Month: June 2021

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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, A new synthetic method of this compound is introduced below., name: 2-Bromo-5-(trifluoromethyl)pyrazine

Step 25 A: 2-[(3R.5R)-3.5-dimethylpiperazin-l -yll-5-(trifluoromethyl)pyrazine (0923) To a solid mixture of (2R,6R)-2,6-dimethylpiperazine dihydrochloride (0924) (0.08 g, 0.44 mmol, 1.0 eq), sodium fert-butoxide (0.21 g, 2.2 mmol, 5.0 eq) and bis(tri- ter/-butylphosphine)palladium(0) (34 mg, 0.07 mmol, 0.15 eq) was added dioxane (4 mL) followed by 2-bromo-5-(trifluoromethyl)pyrazine (0.10 g, 0.44 mmol, 1.0 eq) and the reaction mixture stirred at 50C overnight. The resulting suspension was filtered thru a pad of celite using EtOAc and concentrated. Silica gel column (24 g) was loaded using methylene chloride and run using an increasing gradient of MeOH (0-20%) in methylene chloride over 25 min. Following concentration of the product eluents, 2- [(3R,5R)-3,5-dimethylpiperazin-l-yl]-5-(trifluoromethyl)pyrazine 25a (0.09 g, 0.33 mmol, 75%) was isolated as a yellow oil.

The synthetic route of 1196152-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; HARRIOTT, Nicole; PAGANO, Nicholas; (135 pag.)WO2017/79641; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 274-79-3, These common heterocyclic compound, 274-79-3, name is Imidazo[1,2-a]pyrazine, 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.

The imidazo[1,2-a]pyrazine (7.2 g, 60.44 mmole) was dissolved in 2-methoxyethanol (100 ml) and PtO2 (1.2 g, 5.13 mmole) was added. The reaction mixture was stirred overnight at RT in an autoclave under a hydrogen atmosphere (4 bar). The autoclave was then flushed with nitrogen, the reaction mixture was filtered through filter earth, concentrated, and the solvent residues were then extracted with toluene. Purification was carried out by column chromatography on silica gel (DCM/7 N NH3 in methanol, 95:5)

Statistics shows that Imidazo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 274-79-3.

Reference:
Patent; GRUENENTHAL GmbH; US2009/186899; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 19838-07-4, The chemical industry reduces the impact on the environment during synthesis 19838-07-4, name is 3-Methylpyrazin-2(1H)-one, I believe this compound will play a more active role in future production and life.

[00596] Step A: To a solution of Ph3P (0.1573 g, 0.5999 mmol) and DIAD (0.1182 mL, 0.5999 mmol) in THF (5.713 mL) was added tert-butyl (3-bromo-1-((1r,4r)-4-hydroxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(methyl)carbamate (0.243 g, 0.5713 mmol) and 2-hydroxy-3-methylpyrazine (0.09437 g, 0.8570 mmol) and stirred overnight. One equivalent each of DIAD, Ph3P and 2-hydroxy-3-methylpyrazine were mixed in 0.5 mL THF and the THF mixture was added to the reaction, which was then stirred for1 h. The reaction mixture was partitioned between ethyl acetate (25 mL) and water (25 mL), extracted with ethyl acetate (2x10mL), washed with water (2×10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (5-60% EtOAc in hexanes) to afford tert-butyl (3-bromo-1-((1s,4s)-4-((3-methylpyrazin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(methyl)carbamate (0.319 g, 0.6165 mmol, 107.9 % yield).

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-Methylpyrazin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
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. 767340-03-4, name is (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine, A new synthetic method of this compound is introduced below., Recommanded Product: (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)but-2-en-2-amine

Example-26: Preparation of racemic sitagliptin compound of formula-18:; Sodium borohydride (2.34 grams) was added to a mixture of compound of formula-17 (25 grams) in toluene at 5-100C. Acetic acid (75 ml) was added to it and stirred for 3 hours. The reaction mixture was quenched with water and then layers were separated. The aqueous layer was basified with aqueous sodium hydroxide and then the reaction mixture extracted into methylene chloride. The extracted methylene chloride dried over sodium sulphate and then solvent from it distilled off completely to get the title compound. Yield: 24 grams

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; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; ESWARAIAH, Sajja; SATYANARAYANA, Revu; KONDAL REDDY, Bairy; SRINIVAS, Aluru; WO2010/122578; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 25911-65-3,Some common heterocyclic compound, 25911-65-3, name is 3-Aminopyrazine-2-carbonitrile, molecular formula is C5H4N4, 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.

d) 4-Amino-2-[(2,3-dichlorophenoxy)methyl]pteridine Obtained using the procedure described in section c of Example 2, starting with 3.6 g (0.030 mole) of 3-amino-2-pyrazinecarbonitrile and 6.6 g (0.030 mole) of 2-(2,3-dichlorophenoxy)acetamidine in 100 ml of absolute ethanol. Refluxing time: 14 hours. Yld: 8.1 g (84%), m.p. 216-218 C. (ethanol). NMR (DMSO-d6): delta=5.2 (2H, s); 7.1 (3H, s); 8.3 (2H, peak exchangeable with CF3 COOD); 8.7 (1H, d); 9.0 (1H, d).

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

Reference:
Patent; Lipha, Lyonnaise Industrielle Pharmaceutique; US5167949; (1992); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 59489-71-3, 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. 59489-71-3, name is 2-Amino-5-bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

2-amino-5-bromopyrazine (10g, 57m mol) and 1-bromo-2,2-dimethoxy-propane (15 g) were dissolved in I PA (30 ml_) and heated at 100 C in a sealed tube for 3 days. The reaction was quenched with sodium bicarbonate solution and filtered and extracted with ethyl acetate; the organic layer was dried over sodium sulphate and concentrated to give a brown solid that was used for the next step without further purification.

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

Reference:
Patent; SALVENSIS; GARDNER, John Mark Francis; BELL, Andrew Simon; (78 pag.)WO2018/130853; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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

A microwave vial equipped with a magnetic stirrer was charged with 3,5-dibromo-l- methylpyrazin-2(lH)-one (1.97 g, 7.4 mmol), 4-morpholinobenzenamine (1.97 g, 11.1 mmol), and isopropanol (25 mL). The system was evacuated and then refilled with N2. It was heated at 90°C for 16 h. Then, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash column chromatography eluting with 5: 1 petroleum ether/ethyl acetate to afford 122a (2.3 g, 85percent). LCMS: [M+H]+ 365.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87486-34-8, its application will become more common.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4774-14-5, The chemical industry reduces the impact on the environment during synthesis 4774-14-5, name is 2,6-Dichloropyrazine, I believe this compound will play a more active role in future production and life.

To a solution of fert-butyl azetidin-3-ylcarbamate hydrochloride (LXII) (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 (LXIII) (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 Na2SC>4, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes?hexanes:EtOAc 1 : 1) to yield fert-butyl (l-(6- chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXIV) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17CIN4O2 mlz 285.1 (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, 2,6-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (299 pag.)WO2017/24015; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 768-05-8, 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. 768-05-8, name is Pyrazinoic acid hydrazide belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2.3. General procedure for the synthesis of N’-(2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)pyrazine-2-carbohydrazide(8-14)The quest for the synthesis of N’-(2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)pyrazine-2-carbohydrazide (8-14) wasaccomplished in two steps as outlined in Scheme 1. A mixture of2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-one (1-7) (1 mmol),commercially available pyrazine-2-carbohydrazide (PZH)(1.5 mmol) in methanol and chloroform mixture (1:1 v/v), andcatalytic amount of acetic acid (0.1 mL) was added and refluxed for2-3 h. On the completion of reaction, a solid mass was formed.After cooling to room temperature, the precipitate was filtered offand washed with cold mixture of ethanol and water. The crude product was recrystallized from ethanol [16].

The synthetic route of Pyrazinoic acid hydrazide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mangalam; Sebastian Antony Selvan; Sankar; Journal of Molecular Structure; vol. 1129; (2017); p. 305 – 312;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-28-4,Some common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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 2-amino-6-chloropyrazine (5 g, 38.60 mmol) in a mixture of anhydrous chloroform (120 mL), anhydrous acetonitrile (12 mL) and anhydrous methanol (12 mL) was addedslowly, at 0CC, NBS (7.56 g, 42.45 mmol, 1.1 eq.) and the mixture was warmed to room temper-ature and continuously stirred for 1 h. The excess solvent was removed in vacuo and the obtained crude material (light brown solid) was purified by column chromatography (Hexane/DCM/MeOH = 50/50/0 then 0/1 00/0 then 0/95/5) to afford 5-bromo-6-chloropyrazin-2-amine(6.34 g, 30.42 mmol, 79%) as white crystals. ESI-MS: 209.90 [M+H]+. 1 H NMR (300 MHz,CDCI3) 6 7.69 (s, 1 H), 4.78 (br s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-chloropyrazine, its application will become more common.

Reference:
Patent; SELVITA S.A.; BOBOWSKA (NEE WITKOWSKA), Aneta; GALEZOWSKI, Michal; NOWAK, Mateusz; COMMANDEUR, Claude; SZEREMETA-SPISAK, Joanna; NOWOGRODZKI, Marcin; OBARA, Alicja; DZIELAK, Anna; LOZINSKA, Iwona; DUDEK (NEE SEDLAK), Marcelina; JANIGA, Anita; REUS, Jacek; WRONOWSKI, Marek; ZASTAWNA, Magdalena; RADZIMIERSKI, Adam; SWIRSKI, Mateusz; ZACHMANN, Julian; FABRITIUS, Charles-Henry; PORTER, Rod; FOGT, Joanna; (276 pag.)WO2019/2606; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem