Tag: M.W=100-200

Electric Literature of 5424-01-1, The chemical industry reduces the impact on the environment during synthesis 5424-01-1, name is 3-Aminopyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

Example 1139.1 1 153.14[0257] A slurry of 3-amino-2-pyrazinecarboxylic acid (15 gm, 0.108 moles) in dry methanol (250 mL) was stirred as concentrated sulfuric acid (10 mL, 18.4 gm, 0.188 moles) was added. The addition of the acid caused most of the solid to dissolve. The mixture was stirred at reflux, causing the formation of a clear yellow solution. This solution was stirred at reflux for 5 hours and was then stored at room temperature overnight. The solution was diluted with methylene chloride (500 mL) and was stirred as a solution of potassium carbonate (26 gm, 0.188 moles) in water (75 mL) was slowly added. After stirring for 15 minutes, the organic phase was separated from the aqueous phase and was dried over magnesium sulfate. After filtration to remove the drying agent, the solvents were removed under reduced pressure. The solid residue was recrystallized from isopropyl alcohol to provide the methyl ester as a tan powder in a yield of 7.22 gm (43.7%).

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-Aminopyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANUS BIOTHERAPEUTICS, INC.; LIPFORD, Grayson, B.; ZEPP, Charles, M.; WO2012/167046; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 136927-64-5, 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. 136927-64-5, name is 1-Chloropyrrolo[1,2-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

PREPARATION 21 1-benzyloxypyrrolo[1,2-a]pyrazine (A compound of formula (DD)) To a solution of sodium hydride in anhydrous dimethylformamide was added benzyl alcohol (0.64 g, 5.9 mmol). The reaction mixture was stirred for 15 minutes. 1-chloropyrrolo[1,2-a]pyrazine (0.90 g, 5.9 mmol) in anhydrous dimethylformamide was then rapidly added to the reaction mixture. The reaction mixture was then heated to 100 C. for approximately 30 minutes. It was then allowed to cool to room temperature and water was added. The product was then extracted with methylene chloride, washed with a saturated sodium chloride solution, dried over MgSO4 and evaporated. The product was then purified by recrystallization in ether-hexane to give the title compound,

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, 1-Chloropyrrolo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Syntex (U.S.A.) Inc.; US5041442; (1991); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 23688-89-3, 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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

6-Chloropyrazine-2-carboxylic acid [CAS-RN: 23688-89-3] (300 mg, 1 .89 mmol,1.0 eq) was dissolved in 12 mL THF, and CDI (338 mg, 2.08 mmol, 1 eq) was added. Then, the reaction mixture was heated to 70C for 60 mm. On cooling, asolution of 2-(methylsulfonyl)ethanamine [CAS-RN: 49773-20-8] (256 mg,2.08 mmol, 1.1 eq) in 1.5 mL THF and triethylamine (0.53 mL, 3.78 mmol,2.0 eq) was added. The reaction mixture was stirred at 70C for 2 h. The reaction mixture was partitioned between ethyl. acetate and water. The water phase was extracted with ethyl. acetate and the combined organic phases were washed with brine. The phases were separated by the use of a Whatman filter and the volatile components of the organic phase were removed in vacuo toyield 350 mg (53% yield of theory) of the title compound in 76% purity (UPLC area%) that was used without further purification.UPLC-MS (Method 1): R = 0.61 mm; MS (EI0): m/z = 264 [M+1].

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, 6-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 98-97-5, name is Pyrazine-2-carboxylic acid, 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 98-97-5, name: Pyrazine-2-carboxylic acid

To a solution of Pyrazine-2-carboxylic acid (295mg, 2. [1MMOL,] leq) and triethylamine [(765UL,] 5.4mmol, 2.6eq) in THF (6ml) at [0 C] was added dropwise diphenylphophoryl azide [(L.] 4ml, 2. [8MMOL,] [1.] 3eq). The mixture was stirred under nitrogen at [0 C] for 30 minutes, then warmed to RT and stirring continued for a further 2 hours. The reaction mixture was concentrated under vacuum and purified by flash chromatography [(90/10-60/40] [ISO-HEXANE/ETOAC)] to afford the title compound as white solid (265mg, yield=78%). 1H NMR (400 MHz, [CDC13)] [6] 9.14 (d, 1H, J=1.2) ; 8.50 (dt, 1H, J=1.2, 0.4), 2.62 (s, 3H, broad).

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; MILLENIUM PHARMACEUTICALS, INC.; WO2003/101444; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 55557-52-3, A common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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.

To a solution of 1.50 g (10.75 mmol, 1 equiv) of 2 chloro-3-cyanopyrazine 15 in propanenitrile (10 mL) was added 3.30 g (21.50 mmol, 2 equiv) of bromotrimethylsilane dropwise, and the resulting mixture was stirred for 16 h at room temperature. Subsequently, the reaction mixture was cooled to 0 C and quenched with an aqueous solution of 2 M NaOH (10 mL). Afterward, the aqueous phase was extracted with EtOAc (3¡Á10 mL), and the combined organic phases were washed with brine (2¡Á10 mL). After drying (MgSO4) and evaporation of the solvents in vacuo, the product was recrystallized from Et2O to afford 1.56 g (8.49 mmol, 79% yield) of 3-bromo-2-cyanopyrazine 16 as white crystals (mp=43.5 C). 1H NMR (CDCl3): delta 8.61 (1H, d, J=2.2 Hz, CH); 8.71 (1H, d, J=2.2 Hz, CH). 13C NMR (CDCl3): delta 114.7 (CN); 133.3 (CCN); 143.3 (CBr); 143.4 (CH); 147.0 (CH). IR (ATR, cm-1): nu=3101; 2243 (CN); 1958; 1538; 1515; 1425; 1364; 1336; 1249; 1184; 1161; 1071; 1048; 945; 870; 839; 824; 668; 653. GC-MS (EI) m/z (%): 183/185 (M+, 58); 129/131 (13); 104 (M+-Br, 100); 77 (23); 52 (28). Anal. Calcd for C5H2BrN3: C, 32.64; H, 1.10; N, 22.84. Found: C, 32.78; H, 1.15; N, 22.67.

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:
Article; Piron, Karel; Kenis, Sara; Verniest, Guido; Surmont, Riccardo; Thuring, Jan Willem; Ten Holte, Peter; Deroose, Frederik; De Kimpe, Norbert; Tetrahedron; vol. 68; 34; (2012); p. 6941 – 6947;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33332-28-4, name is 2-Amino-6-chloropyrazine, 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 33332-28-4, Quality Control of 2-Amino-6-chloropyrazine

Example 27; Synthesis of N-(6-chloropyrazin-2-yl)-4-(3-{[5-(trifluoromethyl)pyridin-2-yl]oxy}benzylidene)piperidine-1-carboxamide; Step 1; Phenyl 6-chloropyrazin-2-ylcarbamate; A solution of 2-amino-6-chloropyrazine (2.0 g, 15.44 mmol) in a mix of 1:1 THF:MeCN (20 mL), and pyridine (1.28, 16.2 mmol) was treated dropwise with phenylchloroformate (2.54 g, 16.2 mmol) in THF (10 mL). After stirring for 18 h, the resulting solid was collected and dried to provide the title compound (2 g, 53percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-6-chloropyrazine, and friends who are interested can also refer to it.

Reference:
Patent; FAY, Lorraine Kathleen; Johnson, Douglas S.; Kesten, Suzanne Ross; Lazerwith, Scott E.; Morris, Mark Anthony; Stiff, Cory Michael; Meyers, Marvin Jay; Wang, Lijuan Jane; US2008/261941; (2008); A1;,
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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

A 250ml RB flask is charged with R-7 (5.4 g, 28.99 mmol) in 100 mL of NMP. R-8 (5.00 g, 28.99 mmol) is added followed by triethylamine (4.85 ml, 34.79 mmol). The reaction is heated to 60 C under nitrogen overnight. The reaction is cooled to room temperature, poured into ice water and the precipitated 1-76 (8.60 g) is isolated by filtration; m/z 323.4 [M+H]

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John; LO, Ho Yin; LOKE, Pui Leng; LIU, Weimin; MORWICK, Tina Marie; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee; WO2012/24150; (2012); A1;,
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. 912773-21-8, name is 2-Bromo-5-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Bromo-5-chloropyrazine

Intermediate 30a and 30b: N-[(1S,2S)-2-[(5-Bromopyrazin-2-yl)amino]cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Intermediate 30a) and N-[(1S,2S)-2-[(5-Chloropyrazin-2-yl)amino]cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Intermediate 30b) A solution of N-[(1S,2S)-2-aminocyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 4; 1.00 g, 3.25 mmol), 2-bromo-5-chloropyrazine (CAS number 912773-21-8; 0.691 g, 3.57 mmol) and DIPEA (1.7 ml, 9.75 mmol) in DMSO (11 ml) was subjected to microwave irradiation at 140 C. for 3 hours. The reaction was partitioned between ethyl acetate and water, washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. This was then purified by column chromatography (silica, 0-100% ethyl acetate/petrol then 0-20% methanol ethyl acetate) to afford title compound as a mixture of both products Example 112 N-[(1S,2S)-2-[(5-Cyclopropylpyrazin-2-yl)amino]cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide A mixture of N-[(1S,2S)-2-[(5-bromopyrazin-2-yl)amino]cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide and N-[(1S,2S)-2-[(5-chloropyrazin-2-yl)amino]cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Intermediate 30a and 30b; 100 mg, 0.23 mmol), cyclopropylboronic acid (CAS number 411235-57-9; 60 mg, 0.70 mmol), sodium carbonate (aq. 2 M, 350 mul, 0.70 mmol) and tetrakis(triphenylphosphine)palladium (27 mg, 0.023 mmol) in 1,4-dioxane (778 mul) was sealed, purged and evacuated with nitrogen and then subjected to microwave irradiation at 100 C. for 1 hour. To this was then added further cyclopropylboronic acid (CAS number 411235-57-9; 60 mg, 0.70 mmol) and tetrakis(triphenylphosphine)palladium (27 mg, 0.023 mmol). The reaction was sealed, purged and evacuated with nitrogen and again subjected to microwave irradiation at 140 C. for 20 minutes. The reaction was partitioned between ethyl acetate and water, washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-100% ethyl acetate/petrol) and then purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% formic acid) and further purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol) to afford the title compound. 1H NMR (400 MHz, DCM-d2) delta ppm 0.77-0.92 (m, 4H), 1.40-1.60 (m, 2H), 1.68-1.94 (m, 3H), 2.14-2.29 (m, 2H), 3.80-3.91 (m, 1H), 3.99-4.10 (m, 1H), 6.65-6.73 (m, 1H), 7.43-7.59 (m, 4H), 7.64 (s, 2H), 7.68-7.72 (m, 1H), 7.74-7.78 (m, 1H) and 7.84 (br. s., 1H). MS ES+: 390

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 912773-21-8.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 313339-92-3, These common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, 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.

A solution of 3,5-dichloropyrazine-2-carbonitrile (137 mg, 0.787 mmol), (R)-2-amino-3-(thiophen-2-yl)propanamide hydrochloride (163 mg, 0.789 mmol) and DIEA (0.350 mL, 2.01 mmol) in DMF (4 mL) was stirred at room temperature for 4 h. Water and EtOAc were added. Organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-(thiophen-2-yl)propanamide (185 mg).

Statistics shows that 3,5-Dichloropyrazine-2-carbonitrile is playing an increasingly important role. we look forward to future research findings about 313339-92-3.

Reference:
Patent; Portola Pharmaceuticals, Inc.; Song, Yonghong; Xu, Qing; Jia, Zhaozhong J.; Kane, Brian; Bauer, Shawn M.; Pandey, Anjali; US2013/131040; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4774-14-5, These common heterocyclic compound, 4774-14-5, name is 2,6-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.

General procedure: To the N,N-dimethylformamide (DMF) (4 mL) solution of N,N-dimethylethylenediamine (95 mL, 0.87 mmol) was added K2CO3 (0.19 g, 1.3 mmol). After the reaction mixture was stirred at room temperature (RT) for 30 min, 2,6-dichloropyrazine (0.10 g, 0.67 mmol) was added and the resulting reaction mixture was further stirred at RT for 12 h. After removal of solvent in vacuo, the residue was treated with dichoromethane. Insoluble impurities were removed by filtration. Removal of solvent in vacuo gave the product 0.095 g in 71 % yield;

The synthetic route of 4774-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lee, Jinho; Park, Jongseong; Hong, Victor Sukbong; Chemical and Pharmaceutical Bulletin; vol. 62; 9; (2014); p. 906 – 914;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem