Pyrazines

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

00154] Step 1 : To a suspension of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (2.5 g, 10.8 mmol) in ethanol (50 mL) was added hydrazine hydrate (3.2 g, 3 mL, 64.6 mmol) and the reaction mixture heated at 70 C for 1.5 h forming a thick yellow solid. The reaction mixture was filtered and the solid washed with water (20 mL) and ethanol (40 mL). The solid was dried in vacuo to yield 3-amino-6-bromo-pyrazine-2-carbohydrazide (2.7 g, 94% yield) as a light yellow solid. LC/MS m/z 233.1 [M+H]+. XH NMR (400 MHz, DMSO-i?) delta 9.78 (s, 1H), 8.31 (s, 1H), 7.62 (s, 2H), 4.53 (d, J = 3.5 Hz, 2H).

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; BINCH, Haley, Marie; HURLEY, Dennis, James; CLEVELAND, Thomas; JOSHI, Pramod; FANNING, Lev Tyler, Dewey; PINDER, Joanne; O’DONNELL, Michael; VIRANI, Anisa, Nizarali; KNEGTEL, Ronald, Marcellus Alphonsus; DURRANT, Steven, John; YOUNG, Stephen, Clinton; PIERRE-HENRI; KAY, David; REAPER, Philip, Michael; WO2011/143426; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 312736-50-8, 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 312736-50-8 as follows.

solution of the compound (5.0 g, 13.3 mmol) obtained in Preparation Example 13.1 in MeCN (100 mL) was charged with POCl3 (6.76 mL, 72.3 mmol) and stirred at 80 for 4 h. After dilution with water, the mixture was extracted with EtOAc and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (20% n-hexane/EtOAc) to afford 3,5-dichloropyrazin-2-carbonitrile (2.94 g, 65%) as a solid.

According to the analysis of related databases, 312736-50-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ST Pharm Co. Ltd.; Kim, Kyeong Jin; Kim, Kwang Rok; Kim, Wook Il; Bang, Hyeong Tae; Yoon, Ji Hye; Im, Hwan Jeong; Ho, Cheong Nyeong; (50 pag.)KR2016/7347; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 1174321-06-2, name is 5-(Difluoromethyl)pyrazine-2-carboxylic acid, molecular formula is C6H4F2N2O2, 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. SDS of cas: 1174321-06-2

3Q-(Il) synthesis of ((lS,4aS,5R,7aS)-7a-{5-r(5-Difluoromethyl-pyrazine-2-carbonyl)- aminol-2-fluoro-phenyl|-5-methyl-4-trifluoromethyl-4a,5JJa-tetrahydro-4H-furor3,4- diri,31oxazin-2-yl)-carbamic acid tert-butyl estertert-butyl ((4S,4aS,5R,7aS)-7a-(5-amino-2-fluorophenyl)-5-methyl-4-(trifluoromethyl)- 4a,5,7,7a-tetrahydro-4H-furo[3,4-d][l,3]oxazin-2-yl)carbamate (Preparation Example 30-(1O)) (110.25 mg, 0.25 mmol) dissolved in DCM. 5-(difluoromethyl)pyrazine-2- carboxylic acid (66.43 mg, 0.38 mmol) added. Followed by N-ethyl-N-(propan-2- yl)propan-2-amine (65.75 mg, 0.51 mmol) and N-[(dimethylamino)(3H- [l,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminiumhexafluorophosphate (0.14 g, 0.38 mmol). The reaction was stirred at RT. LCMS (Agilent Method A) Retention time 5.44min, ES+: 535 [MH]+. After 15 min, the reaction mixture was washed with HCl IM (2 x 5mL) then washed with sat. NaHCO3 (2 x 5mL). The organic phase was then concentrated and the crude mixture was purified by flash chromatography. 140 mg (100%) of the title compound (85%) and its isomer (15%) were isolated as a mixture. 1H NMR (400 MHz, CDCl3) ppm 1.45 (d, /=6.19 Hz, 3H) 1.55 (s, 9H) 2.95 (dd, /=8.84, 2.65 Hz, IH) 3.89 (dd, /=8.84, 2.53 Hz, IH) 4.30 (qd, /=6.91, 2.27 Hz, IH) 4.48 (quin, /=6.44 Hz, IH) 4.56 (dd, /=(dd, /=11.68, 9.03 Hz, IH) 6.82 (t, /=54.20 Hz, IH) 7.22 (dd, /=11.6, 7.87 Hz, IH) 7.55 (dd, /=6.88, 2.84 Hz, IH) 8.26 (ddd, /=8.87, 4.14, 2.78 Hz, IH) 8.97 (s, IH) 9.55 (s, IH) 9.70 (s, IH)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1174321-06-2, its application will become more common.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD; ELLARD, John Mark; FARTHING, Christopher Neil; HALL, Adrian; WO2011/9898; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-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 6966-01-4, Product Details of 6966-01-4

The compound 3-amino-6-bromopyrazine-2-carboxylic acid methyl ester 3a (20.0 g, 86.2 mmol) was added to a 500 mL three-necked flask, dioxane (40mL), HBr (200mL) and acetic acid (40mL), stirred and dissolved -5 C dropwise to the reaction system was added NaNO2 (19.6g, 285mmol), the solution was stirred at -5 C (20mL) acetic acid for 4 hours. The system was poured into a solution of Na2SO3 and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous sodium sulfate, and dried under reduced pressure using a rotary evaporator, purified by column to give the title compound 3b (12.0g, 40.8mmol), in a yield of 47.3%

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; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Qiang; Qu Minkai; Zhang Linli; Song Jinqian; Liu Lei; Chen Haiji; Liu Qiang; Wang Yijin; Ge Jian; (67 pag.)CN109535164; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 312736-49-5, 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. 312736-49-5 name is 3,5-Dichloropyrazine-2-carboxylic acid, 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.

Step 2: methyl 3,5-dichloropyrazine-2-carboxylate To a solution of 3,5-dichloropyrazine-2-carboxylic acid (0.304 g, 1.58 mmol) in MeOH (5 mL) and diethyl ether (5 mL) at RT was added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, 4.00 mL, 8.00 mmol). The reaction mixture was stirred at RT for 30 min and then concentrated. Purification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes) gave methyl 3,5-dichloropyrazine-2-carboxylate (0.312 g, 1.51 mmol, 96% yield) as a white solid.

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

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 54013-07-9,Some common heterocyclic compound, 54013-07-9, name is 5-Methoxypyrazin-2-amine, molecular formula is C5H7N3O, 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.

General procedure: A 0.5 – 2.0 mL microwave vessel was charged with carboxylic acid VII (251 mg, 0.534 mmol) and this was dissolved in NMP (2 mL). HATU (223 mg, 0.587 mmol) andDIPEA (0.102 mL, 0.587 mmol) were then added and the resultant mixture was stirred at room temperature for 30 min. 2-amino-5-trifluoromethylpyridine (130 mg, 0.801 mmol) was then added and the vessel was tightly sealed with a crimp top. The resultant mixture was heated thermally in a heating block to 110 C for 16 h. The mixture was then diluted with EtOAc and washed with successively with sat. NH4Cl (aq) (1X), sat. NaHCO3 (aq) (1X), H2O (1X) and brine (1X). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was then purified by FCC (12 g SiO2, gradient elution with 0-5% MeOH/DCM). The semi-pure material obtained was then further purified by FCC (12 g SiO2, gradient elution with 0-100% EtOAc/hexanes) and then purified further by FCC (12 g SiO2, gradient elution with 0-5% MeOH/EtOAc) to provide 170 mg (52%) of 11d.

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

Reference:
Article; Letourneau, Jeffrey J.; Stroke, Ilana L.; Hilbert, David W.; Cole, Andrew G.; Sturzenbecker, Laurie J.; Marinelli, Brett A.; Quintero, Jorge G.; Sabalski, Joan; Li, Yanfang; Ma, Linh; Pechik, Igor; Stein, Philip D.; Webb, Maria L.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3601 – 3605;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5521-58-4, These common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, 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.

[00790] To a mixture of 5-methylpyrazin-2-amine (10 g, 92 mmol) in DCM (300 mL) was added BS (16 g, 91.63 mmol) in one portion at 0 C under N2. The mixture was stirred at 30 C for 1 hr. The resulting mixture was poured into saturated aq. Na2S03 (100 mL) and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to afford 3-bromo-5-methyl-pyrazin-2-amine (12 g, 69% yield,) as a light yellow solid. MR (400 MHz, CDCh-d) delta ppm 7.82 (s, 1H) 4.79 – 5.03 (m, 2 H) 2.39 (s, 3 H).

Statistics shows that 5-Methylpyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 5521-58-4.

Reference:
Patent; REVOLUTION MEDICINES, INC.; BLANK, Brian R.; PITZEN, Jennifer; WANG, Gang; WON, Walter S.; TZITZILONIS, Christos; LI, Jie Jack; KOLTUN, Elena S.; AAY, Naing; BUCKL, Andreas; MELLEM, Kevin; SEMKO, Christopher; JOGALEKAR, Ash; KISS, Gert; GILL, Adrian; (298 pag.)WO2018/136265; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products 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.

,6-Dimethoxypyrazine (V): A mixture of 1,6-dichloropirhoerazine U (3.9g; 26 mmol) and freshly prepared sodium methoxide (62 mmol) in anhydrous methanol (50 ml) was refluxed overnight and the solvent was removed under reduced pressure. The residue was diluted to 100 ml with CH2Cl2 and the solution washed with water, brine and dried over anhydrous MgSO4 and filtered off. The filtrate was evaporated under reduced pressure to give pure 1,6-dimethoxypiperazine V (3.6 g; 98%) as a colourless crystals. 1HNMR (CDCl3) 3.94 (s, 6H); 7.76 (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, 2,6-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIONOMICS LIMITED; WO2008/70908; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 173253-42-4, These common heterocyclic compound, 173253-42-4, name is 2-Amino-5-bromo-6-chloropyrazine, 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.

To a solution of 5-bromo-6-chloropyrazin-2-amine (200 mg, 0.98 mmol, 1 eq.) in DMF (3 mL) was added 3-methyl pyrazole (312 mg, 3.8 mmol, 5.0 eq.) and Cs2CO3 (1.24 g, 3.8 mmol, 5.0 eq.). The reaction mixture was allowed to heat at 100 C. for 16 h. The progress of the reaction was monitored by TLC and LCMS The reaction mixture was diluted with water (30 mL) and extracted using ethyl acetate (2*50 mL). The separated organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by normal phase column chromatography to afford the desired product (16 mg, 54%). LCMS: 309 [M+1]+. 1H NMR: (400 MHz, DMSO-d6) delta 9.35 (s, 1H), 8.06 (s, 1H), 7.96 (d, J=1.32 Hz, 1H), 7.90 (d, J=8.77 Hz, 1H), 7.81 (d, J=2.19 Hz, 1H), 7.13 (dd, J=1.75, 8.77 Hz, 1H), 6.98 (s, 2H), 6.23 (d, J=2.19 Hz, 1H), 2.08 (s, 3H).

Statistics shows that 2-Amino-5-bromo-6-chloropyrazine is playing an increasingly important role. we look forward to future research findings about 173253-42-4.

Reference:
Patent; GiraFpharma LLC; PHAM, Son Minh; CHEN, Jiyun; ANSARI, Amantullah; JADHAVAR, Pradeep S.; PATIL, Varshavekumar S.; KHAN, Farha; RAMACHANDRAN, Sreekanth A.; AGARWAL, Anil Kumar; CHAKRAVARTY, Sarvajit; (120 pag.)US2019/23666; (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. 4858-85-9, name is 2,3-Dichloropyrazine, A new synthetic method of this compound is introduced below., Formula: C4H2Cl2N2

Under a nitrogen atmosphere,To a 25 mL test tube reactor was added substrate 2,3-dichloropyrazine 1 w (0.2 mmol,29.6 mg), KSAc(0.6mmol,68.4mg),DMC(1.0mmol,90mg),Pd(OAc)2(0.01mmol,2.3mg),PPh3 (0.02mmol,5.9mg),tBuOK(0.6mmol,69.2mg),and DMSO(2.0mL)..The reaction was heated to 120 C to carry out the reaction.After the TLC detection reaction was completed,The system was cooled to room temperature.The reaction was quenched with saturated aqueous ammonium chloride,And extracted with ethyl acetate (3 * 10 mL)The product was purified by column chromatography to give 28.2mg(82).of product 2w.

The synthetic route of 4858-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; East China Normal University; Jiang Xuefeng; Qiao Zongjun; (32 pag.)CN106866327; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem