Category: 330786-09-9

These common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, 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. Safety of Methyl 3,5-dichloropyrazine-2-carboxylate

Step 1: [0443] Dichloropyrazine S1.1 (synthesized as described in Yamada, K.; Mastuki, K.; Omori, K.; Kikkawa, K. US Patent Application 2004/0142930A1) (0.46 g, 2.7 mmol) was diluted with 10 mL of acetonitrile. To this was then added DIPEA (0.52 mL, 3.0 mmol) and cyclopropylamine (0.19 mL, 2.7 mmol) and the reactions stirred at rt overnight. The following day the reaction was concentrated by rotary evaporation and the resulting syrup diluted with water and stirred until a filterable precipitate formed. The solid was isolated by filtration and washed with water affording the desired product as a bright yellow solid containing regioisomers S1.2 and S1.3.

The synthetic route of Methyl 3,5-dichloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Portola Pharmaceuticals, Inc.; Song, Yonghong; Xu, Qing; Jia, Zhaozhong J.; Kane, Brian; Bauer, Shawn M.; Pandey, Anjali; US2013/131040; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 330786-09-9, A common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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 500 mL round-bottomed flask, methyl 3,5-dichloropyrazine-2- carboxylate (5.0 g, 24.2 mmol) is dissolved in a 9:1 mixture of dry tetrahydrofuran (242 mL)and methanol (27 mL). The reaction mixture is cooled to 1.5-2 C with an ice/water bath and stirred at this temperature for 10 mm. A 2 M solution of lithium borohydride in THF (13.3 mL, 26.6 mmol) is then added carefully – Caution: reaction temperature must be below 4-5 C. After the end of addition, the reaction mixture is stirred for an additional 10-15 mm at 0-4 C. Methanol (120 mL) is added to the flask and the mixture is stirred for 15 mm at roomtemperature. The reaction is slowly poured into a mixture of 1 M HC1 solution (100 mL) and ethyl acetate (200 mL). The resulting mixture is stirred at room temperature for 15 mm. After this time, the layers are separated. The aqueous layer is extracted with ethyl acetate (3 x 150 mL). The combined organic layers are washed with brine (2 x 100 mL), dried over anhydrous Mg504, filtered and concentrated under reduced pressure. (3,5-dichloropyrazin-2-yl)methanol(4.3 g, 99%) is obtained as a crude yellow oil after drying under high vacuum for 2 h. NMR ?H (500 JVII-Tz, CDC13) oe 8.52 (s, 1H), 4.85 (s, 2H).

The synthetic route of 330786-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; GIORDANETTO, Fabrizio; GREISMAN, Jack, Benjamin; MARAGAKIS, Paul; TAYLOR, Alexander, M.; DIPIETRO, Lucian, V.; KELLEY, Elizabeth, H.; LESCARBEAU, Andre; MURCKO, Mark, Andrew; PIERCE, Levi Charles, Thomas; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; BHAT, Sathesh; THERRIEN, Eric; DAHLGREN, Markus, Kristofer; (156 pag.)WO2018/81091; (2018); 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. 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C6H4Cl2N2O2

Step 1: [0443] Dichloropyrazine S1.1 (synthesized as described in Yamada, K.; Mastuki, K.; Omori, K.; Kikkawa, K. US Patent Application 2004/0142930A1) (0.46 g, 2.7 mmol) was diluted with 10 mL of acetonitrile. To this was then added DIPEA (0.52 mL, 3.0 mmol) and cyclopropylamine (0.19 mL, 2.7 mmol) and the reactions stirred at rt overnight. The following day the reaction was concentrated by rotary evaporation and the resulting syrup diluted with water and stirred until a filterable precipitate formed. The solid was isolated by filtration and washed with water affording the desired product as a bright yellow solid containing regioisomers S1.2 and S1.3. Step 2: [0444] The mixture of regioisomers S1.2 and S1.3 (0.42 g, 1.9 mmol) were diluted with 20 mL of dioxane and 2.0 mL of 1M LiOH. The reaction was stirred at rt until all starting material had been consumed. The reaction was then acidified to pH=2 with 1M HCl and diluted with water to a total volume of 70 mL. The resulting solid was isolated by filtration affording the major isomer, S1.4, as a yellow solid (107 mg, 26%). Upon sitting, a precipitate formed in the filtrate which was then isolated and identified as regioisomer S1.5 (0.17 g, 42%).

The synthetic route of 330786-09-9 has been constantly updated, and we look forward to future research findings.

Related Products of 330786-09-9, A common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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 compound methyl 3,5-dichloropyrazine-2-carboxylate (0.55g, 2.6mmol, l .Oeq) in dimethylformamide (5mL), cesium carbonate (0.8g, 3.1mmol, 1.2eq) and dibenzylamine (0.61g, 3.1mmol, 1.2eq) was added. Reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, reaction mixture transferred into water and extracted with ethyl acetate. Combined organic layer, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain 190.1. (0.5g, 51.16%). MS(ES): m/z 368.54 [M+H]+

The synthetic route of 330786-09-9 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 330786-09-9, name is Methyl 3,5-dichloropyrazine-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 330786-09-9, HPLC of Formula: C6H4Cl2N2O2

Methyl 3,5-dichloropyrazine-2-carboxylate (2.83 g,13.7 mmol), palladium acetate (302 mg, 1.33 mmol), 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (1.63 g, 2.82 mmol), potassium carbonate (18.5 g, 135 mmol), and tert- butyl 3-amino-5-methyl-lH-pyrazole-l-carboxylate (2.70 g, 13.7 mmol) were suspended in anhydrous dioxane (95 mL). The resulting mixture was degassed with nitrogen for5 minutes and stirred at 90C for one hour. The reaction was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (3 x 200 mL), and the organic layers were combined and dried over magnesium sulfate. After filtration, the solvent was removed in vacuo. The residue was purified by silica gel chromatography (0-60% ethyl acetate in hexanes) to give the title compound as a yellow solid (4.2Og, 11.42 mmol, 84% yield); IH NMR (400 MHz, DMSO-^6) delta ppm 1.55 (s, 9 H), 2.21 (s, 3 H), 3.86 (s, 3 H), 6.66 (s, 1 H), 8.57 (s, 1 H), 10.43 (s, 1 H); MS (ESI) m/z 368.3 [M+l]+.

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Application of 330786-09-9, The chemical industry reduces the impact on the environment during synthesis 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

Step 3: ethyl 3,5-dimethoxypyrazine-2-carboxylate To a solution of methyl 3,5-dichloropyrazine-2-carboxylate (0.312 g, 1.51 mmol) in THF (4.5 mL) at room temperature was added sodium hydride (60% wt. dispersion, 0.199 g, 4.98 mmol) and methanol (0.200 mL, 4.94 mmol). The reaction mixture was stirred at room temperature for 30 min, diluted with EtOAc, and quenched with saturated NH4Cl. The reaction mixture was partitioned between brine and EtOAc. The aqueous phase was extracted with EtOAc (3*) and the combined organic extracts were washed with brine (1*), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (10% to 50% EtOAc in hexanes) gave ethyl 3,5-dimethoxypyrazine-2-carboxylate (0.314 g, 1.48 mmol, 98% yield) as an off white solid.

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, Methyl 3,5-dichloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

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 330786-09-9,Some common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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 mixture of methyl 3,5-dichloropyrazine-2-carboxylate (2.0 g, 9.7 mmol, synthesized via Step a of Intermediate A), trimethyl-l,3,5,2,4,6-trioxatriborinane (2.4 g, 19.3 mmol), Pd(PPh3)4 (558 mg, 483 pmol) and Cs2C03 (6.3 g, 19.3 mmol) in dioxane (70 mL) was stirred at 110 C for 12 hours under N2 atmosphere. The reaction mixture was concentrated in vacuo to give a residue, which was purified by silica gel chromatography (ethyl acetate in petroleum ether = 0% to 50% ) to afford methyl 3-chloro-5-methylpyrazine- 2-carboxylate (250 mg, 14% yield) as a yellow solid. LCMS m/z [M+H]+ = 187.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,5-dichloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 330786-09-9,Some common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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.

Step 1 Methyl 3,5-dichloropyrazine-2-carboxylate Jl (lOg, 48.3 mmol) was treated with sodium methoxide in MeOH (97 ml, 48.3 mmol) at RT for 3 hour. It was filtered and the filtrate was concentrated under reduced pressure. The residue was washed with water and dried to give compound J2 (9.79 g). LCMS for J2: m/e = 203 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,5-dichloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Wen-Lian; HE, Shuwen; WALSH, Shawn, P.; CUMMING, Jared, N.; (70 pag.)WO2016/118404; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 330786-09-9,Some common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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.

Step 1 A mixture of methyl 3,5-dichloropyrazine-2-carboxylate (1.30 g, 6.28 mmol) and sodium methoxide (0.5 M in MeOH, 13.8 mL) was stirred at room temperature for 2 h. The mixture was quenched with ice water and extracted with EtOAc (2 x). The combined extracts were dried over sodium sulfate, filtered and concentrated. Si02 column chromatography (5% to 100% EtOAc in hexane) in vacuo to afford compound 2K-2. MS for 2K-2: m/e = 203 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,5-dichloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CUMMING, Jared, N.; HE, Shuwen; TAOKA, Brandon, M.; TRUONG, Quang, T.; WU, Wen-Lian; (122 pag.)WO2015/187437; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem