol. 1201; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-Dichloropyrazine, 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 19745-07-4, HPLC of Formula: C4H2Cl2N2

Step K: (3S,4S)-3-(2-fluoro-4-(methylsulfonyl)phenoxy)-4-hydroxy-l-(piperidin-4-yl)pyrrolidin-2-one hydrochloride (0.03 g, 0.073 mmol) was dissolved in DMF (2 mL) and 2,5-dichloropyrazine (0.012 g, 0.081 mmol) and Hunig’s base (0.040 mL, 0.22 mmol) were added. The reaction was heated at 100 ¡ãC for 4 hours. The reaction was cooled and concentrated. The residue was purified by reverse phase chromatography (5 to 95percent ACN in water) to afford (3S,4S)-l-(l-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(2-fluoro-4- (methylsulfonyl)phenoxy)-4-hydroxypyrrolidin-2-one (0.0027 g, 0.0056 mmol, 7.6percent yield). Mass spectrum (apci) m/z = 485.2 (M+H).

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, 2,5-Dichloropyrazine, 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

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. 1111638-10-8, name is 3-Chloro-5H-pyrrolo[2,3-b]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

Preparation of 3-chloro-5-methyl-5H-pyrrolo[2,3-b]pyrazine (B-10-6).B-10-5 , B-10-6 A solution was made of 310 mg (1.95 mmol) of compound B-10-5 in 3 ml of anhydrous DMF. This mixture was added to a solution of 125 mg (3.05 mmol) of 60% NaH dispersion in mineral oil in 3 ml of anhydrous DMF. Another 6 ml of DMF was used to rinse the container. Let stir reaction mixture stir for 15 min at room temperature. Added another 150 mul (2.40 mmol) of MeI. Let stir for 2 hr. LCMS shows one peak M+H = 168 with Cl isotope pattern. The reaction mixture was poured into saturated NH4CI solution (100 ml) slowly, then extracted with EtOAc (3 x 50 ml). The organics were combined, dried over MgSO4 and filtered. Silicia gel chromoatography using EtOAc/Hexane gave 257 mg (76% yield) of compound B-10-6 as a yellow solid.

According to the analysis of related databases, 1111638-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 13924-95-3, name is Methyl 5-hydroxypyrazine-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 13924-95-3, Safety of Methyl 5-hydroxypyrazine-2-carboxylate

(62b) Methyl 5-Chloropyrazine-2-carboxylate Methyl 5-hydroxypyrazine-2-carboxylate (673 mg, 4.37 mmol) synthesised in Example (62a) was dissolved in phosphorous oxytrichloride (6.1 mL), and a few drops of N,N-dimethylformamide were added, followed by heating to reflux for 2 hours under nitrogen atmosphere. The reaction solution was poured into ice water, and extraction was carried out three times with chloroform (30 mL). The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine (100 mL each), and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure to afford the desired compound (611 mg, yield 81%) as a gray solid. 1H-NMR (CDCl3, 400 MHz): delta 4.05 (3H, s), 8.71 (1H, d, J=1.6 Hz), 9.10 (1H, d, J=1.2 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-hydroxypyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2239253; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem