Category: 313339-92-3

Reference of 313339-92-3,Some common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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 3,5-dichloropyrazine-2-carbonitrile (100 mg, 0.578 mmol), phenylboronic acid (0.635 mmol, 77.5 mg, 1.1 equiv), [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.029 mmol, 5 mol%) in degassed dioxane/water 4:1 (6 mL) was sodium carbonate (0.635 mmol, 1.1 equiv) and the reaction mixture was stirred for 4h under nitrogen at 100oC. Once complete, the reaction was diluted with EtOAc and water. The organic phase was separated and aqueous layer was extracted twice with EtOAc, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give product: ESI-MS (m/z): 215.1

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

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford; ANTCZAK, Monika; READY, Joseph; ZHANG, Youngyou; (332 pag.)WO2018/218251; (2018); 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 313339-92-3 as follows. Recommanded Product: 313339-92-3

(ii) 2,3-Dichloro-N-[4-(6-chloro-5-cyano-pyrazin-2-yl)phenyl]benzenesulfonamide 2,3-Dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide (5.78 g) was added to a reaction vessel containing a magnetic stirring bar together with 3,5-dichloro-pyrazine-2-carbonitrile (2.35 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (Pd(dppf)2Cl2) (791 mg) and cesium carbonate (13.2 g), followed by 100 ml dioxane and 10 ml water, and the mixture heated to 100 C. under stirring. After 3 h the reaction mixture was cooled to RT and quenched with a saturated aqueous sodium bicarbonate solution (100 ml) and extracted with EtOAc (3*200 ml). The combined aqueous phases were dried over sodium sulfate, filtered and evaporated to afford the crude product as a brown oil. Purification by flash chromatography on silica gel using a mixture of EtOAc and heptane as the eluent afforded 2,3-dichloro-N-[4-(6-chloro-5-cyano-pyrazin-2-yl)-phenyl]-benzenesulfonamide as a light brown foam after evaporation of the solvents under reduced pressure. Yield: 4.32 g (73%). MS (ES-): m/e=436.0 (M-H).

According to the analysis of related databases, 313339-92-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI; NAZARE, Marc; Halland, Nis; Schmidt, Friedemann; Weiss, Tilo; Dietz, Uwe; Hofmeister, Armin; US2013/72493; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

313339-92-3, Adding some certain compound to certain chemical reactions, such as: 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, 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 313339-92-3.

To a solution of 3,5-dichloropyrazine-2-carbonitrile (1.00 g, 5.47 mmol) in DMF (10 mL) was added (R)-()-3-amino-1-Boc-piperidine (1.38 g, 6.9 mmol) and DIPEA (2.0 mL, 10.94 mmol) in a dropwise manner. The mixture was stirred at room temperature for 60 min. The reaction mixture was evaporated under reduced pressure and the residue was purified by flash chromatography with 0 to 50% ethyl acetate in cyclohexane to give tert-butyl (3R)-3-[(6-chloro- 5-cyanopyrazin-2-yl)amino]piperidine-1-carboxylate (2.36 g, quantitative yield).

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 313339-92-3.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C5HCl2N3

A nilxture of 3,5-dichloropyrazine-2-carbonitrile (150 mg, 0.87 mmol), 1- methyl-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrazole (180 mg 0.87 mmol, 1.0 equiv), [1,1 ?-bis(diphenylphosphino)ferroceneldichloropalladium(II) (0.04 mmol, 5 mol%) in degassed THF (1.7 mL) and aq. solution of sodium carbonate (2 M, 850 jiL) was stirred for 4h under nitrogen at 100C. Once complete, the reaction was diluted with EtOAc and water. The organic phase was separated and the aqueous layer was extracted twice with EtOAc, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give product: ESI-MS (mlz): 220.1

The synthetic route of 313339-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford; ANTCZAK, Monika; READY, Joseph; ZHANG, Youngyou; (332 pag.)WO2018/218251; (2018); 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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 313339-92-3

Step 1: To a mixture of 3,5-dichloropyrazine-2-carbonitrile (369 mg, 2.09 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (500 mg, 2.3 mmol) in AcCN (7.5 mL) was added DIPEA (0.41 mL, 2.3 mmol). After stirring at room temperature for 5 h, it was diluted with EtOAc, washed with sat. NaHCO3, organic layer was separated and washed with brine, dried and concentrated to give tert-butyl (3R,4R)-4-(6-chloro-5-cyanopyrazin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (880 mg).

The synthetic route of 313339-92-3 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

Some common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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. Application In Synthesis of 3,5-Dichloropyrazine-2-carbonitrile

To a solution of 44 3,5-dichloropyrazine-2-carbonitrile (3) (120mg, 0.69mmol) in 45 formamide (5.3g, 120mmol) were added 46 H2SO4 (37muL, 0.69mmol), FeSO4·7H2O (190mg, 0.69mmol) in 47 H2O (700muL) and 48 H2O2 (230muL, 2.1mmol) in H2O (700muL) dropwise at 0C, and the mixture was stirred at the same temperature for 30min. The reaction mixture was quenched with 49 ice water and extracted with EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water, saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to give 7 4 (99mg, 66%) as a pale yellow solid. 1H NMR (DMSO-d6) delta ppm 8.18 (1H, br s), 8.28 (1H, br s); MS (ESI) m/z 197, 199 [M-HCl+H2O]-

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 313339-92-3, its application will become more common.

Reference:
Article; Kunikawa, Shigeki; Tanaka, Akira; Takasuna, Yuji; Tasaki, Mamoru; Chida, Noboru; Bioorganic and Medicinal Chemistry; vol. 26; 20; (2018); p. 5499 – 5509;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, 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 313339-92-3, Recommanded Product: 3,5-Dichloropyrazine-2-carbonitrile

Example 34 5-(1-carbamoylcyclobutylamino)-3-(quinolin-6-ylamino)pyrazine-2-carboxamide A solution of 3,5-dichloropyrazine-2-carbonitrile (100 mg, 0.574 mmol), 1-aminocyclobutanecarboxamide hydrochloride (108 mg, 0.717 mmol) and DIEA (0.350 mL, 2.01 mmol) in DMF (4 mL) was stirred at room temperature for 70 h. Water and EtOAc were added. Organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give 1-(6-chloro-5-cyanopyrazin-2-ylamino)cyclobutanecarboxamide (22 mg).

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; 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

313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, 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. SDS of cas: 313339-92-3

(4-tert-Butoxycarbonyl-aminophenyl)boronic acid pinacol ester (8.26 g) was added to a reaction vessel containing a magnetic stirring bar together with 3,5-dichloro- pyrazine-2-carbonitrile (5.0 g), 1,1 ?-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (1.68 g) and cesium carbonate (28.1 g), followed by 100 ml dioxane and 10 ml water, and the mixture heated to 100 00 under stirring. After 1 h the reaction mixture was cooled to RT and quenched with a saturated aqueous sodium bicarbonate solution (100 ml) and extracted with EtOAc (3 x 200 ml). The combined organic phases were dried over sodium sulfate, filtered and evaporated to afford the crude product as a brown oil which was purified by flash chromatography on silica gel using a mixture of EtOAc and heptane as the eluent. The obtained product was recrystallized from methyl tert-butyl ether to afford [4-(6-chloro-5-cyano-pyrazin-2-yl)-phenyl]-carbamic acid tert-butyl ester as a pale yellow solid after drying under vacuum. Yield: 6.92 g (73%).

The synthetic route of 313339-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; NAZARE, Marc; HALLAND, Nis; SCHMIDT, Friedemann; WEISS, Tilo; DIETZ, Uwe; HOFMEISTER, Armin; WO2013/41502; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 313339-92-3, A common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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.

Potassium tert-butoxide (0.658 g, 5.86 mmol) and tetrahydrofuran (8 ml) were mixed to give a colorless suspension. The reaction mixture was cooled to 0C and 3,3- difluorocyclobutanol (0,683 g, 6,32 mmol) diluted in tetrahydrofuran (3 ml) were added by a syringe and the reaction mixture was stirred for 30 min at 0C while the color changed to orange. Then, the reaction mixture was cooled to -78C and a solution of 3,5-dichloropyrazine-2-carbonitrile (1 g, 5.75 mmol) in tetrahydrofuran (4 ml) was added over 10 min by syringe. The cooling bath was removed and the reaction mixture was stirred for 2 h at 25C.The reaction mixture was diluted with ethyl acetate and 1M sodium hydroxide was added. The aqueous layer was extracted with ethyl acetate (3 x). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography to give 3-chloro-5-(3,3-difluorocyclobutoxy)pyrazine-2- carbonitrile (1.11 g, 4.54 mmol). LCMS (ESI+) m/z [M+H]+: 246

The synthetic route of 313339-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE DEUTSCHLAND GMBH & CO. KG; BACKFISCH, Gisela; BAKKER, Margaretha; BLAICH, Guenter; BRAJE, Wilfried; DRESCHER, Karla; ERHARD, Thomas; HAUPT, Andreas; HOFT, Carolin; KLING, Andreas; LAKICS, Viktor; MACK, Helmut; OELLIEN, Frank; PETER, Raimund; POHLKI, Frauke; RELO, Ana Lucia; (313 pag.)WO2017/50807; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, 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. Product Details of 313339-92-3

Preparation of compound 2Od: terf-butyl (3/?)-3-[(6-chloro-5-cyanopyrazin-2- yl)amino]piperidine-1-carboxylateTo a solution of 20c (0.6 g, 3.46 mmol) and te/f-butyl (3R)-3-aminopipehdine-1 – carboxylate (0.41 g, 2 mmol) in n-BuOH (20 ml_) was added DIPEA (1.2 ml_, 6.9 mmol) at room temperature. The resulting mixture was stirred at 50 0C for 5 h. The mixture was concentrated to dryness. The residue was purified by column chromatography (CH2CI2: CH3OH from 500:1 to 100:1 ) which gave the title compound 2Od as yellow solid (0.7 g, 60%). 1H NMR (400 MHz, CDCI3) delta ppm 1.37 (s, 9H), 1.56 (m, 1 H), 1.70 (m, 2H), 1.86 (s, 1 H), 3.36 (s, 3H), 3.57 (s, 1 H), 3.96 (s, 1 H), 5.78 (br, 1 H), 7.76 (s, 1 H).

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

Reference:
Patent; PFIZER INC.; NINKOVIC, Sacha; BRAGANZA, John Frederick; COLLINS, Michael Raymond; KATH, John Charles; LI, Hui; RICHTER, Daniel Tyler; WO2010/16005; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem