Category: Pyrazines

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

Application of 36070-75-4,Some common heterocyclic compound, 36070-75-4, name is 5-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.

A solution of rac- I -((2S,3R,4R)-4-am ino-6-fluoro-2,3-dimethyl-3,4-dihyd roquinolin- I (2H )-yl)ethanone(for a preparation see Intermediate 143, 86 mg, 0.364 mmol), 5-chloropyrazine-2-carbonitrile (102mg, 0.728 mmol) and DIPEA (0.127 mL, 0.728 mmol) in NMP (1.5 mL)was heated in a microwave at 200 C for I h. The solution was applied directly and purified by MDAP (formic). The appropriate fractions were combined and concentrated in vacuo to give the title compound (30 mg, 0.088 mmol, 24%). LCMS (2 mm Formic): Rt = 0.88 mi [MH] = 340.

The synthetic route of 36070-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; ATKINSON, Stephen John; HARRISON, Lee Andrew; HIRST, David Jonathan; LAW, Robert Peter; LINDON, Matthew; PRESTON, Alexander; SEAL, Jonathan Thomas; WELLAWAY, Christopher Roland; WO2014/140076; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

43029-19-2, name is 3-Aminopyrazin-2(1H)-one, 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. name: 3-Aminopyrazin-2(1H)-one

A mixture of compound 11A (64.48 mg, 580.41 umol) in DMF (1.5 mL) was added NaH (38.69 mg, 967.35 umol, 60% purity) at 0C. The mixture was stirred at 0C for 0.5 hour. A solution of tert-butyl 7-(2,2-dimethylpropyl)-5-fluoro-2- (methylsulfonyloxymethyl)indole-1-carboxylate (0.2 g, 483.67 umol) in DMF (1.5 mL) was added followed by the addition of KI (40.15 mg, 241.84 umol). The mixture was stirred at 25C for 1.5 hr. The reaction mixture was quenched by addition to the solution of sat. NH4Cl solution (10 mL). The mixture was extracted with EtOAc (5 mL x 2) and the combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-TLC to give tert-butyl 2-[(3-amino-2-oxo- pyrazin-1-yl)methyl]-7-(2,2-dimethylpropyl)-5-fluoro-indole-1-carboxylate (I-409) (80 mg, 39% yield) as a yellow gum.

The synthetic route of 43029-19-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SITARI PHARMA, INC.; CAMPBELL, David; CHAPMAN, Justin; CHEUNG, Mui, H.; DIRAIMONDO, Thoams, R.; DURON, Sergio, G.; (615 pag.)WO2020/33784; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine, 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. HPLC of Formula: C5H5ClN2O

Preparation 299; To a solution of (5-chloro-2-pyrazinyl)methanol (11.0 g) in dioxane(110 mL) was added manganese (IV) oxide (26.5 g) and (carbethoxymethylene)triphenylphosphorane (29.2 g). After stirring for 2 hours at room temperature, a resulting precipitate was filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E) -3-(5-chloro-2-pyrazinyl)acrylate (11.0 g).^-NMR (300 MHz, CDC13) 8 1.35 (3H, t, J = 7 Hz), 4.30 (2H, q, J = 7 Hz), 7.01 (1H, d, J = 15 Hz), 7.66 (1H, d, J = 15 Hz), 8.43 (1H, s), 8.60 (1H, s)

The synthetic route of 72788-94-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2006/16680; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem