Month: August 2021

Synthetic Route of 41110-29-6, A common heterocyclic compound, 41110-29-6, name is Methyl 3-methylpyrazine-2-carboxylate, molecular formula is C7H8N2O2, 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.

To a stirred suspension of methyl 3-methylpyrazine-2-carboxylate (3.6 g, 24 mmol) in benzotrifluoride (71 mL) was added I ,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione (3.7 g, 13mmol) and 2,2-azodiisobutyronitrile [AIBN] (0.39 g, 0.34 mL, 2.4 mmol). The reaction was heated to reflux and monitored by LCMS. After 4 h, LCMS analysis showed consumption of starting material. The reaction was allowed to cool and then concentrated in vacuo. The crude product was purified by flash column chromatography to give the desired bromide (3.6 g, 16 mmol, 66 %) as a yellow oil.1H-NMR (400MHz, CDCI3): oe = 8.72 (d, J=2.3 Hz, 1H), 8.65 (d, J=2.3 Hz, 1H), 5.04 (s, 2H), 4.12 -4.02 (m, 3H).

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; SYNGENTA PARTICIPATIONS AG; SHANAHAN, Stephen Edward; O’RIORDAN, Timothy Jeremiah Cornelius; (60 pag.)WO2016/174073; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 25710-18-3, A common heterocyclic compound, 25710-18-3, name is 2,3-Dichloropyrido[2,3-b]pyrazine, molecular formula is C7H3Cl2N3, 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.

A slurry of 2,3-Dichloropyrido[2,3-b]pyrazine (Intermediate F step 2) (500 mg, 2.500 mmol), 3- fluoro-4-methylphenylboronic acid (847 mg, 5.50 mmol),tetrakis(triphenylphosphine)palladium(0) (173 mg, 0.150 mmol) and potassium carbonate (1520 mg, 1 1 .00 mmol) in dioxane (20 ml) was degassed by bubbling nitrogen through (x3). The reaction mixture was heated using microwave radiation under nitrogen at 150 °C for 4h. The resulting mixture was partitioned between EtOAc and water. The organic portion was separated, dried (sodium sulphate), filtered and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 0-3percent THF in DCM to afford the title compound;LCMS; Rt 1 .28 mins MS m/z 348 [M+H]+ Method 2minl_C_v003

The synthetic route of 25710-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHARLTON, Steven, John; LEBLANC, Catherine; MCKEOWN, Stephen, Carl; WO2012/7539; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 19745-07-4, name is 2,5-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H2Cl2N2

Preparation of N-fdelta-chloroDyrazin^-vD-N-methylethanesulfonamide (SM-9):(SM-9)To a solution of N-methyl-ethanesufonamide (400 mg, 3.25 mmol) in methanol (2.2 ml_) was added potassium hydroxide (85percent, 214 mg, 3.25 mmol). Solvent was removed and the potassium salt was suspended in dimethylsulfoxide (1.0 ml_) and added to a stirred solution of 2,5- dichloropyrazine (484 mg, 3.25 mmol) in dimethylsufoxide (1.0 ml_). The resulting dark colored reaction mixture was stirred at room temp for 45 minutes. The reaction mixture was quenched in ice water and the dark suspension was extracted three times with dichloromethane. The combined organics were washed with brine, dried over sodium sulfate and flash chromatographed eluting with a 0-40percent gradient of ethyl acetate in heptane to afford N-(5-chloropyrazin-2-yl)-N-methyl ethanesulfonamide (SM-9: 195 mg, 25.5percent).1H NMR (400 MHz, CHLOROFORM-d) ppm 1.32 (t, J=7.43 Hz, 3 H), 3.26 (q, J=7.30 Hz, 2 H), 3.42 (s, 3 H), 8.32 (d, J=1.37 Hz, 1 H), 8.56 (d, J=1.17 Hz, 1 H). MS (M+1 ) 236.0.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 19745-07-4.

Reference:
Patent; PFIZER INC.; CORBETT, Jeffrey Wayne; GUZMAN-PEREZ, Angel; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/103438; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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 24241-18-7, Recommanded Product: 2-Amino-3,5-dibromopyrazine

Zinc powder (235 mg, 3.6 mmol) and iodine (12 mg) were mixed under nitrogen and DMF was added. The mixture was stirred at room temperature until the color of the iodine disappeared. Benzyl bromide (0.57 mg, 3 mmol) was then added and the mixture was stirred at 80 ° C for about 3 hours. After the reaction mixture had cooled to room temperature, 2-amino-3,5 dibromopyrazine (506 mg, 2 mmol) and triphenylphosphine palladium dichloride (70 mg, 0.1 mmol) were added. Reaction at room temperature for 24 hours. The reaction mixture was filtered through celite and extracted with ethyl acetate. The ethyl acetate phase was washed with saturated sodium chloride solution. The ethyl acetate phase was dried over anhydrous sodium sulfate, filtered and purified by silica gel column chromatography on 200-300 mesh, The intermediate compound 1-1 was 313 mg of yellow solid with a yield of 59percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-3,5-dibromopyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Shandong University; Li Minyong; Du Lvpei; Jiang Tianyu; (37 pag.)CN105968114; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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 24241-18-7, Computed Properties of C4H3Br2N3

To a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79 mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 110 C. for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na2(SO4) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6%) ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz, CDCl3: delta=8.30 (s, 1H), 8.27 (s, 1H), 4.48 (q, 2H), 1.43 (tr, 3H) ppm.

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; BAYER INTELLECTUAL PROPERTY GMBH; Koppitz, Marcus; Klar, Ulrich; Jautelat, Rolf; Kosemund, Dirk; Bohlmann, Rolf; Bader, Benjamin; Lienau, Philip; Siemeister, Gerhard; US2013/267527; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 939412-86-9, The chemical industry reduces the impact on the environment during synthesis 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, I believe this compound will play a more active role in future production and life.

The latter compound was added to 2-aminomethyl-3- chloropyrazine hydrochloride (content 69%; 3.49 mmol, 0.91 g) in dichloromethane (15 ml) and triethylamine (10.46 mmol, 1.458 ml) and the reaction mixture was stirred over night at room temperature. Then the reaction mixture was filtered over decalite (washed with dichloromethane). The filtrate was concentrated and the crude product was purified using column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol) to give benzyl 4-((3-chloropyrazin-2- yl)methylcarbamoyl)piperazine-1 -carboxylate (1.15 g).

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, (3-Chloropyrazin-2-yl)methanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 28643-16-5, 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. 28643-16-5, name is Methyl 3-amino-5-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

a) 3-Amino-5-(2,2,2-trifluoro-ethoxy)-pyrazine-2-carboxylic acid methyl ester A mixture of 2,2,2-trifluoro-ethanol (6.9 ml, 96 mmol) and cesium carbonate (1.56 g, 4.8 mmol) was stirred for 20 min, 3-amino-5-chloro-pyrazine-2-carboxylic acid methyl ester [28643-16-5] (600 mg, 3.2 mmol) was added and the mixture was stirred at rt for 42 h. To complete the reaction the mixture was heated to reflux for another 3 h. Saturated aq. NH4CI was added and the mixture was extracted with EtOAc, the combined organic layers were washed with saturated aq. sodium chloride, dried with Na2S04 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 3:7) to provide the title compound as colorless solid. HPLC: 0.83 min; ESIMS [M+H]+ = 252.2; 1H-NMR (400 MHz, DMSO-c 6): delta 7.66 (s, 1 H), 7.60 (br. s, 2H), 5.03 (q, 2H), 3.81 (s, 3H).

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

Reference:
Patent; NOVARTIS AG; LUEOEND, Rainer Martin; MACHAUER, Rainer; RUEEGER, Heinrich; VEENSTRA, Siem Jacob; WO2013/27188; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-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. Formula: C6H7ClN4O2

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.

The synthetic route of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

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

Related Products of 24241-18-7, A common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, molecular formula is C4H3Br2N3, 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.

2-Amino-3,5-dibromopyrazine (10 g, 04 mol) was added to aqueous ammonia (50 ml) After heating to 110 C for 16 h, add ethyl acetate and HO The organic layer was separated, dried and concentrated to give the title compound

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NANJING SHENGHE PHARMACEUTICAL CO., LTD.; WANG, YONG; ZHAO, LIWEN; LIU, YANG; ZHANG, JINGZHONG; WANG, DEZHONG; GAO, YIPING; CHEN, HONGYAN; ZHANG, CANG; ZHANG, DI; (68 pag.)TWI523856; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 19745-07-4, A common heterocyclic compound, 19745-07-4, name is 2,5-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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 3: Synthesis of 1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)ethanol To a stirred solution of 2,5-dichloropyrazine (0.09 g, 0.608 mmol) and 1-(piperidin-4-yl)ethanol hydrochloride (0.12 g, 0.729 mmol) in DMF (5 mL) was added potassium carbonate under nitrogen and heated 12 h at 100° C. Progress of reaction was monitored by TLC. After reaction completion reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to give crude product. Crude was purified by silica gel (100-200 mesh) column chromatography using 20percent ethyl acetate in hexane as eluent to obtain 1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)ethanol (0.08 g, 54.6percent) as yellow oil. MS: 242.7 [M++1]

The synthetic route of 19745-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mankind Pharma Ltd.; Patil, Rakesh Ishwar; Verma, Jeevan; Shah, Dharmesh; Ali, Sazid; Bapuram, Srinivasa Reddy; Rai, Santosh Kumar; Kumar, Anil; (146 pag.)US2017/291910; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem