Tag: M.W=100-200

These common heterocyclic compound, 6863-73-6, name is 3-Chloropyrazin-2-amine, 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 3-Chloropyrazin-2-amine

Bromoacetaldehyde diethyl acetal (17.4 ml, 115.8 mmol) was added dropwise to a 48% aqueous solution of hydrobromic acid (4.45 ml, 38.6 mmol) at RT. The mixture was stirred at reflux temperature for 2 h. and then poured onto a suspension of sodium hydrogen carbonate (74.5 g, 0.88 mol) in isopropanol (220 ml). The mixture was stirred for a further 30 min. and then filtered off. 3-Chloro-pyrazin-2-ylamine (5 g, 38.6 mmol) was added to the filtrate and the mixture was stirred at 85 C for 4 h. The solvent was evaporated in vacuo and the crude product suspended in a saturated solution of sodium hydrogen carbonate and extracted with DCM. The organic layer was dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was precipitated from Et20 to yield intermediate 3 (4.1 g, 70%) as a brown solid which was used in the next step without further purification.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose, Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; PASTOR-FERNANDEZ, Joaquin; VAN GOOL, Michiel, Luc, Maria; MARTIN-MARTIN, Maria, Luz; VANHOOF, Greta, Constantia, Peter; WO2011/110545; (2011); A1;,
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Synthetic Route of 313339-92-3, 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.

A solution of BnOH (30.8 g, 0.285 mol, 29.6 mL, 1.1 eq) in THF (450 mL) was cooled to 0 C. NaH (12.4 g, 0.311 mol, 60% oil dispersion, 1.2 eq) was added slowly to the mixture at 0 C. After addition, the mixture was stirred at 25C for 1 hr. The resultant solution was added a solution of 3,5-dichloropyrazine-2-carbonitrile (45.0 g, 258.64 mmol, 1.0 eq) in THF (450 mL) at -78 C and the mixture was stirred at -78 C for 0.5 hr. The reaction was then poured into water (1.00 L) and extracted with EtOAc (1.00 L*3). The combined organic layer was washed with brine (500 mL), dried over Na2S04, filtered and concentrated. The residue was slurryed in petroleum ether/EtOAc = 10: 1 (1.50 L) at 25 C for 0.5 hr. The mixture was filtered and the filter cake was washed with petroleum ether (200 mL). The filter cake was dried under reduced pressure to give 5-(benzyloxy)-3- chloropyrazine-2-carbonitrile (79.3 g, 300 mmol, 58% yield, 93% purity) as a white solid. LCMS m/z [M+H]+ = 245.9. 1H NMR (400MHz CDCl3) d 8.23 (s, 1H), 7.51 – 7.39 (m, 5H), 5.48 (s, 2H).

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

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;,
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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. 4774-14-5, name is 2,6-Dichloropyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H2Cl2N2

To a solution of fert-butyl azetidin-3-ylcarbamate hydrochloride (LXXX) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXXXI) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes?hexanes:EtOAc 1 : 1) to yield fert-butyl (l-(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXXXII) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17CIN4O2 mlz 285.1 (M+H).

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.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (280 pag.)WO2017/23986; (2017); A1;,
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91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, 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. Application In Synthesis of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine

Production Example 3 6,7-Difluoro-7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-1-(thiazol-2-yl)methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (compound No. 51) A mixture of 0.34 g of 1-(thiazol-2-yl)methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.5 g of 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine and 2 ml of N-methylpyrrolidone was stirred at 60 to 70 C. for 2 hours. After the reaction mixture was concentrated under reduced pressure, 10 ml of water was added to the residue, followed by extraction with chloroform (20 ml *3). After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was recrystallized from ethyl ether to yield 0.06 g of the title compound. Melting point: 210-213 C. Elemental analysis (for C20 H15 F2 N5 O3 S.1/2H2 O)

The synthetic route of 91476-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5519024; (1996); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 36070-75-4, 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. 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

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 100C for 4 hours. The reaction mixture was cooled to 20C, 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)pyrazine-2-carbonitrile (310 mg, Yield 82%). The structure was confirmed by LC-MS.

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; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason D.; GUZI, Timothy; WILSON, Kevin J.; DIPIETRO, Lucian V.; ZHANG, Yulian; WILSON, Douglas; FLEMING, Paul E.; (137 pag.)WO2018/17983; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1190927-25-3, 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 1190927-25-3 as follows.

To a solution of 3-morpholin-4-ylmethyl-1 /-/-indol-6-ol sodium salt (130 mg, 0.51 mmol) and 2-chloro-thiazolo[4,5-]pyrazine (70 mg, 0.41 mmol) in DMF (1.4 ml.) was added CS2CO3 (43 mg, 0.12 mmol) and the resulting suspension was stirred (rt, 16 h). The reaction mixture was filtered and the solid was rinsed with EtOAc. The reaction mixture was concentrated in vacuo. The resulting residue was purified via reverse phase HPLC to provide the title compound as a white powder (38.3 mg, 26%). MS (ESI): mass calculated for Ci8H17N5O2S, 367.1 ; m/z found, 368.1 [M+H]+. 1H NMR (600 MHz, CDCI3): 8.51 (d, J = 2.6, 1 H), 8.32 (d, J = 2.6, 1 H), 8.21 (s, 1 H), 7.83 (d, J = 8.6, 1 H), 7.45 (d, J = 2.2, 1 H), 7.21 (d, J = 2.3, 1 H), 7.12 (dd, J = 8.6, 2.2, 1 H), 3.75-3.69 (m, 6H), 2.51 (s, 4H).

According to the analysis of related databases, 1190927-25-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BACANI, Genesis; CHROVIAN, Christa, C.; ECCLES, Wendy; FOURIE, Anna, M.; GOMEZ, Laurent; GRICE, Cheryl, A.; KEARNEY, Aaron, M.; LANDRY-BAYLE, Adrienne, M.; LEE-DUTRA, Alice; SANTILLAN, Alejandro; TANIS, Virginia, M.; WIENER, John, J. M.; WO2010/132599; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 55557-52-3,Some common heterocyclic compound, 55557-52-3, name is 3-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.

Example 345-[(3-Cyanopyrazin-2-y[)amino]-N-(2-ethy[pheny[)-3-methy[- 1 ,2-thiazo[e-4- carboxamide A mixture of 5-amino-N-(2-ethy[pheny[)-3-methy[-1 ,2-thiazo[e-4-carboxamide [Intermediate 1] (150 mg, 0.57 mmo[, 1.4 eq), 3-ch[oropyrazine-2-carbonitri[e [CAS-RN: 55557-52-3] (57 mg, 0.41 mmo[, 1.0 eq) and cesium carbonate (307 mg, 0.94 mmo[, 2.3 eq) in 4.0 mL dioxane/DMF (7/1) was p[aced in a microwave via[ and f[ushed with argon. Then, pa[[adium(II) acetate (9 mg, 0.04 mmo[, 0.1 eq) andXantphos (24 mg, 0.04 mmo[, 0.1 eq) were added. The via[ was capped and the reaction mixture was stirred at an environmenta[ temperature of 110 C overnight. On coo[ing, the reaction mixture was partitioned between dich[oromethane and water. After fi[tration over Ce[ite, the organic phase was separated and concentrated in vacuo. The crude product was purified via preparative HPLC(method A) to give 47 mg (22 % yie[d of theory) of the tit[e compound.UPLC-MS (Method 1): Rt = 1.24 mm; MS (Elneg) m/z = 363 [M-H].1H-NMR (400 MHz, DMSO-d6): oe [ppm] = 1.11 (t, 3H), 2.61 -2.82 (m, 5H), 7.09-7.31 (m, 3H), 7.46 (d, 1H), 8.20 (s br, 1H), 8.77 (d, 1H), 11.72 (s br, 1H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; PRECHTL, Stefan; SIEMEISTER, Gerhard; WENGNER, Antje Margret; ACKERSTAFF, Jens; NOWAK-REPPEL, Katrin; BADER, Benjamin; LIENAU, Philip; STOeCKIGT, Detlef; WO2014/118186; (2014); 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. 14508-49-7, name is 2-Chloropyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloropyrazine

Step A Ethanol (13 ml) and 1.0M Na2CO3 (27.5 ml) were added to a suspension of 2-chloropyrazine (4.0 g, 34.6 mmole), 4-formylphenylboronic acid (6.8 g, 45.0 mmole), and tetrakis(triphenylphosphine)palladium(0) (2.0 g, 1.7 mmole) in toluene (55 ml). The mixture was refluxed for 18 hours then cooled, diluted with EtOAc, washed with NaHCO3, washed with brine, dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 4:1 hexanes/EtOAc) yielded 6.2 g (97%) of 4-(2-pyrazinyl)benzaldehyde.

The synthetic route of 14508-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhu, Bin; Marinelli, Brett; Macielag, Mark J.; US2005/250713; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 768-05-8, 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. 768-05-8, name is Pyrazinoic acid hydrazide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To the solution of pyrazine carboxylic acid hydrazide (0.55 g, 4 mmol) in methanol (30 mL) was added dropwise with continuous stirring, a solution of 2-benzoyl pyridine (0.73 g, 4 mmol) in the same solvent. The reaction mixture was then refluxed for 5 h. The solid product so obtained was filtered and recrystallised in hot methanol.

The chemical industry reduces the impact on the environment during synthesis Pyrazinoic acid hydrazide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Devi, Jai; Batra, Nisha; Malhotra, Rajesh; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 97; (2012); p. 397 – 405,9;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1174321-06-2, These common heterocyclic compound, 1174321-06-2, name is 5-(Difluoromethyl)pyrazine-2-carboxylic acid, 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.

Example 24 N-(3-((2R,5R)-6-amino-3,3,5-trifluoro-2,5-dimethyl-2,3,4,5-tetrahydropyridin-2-yl)-4-fluorophenyl)-5-(difluoromethyl)pyrazine-2-carboxamide Prepared from (3R,6R)-6-(5-amino-2-fluorophenyl)-3,5,5-trifluoro-3,6-dimethylpiperidine-2-thione and 5-(difluoromethyl)pyrazine-2-carboxylic acid LC-MS (m/z) 446 (MH+) tR=0.52 minutes (Method A) 1H NMR (600 MHz, DMSO-d6) delta 11.03 (s, 1H), 9.37 (t, J=2.4 Hz, 1H), 9.09 (s, 1H), 7.89-7.80 (m, 2H), 7.26 (t, J=53.9 Hz, 1H), 7.18 (dd, J=11.9, 8.7 Hz, 1H), 6.34 (s, 2H), 2.62-2.51 (m, 1H), 2.29-2.14 (m, 1H), 1.71 (d, J=23.2 Hz, 3H), 1.68 (s, 3H)

The synthetic route of 1174321-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; Juhl, Karsten; Marigo, Mauro; Tagmose, Lena; Jensen, Thomas; US2015/232449; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem