Month: July 2021

These common heterocyclic compound, 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, 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

A mixture of l-(3-chloropyrazin-2-yl)hydrazine (0.90 g, 62 mmol), triethyl orthoformate (2.3 mL), 14 mmol), and dry xylene (15 mL) was refluxed with stirring for 2 h. The mixture was brought to RT, diethyl ether was added and the suspension was filtered. The solid collected was washed with diethyl ether to afford 8-chloro-[l,2,4]triazolo[4,3- ajpyrazine (0.60 g, 62% yield). MS m/z: 155.0 (M+l).

The synthetic route of 2-Chloro-3-hydrazinylpyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/64418; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

59489-71-3, name is 2-Amino-5-bromopyrazine, 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. COA of Formula: C4H4BrN3

EXAMPLE 1B 5-amino-2-pyrazinecarbonitrile A mixture of Example 1A (19.29 g, 105 mmol), freshly powdered KCN (16.9 g, 260 mmol), CuI (49.5 g, 260 mmol), 18-crown-6 (2.08 g, 7.8 mmol), and (PPh3)4Pd (1.8 g, 1.57 mmol) in N,N-dimethylformamide (600 mL) was stirred at room temperature for 30 minutes and heated to reflux in an oil bath preheated to about 200 C. The solution was stirred at reflux for 3 hours, cooled to room temperature, poured into ethyl acetate (1L), filtered through diatomaceous earth (Celite), treated with silica gel (100 g), and concentrated. The concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes to provide 11.9 g (94.4%) of the desired product. MS (APCI(+)) m/z 121 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta 8.40 (d, J=0.7 Hz, 1H), 7.90 (d, J=0.7 Hz, 1H), 7.47-7.69 (br s, 2H).

The synthetic route of 59489-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Li, Goaquan; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Sham, Hing L.; Wang, Gary T.; US2004/34038; (2004); 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. 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 36070-75-4

General procedure: To a solution of 9 (75 mg, 0.226 mmol) in 1,3-dimethyl-2-imidazolidinone (DMI) (0.75 mL), Et3N (0.13 mL, 0.903 mmol) and 2-chloro-5-cyanopyridine (62.6 mg, 0.451 mmol) were added, andthe mixture was then stirred at 160 C for 1 h. After cooling toroom temperature, EtOAc was added, and the mixture was washedwith H2O, dried over MgSO4, and concentrated under reduced pressure.The residue was purified by column chromatography(CHCl3/MeOH = 100/0 to 95/5) to give the title compound (46 mg,56%).

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

Reference:
Article; Nakajima, Yutaka; Inoue, Takayuki; Nakai, Kazuo; Mukoyoshi, Koichiro; Hamaguchi, Hisao; Hatanaka, Keiko; Sasaki, Hiroshi; Tanaka, Akira; Takahashi, Fumie; Kunikawa, Shigeki; Usuda, Hiroyuki; Moritomo, Ayako; Higashi, Yasuyuki; Inami, Masamichi; Shirakami, Shohei; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4871 – 4883;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 56423-63-3, 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. 56423-63-3, name is 2-Bromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Method B (ii) (Suzuki coupling) [00164] To a solution of methyl- l-(3-fluoro-2-methylphenyl)-3- (((trifluoromethyl)sulfonyl) oxy)cyclopent-2-enecarboxylate (0.2 g, 0.5 mmol) in 1,2 dimethoxyethane (8 mL) was added bis(pinacolato)diboron (0.15 g, 0.6 mmol), potassium acetate (0.060 g, 0.6 mmol), [l,l’-Bis(diphenylphosphino)ferrocene] dichloropalladium(II), complex with dichloromethane (0.03 g, 0.02 mmol) and water (2 mL). The reaction mixture was heated to 80 C under N2 for 2 h. After this time the reaction mixture was cooled to r.t. and aryl bromide (0.57 mmol), potassium carbonate (0.036 g, 1.31 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.03 g, 0.026 mmol) were added and the reaction mixture heated to 110 C under N2 for 2 h. Reaction mixture was cooled to rt and filtered through Celite, washing with EtOAc (3 x 10 mL). Combined organics were extracted with water (15 mL) then brine (20 mL). EtOAc layers were then dried, filtered (phase separation cartridge) and concentrated.

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-Bromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; MUNOZ-SANJUAN, Ignacio; MAILLARD, Michel; LUCKHURST, Christopher, A.; JARVIS, Rebecca, E.; BUeRLI, Roland, W.; ALLEN, Daniel, R.; HAUGHAN, Alan, F.; BRECCIA, Perla; VATER, Huw, D.; STOTT, Andrew, J.; PENROSE, Stephen, D.; WALL, Michael; SAVILLE-STONES, Elizabeth, A.; WISHART, Grant; HUGHES, Samantha, J.; WO2014/159218; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 762240-92-6 as follows. name: 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

General procedure: To the stirred reaction mixture of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyrazine hydrochloride(11) (300 mg, 1.32 mmol), TEA (0.55 mL, 3.95 mmol)and toluene (10 mL), substituted cyanates 12(a-e)/isocyanates12(f-j) (1.32 mmol) were added at ambient temperature.The reaction mass was agitated at 75-80 C until thecompletion of the reaction that was monitored by TLC. Thereaction mass was allowed to cool at ambient temperatureand it was washed sequentially with 3% aqueous HCl(5.0 mL) and then water (5.0 mL). The organic fraction wasconcentrated under vacuum at 50-55 C to obtain crudeproduct. It was purified by column chromatography using10-50% of EtOAc:hexane mixture as a mobile phase.

According to the analysis of related databases, 762240-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mannam, Madhava Rao; Devineni, Subba Rao; Pavuluri, Chandra Mouli; Chamarthi, Naga Raju; Kottapalli, Raja Sekhara P.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 9; (2019); p. 922 – 932;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 33332-29-5, 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. 33332-29-5, name is 2-Amino-5-chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step A: To a solution of 5-chloropyrazin-2-amine (1.0 g, 7.7 mmol) in DCM (60 ml) was added a suspension of bis(difluoromethylsulfinyloxy)zinc (2.3 g, 7.7 mmol) and Fe(N03)3.9H20 (0.3 g, 0.8 mmol) in water (24 ml) and the mixture was stirred. tert-Butylhydroperoxide (2.2 ml, 5.5 M in nonane 12.1 mmol) was added in 0.2 ml portions every 45min for a total reaction time of 8 h. The reaction was diluted with DCM, washed with water, dried (Na2S04) and concentrated. Purification by flash column chromatography on silica gel (DCM:MeOH 1:0-4: 1) afforded 5- chloro-3-(difluoromethyl)pyrazin-2-amine as a yellow crystals (0.6 g, 40%). MS (m/e): 180.0. (M+H+, CI).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GREEN, Luke; PINARD, Emmanuel; RATNI, Hasane; WILLIAMSON, Patrick; (95 pag.)WO2015/197503; (2015); 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. 914452-71-4, name is 2-Bromo-6-methylpyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C5H5BrN2

Pd2(dba)3 (38.4 mg, 0.042 mmol), DavePhos (33.0 mg, 0.084 mmol) and sodium tert-butoxide (60.4 mg, 0.629 mmol) were all placed in a 2 mL microwave vial. To this was added 2-bromo-6- methylpyrazine (81 mg, 0.469 mmol), followed by rac- I -((2S,3R,4R)-4-amino-2-cyclopropyl-3-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (for a preparation see Intermediate 14, 51.2 mg, 0.210 mmol) in I ,4-dioxane (2 mL). The mixture was heated at 120 C for 40 mm in a microwave heater. The reaction mixture was passed through a 2.5 g celite cartridge and washed through with 3 CVs of ethyl acetate. The solution was evaporated in vacuo to afford a deep orange oil. The crude product was taken up in dichloromethane and purified on a silica cartridge (25 g) by flash columnchromatography, eluting with 30% – 70% ethyl acetate in cyclohexane. The appropriate fractions were collected and concentrated in vacuo to afford a yellow solid (40.6 mg).LCMS (2 mm Formic): Rt = 0.91mm, [MH] = 337.

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; 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

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. 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 122-05-4

A suspension of pyrazine-2,5-dicarboxylic acid 1 (5 g, 29.7 mmol) and HCl (1.25 M in MeOH, 50 mL, 62.5 mmol) was stirred at 60 C. for 20 h, after which the reaction was complete. The reaction mixture was concentrated on a rotary evaporator. The crude product was suspended in saturated NaHCO3, extracted with 10% MeOH in dichloromethane (DCM, 3*150 mL). The combined organic extracts were dried with Na2SO4, filtered and concentrated to yield dimethyl pyrazine-2,5-dicarboxylate (4.37 g, 22.28 mmol, 74.9% yield). LCMS ESI: calculated for C8H8N2O4=197.0 (M+H+), found 197.0 (M+H+).

According to the analysis of related databases, 122-05-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; POUDEL, Yam B.; He, Liqi; Gangwar, Sanjeev; Posy, Shoshana L.; Sivaprakasam, Prasanna; (38 pag.)US2019/55245; (2019); 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. 117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, A new synthetic method of this compound is introduced below., Safety of 5-Bromo-3-morpholinopyrazin-2-amine

A mixture of 5-bromo-3-morpholinopyrazin-2-amine (150 mg, 0.70 mmol, 1 eq) and ethyl 3-bromo-4-oxocyclohexanecarboxylate (210 mg, 0.84 mmol, 1.2 eq) in dioxane (1.0 mL) was heated for 18 h at 120C in a sealed tube. Two more batches were progressed. The crude mixtures from different batches were combined and the residue was purified by column chromatography (EtOAc as eluent) to give a brown oil that was repurified by column chromatography (hexanes/EtOAc 10:1) to give intermediate I-05 as a yellow solid (42 mg, 6% combined yield).

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; CENTRO NACIONAL DE INVESTIGACIONES ONC&Oacgr;LOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ ARISTEGUI, Sonsoles; GONZALES CANTALAPIEDRA, Esther; HERNANDEZ HIGUERAS, Ana Isabel; VARELA BUSTO, Carmen; WO2011/36461; (2011); 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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H3ClN2O2

The preparation method is: 0.185 g (ie 1.0 mmol) of 4-phenoxyaniline, 0.158 g (ie 1.0 mmol) of 6-chloropyrazine-2-carboxylic acid and 30 ml of dichloromethane were added to the reaction flask. Then 0.202 g (ie 2.0 mmol) of Et3N was added, followed by 0.287 mg (1.5 mmol) of EDCl, 0.20 g (ie 1.5 mmol) of HOBt, After reacting at 25 C for 2.0 hours, the reaction was completed by TLC, and the reaction was completed. The reaction solution was washed twice with water and once with saturated brine. The organic phase is dried over anhydrous sodium sulfate and de-solued to give a crude product. Recrystallization of ethanol gave a white solid, m.p (melting point): 160-162 C, yield: 83.0%

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 23688-89-3.

Reference:
Patent; Shanghai Kaiai Network Technology Co., Ltd.; Xu Liyong; (8 pag.)CN108892646; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem