Tag: M.W=100-200

Electric Literature of 274-79-3, 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. 274-79-3, name is Imidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

lmidazo[1 ,2-a]pyrazine (1.191 g, 10 mmol, Intermediate 1 ) and sodium acetate (0.984 g, 12.00 mmol) were suspended in methanol (10 ml) saturated with potassium bromide (excess) and cooled to -10 0C. Bromine (0.515 ml_, 10.00 mmol) was added dropwise and the mixture stirred at -10 0C for 10 min. The solution was quenched by the addition of 1 N sodium sulfite solution (10 ml) and concentrated in vacuo. The residue was partitioned between ethyl acetate (100 ml) and 50% saturated sodium bicarbonate solution (100 ml). The aqueous phase was extracted with ethyl acetate (2 x 100 ml), combined, washed with brine (50 ml), dried over anhydrous sodium sulfate and concentrated to give crude 3-bromoimidazo[1 ,2-a]pyrazine (1.66 g, 8.38 mmol, 84 % yield) that was used in subsequent steps without further purification 3- bromoimidazo[1 ,2-a]pyrazine (1.66 g, 8.38 mmol, 84 % yield). LC/MS [M+H]+ = 198, 200, retention time = 0.53 minutes (2 minute method). 1H NMR (CDCI3, 400 MHz) d 9.09 (s, 1 H), 8.08 (s 1 H), 7.94 (s, 1 H), 7.81 (s, 1 H).

The synthetic route of Imidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 38557-72-1, The chemical industry reduces the impact on the environment during synthesis 38557-72-1, name is 2-Chloro-3,5-dimethylpyrazine, I believe this compound will play a more active role in future production and life.

A solution of intermediate 72 (0.24 M in THF, 43 mL, 10.32 mmol) was added to a flask containing 4-bromo-2,6-dimethylpyridine (CAS: 5093-70-9, 1.75 g, 9.38 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.395 g, 0.56 mmol) under N2. Then N,N,N?,N?-tctramcthylcthylcncdiaminc (1.538 mL, 10.32 mmol) was added and the mixture was stirred at 60 C for 18 h. The mixture was quenched with the addition of a 1/1 solution of sat NH4Cl/32% aq NTb and then it was extracted with EtOAc. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (Si02, EtOAc in heptane 0/100 to 80/20). The desired fractions were collected and the solvents evaporated in vacuo to yield intermediate 48 (2.59 g, 955) as a yellow oil.; Intermediate 53 was prepared following an analogous procedure to the one described for the synthesis of intermediate 48 using intermediate 73 and 2-chloro-3,5- dimethylpyrazine (CAS: 38557-72-1) as starting materials.

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-Chloro-3,5-dimethylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; MARTINEZ-VITURRO, Carlos Manuel; DELGADO-JIMENEZ, Francisca; CONDE-CEIDE, Susana; VEGA RAMIRO, Juan, Antonio; (178 pag.)WO2019/243527; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 274-79-3, A common heterocyclic compound, 274-79-3, name is Imidazo[1,2-a]pyrazine, molecular formula is C6H5N3, 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.

Stage 2. The imidazo [1 , 2-a] pyrazine (7.2 g, 60.44 mmole) was dissolved in 2-methoxyethanol (100 ml) and Pttheta2 (1.2 g, 5.13 mmole) was added. The reaction mixture was stirred overnight at RT in an autoclave under a hydrogen atmosphere (4 bar). The autoclave was then flushed with nitrogen, the reaction mixture was filtered through filter earth, concentrated, and the solvent residues were then extracted with toluene. Purification was carried out by column chromatography on silica gel (DCM / 7 N NH3 in methanol, 95:5)

The synthetic route of 274-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; WO2009/90055; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 4744-50-7 as follows. SDS of cas: 4744-50-7

EXAMPLE 1; Preparation of 3-(5-chloropyrid -2-yl) carbamoyl-pyrazine 2 carboxylic acid; In a clean, dry 500 ml R. B. flask charged acetic anhydride (162 gms) and pyrazine- 2,3, dicarboxylic acid (50 gms). The reaction mass was heated to 100-120 C. up to completion of reaction. After completion of reaction, the excess acetic anhydride was distilled under vacuum. Charged methylene dichloride (350 ml) to the above reaction mass followed by 2-amino-5- chloropyridine (40 gms) in a lot wise manner at room temperature in 30 min. The reaction mass was stirred at room temperature for 2 hrs; cooled the reaction mixture to 5-10 C. for 1 hr. The reaction mixture was filtered and washed with chilled methylene dichloride to obtain 3-(5-chloropyrid -2-yl) carbamoyl-pyrazine-2-carboxylic acid.Yield=82 gms.; EXAMPLE 2; Preparation of 6-(5-chloropyrid-2-yl) 5,7-dioxo-5,6-dihydropyrrolo [3,4-b]-pyrazine; In a clean 500 ml R. B.flask charged pyrazine-2,3-dicaroxylic acid (50 gms) and acetic anhydride (162 gms). The reaction mass was heated to 110-120 C. till the completion of reaction to get pyrazine-2,3-dicarboxylic acid anhydride. After completion of the reaction, excess acetic anhydride distilled out under vacuum and furthermore charged methylene dichloride (315 ml) and 2-amino-5-chloropyridine (40 gms) in a lot wise manner at room temperature in 30 min. Further, reaction mixture was stirred for 2 hours at room temperature. The reaction mass was cooled to 5 to 10 C. for one hour, filtered the product and washed with chilled methylene dichloride. The solid was charged with methylene dichloride (235 ml), triethylamine (40.9 ml) at temp. 0-5 C. followed by ethyl chloroformate (28.1 ml). The reaction mass was stirred at 0-5 C. for 1 hr, added water (200 ml) to the reaction mixture and stirred the mass at room temperature for 1 hr to obtain the solids. The title compound thus separated was isolated by filtration.Yield=65 gms.The HPLC purity of this above product was above 99%.

According to the analysis of related databases, 4744-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sawant, Shrikant Dattatraya; Naik, Anil Mahadev; Kavishwar, Girish Arvind; Kavishwar, Smita Girish; US2008/146800; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 33332-25-1, The chemical industry reduces the impact on the environment during synthesis 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

5-Chloro-pyrazine-2-carboxylic acid methyl ester (CAN 33332-25-1; 15 g, 86.92 mmol) was dissolved in dioxane (100 mL). To this solution was added 3,3-difluoroazetidine hydrochloride (CAN 288315-03-7; 13.51 g, 104.31 mmol), and triethyl amine (31.3 mL, 226 mmol). The mixture was stirred 22 hours at 45 C. and afterwards cooled to room temperature. Brine solution (100 mL) was added and the mixture was extracted with ethyl acetate. The organic phases were washed successively with sodium bicarbonate solution (10%, 300 mL) and brine (200 mL); dried with Na2SO4 and filtered and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 200 g, 30% to 50% ethyl acetate in hexane) to give the desired product (15 g, 75.3%) as white solid; LC-MS (UV peak area, ESI) 98.6%, 230.4 (M+H).

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, Methyl 5-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; Bissantz, Caterina; Dhurwasulu, Baledi; Grether, Uwe; Hazra, Anindya; Hebeisen, Paul; Roever, Stephan; Rogers-Evans, Mark; US2013/109665; (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. 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2,3-Pyrazinecarboxylic anhydride

A mixture of 1 -ethyl-7-hydroxy-2,2,4-trimethyl- 1 ,2-dihydroquinoline (1.15 mmole), l-(5- carboxypentyl)-7-hydroxy-2,2,4-trimethyl-l,2-dihydroquinoline (1.15 mmole), 2,3- pyrazinedicarboxylic anhydride (1.15 mmole) and 50 mg p-toluenesulfonic acid is stirred in propionic acid (80 mL) at 140 C for 24 hours. The solvent is removed under vacuum and the product is purified by a silica gel column eluting with MeOH/CHCl3.

The synthetic route of 4744-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTIUM, INC.; MAO, Fei; LEUNG, Wai-Yee; CHEUNG, Ching-Ying; HOOVER, Hye Eun; WO2011/68569; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, 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. Recommanded Product: 33332-25-1

Step 1: methyl 5-{3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl) ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}pyrazine-2-carboxylate (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (0.065 g, 0.10 mmol) was added to a mixture of {3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile dihydrochloride (0.50 g, 1.0 mmol), methyl 5-chloropyrazine-2-carboxylate (0.18 g, 1.0 mmol)(Ark Pharm, Inc., Cat. No.: AK-23920), and cesium carbonate (1.0 g, 3.1 mmol) in toluene (15.0 mL) under nitrogene, followed by palladium acetate (0.023 g, 0.10 mmol). The reaction mixture was stirred at 120 C. for 3 h. After cooled to r.t., the reaction mixture was filtered through a pad of celite, washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in dichloromethane (0-70%) to afford the desired product (0.31 g, 55%). LCMS (M+H)+: m/z=546.3.

The synthetic route of Methyl 5-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Vaddi, Krishna; US2015/246046; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 75907-74-3, These common heterocyclic compound, 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, 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): to a 50 ml three-necked flask, the QR01006-IN-01 (500 mg, 3.29 mmol), dichloromethane (10 mL), chloromethyl chloroformate (460 mg, 3.6 mmol) were added. The resultant mixture solution was controlled at the temperature of -2 C., and then pyridine (0.32 mL) was dropwise added while controlling the temperature of no greater than 3 C. After the dropwise addition, the reaction solution was heated to room temperature and stirred overnight. The TLC (petroleum ether/ethyl acetate=1:3) was used to monitor the reaction until the raw materials were fully reacted. The reaction solution was filtered, and the resulting filtrate was dried by rotary evaporation, to give 1.1 g of yellow oil. The yellow oil was purified by preparative plate to give 620 mg of yellow liquid, with the yield of 77.3%. LCMS and HNMR spectra can confirm the structure of the target compound.

Statistics shows that (3,5,6-Trimethylpyrazin-2-yl)methanol is playing an increasingly important role. we look forward to future research findings about 75907-74-3.

Reference:
Patent; WUHAN LL SCIENCE AND TECHNOLOGY DEVELOPMENT CO., LTD; WUHAN QR PHARMACEUTICALS CO., LTD; GE, Jian; MA, Jianyi; XIANG, Guangya; WANG, Wei; WANG, Chaodong; (46 pag.)US2017/22188; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 27825-21-4, The chemical industry reduces the impact on the environment during synthesis 27825-21-4, name is Methyl 3-chloropyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

The mixture of 1.35 g (7.8 mmol, 1 eq.) of 3-chloro-2-pyrazine methyl carboxylate prepared in example 20a), 0.7 ml (7.8 mmol, 1 eq.) of methyl thioglycolate and 1.62 g (11.7 mmol, 1.5 eq.) of K2CO3 in 60 ml of acetonitrile is heated under stirring for 16 hrs. The solvent is concentrated and immersed in 200 ml of water. After acidifying with 1N HCl, extraction is performed 3 times with CH2Cl2, the organic phase is dried on Na2CO3, filtered and evaporated. 1.21 g (73.5%) of aromatized product is obtained. FP=188 C. NMR (1H, DMSO): 2.50 (s; 3H; SCH3), 3.87 (s; OCH3), 8.81 (d, J=2.3 Hz; 1H, arom. H), 8.86 (d, J=2.3 Hz; 1H; arom. H), 11.67 (m; 1H; OH).

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, Methyl 3-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Imbert, Thierry; Monse, Barbara; Koek, Wouter; US2005/80085; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 59489-71-3,Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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.

Sodium nitrite (1. 35 g, 19. 53 MMOL) was added portionwise to concentrated sulfuric acid (9. 8 mL) at 0 C. The mixture was heated at 50 C until all of the sodium nitrite had dissolved and the mixture was again cooled to 0 C. A solution of 5- BROMO-PYRAZIN-2-YLAMINE (2. 57 g, 14. 68 MMOL) in concentrated sulfuric acid (14. 7 mL) was added dropwise to the nitronium solution at 0 C. The ice bath was removed, the mixture warmed to ambient temperature and stirred for 15 minutes before heating to 45 C for seven minutes. After cooling to ambient temperature, the mixture was poured slowly with precaution into crushed ice water (100 mL). The aqueous phase was neutralized to pH 4 with 20% aqueous sodium hydroxide then extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were washed with water (50 mL), dried (anhydrous magnesium sulfate), filtered, and evaporated to afford the title compound (1. 88 g, 73%) as a yellow solid. ‘H NMR (CDCl3, 300 MHz) ; 8. 07 (1 H, s), 7. 62 (1 H, D, J = 3. 0 Hz).

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

Reference:
Patent; PFIZER INC.; WO2004/92145; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem