Month: June 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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H2BrIN2

Description 66: 2-bromo-5-(trifluoromethyl)pyrazine (D66); Potassium fluoride (238 mg, 4.09 mmol) and copper(I) iodide (779 mg, 4.09 mmol) were mixed and heated under vacuum using heat gun (temperature 360 0C, on display of heating gun) for 20 minutes (until a greenish colour of the mixture appeared). After cooling at room temperature, DMF (4 ml) and NMP (4.00 ml) were added followed by (trifluoromethyl)trimethylsilane (0.603 ml, 3.77 mmol) and 2-bromo-5-iodopyrazine D65 (896 mg). The resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was poured in 200 ml of 6N NH3 water solution and was extracted twice with Et2O(3 x 50 ml). Gathered Et2O layers were dried over Na2SO4.Diethyl ether was distilled by Claisen apparatus. It was recovered the title compound D66(586 mg).1H NMR (400 MHz, CHLOROFORM- d) delta ppm 8.73 – 8.81 (m, 1 H) 8.84 (s, 1 H)

According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, 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 55557-52-3, Safety of 3-Chloropyrazine-2-carbonitrile

(a). (3-Chloropyrazin-2-yl)methanamine hydrochloride was prepared as follows. To a solution of 3-chloropyrazine-2-carbonitrile (160 g, 1 .147 mol) in acetic acid (1.5 L) was added Raney Nickel (50% slurry in water, 70 g, 409 mmol). The resulting mixture was stirred under 4 bar hydrogen at room temperature overnight. Raney Nickel was removed by filtration over decalite and the filtrate was concentrated under reduced pressure and co-evaporated with toluene. The remaining brown solid was dissolved in ethyl acetate at 50C and cooled on an ice-bath. 2M hydrogen chloride solution in diethyl ether (1 .14 L) was added in 30 min. The mixture was allowed to stir at room temperature over weekend. The crystals were collected by filtration, washed with diethyl ether and dried under reduced pressure at 40C. The product brown solid obtained was dissolved in methanol at 60C. The mixture was filtered and partially concentrated, cooled to room temperature and diethyl ether (1000 ml) was added. The mixture was allowed to stir at room temperature overnight. The solids formed were collected by filtration, washed with diethyl ether and dried under reduced pressure at 40C to give 153.5 g of (3-chloropyrazin-2- yl)methanamine.hydrochloride as a brown solid (74.4 %, content 77 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloropyrazine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (732 pag.)WO2016/24230; (2016); 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-6-bromopyrazine-2-carboxylate

Triisopropyl borate (2.7 mL, 11.6 mmol) was added to a solution of 1- [ (4- bromophenyl) SULFONYL]-4-METHYLPIPERAZINE in (1.24 g, 3.87 mmol; described: in Keasling, H. H. et el. J. Med. Chem. 1965, 8, 548-550) in anhydrous tetrahydrofuran (25 mL) at-78 C under an atmosphere of nitrogen, followed by dropwise addition of n-butyllithium (9.8 mL, 15.5 mmol). The resulting mixture was stirred at-78 C for 30 min, then allowed to warm to room temperature. HCl (3 M aq, 7.8 mL, 23.2 mmol) was added and the mixture was stirred at room temperature for 10 min. Sodium carbonate (4.1 g, 38.7 mmol) was added followed by the addition of methyl 3-amino-6-bromo-2-pyrazinecarboxylate (0.79 g, 3.4 mmol; described in: H. Ellingson, J. Amer. Chem. Soc. 1949,2798) and Pd (dppf) Cl2 (95 mg, 0.12 mmol). The resulting mixture was heated at 55 C overnight. Silica was added, the solvent was evaporated and the crude mixture was purified by column chromatography on silica using CHLOROFORM/METHANOL, (99: 1), as the eluent to give 0.923 g (69% yield) of the base as a yellow solid : 1HNMR (DMSO-D6) S 9.0 (s, 1 H), 8.22 (d, J = 7 Hz, 2 H), 7.80 (d, J = 7 HZ, 2 H), 7.62 (BR S, 2 H), 3.90 (s, 3 H) 2.91 (m, 4 H), 2.36 (m, 4 H), 2.12 (s, 3 H); 13CNMR (DMSO-D6) 8 166. 2,155. 1,145. 8,140. 33,127. 5,134. 0,128. 1, 125.7, 109.1, 53.5, 52.3, 45.7, 45.2 ; MS (ESP) M/Z 392 (M++1).

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; ASTRAZENECA AB; WO2004/55006; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 17890-77-6, These common heterocyclic compound, 17890-77-6, name is 3-Amino-6-bromopyrazine-2-carboxamide, 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.

In the equipped with magnetic stirring, of the reflux condensation tube (with drying tail pipe) of 250 ml in three-necked bottle, adding 13.1g (about 0.06 muM) 3 – amino pyrazine -2 – formamide, 60 ml of acetic anhydride, 60 ml ethyl trimethyl orthoformate, stirring under heating to reflux 4h, started when the reflux temperature 136 C, gradually reduced to 95 C, cooling to room temperature, filter, ice laundering, a brown solid.The crude isopropyl alcohol and water (1:1) about 300 ml of mixed the fluid is heavy crystallization, heating completely dissolved, add 2g activated carbon to decolorize 30min, heat filtering, washing. Cooling separating white solid. 60 C drying. Be 11.24g white powder that is 6 – bromo -4 (3H) dihydropteridinones. Yield: 82.5

The synthetic route of 17890-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Li Zhulai; (15 pag.)CN106699759; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-25-1, 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.

Methyl 5-chloropyrazine-2-carboxylate (CAS no. 33332-25-1)(345.1 g) was dissolved in DMF (1.73 l). Lithium chloride (423.9 g) was added and the mixture heated to 140 C. over one hour. The mixture was evaporated, and the residue dissolved in water (3.4 l) by continued stirring. The solution was acidified by addition of 2N HCl (900 ml) and extracted into ethyl acetate (5×1.73 l). The combined organic extracts were washed with water (2×900 ml), brine (900 ml), dried (MgSO4), and evaporated to give the title compound (298.1 g). 1H NMR 6 (400.132 MHz, DMSO) 8.92 (d, 1H), 9.02 (d, 1H), 13.87 (s, 1H).

The synthetic route of 33332-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US2008/153800; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 54608-52-5, name is 2-Hydrazinopyrazine, 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 54608-52-5, Recommanded Product: 54608-52-5

[00462] Step A: 5-amino-4-methyl-l-(pyrazin-2-yl)-lH-pyrazol-3(2H)-one: To a mixture of 2-hydrazinylpyrazine (0.551 g, 5.00 mmol) and ethyl 2-cyanopropanoate (0.669 g, 5.00 mmol) in abs. EtOH (10 mL) was added 3M NaOEt in EtOH (0.167 mL, 0.501 mmol) and the mixture was heated at reflux for 64 hours. The mixture was concentrated and the residual yellow-brown solid was treated with EtOAc (30 mL) and sonicated. The resulting tan suspension was stirred vigorously for 8 hours. The solid was collected via vacuum filtration, washed with EtOAc and dried in vacuum to afford the title compound as a light tan powder (682 mg, 71%). NMR (DMSO d6) delta 10.3 (br s, 1H), 8.82 (s, 1H), 8.30 (d, 2H), 6.55 (s, 2H), 1.71 (s, 3H).

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; ARRAY BIOPHARMA INC.; BRANDHUBER, Barbara, J.; JIANG, Yutong; KOLAKOWSKI, Gabrielle, R.; WINSKI, Shannon, L.; WO2014/78322; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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 6966-01-4, Application In Synthesis of Methyl 3-amino-6-bromopyrazine-2-carboxylate

Palladium acetate (0.145 g) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium complex with DCM (0.702 g) were dissolved in DMF (65 ml) and heated to 50 C for 15 minutes. After cooling to room temperature 3-amino-6-bromo-pyrazine-2-carboxylic acid methyl ester (5.0 g), 4-fluoro-phenyl boronic acid (3.82 g) and triethylamine (4.5 ml ) were added and the mixture heated to 90 C for 20 hours with stirring. The solvent was evaporated and the residue dissolved in DCM. The organic phase was washed with dilute ammonium hydroxide solution and water. After drying with sodium sulphate and filtration the solvent was evaporated and the residue purified by column chromatography on silica gel eluting with hexane: ethyl acetate, 3: 1 to give 3-amino-6-(4-fluorophenyl)-pyrazine-2- carboxylic acid methyl ester (0.670 g). ‘H NMR (CDCI3) 8 ppm: 3.92 (s, 3H), 6.4 (bs,1H), 7.1 (m, 2H), 7.8 (m, 2H), 8.5 (s,1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-6-bromopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2005/123733; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 56423-63-3, 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 56423-63-3 as follows.

Ethyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l-{2-[4-(trifluoromethoxy)phenoxy]ethyl}- lH-indole-2-carboxylate (34 mg, 0.065 mmol), 2-bromoprazine (21 mg, 0.13 mmol), K2C03 (27 mg, 0.2 mmol) and S Phos (2.7 mg, 0.006 mmol) were combined in 1.0 mL of dioxane in a flask. The reaction was degassed and filled with nitrogen. Water (0.2 mL) was added and purged again with nitrogen. Palladium acetate (0.7 mg, 0.003 mmol) was added, and the reaction was heated to 90C overnight. EtOAc was added and the crude mixture was filtered through a pad of Celite. The volatiles were concentrated in vacuo, and the reaction was purified on reverse phase HPLC (25-55% ACN in H20 (w/ 0.1% TFA)) to yield the title product. HRMS: Calc forC22H17F3N304 444.1171. Found 444.1 167

According to the analysis of related databases, 56423-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HANNEY, Barbara; MANLEY, Peter; RUDD, Michael, T.; SANDERS, John, M.; STACHEL, Shawn, J.; HENZE, Darrell; WO2013/9582; (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. 58139-03-0, name is 2-Iodo-6-methoxypyrazine, A new synthetic method of this compound is introduced below., Formula: C5H5IN2O

2. 3-[2-(6-Methoxypyrazin)yl]-1-azabicyclo[2.2.2]octan-3-ol t-Butyllithium (20 ml of a 1.7M solution in pentane, 35.3 mmol) was added dropwise to a rapidly stirred solution of 2-methoxy-6-iodopyrazine (4.17 g, 17.6 mmol) in ether (80 ml), at -40° C. After 0.25 h a solution of quinuclidinone (2.21 g, 17.6 mmol) in ether (60 ml) was added dropwise and the reaction mixture warmed to room temperature and stirred for 2 h. Water (35 ml) was added and extracted with ethylacetate (4*100 ml). The combined extracts were dried (Na2 SO4), the solvent removed under vacuum and, the residue chromatographed through alumina, eluding with dichloromethane/methanol (93:7) to give 3-[2-(6-methoxypyrazin)yl]-1-azabicyclo [2.2.2]octan-3-ol (1.65 g); delta (360 MHz, CDCl3) 1.37-1.51 (3H,m, –CH2 and CH of CH2); 1.70-1.90(1H, brs, OH); 1.94-1.96-(1H,m,CH); 2.20-2.32(1H,m,CH of CH2); 2.80-3.10(5H,m,2*CH2 and CH of CH2) 3.74(1H,dd, J=2 and 14.6 Hz, CH of CH2); 3.99(3H,s,Me); 8.15(1H,s,pyrazine-H); 8.39(1H,s,pyrazine-H).

The synthetic route of 58139-03-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Limited; US5260293; (1993); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 57948-41-1, These common heterocyclic compound, 57948-41-1, name is 3-Bromoimidazo[1,2-a]pyrazine, 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.

3-Bromoimidazo[1 ,2-a]pyrazine (1.66 g, 7.13 mmol, Intermediate 2), sodium carbonate (3.78 g, 35.6 mmol) and phenylboronic acid (1.043 g, 8.55 mmol) were dissolved in 1 ,2-dimethoxyethane (DME) (40 ml) and water (20 ml). Bis(triphenylphosphine)palladium (II) chloride (0.250 g, 0.356 mmol) was added and the biphasic solution heated at 80 0C for 16 h. The aqueous phase was extracted with ethyl acetate (3 x 100ml) and the combined extracts washed with saturated sodium bicarbonate solution (100 ml), water (100 ml), brine (100 ml) and dried by passing through a hydromatrix cartridge (Varian). The filtrate was concentrated in vacuo to afford a crude oil (2.44g). The crude product was purified by flash chromatography (Biotage SP4, 40+M, eluting with a 0-100% gradient of ethylacetate in hexane) – (the product elutes in 100% ethyl acetate), to afford 3- phenylimidazo[1 ,2-a]pyrazine (1.22 g, 6.25 mmol, 88 % yield). LC/MS [M+H]+ = 196, retention time = 1.63 minutes (5 minute method).

Statistics shows that 3-Bromoimidazo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 57948-41-1.

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