Category: 23688-89-3

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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 6-Chloropyrazine-2-carboxylic acid

Example 25; N-(tert-Butyl)-6-chloropyrazine-2-carboxamide Thionyl chloride (1 mL, 13. 7 mmol) was added to a suspension of the acid (325 mg, 2 mmol) in toluene (5 mL). A drop of DMF was then added and after stirring at RT for 10 min. the mixture was heated at reflux for lh. The reaction was cooled to RT and toluene and excess thionyl chloride were removed under reduced pressure. Toluene (1 mL) was then added to the residue and this was removed under reduced pressure. This process was repeated, and then CtiCIz (10 mL) was added and the resulting solution cooled to QC. t-Butylamine (0. 45 mL, 4.3 mmol) and triethylamine (1.1mL, 8.0 mmol) were then added and the solution stirred at RT overnight. The solution was diluted with 10 mL) and H20 (10 mL) and the organic layer collected and washed with aq. Na2CA and then dried (Na2SO4). The solvent was removed in vacuo and flash chromatography of the residue using CH2Cl2-MeOH (95: 5) separated the pure product as an oil (290 (at) mg, 68 %).

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; CYTOPIA RESEARCH PTY LTD; WO2005/66156; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, 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. Recommanded Product: 23688-89-3

6-Chloropyrazine-2-carboxylic acid [CAS-RN: 23688-89-3] (300 mg, 1 .89 mmol,1.0 eq) was dissolved in 12 mL THF, and CDI (338 mg, 2.08 mmol, 1 eq) wasadded. Then, the reaction mixture was heated to 70C for 60 mm. On cooling, asolution of 1 -(2,2-difluoroethyl)piperazine [CAS-RN: 767609-14-3] (313 mg,2.08 mmol, 1 .03 eq) in 1 .5 mL THF was added. The reaction mixture was stirredat 70C for 2 h. The reaction mixture was partitioned between ethyl acetateand water. The water phase was extracted with ethyl acetate and the combinedorganic phases were washed with brine. The phases were separated by the useof a Whatman filter and the volatile components of the organic phase wereremoved in vacuo. Purification was conducted via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane -> hexane/ethyl acetate 2/1) to give 300 mg (55% yield of theory) of the title compound.UPLC-MS (Method 1): R = 0.75 mm; MS (EI0): m/z = 292 [M+1].

The synthetic route of 6-Chloropyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 23688-89-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 23688-89-3 name is 6-Chloropyrazine-2-carboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate 136-Ch[oro-N,N-dimethy[pyrazine-2-carboxamide A mixture of 6-ch[oropyrazine-2-carboxy[ic acid [CAS-RN: 23688-89-3] (510 mg,3.22 mmo[, 1.0 eq), dimethy[amine [CAS-RN: 124-40-3] (1.61 mL, 2M so[ution inTHF, 3.22 mmo[, 1.0 eq), HATU (1.47 g, 3.86 mmo[, 1 .2 eq) and DIPEA (1 .78 mL, 9.65 mmo[, 3.0 eq) was disso[ved in 15 mL DMF and stirred at rt overnight. The reaction mixture was partitioned between ethy[ acetate and water. The organic phase was washed with brine and separated by the use of a Whatman fi[ter. Thevo[ati[e components were removed in vacuo and the crude materia[ obtained was purified via preparative MPLC (Biotage Iso[era; 25 g SNAP cartridge: hexane/ethy[ acetate 8/2 -> hexane/ethy[ acetate 4/6) to give 330 mg (50% yie[d of theory) of the tit[e compound.UPLC-MS (Method 1): R = 0.67 mm; MS (EI0): m/z = 186 [M]¡Â.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Chloropyrazine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; PRECHTL, Stefan; SIEMEISTER, Gerhard; WENGNER, Antje Margret; ACKERSTAFF, Jens; NOWAK-REPPEL, Katrin; BADER, Benjamin; LIENAU, Philip; STOeCKIGT, Detlef; WO2014/118186; (2014); 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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Chloropyrazine-2-carboxylic acid

SOCl2 (0.71 mL, 2.84 mmol) and DMF (0.025 mL) were added dropwise to a suspension of 6-chloro-pyrazine -2-carboxylique acid (0.450 g, 2.84 mmol) in toluene (1 mL) and the RM was stirred at 80-90C for 2 h. The solvent was evaporated off under reduced pressure and the residue was dissolved in THF (10 mL) and acetone ( 20 mL), cooled to 0 under argon atmosphere, pyridine ( 0.689 mL, 8.52 mmol), a solution of 4-(trifluoromethoxy)aniline (0.593 mL, 4.42 mmol) in acetone (5 mL) and DMF (1 mL) were added and the RM was stirred at RT overnight. The mixture was treated with aq. 1M HC1 (40 mL) and extracted with EtOAc/TBME (1 :4). The combined extracts were washed with aq. 1M HC1, water, brine and dried over MgSC and the solvent was evaporated off under reduced pressure. The residue was purified by flash chromatography (Silica gel column, 25 g, cyclohexane / EtOAc from 5% to 30% EtOAc) and afforded 6-chloro-N-(4-(trifluoromethoxy)phenyl)pyrazine-2-carboxamide as a yellow oil of which (50 mg, 0.157 mmol), pyrimidin-5-ylboronic acid (39.0 mg, 0.315 mmol), Pd(PPh3)2Cl2 (6.63 mg, 0.0094 mmol), Na2C03 (66.7 mg, 0.630 mmol), DME (668 muGamma), water (191 muGamma) and EtOH (95 mu) was stirred at 80-85C for 1 h. The RM was diluted with THF (2 mL), stirred overnight with Si-Thiol (Silicycle, 124 mg, 0.157 mmol), filtered and the filtrate was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (Silica gel column, 4 g, DCM / EtOAc + 0.1% NH4OH from 20% to 80% EtOAc+ 0.1% NH4OH) Crystallization from MeOH afforded the title product as white needles. UPLC-MS (Condition 1) tR= 2.68 min, m/z =362.0 [M+H]+, m/z = 360.0 [M-H]”; XH-NMR (400 MHz, DMSO-d6) d ppm 7.45 (d, J=8.6 Hz, 2 H) 8.01 (d, J=9.0 Hz, 2 H) 9.35 (s, 1 H) 9.38 (s, 1 H) 9.69 (s, 1 H) 9.88 (s, 2 H) 10.85 (s, 1 H) .

The synthetic route of 23688-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GROTZFELD, Robert Martin; JONES, Darryl Brynley; MANLEY, Paul; MARZINZIK, Andreas; MOUSSAOUI, Saliha; PELLE, Xavier Francois Andre; SALEM, Bahaa; SCHOEPFER, Joseph; WO2013/171641; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 23688-89-3, 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 23688-89-3 as follows.

Intermediate 13 was prepared from the indicated bromide and boronic acid by methods analogous to those described for Intermediate 12.:_To a solution of ethyl 2-ethoxy-4-(4,4, 5, 5-tetramethyl- 1, 3,2-dioxaborolan-2- yl)benzoate (439 mg, 1.37 mmol) and 6-bromo-5-fluoropicolinic acid (302 mg, 1.37 mmol) in 1,4-dioxane (6.9 ml) was added a solution of sodium carbonate (436 mg, 4.11 mmol) in water (2 ml). The reaction was purged with nitrogen and PdCI2(dppf)-CH2CI2 adduct (112 mg, 0.14 mmol) was added and the reaction then heated at 80 00 for 18 hours. The reactionwas then cooled to room temperature and concentrated. The residue was partitioned between water and EtOAc and the aqueous phase acidified. The layers were separated, and the aqueous phase was extracted with further EtOAc (3 x 20 ml). The combined organic extracts were dried over Mg504, filtered, and concentrated to give the title compound as an orange solid (129 mg, 28 % yield).

According to the analysis of related databases, 23688-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara S.; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; (274 pag.)WO2017/6295; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

23688-89-3,Some common heterocyclic compound, 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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: 5-Chloropyrazine-2-carboxamide (1). 5.0 g of 5-hydroxypyrazine-2-carboxylic acid (0.036 mol) was suspended in 50 mL of dry toluene and treated with thionyl chloride (3 eq., 7.9 mL, 0.108 mol). DMF (10 drops) was added to the reaction mixture as a catalyst. The reaction mixture was heated to reflux for about 1 h. The excess of thionyl chloride was removed by repeated evaporation with dry toluene in vacuo.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloropyrazine-2-carboxylic acid, its application will become more common.

Reference:
Article; Servusova, Barbora; Paterova, Pavla; Mandikova, Jana; Kubicek, Vladimir; Kucera, Radim; Kunes, Jiri; Dolezal, Martin; Zitko, Jan; Bioorganic and Medicinal Chemistry Letters; vol. 24; 2; (2014); p. 450 – 453;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, 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. 23688-89-3

Preparation of compound 8a: 6-Chloropyrazine-2-carbonyl chloride A mixture of 2-chloro-6-carboxy-pyrazine (1000 mg, 6.3 mmol) in ACN (20 ml_) was treated with thionyl chloride (800 uL). The resulting mixture, which became homogeneous upon heating, was refluxed for 2 h. The solvent was removed under reduced pressure which gave an oil. The crude product was used in the next step.

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; PFIZER INC.; NINKOVIC, Sacha; BRAGANZA, John Frederick; COLLINS, Michael Raymond; KATH, John Charles; LI, Hui; RICHTER, Daniel Tyler; WO2010/16005; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 23688-89-3

General procedure: The compounds were prepared following a literature procedure.57 To a solution of carboxylic acid (1.0 equiv.) in anhydrous CH2Cl2(0.1 M) was added oxalyl chloride (1.5 equiv.) and DMF (0.1 equiv.) at0 C, and the resulting mixture was allowed to warm to RT for 2 h. Thenthe volatiles were concentrated under reduced pressure, and the residuewas dissolved in anhydrous CH2Cl2 (0.1 M), followed by the addition ofaniline (1.0 equiv.) and triethylamine (1.1 equiv.), and the resultingmixture was stirred at RT for another 2 h. After completion monitoredby TLC, the reaction mixture was quenched with H2O and extractedwith CH2Cl2 (3¡Á20 mL), and washed with 1% HCl solution, and thensat. Na2CO3 (aq.). The combined organic layers were dried over MgSO4and concentrated in vacuo.

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, 23688-89-3, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhou, Qingqing; Reekie, Tristan A.; Abbassi, Ramzi H.; Indurthi Venkata, Dinesh; Font, Josep S.; Ryan, Renae M.; Munoz, Lenka; Kassiou, Michael; Bioorganic and Medicinal Chemistry; vol. 26; 22; (2018); p. 5852 – 5869;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

23688-89-3, Adding some certain compound to certain chemical reactions, such as: 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, 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 23688-89-3.

To a 100 ml round bottom flask, 6-chloropyrazine-2-carboxylic acid (Ig, 6.31 mmol) was suspended in dry CH2Cl2 (30ml). Oxalyl chloride (3.78 ml, 7.57 mmol) was added along with a few drop of DMF, the mixture was stirred at room temperature for 12 hrs, N, O- Dimethylhydroxylamine hydrochloride (0.800 g, 8.20 mmol) was added, the resulting mixture was cooled down to 5C, TEA (2.64 ml, 18.92 mmol) was added via a droping funal, the reaction mixture was stirred at room temperature for 30 minutes, filtered and the filter cake was washed with EtOAc, the combinded filtrate was washed with saturated sodium bicarbonate and brine, concentrated to an oil, purified on silica gel with Hexanes/EtOAc solventsto give product (1.06g). MS (ES) MH+: 202 for C7H8ClN3O2

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARVIAN, Kevin; BASARAB, Gregory, Steven; GOWRAVARAM, Madhusudhan, Reddy; HAUCK, Sheila, Irene; ZHOU, Fei; WO2010/43893; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem