Tag: M.W=100-200

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. 5521-58-4, name is 5-Methylpyrazin-2-amine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 5521-58-4

l-Chloro-N,N,2-trimethyl-l-propenylamine (2.67 mL, 20 mmol) was added to a solution of 3-{[6-(azetidin-l-ylcarbonyl)pyridin-3-yl]oxy}-5-[(phenylmethyl)oxy]benzoic acid (6.18 g, 15.3 mmol) in DCM (100 mL) and the reaction stirred at RT for 50mins. 2-Amino-5- methylpyrazine (3.34 g, 30.6 mmol) and pyridine (2.5 mL, 30.6 mmol) were added and the reaction stirred overnight. The solvent was removed in vacuo, and the residue taken up in ethyl acetate(350 mL). The organic phase was washed with water (2 x 100 mL), brine (100 mL), dried (MgSO4), filtered, and evaporated in vacuo. The residue was chromatographed on silica, eluting with a gradient of 50-75% ethyl acetate in isohexane, to give the desired material (4.01 g). 1H NuMR delta (CDCl3): 2.28 (quin, 2H), 2.49 (s, 3H), 4.18 (t, 2H), 4.63 (t, 2H), 5.05 (s, 2H), 6.78 (s, IH), 7.10 (s, IH), 7.25 – 7.37 (m, 7H), 8.04 (d, IH), 8.07 (s, IH), 8.25 (s, 2H), 9.46 (s, IH); m/z 496 (M+H)+

The synthetic route of 5521-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7041; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

122-05-4, The chemical industry reduces the impact on the environment during synthesis 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, I believe this compound will play a more active role in future production and life.

A solution of ScCl3¡¤6H2O (30 mg, 0.116 mmol) in distilled water(1.0 ml) was mixed with a solution of H2pzc dihydrate (35 mg, 0.171 mmol) in N,N-dimethylacetamide (1.0 ml). Acetonitrile(2.0 ml) and 0.25 ml of concentrated hydrochloric acid were added to the mixture. The prepared reaction mixture was placedinto a sealed glass tube and kept at 100 C for 48 h. The obtained colorless needle-like crystals were filtered off, washed bytwo portions (2 ml) of acetonitrile and dried in air. The product yield was 18 mg (43%). Elemental analysis: found (%)C 37.2, H 2.8, N 15.2. Calculated for C22H18N8O15Sc2 (%): C 36.8, H 2.5, N 15.5. IR spectrum (KBr), v, cm-1: 417 (w),489 (m), 509 (m), 532 (m), 510 (w), 773 (s), 845 (s), 949 (w), 1016 (w), 1051 (s), 1180 (s), 1200 (w), 1298 (s), 1385 (s),1479 (s), 1666 (s), 2250 (w), 2816 (w), 3100 (w), 3375 (w), 3470 (w).

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

Reference:
Article; Barsukova; Sapianik; Samsonenko; Fedin; Journal of Structural Chemistry; vol. 60; 5; (2019); p. 823 – 829; Zh. Strukt. Kim.; vol. 60; 5; (2019); p. 857 – 863,7;,
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. 19745-07-4, name is 2,5-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., 19745-07-4

To a solution of l-(2,5-difluoro-4-(methylsulfonyl)benzyl)-3-(piperidin-4- yl)imidazolidin-2-one 2,2,2-trifluoroacetate (Intermediate 10; 0.2 g, 0.410 mmol) in DMF (2 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.300 mL, 1.641 mmol) and 2,5- dichloropyrazine (0.0917 g, 0.615 mmol) and the reaction was heated to 100 ¡ãC for 8 hours. The reaction was diluted with EtOAc (100 mL), washed with water (50 mL) and brine (50 mL), dried over MgS04, filtered and concentrated in vacuo. The crude material was chromatographed eluting with 7:3 EtOAc/Hexane to yield a solid, which was further purified by reverse phase preparative HPLC to give l-(l-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(2,5- difluoro-4-(methylsulfonyl)benzyl)imidazolidin-2-one (0.0071 g, 0.0146 mmol, 3.6percent yield). Mass spectrum 485.7, 487.7 (M+H).

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:
Patent; ARRAY BIOPHARMA INC.; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald J.; WO2013/74641; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 4858-85-9, name is 2,3-Dichloropyrazine, 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 4858-85-9. 4858-85-9

2,3-Dichloropyrazine (448 mg, 3 mmol) and 1 -[2-(4-fluorophenoxy)ethyl] piperazine (CAS 77602-92-7, 2.9 mmol) were dissolved in DMSO (0.4 ml). Subsequently, NaOH pellets (1 g, 25 mmol) were added. The reaction was stirred at 150 0C under microwave irradiation for 0.5 hours. Then, 0.4 ml of NaOH (4M) and 0.4 ml of DMSO were added, heating at 150 0C in microwave for 0.5 hours more. The mixture was dissolved in AcOEt, washed with H2O and brine, dried with MgSO4 and evaporated under vacuum. The product was used without any further purification, yielding 710 mg of the desired final compound 13-1 (77 %).

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 2,3-Dichloropyrazine.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/135131; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, 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. 4858-85-9

To a flame dried 25 mL flask with zinc dust (217 mg, 3.31 mmol) and N,N-dimethylacetamide (2 mL) was added chlorotrimethylsilane (33.5 muL, 0.265 mmol) and 1,2- dibromoethane (22.83 muL, 0.265 mmol). The resulting slurry was stirred 15 min, then tert-butyl 3-iodoazetidine-l-carboxylate (753 mg, 2 66 mmol) was added to the above mixture (mild exotherm). The suspension was stirred at rt 30 min. [00422] The zinc solution was added via syringe to a solution of 2,3-dichloropyrazine (277 mg, 1.862 mmol), (dppf)PdCl2-CH2Cl2 (65.2 mg, 0.080 mmol), and copper(I) iodide (30.4 mg, 0.160 mmol) in N,N-dimethylacetamide (1.0 mL) that was degassed with N2 (3 x). The solution was heated to 80 0C and stirred 1 h. The reaction was quenched with NH4Cl (10 mL) and extracted with EtOAc (3 x 10 mL). The combined organic fractions were dried (MgSO4), concentrated, and purified by ISCO (40 g SiO2, 10-100% EtOAc/Hexane) to give tert-butyl 3-(3- chloropyrazin-2-yl)azetidine-l-carboxylate (262 mg, 0.971 mmol, 36.5 % yield) as a clear, colorless oil.

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 4858-85-9.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; BOURBEAU, Matthew P.; CHEN, Ning; HU, Essa; KUNZ, Roxanne; RUMFELT, Shannon; WO2010/57121; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, 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. 55557-52-3

Step 7: synthesis of Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate (7) A mixture of 3-chloropyrazine-2-carbonitrile (17.9 g, 128 mmol), sodium carbonate (17.7 g, 167 mmol) and ethyl-2-mercaptoacetate (18.4 mL, 167 mmol) in ethanol (120 mL) was heated to reflux for 4.5 h. Quenched with water (1.5 L) and stirred for 30 min. The resulting precipitate was collected and washed with water. The residue was dissolved in diethyl ether and a black precipitate was filtrated off. Ether was evaporated to give pure compound ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate 7 (19.6 g, 68.5%). 1H-NMR (400 MHz, CDCl3) 1.42 (t, J=7.2 Hz, 3H), 4.40 (q, J=7.2 Hz, 2H), 6.19 (br s, 1H), 8.58 (d, J=2.2 Hz, 1H), 8.63 (d, J=2.2 Hz, 1H).

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, 55557-52-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Folmer, Brigitte Johanna Bernita; Man, de Adrianus Petrus Antonius; Gernette, Elisabeth Sophia; Corte Real Goncalves Azevedo, Rita; Ibrahim, Hemen; US2013/79341; (2013); 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. 3149-28-8, name is 2-Methoxypyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 3149-28-8

1.9 g (0.017 mol) of 30 % hydrogen peroxide are added to a solution of 1.1 g (0.01 mol) of 2-methoxy-pyrazine in 3 ml of glacial acetic acid and the resulting solution is heated at 65-68C for 17 hours. The solution is concentrated to 1/3 of the original volume, diluted with the same amount of water and concentrated again. The residue is extracted with chloroform and the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. After concentration, two amounts, each of 25 ml, of toluene are added to the residue obtained and are concentrated again. The desired title compound, which can be used directly for further reactions, is obtained in a yield of 0.98 g (77 % of theory). ‘H NMR (300 MHz, CDCI3) : 7.988 ppm (d (J=4.2 Hz), 1 H) ; 7.766-7. 773 ppm (m, 1 H) ; 7.745 ppm (dxd (J=4.2 and 1.5 Hz), 1 H) ; 3.995 ppm (s, 3H).

The synthetic route of 3149-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2003/87067; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 55557-52-3

General procedure: alpha,beta-unsaturated tosylhydrazones 1 (0.11 mmol, 1.1 equiv), heteroaryl chlorides 2 (0.1 mmol, 1 equiv), Cs2CO3 (0.25 mmol, 2.5 equiv) and MeCN (1 mL) were added to a tube. The mixture was stirred at 60 C until the heteroaryl chlorides was completely disappeared for 4-8h. After cooling to room temperature, the mixture was quenched with NH4Cl (2 mL, saturated aqueous solution) and extracted with CH2Cl2 (3 ¡Á 2 mL). The combined organic phases were dried over Na2SO4 and solvents removed in vacuo. The residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether (1:10-1:4, V/V) as the eluent, affording the desired product 3 and 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 55557-52-3, its application will become more common.

Reference:
Article; Zeng, Lin; Guo, Xiao-Qiang; Yang, Zai-Jun; Gan, Ya; Chen, Lian-Mei; Kang, Tai-Ran; Tetrahedron Letters; vol. 60; 33; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

19745-07-4, 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. 19745-07-4, name is 2,5-Dichloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step C: To a solution of (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenylamino)- l-(piperidin-4-yl)pyrrolidin-2-one (Table 2, compound 1; 1.5 g, 4.02 mmol) and DIEA (3.50 mL, 20.1 mmol) in DMF (15mL) was added 2,5-dichloropyrazine (1.20 g, 8.03 mmol) . This mixture was heated to 100 ¡ãC for 3 hours under nitrogen. The mixture was poured into brine (150 mL) and extracted into ethyl acetate (3 x 500 mL). The combined organic layers were dried over MgS04, filtered and concentrated in vacuo to give an oil. Ether (100 mL) was added and a precipitate formed overnight. The ether was decanted and the solid was triturated using ethanol (100 mL) at reflux with stirring for 5 minutes. The material was purified by column chromatography using 50percent to 100percent ethyl acetate/hexane. The resulting solid was dried over the weekend under high vacuum to provide the title compound (0.83 g, 39percent yield). Mass spectrum (apci) m/z = 486.1 (M+H).

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

Reference:
Patent; ARRAY BIOPHARMA INC.; AICHER, Thomas Daniel; BENCSIK, Josef Roland; BOYD, Steven Armen; CONDROSKI, Kevin Ronald; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald Jay; PRATT, Scott Alan; SINGH, Ajay; TURNER, Timothy M.; WO2011/146335; (2011); 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. 4858-85-9

To a solution of l-(quinolin-2-yl)piperidin-4-ol (see PREPARATION Pl . l ; 2.0 g, 8.7 mmol) in DMF (30 mL) at room temperature was added sodium hydride (60% wt in mineral oil) (0.47 g, 17.4 mmol) at 0 C. The mixture was stirred at room temperature for 60 min and then 2, 3-dichloro-pyrazine (1.2 g, 8.7 mmol) was added. The reaction mixture was heated to 90 C overnight and then diluted with water (60 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with water (40 mL) and brine (40 mL), dried over Na2S04, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (10% to 30% EtOAc in petroleum ether) to give the title product ( 2.0 g, 5.8 mmol, 70% yield ) as white solid. ESI-MS (M+l): 341 calc. for

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

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; HORNE, Daniel B.; HU, Essa; KALLER, Matthew R.; MONENSCHEIN, Holger; NGUYEN, Thomas T.; REICHELT, Andreas; RZASA, Robert M.; WO2011/143495; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem