Category: 6863-73-6

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;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6863-73-6, name is 3-Chloropyrazin-2-amine, 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. Quality Control of 3-Chloropyrazin-2-amine

Bromoacetaldehyde diethyl acetal (45 ml, 0.29 mol) was treated with water (33 ml) and 48% hydrobromic acid (33 ml) and this mixture was heated at 95C for 90 min. The reaction was cooled, diluted with propan-2-ol (300 ml) and treated with sodium hydrogencarbonate (33 g) added in portions. This mixture was stirred for 30 min then filtered. The filtrate was treated with 2-amino-3- chloropyrazine (25 g, 0.19 mol) and then heated at 90C for 16 h. The reaction was cooled to ambient temperature, concentrated to about one-third volume and then treated with 48% hydrobromic acid (25 ml). More propan-2-ol (300 ml) was added and the mixture aged for 1 h. The resulting solid was collected by filtration, washed with propan-2-ol and then dissolved in water (500 ml). This solution was made basic by adding solid sodium hydrogencarbonate and then extracted with chloroform (3 x 250 ml). The organics were combined, dried over anhydrous magnesium sulphate, filtered and concentrated to give a solid. Trituration with diethyl ether afforded 8-CHLOROIMIDAZO [1, 2-A] PYRAZINE as an off- white solid (18.6 g, 63%)

The synthetic route of 6863-73-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/41826; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6863-73-6, 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.

Second generation imidazo[1,2-a]pyrazineinhibitors, variants at 2- and 6-positions.8-Chloroimidazo[1,2-a]pyrazine 2-Amino-3-chloropyrazine (200 mg, 1.54mmol) and NaHCO3 (162 mg, 1.93 mmol) were suspended in tBuOH. Chloroacetaldehyde (50% w/v in H2O;200 muL, 1.54 mmol) was added and the reaction mixture was stirred under refluxfor 40 h. The reaction was then cooledto RT and solvent removed in vacuo. The residual material was taken up in CH2Cl2(100 mL) washed H2O (40 mL) and brine (40 mL), dried (MgSO4),filtered and concentrated in vacuo. Flash chromatography (applied in pet. ether;eluted 3:1 to 2:1 to 1:3 pet. ether/EtOAc) afforded the title compound as anoff white solid (118 mg, 0.773 mmol, 50%). Mpt: Decomposed before melting; Rf = 0.17 (2:1 EtOAc/pet.ether); IR (numax/cm-1, thin film): 3144, 3105, 1432; 1H NMR (600 MHz,(CD3)2SO): deltaH = 7.73 (d, J= 4.5 Hz, 1H, 6-H), 7.87 (d, J = 0.9 Hz, 1H, 2-H), 8.28 (d, J = 0.9Hz, 1H, 3-H), 8.66 (d, J = 4.5 Hz, 1H, 5-H); 13C NMR (150 MHz, (CD3)2SO): deltaC = 117.3 (C-3),120.8 (C-5), 127.3 (C-6), 135.5 (C-2), 137.1 (C-9), 141.7(C-8); LRMS m/z (CI+):154 [M(35Cl)+H]+, 156 [M(37Cl)+H]+;HRMS m/z (CI+): Found 154.0166 [M(35Cl)+H]+; C6H5ClN3requires154.0172.

The synthetic route of 6863-73-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sayer, James R.; Walldn, Karin; Pesnot, Thomas; Campbell, Frederick; Gane, Paul J.; Simone, Michela; Koss, Hans; Buelens, Floris; Boyle, Timothy P.; Selwood, David L.; Waksman, Gabriel; Tabor, Alethea B.; Bioorganic and Medicinal Chemistry; vol. 22; 22; (2014); p. 6459 – 6470;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6863-73-6, name is 3-Chloropyrazin-2-amine, 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: C4H4ClN3

3-chloropyrazine-2-amine (1.29 g, 10 mmol)And chloroacetaldehyde (40% aqueous solution, 9.8 g, 50 mmol) were added to 30 mL of isopropanol, and heated under reflux overnight.The solvent was removed by rotary evaporation, and 30 mL of water was added to dissolve.Adjust pH = 7 with saturated sodium bicarbonate solution, extract with ethyl acetate (20mL * 3), combine the organic phases,It was washed with 20 mL of saturated brine, dried over anhydrous sodium sulfate, and concentrated.1.07 g of a pale yellow solid was isolated through a silica gel column with a yield of 70%.

The synthetic route of 6863-73-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Xing Qingfeng; Ai Yixin; (85 pag.)CN110272426; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6863-73-6, 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. 6863-73-6, name is 3-Chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Bromoacetaldehyde diethyl acetal (200 ml_, 1.3 mol) and a solution of 48% HBr (48 ml) are heated at reflux for 1.5 hours, then poured onto a suspension of NaHCO3 (10Og) in propan-2-ol (1.6 L). The resulting solid is filtered off and 2-amino-3-chloropyrazine (51.8 g, 0.4 mol) is added to the solution then heated to reflux, during which time a clear solution forms which precipitates over 2 hours. The reaction mixture is cooled and allowed to stand overnight, and the solid may be collected by filtration and washed with propan-2-ol and Et2O. The solid is added to a saturated solution of NaHCO3 (500 ml.) and DCM (1 L). The aqueous layer is separated from the organic solvent and re-extracted with DCM (2 x 250 mL). The organic layers are combined and dried over MgSO4, filtered and evaporated to dryness, to afford a light brown solid. The propan-2-ol and Et2O liquors from washing the filter cake, are evaporated to give a pale brown solid which is washed with a saturated solution of NaHCO3 and extracted with DCM (X 3). The two solids were combined to afford compound 8-chloro-imidazo[l,2-a]pyrazine (59.1 g, 96%).

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

Reference:
Patent; BIOFOCUS DPI LIMITED; WO2009/24585; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6863-73-6,Some common heterocyclic compound, 6863-73-6, name is 3-Chloropyrazin-2-amine, molecular formula is C4H4ClN3, 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 25 (5.20 g, 40.1 mmol) and CuSO4 (640 mg, 4.01 mmol) in 12 M methanamine aqueous solution (40.0 mL, 480 mmol) was stirred at 120 C for 3 h under microwave irradiation. The reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0-5% MeOH in CHCl3) to give 26 (3.99 g, 80%) as a yellow solid. 1H NMR (DMSO-d6) delta 2.81 (d, 3H, J = 4.7 Hz), 5.84 (s, 2H), 6.13 (q, 1H, J = 4.7 Hz), 7.09 (d, 1H, J = 3.1 Hz), 7.23 (d, 1H, J = 3.1 Hz); MS (ESI) m/z 125 [M+H]+.

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

Reference:
Article; Chino, Ayaka; Masuda, Naoyuki; Amano, Yasushi; Honbou, Kazuya; Mihara, Takuma; Yamazaki, Mayako; Tomishima, Masaki; Bioorganic and Medicinal Chemistry; vol. 22; 13; (2014); p. 3515 – 3526;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

6863-73-6, A common compound: 6863-73-6, name is 3-Chloropyrazin-2-amine, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

EXAMPLE 1; Tert-butyl 4-(8-(2-fluoro-4-(methylsulfonyl)phenylamino)imidazo[l,2- a]pyrazin-3-yl)-5,6-dihydropyridine-l(2H)-carboxylateStep 1: 8-Chloroimidazo[l,2-a]pyrazine[0313] 3-chloropyrazin-2-amine (21.0 g, 161.54 mmol, 1.00 equiv) was dissolved in isopropyl alcohol (200 mL) in a 500 mL round-bottom flask equipped with a reflux condenser. To this solution was added 2-bromo-l,l-diethoxyethane (160.3 g, 813.71 mmol, 5.00 equiv) in small portions over 10 minutes. The resulting mixture was then allowed to reflux for 2 hours in an oil bath. The reaction was monitored by TLC (EtOAc/PE = 1:1). The mixture was cooled down to room temperature and filtered off to give a yellow cake. The solid was added to a saturated solution of NaHCC>;3 (200 mL) and DCM (IL). Aqueous layer was separated from organic phase and re-extracted with DCM (2x 250 mL). The combined organics were dried over MgSO4, filtered and evaporated to dryness affording 8-chloroimidazo[l,2-a]pyrazine (25 g) as a yellow solid.

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-Chloropyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KALYPSYS, INC.; KAHRAMAN, Mehmet; SMITH, Nicholas, D.; BONNEFOUS, Celine; NOBLE, Stewart, A.; PAYNE, Joseph, E.; WO2010/88518; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem