Category: 132426-19-8

132426-19-8, name is 2-Bromo-1-(pyrazin-2-yl)ethanone, 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. Recommanded Product: 2-Bromo-1-(pyrazin-2-yl)ethanone

To a solution of 1-(pyridin-2-yl)thiourea (0.129 g, 0.85 mmol) in DMF (7 mL), 2-bromo-1-(pyrazin-2-yl)ethan-1-one (0.20 g,0.99 mmol) and triethylamine (0.3 mL, 2.0 mmol) were added successively and heated the mixtureat 70C for 2 hours. After TLC showed completion, reaction mixture was diluted withEtOAc (20 mL) and washed with water (3 x 10 mL). The organic layer was dried over Na2SO4and concentrated. The resulting residue was purified by column chromatography (silicagel,100-200) and the desired product was eluted with 3% CH3OH in CH2Cl2. Concentration ofthe pure fractions afforded 58 (35 mg, 13.8% yield), as a greenish solid; 1H NMR: (400 MHz,DMSO-d6): delta 6.95 (d, J = 4.8 Hz, 1H), 7.11 (d, J = 8.4 Hz, 1H), 7.71-7.76 (m, 1H), 7.79 (s, 1H),8.32-8.33 (m, 1H), 8.58 (d, J = 2.4 Hz, 1H), 8.65-8.66 (m, 1H), 9.16 (d, J = 1.6 Hz, 1H), 11.57(s, 1H); 13C NMR: (300 MHz, DMSO-d6): 111.3, 114.5, 116.8, 117.0, 138.6, 146.8, 147.2, 152.0,158.8, 158.9, 159.0, 160.7; LCMS m/z (M+H) 256.04, purity 98.9%; HRMSMS ESI m/z calcdfor C12H9N5S (M+H)+ 256.06122, found 256.0634 (Delta 2.2 ppm).

The synthetic route of 132426-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kesicki, Edward A.; Bailey, Mai A.; Ovechkina, Yulia; Early, Julie V.; Alling, Torey; Bowman, Julie; Zuniga, Edison S.; Dalai, Suryakanta; Kumar, Naresh; Masquelin, Thierry; Hipskind, Philip A.; Odingo, Joshua O.; Parish, Tanya; PLoS ONE; vol. 11; 5; (2016);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 132426-19-8, name is 2-Bromo-1-(pyrazin-2-yl)ethanone, 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 132426-19-8, Recommanded Product: 132426-19-8

Step 1. 3-Amino-6-chloro-1-(ethoxycarbonyl)-2-(pyrazine-2-carbonyl)indole The title compound was prepared according to the procedure described in step 2 of Example 1 from 4-chloro-2-(ethoxycarbonylamino)benzonitrile (Example 1, step 1) and 2-(bromoacetyl)pyrazine (prepared according to the method of F. H. Case et al., J. Am.Chem.Soc., 1956, 78, 5842). 1H-NMR (CDCl3) delta: 9.26 (1H, d, J=1.5 Hz), 8.67 (1H, d, J=2.6 Hz), 8.56 (1H, dd, J=1.5, 2.6 Hz), 8.21 (1H, d, J=1.8 Hz), 7.55 (1H, d, J=8.4 Hz), 7.27 (1H, dd, J=1.5, 8.4 Hz), 6.18 (2H, br s), 3.87 (2H, q, J=7.0 Hz), 0.93 (3H, t, J=7.0 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-(pyrazin-2-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US6300363; (2001); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

132426-19-8, 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. 132426-19-8, name is 2-Bromo-1-(pyrazin-2-yl)ethanone belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a 1 dram vial was added 4-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2- yl)pyridin-2-amine, 2 HCl (50 mg, 0.160 mmol), 2-bromo-1-(pyrazin-2-yl)ethanone (48.1 mg, 0.239 mmol) and Hunig’s Base (0.1 12 mL, 0.639 mmol) in EtOH (1 mL). The vial was sealed and heated to 90 C overnight. The next day the reaction was cooled to rt and analyzed by LC/MS. The reaction was complete and the solution was cooled to rt and the crude solid was filitered off and washed with cold Ethanol. The resulting solid was pure by LC/MS. The solid was then dissolved in hot methanol containing TFA. The solvent was then evaporated in vacuo affording 5,8-dimethyl-2-(2-(pyrazin-2-yl)imidazo[1,2-a]pyridin-7-yl)-[1,2,4]triazolo[1,5-a]pyrazine, 2 TFA (48 mg, 0.077 mmol, 48.5 % yield). 1H NMR (400MHz, DMSO-d6) delta 9.35 (s, 1H), 8.80 (d, J=7.3 Hz, 1H), 8.75 (s, 1H), 8.72 (s, 1H), 8.64 (d, J=2.5 Hz, 1H), 8.43 (s, 1H), 8.08 (s, 1H), 7.79 (d, J=6.8 Hz, 1H), 2.87 (s, 3H), 2.78 (s, 3H), LC/Mass spec. (Method 1) RT=1.87 min. Mass = 343.3 (MH)+.

The synthetic route of 2-Bromo-1-(pyrazin-2-yl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SCHMITZ, William D.; DEBENEDETTO, Mikkel V.; KIMURA, S. Roy; WO2013/3298; (2013); A2;,
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. 132426-19-8, name is 2-Bromo-1-(pyrazin-2-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., 132426-19-8

To a solution of 1-(pyrazin-2-yl)ethan-1-one (250 mg, 2.03 mmol) in AcOH (5 mL), pyridinium bromide perbromide(780 mg, 2.4 mmol) was added and allowed the mixture to stir at room temperature for 48hours. After TLC showed completion, diluted the mixture with EtOAc (20 mL) and washedwith water (3 x 10 mL). The organic layer was dried over Na2SO4 and concentrated to obtaincrude 2-bromo-1-(pyrazin-2-yl)ethan-1-one, which was used in next step without further purification(300 mg, crude). To a solution of 1-(2,6-dimethylphenyl)thiourea (134 mg, 0.7 mmol)in DMF (5 mL), crude 2-bromo-1-(pyrazin-2-yl)ethan-1-one (300 mg, 0.7 mmol) and triethylamine(0.31 mL, 2.2 mmol) were added successively and heated the mixture at 70C for 2hours. After TLC showed completion, reaction mixture was diluted with EtOAc (20 mL) andwashed with water (3 x 10 mL). The organic layer was dried over Na2SO4 and concentrated.The resulting residue was purified by column chromatography (silicagel, 100-200) and thedesired product was eluted with 20% EtOAc in hexane. Concentration of the pure fractionsafforded 52 (135 mg, 32% yield), as a pale yellow solid; 1H NMR: (400 MHz, DMSO-d6): delta 2.23(s, 6H), 7.14-7.20 (m, 3H), 7.45 (s, 1H), 8.54 (d, J = 2.4 Hz, 1H), 8.61 (t, J = 1.6 Hz, 1H), 8.99 (d, J = 1.6 Hz, 1H), 9.43 (1H, s); 13C NMR: (300 MHz, CDCl3) delta 18.1, 107.7, 128.1, 128.9, 137.0,137.4, 142.5, 142.7, 143.8, 148.3, 148.8, 171.0; LCMS m/z (M+H) 283.08, purity 99.8%; HRMSMS ESI m/z calcd for C15H14N4S (M+H)+ 283.1012, found 283.1001 (Delta 1.1 ppm).

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:
Article; Kesicki, Edward A.; Bailey, Mai A.; Ovechkina, Yulia; Early, Julie V.; Alling, Torey; Bowman, Julie; Zuniga, Edison S.; Dalai, Suryakanta; Kumar, Naresh; Masquelin, Thierry; Hipskind, Philip A.; Odingo, Joshua O.; Parish, Tanya; PLoS ONE; vol. 11; 5; (2016);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 132426-19-8, name is 2-Bromo-1-(pyrazin-2-yl)ethanone, 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 132426-19-8, 132426-19-8

Example 76N-(2-amino-phenyl)-4-[4-(4-pyrazin-2-yl-1H-imidazol-2-yl)-tetrahydro-pyran-4-yl]-benzamide; 4-(4-Cyano-tetrahydro-pyran-4-yl)-benzoic acid methyl ester (1.0 g, 4.08 mmol) was suspended in 4.0N NaOH and heated at 110 C. for 1 hour. After the reaction was complete, 2N HCl was slowly added to form a precipitate. The precipitate was then filtered, dried under vacuum, and used for next step without purification. 4-(4-Carboxy-phenyl)-tetrahydro-pyran-4-carboxylic acid (0.4 g, 1.6 mmol) was dissolved in NMP. HATU (1.28 g, 2.1 eq) and DIPEA (0.8 mL, 3.0 eq) were added and stirred at 50 C. for 1 hour. The reaction mixture was cooled down to room temperature and benzyl alcohol (172 mg, 1.0 eq) was added. The reaction mixture was stirred at room temperature overnight. Saturated aqueous solution of NaHCO3 was added to the mixture and was then extracted with EtOAc. The organic phase was dried, evaporated and used for next step without further purification.To a solution of 4-(4-benzyloxycarbonyl-phenyl)-tetrahydro-pyran-4-carboxylic acid (0.3 g, 0.88 mmol) and 2-bromo-1-pyrazin-2-yl-ethanone (210 mg, 1.2 eq) in acetonitrile, TEA (0.18 mL, 1.2 eq) was added and heated in the microwave at 80 C. for 1 hour. The reaction mixture was evaporated and purified by silica gel chromatography (Hex:EtOAc 25:75). 4-(4-benzyloxycarbonyl-phenyl)-tetrahydro-pyran-4-carboxylic acid 2-oxo-2-pyrazin-2-yl-ethyl ester (0.3 g, 0.65 mmol), NH4OAc (110 mg, 2.2 eq) and 3 molecular sieves were mixed together in xylene and heated in the microwave at 160 C. for 1 hour. After the reaction was done, it was extracted with EtOAc and the organic phase was dried and evaporated to be used in the next step without further purifications.Hydrogenation of 4-[4-(4-pyrazin-2-yl-1H-imidazol-2-yl)-tetrahydro-pyran-4-yl]-benzoic acid benzyl ester (0.2 mg, 0.45 mmol) in EtOH, was carried out in the presence of excess Pd/C (10%, dry basis) at a pressure of 1 atmosphere. After 16 hours, the reaction mixture was filtered through a celite pad and washed with hot ethanol. The solution was evaporated and used for next step without further purification.The above acid was then coupled with 1,2-phenylenediamine in the presence of HATU and DIPEA in DMF and purified by reverse phase chromatography to give the title compound. MS found for C25H24N6O2 as (M+H)+ 441.21 1H NMR (400 MHz, dmso-d6): 1H-NMR (DMSO) delta: 10.42 (s, 1H), 9.32 (s, 1H), 8.68-8.64 (m, 2H), 8.37 (s, 1H), 8.07 (d, J=8.4 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.46-7.28 (m, 5H), 3.82-3.79 (m, 2H), 3.52-3.46 (m, 2H), 2.98-2.95 (m, 2H), 2.40-2.29 (m, 2H).

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, 2-Bromo-1-(pyrazin-2-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Melvin, JR., Lawrence S.; Graupe, Michael; Venkataramani, Chandrasekar; US2010/22543; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem