Month: April 2021

Related Products of 912773-21-8, 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. 912773-21-8, name is 2-Bromo-5-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-bromo-5-chloro-pyrazine (4 g, 20.68 mmol), 2-benzyloxy-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (7.08 g, 22.75 mmol), CS2CO3 (l3.47g, 4l.36mmol) and Pd(dppf)Cl2 (1.51 g, 2.07 mmol) in l,4-dioxane (50mL) and water (lOmL) was stirred at 50 C under N2 for 3 hours. After cooling to room temperature, the mixture was filtered and concentrated to give a residue. To the residue was added water (100 mL), extracted with EtOAc (150 mL x 2). The combined organic phase was washed with brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated to give the crude product. The crude product was filtered through silica gel (~ 50 g) and eluted with DCM (150 mL x 3). The filtrate was concentrated to give the impure product. The impure product was triturated from /-Pi O (15 mL) to give the product of (4 g, 13.44 mmol, 65% yield) as a solid. LCMS Rt= 1.03 min in 1.5 min chromatography, 5-95AB, MS ESI calcd. for Ci6H13ClN30 [M+H]+298.1, found 297.9.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-chloropyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; MARTINEZ BOTELLA, Gabriel; REDDY, Kiran; WITTMANN, Marion; (0 pag.)WO2019/232209; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 5521-55-1,Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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 boron trifluoride-diethyl ether complex (91.7 muL) was added dropwise to a suspension of 2-methylpyrazine-5-carboxylic acid (1 g) and tert-butyl 2,2,2-trichloroacetimidate (4.75 g) in THF (20 mL) under ice-cooling. The reaction solution was warmed to RT, followed by stirring for 2 h. A saturated NaCl solution and EtOAc were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous MgSO4, and the insoluble matter was separated by filtration. The filtrate was concentrated and purified by silica gel column chromatography to obtain the title compound (1.4 g). 1H-NMR (CDCl3) delta (ppm): 1.65 (s, 9H), 2.65 (s, 3H), 8.57 (d, J=1.2 Hz, 1H), 9.10 (d, J=1.6 Hz, 1H).

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

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; HALL, Adrian; FARTHING, Christopher Neil; CASTRO PINEIRO, Jose, Luis; WO2012/98213; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 19745-07-4,Some common heterocyclic compound, 19745-07-4, name is 2,5-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

In a sealed vessel, a mixture of tert-butyl (4-methylpiperidin-4-yl)carbamate (1.44 g, 6.71 mmol), 2,5-dichloropyrazine (1.00 g, 6.71 mmol) and K2C03(S) (4.64 g, 33.6 mmol) in dioxane (67.1 mL) was stirred for 60 h at 60 ¡ãC. After cooling to ambient temperature, the resulting suspension was diluted with EtOAc, filtered through Celite ? then concentrated in vacuo. The crude residue was purified by silica chromatography (0-100percent) EtOAc in hexanes) to afford the title compound (657 mg, 30percent yield). MS (apci) m/z = 327.1 (M+H).

The synthetic route of 19745-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 95-89-6, name is 3-Chloro-2,5-dimethylpyrazine, 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. name: 3-Chloro-2,5-dimethylpyrazine

Ammonia in water (3 mL, 48.5 mmol) was added to 3-chloro-2,5-dimethylpyrazine (0.121 mL, 1 mmol) and the mixture heated by microwaves to 165 C. for 7 hours. Following LCMS analysis, the reaction was then reheated to 165 C. for a further 16 hours, by microwaves. After cooling, the solvent was removed under a stream of nitrogen and the crude redissolved in dichloromethane (20 mL). Water (25 mL) was added and the mixture basified to pH14 using sodium hydroxide solution (18 N). The organic layer was removed and the aqueous layer extracted with dichloromethane (5¡Á25 mL). The organic phases were combined and dried using a hydrophobic frit, then evaporated in vacuo to give the title product (109 mg). This was used directly in the next step with no further purification. LCMS (2 min, high pH) Rt 0.47 min, m/z (ES+) 124 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 7.73 (s, 1H), 4.42 (br. s., 2H), 2.37 (s, 3H), 2.35 (s, 3H).

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

Reference:
Patent; Glaxo Group Limited; Birault, Veronique; Campbell, Amanda Jennifer; Harrison, Stephen; Le, Joelle; Shukla, Lena; US2015/65507; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 14508-49-7,Some common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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 2-chloropyrazine (2.13g, 18.7mmol), tert-butyl piperazine-1-carboxylate(3.16g,17mmol) and caesium carbonate (7.7g, 23.7mmol) in DMF (35ml) was heated at 100C for16 hours. Cooled toRT and diluted with ether. Ether layer was washed with water and brine,dried over sodium sulphate and distilled off the solvent to afford 2g ( 40.7% yield) of the25 titled product after purification with (601120 silica gel) column chromatography using 40%ethyl acetate in hexane as eluent.

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

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; UM PHARMAUJI SDN. BHD; GUMMADI, Venkateshwar, Rao; HOSAHALLI, Subramanya; NANDURI, Srinivas; AGGUNDA RENUKAPPA, Girish; WO2014/6554; (2014); 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. 4858-85-9, name is 2,3-Dichloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H2Cl2N2

2,3-Dichloropyrazine (5.0 g, 33.6 mmol) and 28% ammonia water (20 mL) were placed in a tube, sealed and stirred at 100 C. for 18 hours. The reaction solution was diluted with water, the resultant solid substance was obtained by filtration to obtain 3-chloropyrazine-2-amine (3.46 g, 100%) as a white solid substance.MS (ESI) m/z=130 (M+H)+.

The synthetic route of 4858-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Oncotherapy Science, Inc.; US2012/59162; (2012); 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. 56423-63-3, name is 2-Bromopyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Bromopyrazine

To a reaction flask were added compound 5 (200 mg, 0.392 mmol), 2-bromopyrazine (92.9 mg, 0.588 mmol),Pd(dppf)Cl2 (32 mg, 0.02 mmol) and sodium carbonate (126 mg, 1.18 mmol), 2 mL glycol dimethyl ether and 0.4 mLwater were added, bubbled with nitrogen gas for 10 minutes, heated to 120 C in microwave and reacted for 0.5 hour.After TLC detected the reaction was complete, the reaction was concentrated, purified by silica gel column chromatographyto afford 83 mg of a product, yield: 46%. LC-MS(APCI): m/z = 462.1 (M+1)+; 1H NMR (400 MHz, DMSO) delta 10.23(s, 1H), 8.87 – 8.79 (m, 2H), 8.76 – 8.70 (m, 1H), 8.63 (d, J = 2.5 Hz, 1H), 8.21 (d, J = 2.3 Hz, 1H), 7.87 (d, J = 9.1 Hz,2H), 7.34 (d, J = 8.9 Hz, 2H), 4.87 (d, J = 3.3 Hz, 1H), 4.21 (s, 1H), 3.41 (dd, J = 17.1, 10.5 Hz, 1H), 3.21 (dd, J = 11.3,4.5 Hz, 2H), 2.85 (d, J= 11.6 Hz, 1H), 1.86 (dd, J = 8.7, 4.1 Hz, 1H), 1.75 (s, 1H).

The synthetic route of 56423-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Targetrx, Inc.; WANG, Yihan; ZHAO, Jiuyang; AL, Yixin; (55 pag.)EP3553056; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4858-85-9, 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. 4858-85-9, name is 2,3-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

A 100 mL round bottom flask was charged with 2,3-dichloropyrazine (10 g, 67.6 mmol), hydrazine hydrate (6.76 g, 135 mmol) and ethanol (40 mL). The resulting mixture was stirred at reflux for 3 h. Reaction progress was monitored by TLC (EtO Ac/petroleum ether = 2:1). Work-up: the reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with water (30 mL x 2) and dried, to afford 8.4 g (87%) of the product as a yellow solid.

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

Reference:
Patent; KALYPSYS, INC.; BORCHARDT, Allen; DAVIS, Robert; NOBLE, Stewart, A.; WO2011/112766; (2011); 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. 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. Computed Properties of C7H3Cl2N3

(D) (S)-1 -(1 -(7-chloropyrido[4,3-ib]pyrazi n-5-yl)pyrrolidi n-3-yl)ethanol .[01 60] (S)-teri-butyl 3-(1 -hydroxyethyl)pyrrolidine-1 -carboxylate was treated with HCI solution (in EtOAc, 5 mL) at room temperature for 2 hours . The volatiles were removed under reduced pressure, and the residue was dissolved in anhydrous THF (10 mL). To the resulted THF solution, DIPEA (570 mg, 4.4 mmol) and 5,7- dichloropyrido[4,3-?>]pyrazine (400 mg, 2.0 mmol) were added, and the reaction was stirred at room temperature overnight. The volatiles were removed under reduced pressure, and the residue was dissolved in ethyl acetate, washed with brine and dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography to afford the title compound. MS (m/z): 279 (M+H)+.

The synthetic route of 1379338-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; JI, Jianguo; WO2012/167423; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 5521-55-1, A common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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.

Step 1. tert-butyl 5-methylpyrazin-2-ylcarbamate To solution 5-methylpyrazine-2-carboxylic acid (2.5 g, 18.1 mmol), tert-butanol (6.92 mL, 72.4 mmol), Et3N (3.78 mL, 27.1 mmol) in 1,4-dioxane (12.5 mL) at 95 C. was dropwise added diphenylphosphoryl azide (DPPA, 3.23 mL, 18.1 mmol), and the reaction was heated at 95 C. for 1.5 h, followed by a 2nd portion of DPPA (1 mL, 5.6 mmol) and heated for additional 1.5 h. The reaction mixture was cooled down, concentrated and the residue was diluted with EtOAc (50 mL), washed with water (30 mL), 3 M NaOH (30 mL), sat. NaHCO3 (30 mL) and brine (30 mL), dried over Na2SO4, and concentrated. The residue was purified by flashed chromatography on silica gel eluting with gradient EtOAc/CH2Cl2 (0-20%) to afford tert-butyl 5-methylpyrazin-2-ylcarbamate as white solid. LCMS (m/z): 210.1 (MH+), 0.69 min; 1H NMR (400 MHz, CDCl3) delta ppm 9.17 (s, 1H), 8.09 (s, 1H), 7.75 (br. s., 1H), 2.51 (s, 3H), 1.56 (s, 9H).

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem