Month: March 2021

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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

According to the analysis of related databases, 1458-01-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 873-42-7, name is 2-Amino-3,5-dichloropyrazine, 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 873-42-7, name: 2-Amino-3,5-dichloropyrazine

Benzyl alcohol (7.60 mL, 73.2 mmol) was added slowly to a stirred suspension of sodium hydride (60% dispersed in mineral oil) (2.95 g, 73.2 mmol) in dry THF (122 mL). The mixture was stirred at rt for 10 min, after which 10 (7.30 g, 44.5 mmol) was added and the mixture was heated at reflux for 24 h. The cooled solution was concentrated, and ethyl acetate (500 mL) and water (200 mL) were added to the resulting gum. The mixture was filtered through Celite. The organic layer was separated, washed with brine (2*100 mL), dried, filtered and concentrated. Flash column chromatography on silica, eluting with 1:1 ethyl acetate/hexanes, gave a solid, which was recrystallised from water (200 mL) to give 11 (6.00 g, 57%) as an orange solid. Mp 285-287 C (from water); Rf (50% EtOAc/hexanes) 0.41; numax (thin film/cm-1) 3409 (NH2), 3019 (Ar CH), 929 (C-O); (found: C, 56.19; H, 4.26; N, 17.65; C11H10N3OCl requires C, 56.06; H, 4.28; N, 17.83%); deltaH (500 MHz; CDCl3) 4.77 (2H, br s, NH2), 5.32 (2H, s, OCH2), 7.30-7.39 (5H, m, Ph), 7.51 (1H, s, 6-H); deltaC (125 MHz; CDCl3) 69.0, 128.5, 128.6, 128.6, 131.7, 131.9, 135.7, 143.8, 146.7; LC-MS (15 min) m/z 236 (MH+) HPLC tR 7.49 min; purity 99% HRMS (found: MH+ m/z 236.0585; requires 236.0585).

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-Amino-3,5-dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728,16;; ; Article; Caldwell, John J.; Veillard, Nicolas; Collins, Ian; Tetrahedron; vol. 68; 47; (2012); p. 9713 – 9728;,
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

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

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

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

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

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

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

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