Category: 313339-92-3

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, SDS of cas: 313339-92-3

[00229] Step 1 : To a mixture of 3,5-dichloropyrazine-2-carbonitrile (68 mg, 0.39 mmol) in 2-methylpropan-2-ol (2 mL) was added tert-butyl l-amino-3-(methylthio)propan-2- ylcarbamate (50 mg, 0.23 mmol), Hunig’s base (101 mg, 0.780 mmol) under N2. The mixture was heated to 50 C under a 2 atmosphere for 5 hours. Upon cooling to 25 C, the mixture was diluted with brine (50 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by prep-TLC (1: 1 petroleum ether/EtOAc) to afford tert-butyl l-(6-chloro- 5-cyanopyrazin-2-ylamino)-3-(methylthio)propan-2-ylcarbamate as a solid. MS ESI calc’d. for Ci4H21ClN502S [M + H]+ 358, found 358. XH NMR (400MHz, DMSO-d6) delta 7.80 (s, 1H), 6.84 (s, 1H), 5.06 (s, 1H), 3.99 – 3.93 (m, 1H), 3.64 – 3.51 (m, 2H), 2.68 – 2.67 (m, 2H), 2.13 (s, 3H), 1.38 (s, 9H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CASH, Brandon; ELLIS, John Michael; MADDESS, Matthew, L.; NORTHRUP, Alan, B.; OTTE, Ryan, D.; SUN, Binyuan; WO2015/138273; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 313339-92-3, 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.

Example 35 Preparation of 5-((1R,2S)-2-aminocyclohexylamino)-3-(tetrahydro-2H-pyran-4-ylamino)pyrazine-2-carboxamide The title compound was prepared according to the synthetic scheme illustrated below: To the solution of 3,5-dichloropyrazine-2-carbonitrile (2.00 g, 11.5 mmol) in 30 mL NMP were added tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (2.71 g, 12.6 mmol) and DIEA (4.07 mL, 13.8 mmol). The mixture was stirred at RT for 1.5 h. To it was poured 300 mL water. After stirring vigorously for 2 h, the solid was isolated by filtration, washed with water and dried in vacuum oven for overnight to afford tert-butyl (1S,2R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)cyclohexylcarbamate in quantitative yield.

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; 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

Synthetic Route of 313339-92-3, 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.

A solution of 3,5-dichloropyrazine-2-carbonitrile (150 mg, 0.862 mmol), (R)-2-amino-2-phenylacetamide hydrochloride (160 mg, 0.858 mmol) and DIEA (0.400 mL, 2.30 mmol) in DMF (5 mL) was stirred at room temperature for 6 h. Water and EtOAc were added. Organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-2-phenylacetamide (245 mg).

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; 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

Reference 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.

3,5-Dichloropyrazine-2-carbonitrile (Example 12, Step 2, 31.0 g, 178.18 mmol) was dissolved in anhydrous diethyl ether (890 mL, 0.2M) and cooled to -78 C. Then MeMgBr in diethyl ether (3.0 M, 65.33 mL, 190.0 mmol) was added slowly to maintain low temperature. After the addition was complete, the mixture was slowly warmed room temperature and stirred 1 h. The mixture was poured into a beaker containing a mixture of HCl in water (1.0 M, 1 L) and ice (1 kg). The mixture was stirred vigorously for 10 min. The mixture was extracted with diethyl ether (3*1 L), the combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford the title compound as an orange oil (34 g, 99% yield). The mixture was used for the next reaction without further purification.

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

Reference:
Patent; FLX Bio, Inc.; Beck, Hilary Plake; Biannic, Berenger; Bui, Minna Hue Thanh; Hu, Dennis X.; Jackson, Jeffrey J.; Ketcham, John Michael; Powers, Jay Patrick; Reilly, Maureen Kay; Robles-Resendiz, Omar; Shunatona, Hunter Paul; Walker, James Ross; Wustrow, David Juergen; Younai, Ashkaan; Zibinsky, Mikhail; (339 pag.)US2018/72743; (2018); A1;,
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, category: Pyrazines

5-Chloro-2-fluoro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide (709 mg) was added to a reaction vessel containing a magnetic stirring bar together with 3,5-dichloro-pyrazine-2-carbonitrile (300 mg), 1,1-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (Pd(dppf)2Cl2) (100 mg) and cesium carbonate (1.69 g), followed by 6 ml dioxane and 1 ml water, and the mixture heated to 100 00 under stirring. After 3 h the reaction mixture was cooled to RT and quenched with a saturated aqueous sodium bicarbonate solution (40 ml) and extracted with EtOAc (3 x 80 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 5-chloro-N-[4-(6-chloro-5-cyano-pyrazin-2-yl)-phenyl]- 2-fluoro-benzenesulfonamide as a brown foam after evaporation of the solvents under reduced pressure. Yield: 160 mg (22%). MS (ES-): m/e = 421.0 (M-H).

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, 3,5-Dichloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

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,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 6-cyclopropyl-2-[(3R)-piperidin-3-yl]isoquinolin-1-one hydrochloride (111.0 mg, 0.36 mmol) in DMF (2 mL), DIPEA (0.2 mL, 1.08 mmol) and 3,5-dichloropyrazine- 2-carbonitrile (68.9 mg, 0.39 mmol) were added. The mixture was stirred at room temperature for 2 h, then it was concentrated and purified by silica flash chromatography with 20 to 40% ethyl acetate in cyclohexane to give 3-chloro-5-[(3R)-3-(6-cyclopropyl-1-oxoisoquinolin-2- yl)piperidin-1-yl]pyrazine-2-carbonitrile (138.0 mg, 94% yield) as a pink solid. MS found for C22H20ClN5O as (M+H)+ 406.3.

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; 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

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. category: Pyrazines

3,5-Dichloropyrazine-2-carbonitrile (487.14 mg, 2.8 mmol) was added to a solution of tert-butyl N-[(2S,3S)-2-methylpiperidin-3-yl]carbamate (600.0 mg, 2.8 mmol) and DIPEA (1.0 mL, 5.6 mmol) in DMF (5mL) and stirred at room temperature for 2 hours. The mixture was poured into ice and extracted with ethyl acetate (3×50 mL), the organic phase dried on Na2SO4, filtered and concentrated under reduced pressure. The residue purified by flash chromatography (silica) eluting with ethyl acetate in cyclohexane from 0 to 60% to obtain tert-butyl N-[(2S,3S)- 1-(6-chloro-5-cyanopyrazin-2-yl)-2-methylpiperidin-3-yl]carbamate (274.3 mg, 28% yield).

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; 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

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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 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 313339-92-3 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

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. 313339-92-3 name is 3,5-Dichloropyrazine-2-carbonitrile, 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. 313339-92-3

3,5-dichloropyrazine-2-carbonitrile (500 mg, 2.9 mmol), tert-butyl (R)-2-methylpiperazine-1-carboxylate (460 mg, 2.3 mmol), and K2CO3 (794 mg, 5.75 mmol) were combined in a 40 mLpressure vial. DMF (28 mL) was added and the reaction mixture was allowed to stir at rtovernight. The reaction mixture was then diluted with 3:1 chloroform/IPA (isopropyl alcohol)and washed with saturated, aqueous NH4Cl. The combined organic layers were washed withbrine, dried over magnesium sulfate (MgSO4), and concentrated in vacuo while loading ontosilica gel. The residue was purified by column chromatography (silica gel, eluting with agradient of 0-50% 3:1 EtOAc/EtOH in hexanes to afford tert-butyl (R)-4-(6-chloro-5-cyanopyrazin-2-yl)-2-methylpiperazine-1-carboxylate (I-1, 1.11 g, 3.29 mmol, 114 % yield), which needed to be dried further on the genevac to afford a pale yellow solid. MS (ESI) Calc?dfor (C15H21ClN5O2) [M+H]+, 338; found, 338.

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

Reference:
Article; Achab, Abdelghani; Augustin, Martin A.; Bass, Alan; Chen, Dapeng; Christopher, Matthew; Fradera, Xavier; Goldenblatt, Peter; Katz, Jason D.; Lampe, John; Lesburg, Charles A.; Li, Chaomin; Lipford, Kathryn; McGowan, Meredeth A.; Methot, Joey L.; Schroeder, Gottfried; Shaffer, Lynsey; Shah, Sanjiv; Witter, David; Zeng, Haoyu; Zhou, Hua; Bioorganic and medicinal chemistry letters; vol. 30; 1; (2020);,
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