Category: 4858-85-9

Adding a certain compound to certain chemical reactions, such as: 4858-85-9, name is 2,3-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 4858-85-9, Recommanded Product: 4858-85-9

To a mixture of 2,3-dichloro-pyrazine ( 3.0 g, 20 mmol ) and tert-butyl ((1S,3S)- 3-hydroxycyclobutyl)carbamate (see PREPARATION 4A; 3.65 g, 20 mmol) in DMSO (50 mL) was added CS2CO3 ( 13.2 g, 40 mmol), and then the mixture was stirred at 80C overnight. The reaction mixture was diluted with water and filtered. The filter cake was washed with water, and dried to give tert-butyl ((lS,3S)-3-((3-chloropyrazin-2-yl)oxy)cyclobutyl)carbamate (5.7 g, 19.0 mmol, 96.6%). ESI-MS (M+l): 300 calc. for Ci3Hi8ClN303 299.

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

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4858-85-9,Some common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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 vial containing 1-tert-butyl 4-methyl piperidine- 1 ,4-dicarboxylate (408 mg, 1.678 mmol) and 2,3-dichloropyrazine (250 mg, 1.678 mmol) in THF (2.5 mL) at rt under N2 is added dropwise LiHMDS (1.678 mL, 1.678 mmol). The reaction was stirred at rt 16 h. The reaction mixture was poured into H2O (10 mL) and extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with saturated NaCl (10 mL), dried (MgSO4), and concentrated. Purification by ISCO (40 g SiO2, 0-75% EtOAc/Hexane) gives 1-tert-butyl 4- methyl 4-(3-chloropyrazin-2-yl)piperidine-l,4-dicarboxylate (565 mg, 1.588 mmol, 95 % yield) as a clear, colorless oil. [M+Na] = 378.0

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

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; BOURBEAU, Matthew P.; CHEN, Ning; HU, Essa; KUNZ, Roxanne; RUMFELT, Shannon; WO2010/57121; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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 12L 3 -neck round bottom flask fitted with a magnetic stirrer under nitrogen was charged with zinc dust (745 g, preactivated according to the above Preparation 1 , 11.4 mol, 2 eq.) and DMA (2 L, anhydrous). 1, 2-dibromoethane (71 mL, 0.855 mol, 0.15 eq, Aldrich) was then added over 10 min, followed by TMSC1 (108 mL, 0.855 mol, 0.15 eq, Acros) over 20 min. The reaction mixture was stirred for 25 min at RT. A solution of N-Boc-3-iodoazetidine (2) (2420 g, 8.55 mol, 1.5 eq, CNH Technologies) in DMA (5 L, anhydrous) was added via a 2L addition funnel over 2 h keeping the internal temperature below 65 C using a water bath. The suspension was stirred for 1 h at RT at which point it was degassed with nitrogen. Stirring was stopped and the suspension was allowed to stand. A 22L 3 -neck round bottom flask fitted with a mechanical stirrer was charged with 2, 3-dichloropyrazine (6) (850 g, 5.70 mol, 1.0 eq, AK Scientific), PdCl2dppf-CH2Cl2 (140 g, 171 mmol, 0.03 eq, Aldrich), Cul (67.3 g, 353 mmol, 0.062 eq, Aldrich), and DMA (5 L, anhydrous). The solution was degassed with nitrogen. The clear zinc reagent solution above the residual solid zinc was poured into the 22L flask under nitrogen. The brown solution was degassed with nitrogen and heated to 80 C for 16 h at which point LCMS indicated complete conversion of 2, 3-dichloropyrazine (6). The reaction mixture was transferred to brine (8 L) in 50L separatory funnel. Water (8 L) and EtOAc (15 L) were added and the layers were separated. The aqueous layer was extracted with EtOAc (2 x 10 L). The combined organics were washed with water (3 x 10 L) and brine (5 L), dried over sodium sulfate and evaporated. The resulting residue was purified by column chromatography (eluting with hexanes/ethyl acetate = 10: 1) to obtain 536 g of pure tert-butyl 3-(3-chloropyrazin-2- yl)azetidine-l-carboxylate (7) and 121 g of mixed fractions. The impure material was distilled under high vacuum to remove the impurity (N-Boc-azetidine) to give 81 g of pure tert-butyl 3-(3- chloropyrazin-2-yl)azetidine- 1 -carboxylate (7).Total: 617g, Yield: 40%.

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

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; CHEN, Jian J.; FROHN, Michael J.; HU, Essa; LIU, Qingyian; PICKRELL, Alexander J.; RUMFELT, Shannon; RZASA, Robert M.; ZHONG, Wenge; WO2011/143365; (2011); 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. 4858-85-9, name is 2,3-Dichloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4858-85-9

59.6 g (0.40 mol) of 2,3-dichloropyrazine, 37.3 g (0.40 mol) of aniline, and 42.4 g (0.40 mol) of sodium carbonate are suspended in 250 ml of 1-methyl-pyrrolidone and heated at 151C during 24 hours. The black suspension is cooled down to 100C, filtered, and the solid residue further washed with ethyl acetate. The filtrate is concentrated under vacuum and the residual oil further purified by distillation (125-128C, 0.3 mbar) giving the title productas light yellow solid (yield: 58.3 g (71%)).1HNMR (300 MHz, CDCI3): = 7.05-7.22 (m, 2 H), 7.32-7.45 (m, 2 H), 7.57-7.68 (m, 2 H),7.75 (d, I H), 8.05 (d, H).

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

Reference:
Patent; BASF SE; MURER, Peter; BATTAGLIARIN, Glauco; DORMANN, Korinna; METZ, Stefan; WAGENBLAST, Gerhard; BENEDITO, Flavio Luiz; WATANABE, Soichi; LENNARTZ, Christian; GESSNER, Thomas; WO2015/14835; (2015); 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. 4858-85-9, name is 2,3-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 4858-85-9

2- Amino-3 -chloro-pyrazine[00236] 2,3-Dichloropyrazine (2.5 g, 16.78 mmol) was dissolved in NH4OH (aq.) and the reaction mixture heated for 15 minutes at 150 C under microwave activation. Upon cooling a precipitate formed which was collected by filtration, washed with water and dried in vacuo at room temperature for 16 hours to give the title compound as a white, crystalline solid

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 4858-85-9.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; PRICE, Paul Damien; MIDDLETON, Penny; WO2010/69684; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4858-85-9, 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. 4858-85-9, name is 2,3-Dichloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2,3-dichloropyrazine (I-94) (45 g, 300 mmol) in NuEta3·Eta20 (1000 mL) was stirred at 120 C in a 2 L autoclave overnight. The mixture was filtered, and the filter cake was washed with water (400 mL) and CH2CI2 (400 mL), and dried in vacuum to afford 2-amino-3-chloropyrazine (I-95) (36.85 g, 94%) as a gray solid, which was used directly without further purification.

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, 2,3-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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 (E)-methyl 4-((benzhydrylimino)methyl)benzoate (67 g, 204 mmol) in THF (700 mL) was cooled to 0 C and added dropwise NaHMDS (244 mL, 244 mmol). The mixture was stirred at this temperature for 30 minutes, and added a solution of 2,3-dichloropyrazine (33.2 g, 224 mmol) in THF (40 mL). The reaction mixture was stirred at 0 C for 20 minutes and RT for 40 minutes. After the reaction was completed, the reaction mixture was extracted with EA and water. The organic layer was treated with 3M HCl (500 mL) for 10 minutes. The phases were separated and the organic layer was extracted with 3M HCl. The aqueous was washed with EA and then alkalified with Na2CO3 to pH = 9. The aqueous solution was extracted with EA and the combined organics were dried and concentrated to give methyl 4-(amino(3-chloropyrazin-2- yl)methyl)benzoate (46 g, yield 81 %). MS-ESI (m/z): 278 (M+1) + (Acq Method: 10-80AB_2min; Rt: 0.75 min).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald, M.; LIU, Jian; LIU, Shilan; YANG, Chundao; ZHENG, Shuling; WO2014/116504; (2014); 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., name: 2,3-Dichloropyrazine

A suspension of 2,3-dichloropyrazine (3.5 g, 0.023 mol) in 25 % aqueous ammonia (20 mL) and THF (20 mL) was heated at 100C for 18 h in a steel bomb. The reaction was cooled to ambient temperature and the resulting crude material was evaporated to minimum. The residual material was triturated with water (15 mL), filtered and dried to afford 2-amino-3-chloropyrazine as a buff- coloured crystalline solid (2.75 g, 90%). MS (ES+) m/z: 130. 1H NMR (400 MHz, CDCl3): delta 7.94 (d, J=2.53 Hz, 1H), 7.72 (d, J=2.53 Hz, 1H), 4.90-5.12 (br. s, 2H).

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

Reference:
Article; Surase, Yogesh B.; Samby, Kirandeep; Amale, Sagar R.; Sood, Ruchi; Purnapatre, Kedar P.; Pareek, Pawan K.; Das, Biswajit; Nanda, Kamna; Kumar, Subodh; Verma, Ashwani K.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3454 – 3459;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

2,3-Dichloro-pyrazine (1.48 g, 0.01 mol),and Ethynyl-benzene (1.53 g, 0.015 mol) was added in a lOOmL flask which contained 30mL of Et3N with stirring, and then the catalyst of Cul(0.38 g, 0.002 mol)and Pd(PPh3) 2C12(2 g, 0.002 mol) was added into the mixture. The reaction mixture was warmed to 80C for 0.5h, lc-ms indicated 2,3-Dichloro-pyrazine was consumed. The reaction mixture was cooled to room temperature. Filtrated, the filtrate was concentrated to give the crude product, the crude product was further purified by flash chromatography to afford 2-Chloro-3-phenylethynyl-pyrazine. (1.5 g, yield: 71%). LC/MS (ESI+): 215 [M+l]+ 217 [ +3]+

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

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

Starting material A-1 (15 g; 100.68 mmol) and hydrazine hydrate 65 % (15.509 ml201.37 mmol) are dissolved in 45 ml_ ethanol and stirred for 1 h at 80 C. While cooling down, a precipitate is formed. It is slurred up with a small amount of water and filtered off. It is washed with water and then dried to afford the product. Yield: 93 % (13.6 g; 94.07mmol) (0279) HPLC-MS: (M+H)+ = 145/147; tRet = 0.34 min; method FECB5

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; TONTSCH-GRUNT, Ulrike; BAUM, Anke; RUDOLPH, Dorothea Ingrid; (85 pag.)WO2019/145410; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem