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. 57948-41-1, name is 3-Bromoimidazo[1,2-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H4BrN3

A round bottom flask was charged with 12a (250 mg, 0.86 mg), 3-bromoimidazo[1,2-a]pyrazine (255 mg, 1.29 mmol), Pd(PPh3)2Cl2 (30 mg, 0.043 mmol), CuI (16 mg, 0.086 mmol). 80 mL dry DMF and DIPEA (333 mg, 2.58 mmol) were added to the flask and the solution was degassed with argon for 5 min. The solution was stirred under argon atmosphere at 80 C for 18 h. The reaction solution was filtered through Celite and the solvent was removed by rotary evaporation to get crude mixture. The crude mixture was purified with silica gel column chromatography (MeOH/DCM, v/v = 1/100) to provide Mthyl 3-(imidazo[1,2-a]pyrazin-3-ylethynyl)-2-methylbenzoate (160 mg, 0.55 mmol) as light yellow solid, yielded 64%. 1H NMR (400 MHz, DMSO-d6) delta 9.20 (s, 1H), 8.81 (dd, J1 = 4.4 Hz, J2 = 1.2 Hz), 8.23 (s, 1H), 8.12 (d, J = 4.4 Hz), 8.06 (s, 1H), 7.85 (s, 1H), 7.82 (s, 1H). LC-MS (ESI) m/z 292 [M + H] +.

The synthetic route of 57948-41-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cui, Shengyang; Wang, Yongjin; Wang, Yuting; Tang, Xia; Ren, Xiaomei; Zhang, Lei; Xu, Yong; Zhang, Zhang; Zhang, Zhi-Min; Lu, Xiaoyun; Ding, Ke; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 470 – 482;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, A new synthetic method of this compound is introduced below., category: Pyrazines

Method BStep 12 -Bromo -5 -(2 -trimethylsilanyl-ethoxymethyl)-5 H-pyrro lo [2,3 -b]pyrazine In a dry round-bottomed flask, 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.0 g, 25.2 mmol) was dissolved in DMF (50 mL). The reaction mixture was cooled to 0C and sodium hydride (60% dispersion in mineral oil, 1.22 g, 30.6 mmol). The reaction mixture was warmed to room temperature and stirred for 15 min then cooled back to 0C and SEM-C1 (5.4 mL, 30.4 mmol) was slowly added. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was quenched with 50 mL water and extracted with 150 mL diethyl ether (2x). The combined organic layers were washed twice with 30 mL water and once with 30 mL brine then dried over sodium sulfate, filtered and concentrated. The residue was absorbed on -20 g Si02 and chromato graphed over 200g Si02 with EtOAc/Hexanes (gradient: 0-15% EtOAc). All fractions containing product were combined and concentrated to afford 6.61 g (80%) of 2-bromo-5-(2-trimethylsilanyl- ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine as a pale yellow oil which gradually solidified. 1H NMR (CDCI3, 300 MHz): delta (ppm) 8.38 (s, 1H), 7.70 (d, J=3.8 Hz, 1H), 6.76 (d, J=3.8 Hz, 1H), 5.68 (s, 2H), 3.50 – 3.65 (m, 2H), 0.88 – 1.03 (m, 2H), 0.00 (s, 9H).

The synthetic route of 875781-43-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O’YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu; WO2013/30138; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 14667-55-1, 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 14667-55-1 as follows.

General procedure: AgNO3 (34.2 mg, 0.2 mmol), tpyz (38 ml, 0.2 mmol) and H2L(313.6 mg, 0.2 mmol) were took place in CH3CN-DMF (N,Ndimethylformamide)mixed solvent (6 ml, v/v: 3/3) under stirring.Then, ammonia (14 M, 10 d) was dropped into the mixture to give aclear solution under ultrasonic treatment (160 W, 40 KHz, 30 min) atroom temperature. The resultant solution was allowed to evaporateslowly in darkness at room temperature for several days to giveirregular-yellow crystals of 1 (Yield: 32%, based on Ag).

According to the analysis of related databases, 14667-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Hua-Qi; Cheng, Xiao-Yue; Zhang, Ting; Huang, Rong-Bin; Inorganic Chemistry Communications; vol. 68; (2016); p. 21 – 28;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route 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.

General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a-k, and4m are known compounds [6,9] except for 4l and 4n.

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

Reference:
Article; Xu, Chen; Li, Hong-Mei; Wang, Zhi-Qiang; Fu, Wei-Jun; Inorganica Chimica Acta; PA; (2014); p. 11 – 15;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 870787-06-7, name is 3-(Trifluoromethyl)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 870787-06-7, Recommanded Product: 870787-06-7

PREPARATION EXAMPLE 7: 3-trifluoromethyl-pyrazine-2-carboxylic acid ri-(5-bromo-3-50 mg of C-[1 -(5-bromo-3-chloro-pyridin-2-yl)-cyclopropyl]-methylamine (step 1 of PREPARATION EXAMPLE 2) was dissolved in 0.9 ml of dichloromethane and 0.085 ml of triethylamine was added at ambient temperature. Then 383 mg of 3- (trifluoromethyl)pyridine-2-carboxylic acid, 54 mg of HOBT hydrate, 76 mg of EDCI.HCI and 37 mg of 3-trifluoromethyl-pyrazine-2-carboxylic acid were added sequentially. The reaction mixture was stirred at ambient temperature for 14 hours and then water was added, the phases were separated and the aqueous phase was extracted withdichloromethane. The organic phases were combined, dried with anhydrous sodium sulphate, filtered and concentrated. Crude material was obtained as a yellow sticky solid, which was purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (1 :1 ) as a solvent. Thus, 76 mg of 3-trifluoromethyl-pyrazine-2-carboxylic acid [1 -(5-bromo- 3-chloro-pyridin-2-yl)-cyclopropylmethyl]-amide was obtained as a sticky solid. . 1H-NMR (CDCIs): 8.80 ppm (s, 1 H), 8.75 ppm (s, 1 H), 8.65 ppm (s, 1 H), 7.95 ppm (s, 1 H), 7.70 ppm (m, 1 H), 3.72 ppm (d, 2H), 1 .18 ppm (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Trifluoromethyl)pyrazine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; PITTERNA, Thomas; LOISELEUR, Olivier; WORTHINGTON, Paul, Anthony; O’SULLIVAN, Anthony, Cornelius; LUKSCH, Torsten; BOBOSIK, Vladimir; WO2013/64521; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 14508-49-7, name is 2-Chloropyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C4H3ClN2

2-Chloropyrazine (7.79 mL, 87 mmol, commercially available e.g. from Sigma- Aldrich or Haiso PharmChem) was dissolved in ethanol (50 mL), and hydrazine hydrate (6.85 mL, 218 mmol) was added. The solution was refluxed for 6 hours. The mixture was cooled to room temperature and the solvent was partially evaporated. The residue was diluted with water and extracted with 10% (v/v) of 2-propanol/Dichloromethane solution (5 extractions). The combined organic phases were then dried and evaporated to give a yellow solid which was triturated with diethyl ether to give 2-hydrazinopyrazine as a yellow solid (3.32 g).

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:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 55557-52-3, These common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-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.

General procedure: In a degassed solution of DME/H2O (2:1) (12mL/mmol of diazine), were successively introduced S-Phos (10mol%) and Pd(OAc)2 (5mol%). The solution was heated at 80C for 10min then sodium carbonate (4.0equiv), appropriate boronic acid (1.05 or 1.5equiv) and appropriate diazine (1.0equiv) were added. The solution was then refluxed (15min or overnight) under Ar. The resulting mixture was filtered on Celite and washed with ethyl acetate and water. The aqueous phase was then extracted three times with ethyl acetate. The combined organic phase was dried over MgSO4 and evaporated to dryness. The residue was purified by column chromatography (eluent: PE/EtOAc) to give the desired product.

The synthetic route of 55557-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fresneau, Nathalie; Cailly, Thomas; Fabis, Frederic; Bouillon, Jean-Philippe; Tetrahedron; vol. 69; 26; (2013); p. 5393 – 5400;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 313339-92-3,Some common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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 3,5-dichloropyrazine-2-carbonitrile (910 mg, 5.2 mmol) in DMF (15 mL) was added tert-butyl N-[(2R,3R)-2-methylpiperidin-3-yl]carbamate (1.1 g, 1.13 mmol) and DIPEA (1.79 mL, 10.26mmol). The mixture was stirred at 60oC for 2 hours. The mixture was concentrated in vacuo. The residue was purified by flash chromatography with 20% ethyl acetate in cyclohexane to isolate tert-butyl N-[(2R,3R)-1-(6-chloro-5-cyanopyrazin-2-yl)-2- methylpiperidin-3-yl]carbamate (1.73 g, 96% yield). MS found for C16H22ClN5O2 as (M+H)+ 352.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloropyrazine-2-carbonitrile, its application will become more common.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 19847-12-2, name is Pyrazinecarbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 19847-12-2

General procedure: Sodium metal (23 mg) was dissolved in absolute methanol (20 ml) and was labeled as sodium methoxide solution in methanol. 2-Cyanopyridine (0.210 ml, 2 mmol) was dissolved in absolute methanol (10 ml) and to it was added sodium methoxide solution (0.5 ml) prepared above, the reaction contents were stirred at room temperature for 2 h. 4-(2-Aminoethyl) morpholine (0.26 ml, 2 mmol) was added to the reaction mixture. The reaction contents were heated under reflux for 8 h. Solvent was removed under reduced pressure and to the residue left behind was added diethyl ether, solid so obtained was filtered and washed with diethyl ether to give crude product. This crude product was purified by crystallization from ethyl acetate/methanol to give pure N-(2-morpholin-4-yl-ethyl)-pyridine-2-carboxamidine (3a).

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; Arya, Surbhi; Kumar, Nikhil; Roy, Partha; Sondhi; European Journal of Medicinal Chemistry; vol. 59; (2013); p. 7 – 14;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, 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. category: Pyrazines

DMAP (5%) was added to a solution of 5-methyl-pyrazin-2-ylamine (10 mmoles) in pyridine (50 ml) which was further treated with phenyl chloroformate (1.2 eq) and the reaction stirred at room temperature overnight. The mixture was added to 10Og of ice and the precipitate was filtered and washed with water and dried to give the title compound.

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

Reference:
Patent; SENTINEL ONCOLOGY LIMITED; WO2007/144579; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem