Category: 27398-39-6

Electric Literature of 27398-39-6, A common heterocyclic compound, 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

9.3 3-Chloro-pyrazine-2-carboxylic acid[1-imino-2-(2-naphthalen-2-yl-ethoxy)-ethyl]-amide; Under an atmosphere of nitrogen, 3-chloro-2-pyrazinecarboxylic acid (Tyger, 250 mg), TBTU (532 mg), and diisopropylethylamine (1.34 ml) were added to a solution of 2-(2-naphthalen-2-yl-ethoxy)-acetamidine hydrochloride (417 mg) in DMF (5 ml). The reaction mixture was stirred for 2 h at r.t., diluted with dichloromethane and washed with water. The organic layer was dried (Na2SO4), filtered, and the solvent was evaporated. The obtained, crude title compound (567 mg) was used without further purification in the next step.

The synthetic route of 27398-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Conte, Aurelia; Dehmlow, Henrietta; Grether, Uwe; Kratochwil, Nicole A.; Kuehne, Holger; Narquizian, Robert; Panousis, Constantinos G.; Peters, Jens-Uwe; Ricklin, Fabienne; US2008/234277; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 27398-39-6, name is 3-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. 27398-39-6

Intermediate 17 (50 mg, 0.079 mmol) was dissolved in NMP (300 uL) and N-ethyl-N- isopropylpropan-2-amine (41.3 mu, 0.237 mmol) and 3-chloropyrazine-2-carboxylic acid (13.78 mg, 0.087 mmol) were added, followed by HATU (36.1 mg, 0.095 mmol). The reaction was allowed to stand for 10 min and then analysed by LCMS and found to be complete. 2,2,2-Trifluoroacetic acid (151 mu, 1.975 mmol) was added and the mixture heated at 120 ¡ãC for 20 min. The mixture was poured into water and extracted with DCM. The organics were dried, filtered and evaporated to give a gum which was purified by RP HPLC (solvent B – minimum 10percent, intermediate 55percent, maximum 95percent) to give compound 48 as a white solid (10 mg, 24percent).

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 27398-39-6.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VAN BRANDT, Sven, Franciscus, Anna; GIJSEN, Henricus, Jacobus, Maria; VOS, Ann, Marleen; OEHLRICH, Daniel; (77 pag.)WO2018/162445; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

27398-39-6, Adding a certain compound to certain chemical reactions, such as: 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, 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 27398-39-6.

3-Chloropyrazin-2-carboxylic acid (1 equiv.) was dissolved in abs. dichloromethane (10 ml/mmol), and triethylamine (3 equiv.) was added. After stirring at room temperature for 5 minutes, N,N-dimethylhydrazine (1.3 equiv.) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane 2,4,6-trioxide (1.5 equiv., 50percent solution in tetrahydrofuran) were added. The resulting reaction mixture was stirred at room temperature for a further 30 minutes, and then water, sat. sodium hydrogencarbonate solution and dichloromethane were added. The aqueous phase was repeatedly extracted vigorously with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification of the resulting crude product by column chromatography gave 3-chloro-N?,N?-dimethylpyrazine-2-carbohydrazide in the form of a colorless solid. 3-Chloro-N?,N?-dimethylpyrazine-2-carbohydrazide (250 mg, 1.25 mmol) was then dissolved in abs. N,N-dimethylformamide (10 ml) under argon, and sodium hydride (60 mg, 1.50 mmol, 60percent purity) was added at room temperature. Stirring at room temperature for 15 minutes was followed by the addition of 3-(2,6-difluorophenyl)propyl bromide (352 mg, 1.50 mmol), and the resulting reaction mixture was stirred under reflux conditions for two hours. After cooling to room temperature, sat. sodium hydrogencarbonate solution, water and dichloromethane were added. The aqueous phase was repeatedly extracted vigorously with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification of the resulting crude product by column chromatography gave 3-chloro-N-[3-(2,6-difluorophenyl)propyl]-N?,N?-dimethylpyrazine-2-carbohydrazide in the form of a colorless viscous oil (118 mg, 26percent of theory).

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-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FRACKENPOHL, Jens; BOJACK, Guido; BRUeNJES, Marco; HELMKE, Hendrik; ADELT, Isabelle; LEHR, Stefan; BRUeCHNER, Peter; DITTGEN, Jan; SCHMUTZLER, Dirk; HEINEMANN, Ines; BICKERS, Udo; HILLS, Martin Jeffrey; RUIZ-SANTAELLA, Juan Pedro; STREK, Harry; DESBORDES, Philippe; (119 pag.)US2018/206495; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

27398-39-6, A common heterocyclic compound, 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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: To a solution of ethyl 5-(piperazin-1-yl) benzofuran-2-carboxylate (1 mmol) in dry dichloromethane (3 mL) was added triethylamine (2 mmol) and corresponding acid (1 mmol) at 0¡ãC. Propylphosphonic anhydride solution (50 wtpercent in ethyl acetate; 2.5 mmol) was then added drop wise to the reaction mixture and was stirred at rt for 6 h (monitored by TLC & LCMS for completion). The reaction mixture was then washed with water (2 mL), brine (2 mL), and dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained was then recyrstallised from diethyl ether.

The synthetic route of 27398-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Renuka, Janupally; Reddy, Kummetha Indrasena; Srihari, Konduri; Jeankumar, Variam Ullas; Shravan, Morla; Sridevi, Jonnalagadda Padma; Yogeeswari, Perumal; Babu, Kondra Sudhakar; Sriram, Dharmarajan; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4924 – 4934;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

27398-39-6, Name is 3-Chloropyrazine-2-carboxylic acid, 27398-39-6, 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.

Step 4: 3-chloro-N-[[1 -r3-chloro-5-r2-(trifluoromethyl)cvclopropyll-2-Pyridyllcvclopropyllmethyllpyrazine-2-carboxamide (compound A.1 1 1 )147 mg [1 -[3-chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamine (step 3) was dissolved in 3 ml of dichloromethane and 0.142 ml triethylamine was added. After cooling to 0¡ãC, 193 mg 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine hydrochloride, 84 mg 3-chloropyrazine-2-carboxylic acid and 141 mg 1- hydroxybenzotriazole were added. The mixture was stirred overnight at ambient temperature. Then water was added. The layers were separated, the organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. Crude material was obtained as an orange oil, which was purified by flash chromatography on silica gel with heptane/ethyl acetate as a solvent. Thus, 161 mg of 3-chloro-N-[[1-[3-chloro-5-[2- (trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methyl]pyrazine-2-carboxamide was obtained as a yellow sticky solid. 1H-NMR (CDCI3): 8.42 ppm (d, 1 H), 8.38 ppm (d, 1 H), 8.18 ppm (s, 1 H), 7.78 ppm (s, 1 H, broad), 7.31 ppm (s, 1 H), 3.66 ppm (d, 1 H), 2.26 ppm (m, 1 H), 1 .78 ppm (m, 1 H), 1.57 ppm (m, 1 H), 1.39 ppm (m, 1 H), 1.18 ppm (m, 4H).

Statistics shows that 3-Chloropyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 27398-39-6.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; PITTERNA, Thomas; LOISELEUR, Olivier; WORTHINGTON, Paul, Anthony; O’SULLIVAN, Anthony, Cornelius; LUKSCH, Torsten; BOBOSIK, Vladimir; WO2013/64521; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, 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. 27398-39-6

To a solution of 3-chloropyrazine-2-carboxylic acid (100 mg, 0.63 mmol) in DCM/MeOH (2 mL : 0.2 mL) was added TMSCH1?2 (0.47 mL, 0.95 mmol) at RT and the resulting mixture was stirred at RT for 2 h. Acetic acid (0.2 mL) was added and the mixture was diluted with water (2 mL) and extracted with DCM (4 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. LRMS m/z (M+H) 173.0 found, 173.0 required.

Statistics shows that 27398-39-6 is playing an increasingly important role. we look forward to future research findings about 3-Chloropyrazine-2-carboxylic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (97 pag.)WO2016/100157; (2016); A2;,
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. 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., 27398-39-6

102901 To a solution of 3-chloropyrazine-2-carboxylic acid (2.0 g, 12.70 mmol, 1.0 eq.) andTEA (3.50 mL, 25.40 mmol, 2.0 eq.) in THF (50 mL) was added methyl chloroformate (1.2 mL,15.20 mmol, 1.2 eq.) atO ¡ãC. The mixture was stirred at 0¡ãC for 10 mm and filtered. To thisfiltrate was added a suspension of NaBH4 (0.97 g, 25.40 mmol, 2 eq.) in water (1.0 mL) at 0 ¡ãC. The mixture was stirred at 0 ¡ãC for 1 h, quenched with NH4C1 (aq) solution, and extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-chloropyrazin-2- yl)methanol (400 mg, 22percent) as a white solid. 1H NMR (400 MHz, MeOD) 8.58 (d,J 2.5 Hz,1H), 8.38 (d,J= 2.5 Hz, 1H), 4.84 (s, 2H). LRMS (M+H+) m/z 145.1.

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; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102145; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 27398-39-6 name is 3-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. 27398-39-6

[00142] A mixture of 19 (1.50 g, 9.49 mmols, 1.0 eq), 1-(4-fluorophenyl)ethanamine (2.64 g, 19.0 mmols, 2.0 eq) and K2C03 (3.93 g, 28.5 mmols, 3.0 eq) in NMP (30 mL) was degassed, purged with nitrogen, and stirred at 140 ¡ãC for 16 hours. The mixture was diluted with ethyl acetate (100 mL) and washed with 2 N aqueous HC1 (30 mL x 3). The organic layer was dried over Na2SO4, filtered, and concentrated, the residue was purified by recrystallization (Petroleum ether/ethyl acetate) to give the desired product 20 (2.00 g, 7.66 mmols, 80.6percent) as a white solid.[00143] LCMS: ESI-MS: m/z: 262.2 [M+H1 RT = 1.87 mm. (Method A).

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

Reference:
Patent; ALPHARMAGEN, LLC; PUTMAN, David, G.; DASSE, Olivier; HOGENKAMP, Derk; (154 pag.)WO2016/144792; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem