Pyrazines

Application of 1111638-10-8,Some common heterocyclic compound, 1111638-10-8, name is 3-Chloro-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4ClN3, 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-chloro-5H-pyrrolo[2,3-]pyrazine (1.00 g, 6.51 mmol) in DMF (33 mL) was added N-bromosuccinimide (1.159 g, 6.51 mmol). The reaction mixture was stirred at room temperature for 18 h. At completion, the reaction was concentrated and the resulting residue was treated with water (30 mL). The resulting slurry was stirred for 30 min, then filtered and washed with water (20 mL). The precipitate was dried for 3 h under vacuum at 70 C to afford crude 7-bromo-3-chloro-5H-pyrrolo[2,3-]pyrazine as brown solid (1.136 g, 48% yield). LCMS: m/z 232 (M+H)+, Rt= 0.80 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-5H-pyrrolo[2,3-b]pyrazine, its application will become more common.

Reference:
Patent; NOVARTIS AG; BAGDANOFF, Jeffrey T.; CHEN, Zhuoliang; DORE, Michael; FORTANET, Jorge Garcia; KATO, Misunori; LAMARCHE, Matthew J.; SARVER, Patrick James; SHULTZ, Michael; SMITH, Troy Douglas; WILLIAMS, Sarah; (156 pag.)WO2016/203404; (2016); 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. 5049-61-6, name is Pyrazin-2-amine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H5N3

Pyrazin-2-amine (2.85 g,30 mmol, 1 eq.) was dissolved in CH2Cl2 (150 mL) and cooled in icewaterbath. N-bromosuccinimide (NBS, 5.4 g, 30 mmol, 1 eq.) wasadded portionwise and stirred for 3 h at the same temperature. Themixture was filtered through a Celite, and the filtrate was washed withsaturated aqueous NaHCO3 solution (30 mL×3) and brine, dried overanhydrous Na2SO4 and concentrated under reduced pressure to obtain alight yellow solid 11a (2.7 g, 52%).1H NMR (300 MHz, DMSO-d6): delta8.01 (s, 1H), 7.66 (s, 1H), 6.62 (s, 2H). Compound 12a was synthesizedfrom 11a following the above diazotization and hydrolysis procedure.Yellow solid, yield: 57%. 1H NMR (300 MHz, DMSO-d6): delta 12.21 (br,1H), 8.07 (s, 1H), 7.90 (s, 1H). ESI–MS m/z: 173.0 [M – 1].

The synthetic route of 5049-61-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Shuang; Xu, Mingshuo; Guo, Qi; Zhu, Fuqiang; Jiang, Xiangrui; Xie, Yuanchao; Shen, Jingshan; Bioorganic and Medicinal Chemistry; vol. 27; 5; (2019); p. 748 – 759;,
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Pyrazine | C4H4N2 – PubChem

Synthetic Route of 117103-53-4,Some common heterocyclic compound, 117103-53-4, name is 2-Bromo-5-nitropyrazine, molecular formula is C4H2BrN3O2, 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.

Example 40 2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-N- [5- (2-HYDROXY-L- hydroxymethyl-ethyl)-pyrazin-2-yl]-propionamide [000237] A solution of 2-BROMO-5-NITROPYRAZINE (3.0 g, 14.7 mmol) in tetrahydrofuran (24.5 mL) was treated with DIETHYLMALONATE (3.35 mL, 22.0 mmol) and potassium carbonate (5.08g, 36.7 MMOL). The mixture was then stirred at 90-95C overnight. At this time, the reaction was cooled to 25C and then poured onto a 1N aqueous hydrochloric acid solution (60 mL). This solution was diluted with a saturated aqueous sodium chloride solution (50 mL) and then was extracted with ethyl acetate (3 x 75 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica 25% ethyl acetate/hexanes) afforded 2- (5-NITRO-PYRAZIN-2-YL)-MALONIC acid diethyl ester (3.28 g, 78%) as a pale yellow oil: EI-HRMS M/E calcd for CILHL3N306 (M) 283. 0804, found 283.0801.

The synthetic route of 117103-53-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/52869; (2004); 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 3-amino-6-bromopyrazine-2-carboxylate

A-7: 6-Cvclopropyl-3-fpyrimidin-5-ylamino)-pyrazine-2-carboxylic acid methyl esterStep 1: 3-amino-6-cyclopropylpyrazine-2-carboxylic acid methyl esterTo a suspension of 3-amino-6-bromopyrazine-2-carboxylic acid methyl ester (17.8 g, 76.7 mmol), cyclopropylboronic acid (8.57 g, 99.7 mmol), potassium phosphate (57.0 g, 268 mmol) and tricyclohexylphosphine (2.15 g, 7.67 mmol) in toluene (445 ml) and water (22 ml) was added palladium(II) acetate (0.86 g, 3.84 mmol). The reaction mixture was heated to 100 C and stirred for 20 h. Water (200ml) was added, the organic layer was washed with water and brine and the aqueous layer was back-extracted with ethyl acetate. The combined organic phases were dried and the solvent was evaporated. The product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as yellow solid (1.69 g, 11.4 %).MS: M = 194.1 (M+H)+

According to the analysis of related databases, 6966-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; VIEIRA, Eric; WO2011/89132; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1379338-74-5, 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. 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 32: 1 ,1-Dimethylethyl {4-r(7-chloropyridor3,4-blpyrazin-5- vDaminolbutvDcarbamate; To 5,7-dichloropyrido[3,4-b]pyrazine (650mg, 3.25mmol) was added 1 , 1- dimethylethyl (4-aminobutyl)carbamate (0.622ml, 3.25mmol) (Fluka) and diisopropylethylamine (0.851 ml, 4.87mmol). To the mixture was added N-methyl-2- pyrrolidone (NMP) (10ml). The microwave vial was sealed and heated to 130C for 30min. The reaction mixture was partitioned between water (70ml) and ethyl acetate (70ml) and then separated. The aqueous layer was extracted with ethyl acetate (2x50ml). The combined organics were passed through a phase separation cartridge and reduced in vacuo. The residue was dissolved in DCM and loaded onto a silica cartridge (50g) and purified via SP4 using a 15-75% EtOAc in cyclohexane gradient. The appropriate fractions were combined and concentrated to give the title compound as a yellow film (1.01g).LCMS (Method C): Rt = 1.11 min, MH+ = 352.0

The synthetic route of 5,7-Dichloropyrido[3,4-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; ATKINSON, Stephen John; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander G; SHIPLEY, Tracy Jane; WILSON, David Matthew; WATSON, Robert J; WO2012/123312; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 723286-68-8, The chemical industry reduces the impact on the environment during synthesis 723286-68-8, name is Ethyl 5,6,7,8-Tetrahydro-1,2,4-triazolo[4,3-a]pyrazine-3-carboxylate, I believe this compound will play a more active role in future production and life.

Example 240: Preparation of 7-[(S)-4-(2,3-dihydro-[l,4]dioxino[2,3-b]pyridin-3-yl)- benzyl]-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyrazine-3-carboxylic acid ethyl ester (240) A solution of Intermediates C (4.88 g, 20.0 mmol) and X (4.76 g, 24.3 mmol) in dry DCE (145 mL) is stirred for 20 min. Sodium triacetoxyborohydride (8.58 g, 40.5 mmol) is added, and the reaction is stirred at rt overnight. The mixture is diluted with DCM and washed with sat. NaHCC>3 and brine, dried over Na2S04, filtered and concentrated. The residue is purified by silica gel chromatography eluting with 0-10% MeOH in DCM to afford the title product 240. (LC/MS method 16: ES+ m/z 422.3 [M+H]+, Rt = 2.81 min).

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, Ethyl 5,6,7,8-Tetrahydro-1,2,4-triazolo[4,3-a]pyrazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRUNETTE, Steven, Richard; ABEYWARDANE, Asitha; BURKE, Michael, J.; KAPADIA, Suresh, R.; KIRRANE, Thomas, Martin, Jr.; NETHERTON, Matthew, Russell; RAZAVI, Hossein; RODRIGUEZ, Sonia; SAHA, Anjan; SIBLEY, Robert; SMITH KEENAN, Lana, Louise; TAKAHASHI, Hidenori; TURNER, Michael, Robert; WU, Jiang-Ping; YOUNG, Erick, Richard, Roush; ZHANG, Qiang; ZHANG, Qing; ZINDELL, Renee, M.; WO2013/134226; (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

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. 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 136927-64-5

The mixture of 1-chloropyrrolo[1,2-a]pyrazine (200 mg, 1.31 mmol) and pivalohy-drazide (346.47 mg, 2.62 mmol) in MeCN (20 mL) was stirred at 80 C. for 24 h. The solvent was removed to give the crude product, the crude product was purified by FCC (petroleum ether/ethyl acetate=100:0 to 70:30).

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 136927-64-5.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 2727-13-1, 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. 2727-13-1, name is 3-Amino-6-chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

DIPEA (200 muIota, 1.15 mmol) was added to a solution of 3-amino-6-chloropyrazine-2- carboxylic acid (50 mg, 0.29 mmol), 2-(aminomethyl)-1-ethyl-6-methoxy-3-methyl-1H-1 ,3- benzodiazol-3-ium iodide, Intermediate 13 (100 mg, 0.29 mmol) and HBTU (142 mg, 0.37 mmol) in anhydrous DMF (1 ml). The resulting mixture was stirred at ambient temperature for 18 h. The reaction mixture was concentrated under a flow of nitrogen to afford the crude product as an oil. The crude material was purified by flash column chromatography on C18 (12 g). The column was eluted with MeCN:H20 + 0.1 % formic acid using the following gradient (%MeCN, column volumes): 10%, 2 CV; 10-100%, 20 CV; 100%, 2 CV. The desired fractions were combined and lyophilised to yield the product as an off-white solid (84 mg, 58%).1H NMR (250 MHz, DMSO-de) delta 9.57 (t, J = 5.3 Hz, 1 H), 8.38 (s, 1 H), 7.93 (d, J = 9.1 Hz, 1 H), 7.66 (s, 2H), 7.57 (d, J = 2.2 Hz, 1 H), 7.29 (dd, J = 9.1 , 2.3 Hz, 1 H), 4.99 (d, J = 5.3 Hz, 2H), 4.62 (q, J = 7.0 Hz, 2H), 4.09 (s, 3H), 3.91 (s, 3H), 1.38 (t, J = 7.1 Hz, 3H). LC/MS (System C): m/z (ESI+) = 375 [M(35CI)+], 377 [M(37CI)+]), R = 1.83 min, UV purity = 100%.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-6-chloropyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 24241-18-7, These common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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.

5-Bromopyrazine-2,3-diamine (27) was preparedfrom 2-amino-3,5-dibromopyrazine and NH4OH (25%) in sealedtube according to lit.33 1H-NMR delta ppm (CD3OD): 4.90 (s,4H,NH2),7.24 (s,2H,H-5,6). 13C-NMR (CD3OD): 123.3, 129.8, 144.3, 145.9. MS(ESI+) m/z: 189(M + H, 100%), 191(M + H+2, 97%). 27 (0.303 g,1.6 mmol) in EtOH (10 mL) was reduced by hydrogenation using 40psi of H2 and 10% Pd-C (15 mg) for 8 h. The catalyst was filtered ona bed of Celite, the filtrate was concentrated in vacuo. Purplecolored powder 28 were used for the further steps without purification.1H-NMR delta ppm (CD3OD): 4.90 (s,4H,NH2), 7.24 (s,2H, H-5,6). 13C-NMR (CD3OD): 123.7, 145.1. MS (ESI) m/z: 110(M + H,100%). 29 was prepared from 28 (0.11 g) and Na2S2O5 adduct of 4-(morpholin-4-ylcarbonyl) benzaldehyde (0.323 g) as described ingeneral method. Resulting precipitate (0.155 g) was purified withcolumn chromatography using CH2Cl2: MeOH (95 : 5) as eluant,yield 0.056 g, (18%), mp > 300 C. 1H-NMR delta ppm (DMSO-d6+D2O):3.27-3.61 (m,8H), 7.62 (d,2H,J – 8.4 Hz), 8.33 (d,2H,J – 8.4 Hz), 8.40(s,2H,H-5,6). 13C-NMR (DMSO-d6+D2O): 66.0, 127.3, 127.8, 129.9,138.2, 139.0, 154.7, 168.2. MS (ESI) m/z: 310(M + H, 100%). AnalCalcd for C16H15N5O2H2O: C, 58.70; H, 5.23; N, 21.39. Found: C,58.97; H, 5.01; N, 20.91.

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karaaslan, Cigdem; Doganc, Fatima; Alp, Mehmet; Koc, Asli; Karabay, Arzu Zeynep; Goeker, Hakan; Journal of Molecular Structure; vol. 1205; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem