Month: November 2020

33332-29-5, 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.

Intermediate 22 5-Methoxypyrazin-2-amine [0242] To a solution of 5-chloropyrazin-2-amine (0.2 g, 1.54 mmol) in MeOH (3 mL) was added Cu powder (0.13 g, 2.07 mmol), followed by a solution of sodium methoxide in MeOH (0.38 mL, 1.75 mmol). The reaction mixture was stirred at 150 C. in a sealed tube for 24 h. The reaction mixture was then filtered through Celite, and the filtrate was concentrated in vacuo. The crude product obtained was purified by column chromatography (silica: 100-200 mesh, MeOH: DCM 2-3%) to afford the title compound (0.13 g, 67%). LCMS (ES+) 126 (M+H)+, RT 1.06 minutes (method 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; Brookings, Daniel Christopher; Ford, Daniel James; Franklin, Richard Jeremy; Ghawalkar, Anant Ramrao; Kulisa, Claire Louise; Neuss, Judi Charlotte; Reuberson, James Thomas; US2014/315885; (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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., 55557-52-3

To a solution of 3-chloropyrazine-2-carbonitrile (15.0 g, 108 mmol) in AcOH (200 mL) was added Raney Ni (3 g, in water), and the mixture was stirred for 48 h under an atmosphere of hydrogen with a balloon at rt. The mixture was filtered and the filtrate was concentrated in vacuo to give a crude product, which was dissolved in 250 mL of aqueous HC1 (2M) and extracted with EtOAc (200 mL x 2). The aqueous layer was concentrated under vacuo to give 14.5 g of (3-chloropyrazin-2-yl)methanamine hydrochloride as a brown solid which was used in the next step without further purification.

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; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David; OWENS, Timothy D.; (121 pag.)WO2016/210165; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

132426-19-8, 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. 132426-19-8, name is 2-Bromo-1-(pyrazin-2-yl)ethanone belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a 1 dram vial was added 4-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2- yl)pyridin-2-amine, 2 HCl (50 mg, 0.160 mmol), 2-bromo-1-(pyrazin-2-yl)ethanone (48.1 mg, 0.239 mmol) and Hunig’s Base (0.1 12 mL, 0.639 mmol) in EtOH (1 mL). The vial was sealed and heated to 90 C overnight. The next day the reaction was cooled to rt and analyzed by LC/MS. The reaction was complete and the solution was cooled to rt and the crude solid was filitered off and washed with cold Ethanol. The resulting solid was pure by LC/MS. The solid was then dissolved in hot methanol containing TFA. The solvent was then evaporated in vacuo affording 5,8-dimethyl-2-(2-(pyrazin-2-yl)imidazo[1,2-a]pyridin-7-yl)-[1,2,4]triazolo[1,5-a]pyrazine, 2 TFA (48 mg, 0.077 mmol, 48.5 % yield). 1H NMR (400MHz, DMSO-d6) delta 9.35 (s, 1H), 8.80 (d, J=7.3 Hz, 1H), 8.75 (s, 1H), 8.72 (s, 1H), 8.64 (d, J=2.5 Hz, 1H), 8.43 (s, 1H), 8.08 (s, 1H), 7.79 (d, J=6.8 Hz, 1H), 2.87 (s, 3H), 2.78 (s, 3H), LC/Mass spec. (Method 1) RT=1.87 min. Mass = 343.3 (MH)+.

The synthetic route of 2-Bromo-1-(pyrazin-2-yl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SCHMITZ, William D.; DEBENEDETTO, Mikkel V.; KIMURA, S. Roy; WO2013/3298; (2013); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

19838-08-5, Name is 3-Methylpyrazin-2-amine, 19838-08-5, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

(iii) A solution of bromine (0.26 ml) in chloroform (40 ml) was added dropwise to a stirred solution of 2-amino-3-methylpyrazine (0.453 g) and pyridine (0.4 ml) in chloroform (100 ml) with shielding from sunlight, over a period of 1 hour. The reaction mixture was stirred for a further 30 minutes and then water (25 ml) was added. The organic layer was separated, dried (MgSO4) and evaporated to afford a brown oil. The oil was purified by chromatography on silica gel, eluding with dichloromethane, to give 2-amino-5-bromo-3-methylpyrazine as a white solid (0.312 g, 28%), m.p. 51-52 C.; mass spectrum (+ve CI): 188 (M+H)+.

Statistics shows that 3-Methylpyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 19838-08-5.

Reference:
Patent; Zeneca Limited; US5861401; (1999); A;,
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. 4858-85-9, name is 2,3-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., 4858-85-9

A. Preparation of the intermediate compounds; Example Al; a) Preparation of intermediate compound 1; Reaction in microwave oven. A mixture of 2-phenoxyethanamine (0.010 mol), 2,3- dichloropyrazine (0.012 mol) and l,8-diazabicyclo(5.4.0.)undec-7-ene (DBU) (0.012 mol) in CH3CN (20 ml) was heated for 20 minutes at 180 0C. The solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2). The product fractions were collected and the solvent was evaporated. Yield: 2.5 g of intermediate compound 1 (quantitative yield; used in next reaction step, without further purification).

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; JANSSEN PHARMACEUTICA N.V.; WO2007/71646; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 38557-72-1, name is 2-Chloro-3,5-dimethylpyrazine, 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 38557-72-1. 38557-72-1

General procedure: l-Boc-3-hydroxypiperidine (CAS 85175-45-2, 0.41 g, 2.05 mmol) was stirred in DMF (1.65 mL), at rt, and then a 60% NaH dispersion in mineral oil (0.082 g, 2.05 mmol) was added. Then 4-chloro-2,6-dimethylpyridine (CAS 3512-75-2, 0.26 mL, 2.05 mmol) in DMF (0.64 mL) was added dropwise at rt. The mixture was stirred overnight at 60 C. The mixture was evaporated diluted with FLO and was extracted with EtOAc. The organic layer was separated, dried (Na2S04), filtered and evaporated, in vacuo. The residue was purified by flash column chromatography (silica; EtOAc in heptane 0/100 to 30/70). The desired fractions were collected and concentrated in vacuo to yield intermediate 22 (0.32 g, 51%) as a colorless oil(0656) Intermediate 129 was prepared following an analogous procedure to the one described for the synthesis of intermediate 22 using 2-chloro-3,5-dimethylpyrazine (CAS 38557- 72-1) as starting material and THF as solvent.

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-Chloro-3,5-dimethylpyrazine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DELGADO-JIMENEZ, Francisca; DE LUCAS OLIVARES, Ana Isabel; VEGA RAMIRO, Juan, Antonio; (224 pag.)WO2019/243531; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6705-33-5, A common compound: 6705-33-5, name is Pyrazin-2-ylmethanol, 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.

Step 2 – 2-(Bromomethyl)pyrazine (0524) [00341] To a solution of pyrazin-2-ylmethanol (750 mg, 6.81 mmol) in dichloromethane (10 mL) was added phosphorus tribromide (2.77 g, 10.2 mmol) dropwise and the reaction mixture was stirred at 15 C for 16 hrs. On completion, methanol (20 mL) was added to the reaction mixture. Then the mixture was concentrated in vacuo and the resulting solid was purified by silica gel chromatography (dichloromethane:methanol = 50:1) to give the title compound. 1H NMR (300MHz, CD3OD) delta = 8.86 (s, 1H), 8.74 (br. s., 1H), 8.63 (d, J = 2.6 Hz, 1H), 4.72 (s, 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, Pyrazin-2-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; MOYER, Mikel P.; SAIAH, Eddine; (264 pag.)WO2017/156181; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 63744-22-9, name is 6,8-Dibromoimidazo[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 63744-22-9, 63744-22-9

[0276] 6-Bromo-N-(4-(4-(oxetan-3-yI)piperazin-1-yl)phenyl)imidazo[1,2- a]pyrazm-8-amine III: To 4-(4-(oxetan-3-yl)piperazin-1-yl)aniline II (2.00 g, 8.57 mmoles), hunig’s base (3.29 mL) and 6,8-dibromoimidazo[ 1,2-a]pyrazine (2.37 g, 8.57 mmoles) was added in DMF (43 mL). The reaction was stirred at 85 C in a pressure tube for overnight. The material was quenched with saturated sodium bicarbonate, extracted with DCM (120 mL x 3) and the organic layers were combined and washed with water (120 mL x 3), dried over anhydrous sodium carbonate and concentrated. The crude material was purified using a 120 g Isco column and eluted off using a stepwise gradient of 0-60% (10% MeOH/DCM). The desired fractions were combined and concentrated to provide the title compound PiIota as a light yellow solid (3.00 g, 6.99 mmoles, 82%).

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, 6,8-Dibromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter, A.; CLARKE, Astrid; CURRIE, Kevin, S.; DI PAOLO, Julie; KROPF, Jeffrey, E.; LEE, Seung, H.; LO, Jennifer, R.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; SWAMINATHAN, Sundaramoorthi; XIONG, Jin-Ming; XU, Jianjun; ZHAO, Zhongdong; (169 pag.)WO2016/10809; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 486460-21-3 as follows. 486460-21-3

The compound of formula 7 (1.3 g, 0.01 mol) was reacted withCompound 9 (1.9 g, 0.01 mol) was added to a 50 ml two-necked flask,Join20 ml of methylene chloride,Added HOBt at -10-10 (1.49,0.011mol) andEDC.HCl (2.9 g, 0.015 mol) The reaction mixture was stirred at room temperature for 8 hours,After completion of the reaction, 15 mL of aqueous NaHCO3 solution was added and the organic phase was saturatedWashed with brine, dried over anhydrous sodium sulfate, concentrated, purified by column chromatography,To give 2.67 g of the compound of formula b,The yield was 89.1%.

According to the analysis of related databases, 486460-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Jiuzhou Pharmaceutical Co., Ltd.; Zhu Guoliang; He Qian; Qian Lingfeng; Xu Yingzhou; Yan Pucha; (13 pag.)CN106146514; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6966-01-4, 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. 6966-01-4 name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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.

Methyl beta-bromo-S-chloropyrazine-l-carboxylate (1-2)To a suspension of copper (II) chloride (3.48 g, 25.9 mmol, 2.0 equiv) in acetonitrile (43 mL) was added te/t-butylnitrite (3.06 mL, 25.9 mmol, 2.0 equiv). The reaction was heated to 600C for 30 minutes and then cooled to ambient temperature. To this suspension was added methyl 3-amino-6-bromopyrazine-2-carboxylate (Ll, 3.O g, 12.9 mmol, 1.0 equiv, commercially available from SynChem Inc.) as a solid in portions with gas evolution. The reaction mixture was heated to reflux for 18 hours and the reaction was cooled to ambient temperature. The reaction was partitioned between EtOAc and saturated NaHCO3. The organic phase was washed with NaHCO3 and dried over MgSO4. After concentration, the residue was purified by normal phase column chromatography (0 to 50% EtOAc in hexanes) to afford the product CL2) as a clear oil. ESI+ MS [M+H]+ C6H4BrClN2O2: 250.7 found, 250.9 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-6-bromopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; MERCER, Swati, P.; ROECKER, Anthony, J.; WO2010/141275; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem