Category: 36070-75-4

Adding a certain compound to certain chemical reactions, such as: 36070-75-4, name is 5-Chloropyrazine-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 36070-75-4, category: Pyrazines

A 0.5-2 mL microwave vial was evacuated and back filled with N2. rac-1-((2S,3R,4R)-4-amino-6-(3,6-dihydro-2H-pyran-4-yl)-2,3-dimethyl-3,4-dihyd roquinolin- I (2H)-yl)ethanone (for a preparation seeIntermediate 150, 23.3 mg, 0.078 mmol) in N-methyl-2-pyrrolidone (NMP) (0.7 mL) was then added. To this was added 5-chloropyrazine-2-carbonitrile (21.65 mg, 0.155 mmol), and DIPEA (0.041 mL, 0.233 mmol) and the resultant solution then heated to 150 C for 30 mm in a microwave. The reaction mixture was filtered through a cotton wool plug directly into an LCMS vial and was thenpurified by MDAP (Formic). The appropriate fraction was collected and concentrated in vacuo to afford the desired product as a yellow gum which was still impure. Therefore the crude product was taken up in DCM and loaded onto a silica cartridge (10 g). This was purified by flash chromatography, eluting with 0-100% EtOAc/cyclohexane. The appropriate fractions were collected and concentrated in vacuo to afford the desired product as a colourless oil (6.3 mg, 0.016 mmol, 20.13%). LCMS (2 mm Formic): Rt = 0.90 mi [MH] = 404.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 36070-75-4, name is 5-Chloropyrazine-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. Quality Control of 5-Chloropyrazine-2-carbonitrile

Step 1: 5-(4-fluoro-1H-pyrazol-1-yl)pyrazine-2-carbonitrile To a solution of 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-1H-pyrazole (170 mg, 2.0 mmol), and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at the 100 C. for 4 hours. The reaction mixture was cooled to 20 C., poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and purified by column chromatography (hexane:ethyl acetate=5:1) to give 5-(4-fluoro-1H-pyrazol-1-yl)pyrazin-2-carbonitrile (310 mg, Yield 82%). The structure was confirmed by LC-MS.

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

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Kim, Joseph L.; Kevin, Douglas J.; Brubaker, Jason D.; (57 pag.)US2017/267661; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 36070-75-4, The chemical industry reduces the impact on the environment during synthesis 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, I believe this compound will play a more active role in future production and life.

The rac-I -((2S,3R,4R)-4-amino-2-ethyl-6-fluoro-3-methyl-3,4-dihyd roquinolin- I (2H )-yl)ethanone (forpreparation see Intermediate 40, 100 mg, 0.400 mmol), 5-chloropyrazine-2-carbonitrile (III mg,0.799 mmol), DIPEA (0.140 mL, 0.799 mmol) and N-methyl-2-pyrrolidone (NMP) (2 mL) were placeda microwaveable vial and irradiated in a microwave at 200 C for 2.5 h. The reactions purified directly using a MDAP (Formic) to give a solid, this solid was eluted through a NH2 SPE (5 g) with MeOH, the eluent was concentrated and dried to give the product (77 mg, 0.218 mmol, 54.5%) as an orange solid. LCMS (2 mm Formic): Rt = 0.93 mi [MH] = 354.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36070-75-4, name is 5-Chloropyrazine-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 36070-75-4, Recommanded Product: 5-Chloropyrazine-2-carbonitrile

General procedure: To an oven-dried round-bottom flask containing tert-butyl 2-[(R)-5-bromo-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate 3 (1.0 mmol) was added bis(pinacolato)diboron (1.1 mmol), potassium acetate (4.0 mmol) and 10 mL of anhydrous 1,4-dioxane. The resulting mixture was purged with N2 for three times. Pd(dppf)Cl2 (0.05 mmol) was added, the reaction mixture was purged with N2 again three times and heated under N2 at 110 C for 46 h. The course of the reaction was followed by TLC (5% MeOH in CH2Cl2) and LCMS. The reaction mixture was cooled to room temperature, and the aryl halide 5 (1.1 mmol)], Pd(dppf)Cl2 (0.05 mmol) and 3.5 mL of 2M aqueous solution of potassium carbonate (de-oxygenated by bubbling through N2 for 15 minutes before addition) were added. The reaction mixture was purged with N2 three times and then heated under N2 for 618 h at 110 C. The course of the reaction was followed by LCMS. The reaction mixture was cooled to room temperature, and the solvent removed under reduced pressure. The residue was partitioned between EtOAc (100 mL) and 1N NaOH solution (100 mL). The organic layer was washed with brine (100 mL), dried over Na2SO4 and the solvent was removed under reduced pressure to afford the crude product as a dark brown oil. The crude product was purified by silica gel chromatography, eluting with 010% MeOH in CH2Cl2 to afford the desired product.

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

Reference:
Article; Fernando, Dilinie P.; Jiao, Wenhua; Polivkova, Jana; Xiao, Jun; Coffey, Steven B.; Rose, Colin; Londregan, Allyn; Saenz, James; Beveridge, Ramsay; Zhang, Yingxin; Storer, Gregory E.; Vrieze, Derek; Erasga, Noe; Jones, Ryan; Khot, Vishal; Cameron, Kimberly O.; McClure, Kim F.; Bhattacharya, Samit K.; Orr, Suvi T. M.; Tetrahedron Letters; vol. 53; 47; (2012); p. 6351 – 6354,4;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36070-75-4, name is 5-Chloropyrazine-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 36070-75-4, COA of Formula: C5H2ClN3

To a microwave vial was added (2S,3R,4R)-ethyl 1-acetyl-4-amino-2,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (for a preparation see Intermediate 4, 200 mg, 0.689 mmol) and 5-chloropyrazine-2-carbonitrile (192 mg, 1.378 mmol). DMSO (1 mL) was added, followed by DIPEA (0.361 mL, 2.066 mmol) and the microwave vial sealed and heated to 160 C for 30 min in a microwave reactor. H20 (20 mL) was added, followed by Et20 (20 mL) and the layers separated. The aqueous layer was further extracted with Et20 (2 x 20 mL) and the combined organics then back extracted with brine (2 x 20 mL). The combined organics were then dried (Na2S04) and concentrated in vacuo to afford a brown oil. This was loaded in DCM and purified by column chromatography (25 g silica) using a gradient of 0-60% EtOAc / cyclohexane. The appropriate fractions were collected and concentrated in vacuo to afford the product as a brown oil (268 mg). LCMS (2 min Formic): Rt = 1.01 min, [MH]+ = 394.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen, John; HIRST, David, Jonathan; HUMPHREYS, Philip, G.; LINDON, Matthew, J.; PRESTON, Alexander, G.; SEAL, Jonathan, Thomas; WELLAWAY, Christopher, Roland; (66 pag.)WO2016/38120; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36070-75-4, name is 5-Chloropyrazine-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 36070-75-4, Application In Synthesis of 5-Chloropyrazine-2-carbonitrile

To a mixture of 5-chloropyrazine-2-carbonitnle (140mg, l.Olmmol) and [(3R,45)-4- (2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid rerf-butyl ester (Preparation 48, 300mg, l.Olmmol) in DMSO (ImL) was added DBU (150muL, l.Olmmol). The mixture was bubbled with argon for 5 min and then heated to 700C for 3 h. After cooling to r.t. the crude reaction mixture was partitioned between EtOAc (20OmL) and water (75mL), then the organic phase was separated, washed with brine, dried (MgSO.4), and the solvent removed in vacuo Purification by column chromatography (IH:EtOAc, 60:40) afforded the title compound: RT = 3.93 mm; m/z (ES+) = 402 1 [M + H]+.

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; PROSIDION LIMITED; BARBA, Oscar; DAVIS, Susan, Helen; FYFE, Matthew, Colin, Thor; JEEVARATNAM, Revathy, Perpetua; SCHOFIELD, Karen, Lesley; STAROSKE, Thomas; STEWART, Alan, John, William; SWAIN, Simon, Andrew; WITHALL, David, Matthew; WO2010/103335; (2010); 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. 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Formula: C5H2ClN3

Combine a THJF solution (22%) of fcrt-butyl (3-(2-(2-cyanoacetyl)-3- memoxyphenoxy)propyl)carbamate (1.0 eqv, this is define as one volume) with hydrazine (35%, 1.5 eqv), acetic acid (glacial, 1.0 eqv), water (1 volume based on the THF solution) and methanol (2 volumes based on the THF solution). This is a continuous operation. Heat the resulting mixture to 130 C and 1379 kPa with a rate of V/Q = 70 minutes, tau = 60. Extract the solution with toluene (4 volumes), water (1 volume), and sodium carbonate (10% aqueous, 1 eqv). Isolate Ihe toluene layer and add to DMSO (0.5 volumes). Collect a solution of the intermediate compound tert-butyl (3-(2-(3-amino-lH- pyrazol-5-yl)-3-methoxyphenoxy) propyl)carbamate (26.59 kg, 91%) in 10 days, mp = 247.17 C as a DMSO solution (3 volumes of product). N-Eftylmorpholine (1.2 eqv) and 5-chloropyrazine-2-carbonitrile (1.15 eqv) in 2 volumes of DMSO is combined in a tube reactor at 80 C, V/Q = 3 and tau = 170 minutes at ambient pressure. Add the product stream to methanol (20 vol). As a continuous process, filter the mixture and wash with methanol followed by MTBE. Air dry the material on the filter to give tert-butyl (3-(2- (3-((5-cyanopyrazm-2-yl)arnino)-lH-pyrazol-5-yl)-3-methox>’phenoxy) propyl)carbamate in a continuous fashion (22.2 kg, 88.7%, 8 days). Dissolve a solution of fcrt-butyl (3-(2- (3-((5-cyanopyrazin-2-yl)amino)-lH-pyrazol-5-yl)-3-methoxyphenoxy) propyl)carbamate in formic acid (99%, 142 kg) at ambient temperature and agitate for 4 hours to provide an intermediate of 5-((5-(2-(3-aminopropoxy)-6-methoxyphenyl)-lH-pyrazol-3- yl)amino)pyrazine-2-carbonitrile formate. Dilute the solution with water (55 kg), (S)- lactic acid (30%, 176 kg) and distill the resulting mixture until 10% relative humidity to give the title product as a white to yellow solid (24.04 kg, 85-90%), mp. 157 C.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Some common heterocyclic compound, 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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. COA of Formula: C5H2ClN3

EXAMPLE 54 5-((3 ?)-3-{[5-fluoro-6-(2-hydroxyethoxy)-2^yrazolo[1 ,5-a]pyridin-3-ylpyrimidin-4- yl]amino}piperidin-1-yl)pyrazine-2-carbonitrile A mixture of (R)-2-((5-fluoro-6-(piperidin-3-ylamino)-2-(pyrazolo[1 ,5-a]pyridin-3- yl)pyrimidin-4-yl)oxy)ethanol dihydrochloride (Example 40b, 0.050 g, 0.13 mmol), 2- chloro-5-cyanopyrazine (0.025 g, 0.18 mmol) and triethylamine (0.056 mL, 0.4 mmol) in N,N-dimethylformamide (1 .0 mL) was heated in a microwave at 120 C for 2 hours. The reaction mixture was cooled to ambient temperature and ethyl acetate (10 mL) was added. The solution was washed with water (10 mL) and brine (20 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was taken up in dichloromethane (5 mL), the suspension was filtered and dried in vacuo to give the title compound (0.012 g, 19%) as a solid. LRMS (m/z): 476 (M+1 )+. 1H-NMR delta (300 MHz, DMSO-d6): 1 .50 – 1 .98 (m, 4H), 2.00 – 2.17 (m, 1 H), 3.02 (dd, 2H), 3.68 – 3.87 (m, 2H), 4.14 (br. s., 1 H), 4.42 (d, 1 H), 4.50 (d, 2H), 4.75 (br. s., 1 H), 4.93 (d, 1 H), 6.94 – 7.10 (m, 1 H), 7.30 (dd, 2H), 8.32 (d, 1 H), 8.46 (d, 1 H), 8.58 (s, 1 H), 8.80 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36070-75-4, its application will become more common.

36070-75-4, name is 5-Chloropyrazine-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. COA of Formula: C5H2ClN3

The tert-butyl 4-(5-cyanopyrazin-2-yl)piperazine-1-carboxylate required for the synthesis was prepared in the following manner: To a solution of 5-chloropyrazine-2-carbonitrile (200 mg, 1.43 mmol) and tert-butyl piperazine-1-carboxylate (266.95 mg, 1.43 mmol) in anhydrous DMA (5 ml) under N2 was added DIPEA (748.95 muL, 4.3 mmol). The mixture was stirred and heated at 150C in a microwave for 90 mins. The mixture was allowed to cool to RT, prior to adding water until a significant amount of precipitate was observed. This was filtered under vacuum, washed with water and dried to afford 363mg, 87% of titled compound as a light brown solid. METCR1673 Generic 2 minutes M/Z (ES+) 233.9, Retention time 1.28. 1H NMR (500 MHz, DMSO-d6) delta 8.35 (d, J = 1.3 Hz, 1H), 8.12 (d, J = 1.3 Hz, 1H), 3.78 – 3.71 (m, 4H), 3.61 – 3.55 (m, 4H), 1.49 (s, 9H).

The synthetic route of 36070-75-4 has been constantly updated, and we look forward to future research findings.

Related Products of 36070-75-4,Some common heterocyclic compound, 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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 (R)-3-(3-amino-4-(isobutyl(tetrahydro-2H-pyran-4-yl)amino)phenyl) butanoate (220 mg, 0.63 mmol), 5-chloropyrazine-2-carbonitrile (177 mg, 1 .27 mmol), Pd2(dba)3 (58 mg, 0.064 mmol), Xantphos (74 mg, 0.13 mmol) and K2C03 (262 mg, 1 .9 mmol) in toluene (10 mL) was stirred at 100C under N2 atmosphere overnight. The resulting mixture was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated to give the crude product which was purified by flash chromatography (silica gel, 0-40% EtOAc in PE) to afford the title compound (70 mg, 25% yield). LCMS (ESI) m/z calcd for C25H33N5O3: 451 .26. Found: 452.46 (M+1)+.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DE LA ROSA, Martha Alicia; KAZMIERSKI, Wieslaw Mieczyslaw; SAMANO, Vicente; (369 pag.)WO2018/116107; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem