Category: 59303-10-5

Electric Literature of 59303-10-5, 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 59303-10-5 as follows.

A mixture of 2-chloro-5-methylpyrazine (300 mg, 1.6 mmol), (R)-tert-butyl 3-aminopyrrolidine-l- carboxylate (206 mg, 1.6 mmol), BINAP (199 mg, 0.3 mmol), Pd2(dba)3 (73 mg, 0.08 mmol) and t- BuONa (307 mg, 3.2 mmol) in toluene (10 mL) was stirred at 80C under N2 for 3 hours. The mixture was cooled to RT and concentrated. The residue was purified by reverse phase chromatography to afford (R)-tert-butyl 3-((5-methylpyrazin-2-yl)amino)pyrrolidine-l-carboxylate (240 mg, 54%) as yellow oil. [M+H] Calc?d for Ci4H22N402, 279.1; Found, 279.1.

According to the analysis of related databases, 59303-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 59303-10-5, name is 2-Chloro-5-methylpyrazine, 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 59303-10-5, Product Details of 59303-10-5

To a solution of rac- I -((2S,3R,4R)-4-amino-2-ethyl-3-methyl-6-morpholino-3,4-dihydroqu inolin1(2H)-yl)ethanone (for a preparation see Intermediate 73, 50 mg, 0.158 mmol) in 1,4-dioxane (1.5 ml) was added tris(dibenzylideneacetone)dipalladium(0) (28.8 mg, 0.032 mmol), Davephos (12.40mg, 0.032 mmol), sodium tert-butoxide (30.3 mg, 0.315 mmol) and 2-chloro-5-methylpyrazine (40.5 mg, 0.315 mmol). The reaction mixture was heated under microwave conditions, using initial normal absorption setting, to 120 C for 30 mm. The sample was diluted with ethyl acetate (5 mL) and loaded onto a celite cartridge (2.5 g). The cartridge was washed with further ethyl acetate (2×10 mL), and the combined fractions dried under a stream of nitrogen. The sample was dissolved in DMSO(2×1 mL) and purified by MDAP (HpH). The solvent was blown down under a stream of nitrogen to give the required product (14 mg) as a yellow gum. LCMS (2 mm HpH): Rt = 0.87 mi [MH] = 410.

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-Chloro-5-methylpyrazine, other downstream synthetic routes, hurry up and to see.

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

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 59303-10-5 as follows. Application In Synthesis of 2-Chloro-5-methylpyrazine

A mixture of N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide (600 mg), 2-chloro-5-methyl-pyrazine (100 mg), and cesium carbonate (300 mg) in N,N-dimethylformamide (10 mL) is stirred for 3 days at 80 C. After cooling to room temperature ethyl acetate and water are added. The organic phase is separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (ethyl acetate/methanol 7:3) to give the title compound. LC (method 1): tR=1.08 min; Mass spectrum (ESI+): m/z=404 [M+H]+.

According to the analysis of related databases, 59303-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NOSSE, Bernd; BLUM, Andreas; BREITFELDER, Steffen; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; WELLENZOHN, Bernd; ASHWEEK, Neil J.; HARRIOTT, Nicole; US2013/65906; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 59303-10-5, 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 59303-10-5 as follows.

Example 192-(2-Methyl-imidazol-1 -yl)-pyrimidine-5-carboxylic acid cvclopropyl-H -(5-methyl- pyrazin-2-yl)-pipehdin-4-vH-amideA mixture of 2-(2-methyl-imidazol-1 -yl)-pyrimidine-5-carboxylic acid cyclopropyl- piperidin-4-yl-amide (44 mg, Intermediate 20), 2-chloro-5-methylpyrazine (15 mg) and ethyldiisopropylamine (35 muIota_) in N-methyl-2-pyrrolidinone (1 .0 ml_) is heated in a microwave oven for 30 min at 200C. After removal of the solvent the residue is purified by HPLC (H2O/MeOH/TFA) to give the title compound. LC (method 3): tR = 0.92 min; Mass spectrum (ESI+): m/z = 419 [M+H]+.

According to the analysis of related databases, 59303-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/168315; (2012); 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. 59303-10-5, name is 2-Chloro-5-methylpyrazine, A new synthetic method of this compound is introduced below., Product Details of 59303-10-5

Example 1.18: Preparation of 2-(4-(((lr,4r)-4-(2-Fluoro-4-(methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidin-l-yl)-5-methylpyrazine (Compound 9).; A mixture of 4-(((l r,4r)-4-(2-fluoro-4- (methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidine hydrochloride (36.1 mg, 0.089 mmol), prepared in Example 1.17, Step A, 2-chloro-5-methylpyrazine (25 mg, 0.194 mmol), and triethylamine (50 muEpsilon, 0.359 mmol) in iPrOH (2 mL) was heated under microwave at 150 C for 1 h, at 200 C for 1 h, and then at 180 C for 14 h. The mixture was purified by HPLC (5- 95% CH3CN). Fractions containing the title compound were partly concentrated and the residue was extracted with 1M NaOH and CH2C12 (three times). The combined organic phases were dried over MgS04, filtered, and concentrated to give the title compound (24.1 mg, 0.052 mmol, 58.7 % yield) as a white solid. Exact mass calculated for C24H32FN3O3S: 461.21 , found: LCMS m/z = 462.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.24-1.58 (m, 6H), 1.81-1.96 (m, 5H), 2.17-2.20 (m, 2H), 2.40 (s, 3H), 2.84-2.95 (m, 3H), 3.05 (s, 3H), 3.25-3.31 (m, 1H), 3.37 (d, = 6.2 Hz, 2H), 4.25-4.28 (m, 2H), 7.40-7.43 (m, 1H), 7.58-7.60 (m, 1H), 7.66-7.68 (m, 1H), 7.95 (s, 1H), 8.06 (s, 1H).

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; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 59303-10-5,Some common heterocyclic compound, 59303-10-5, name is 2-Chloro-5-methylpyrazine, molecular formula is C5H5ClN2, 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.

NaH (60% in mineral oil, 103 mg, 2.57 mmol) was added to a stirred solution of l-Boc- 4-hydroxypiperidine (CAS: 109384-19-2; 470 mg, 2.33 mmol) in DMF (10 mL) at 0 C under N2 atmosphere. The mixture was stirred at room temperature for 1 h. 2-Chloro-5- methylpyrazine (CAS: 59303-10-5; 300 mg, 2.33 mmol) was added to the mixture under N2 atmosphere and the reaction mixture was stirred at 50 C for 16 h. A solution of 1- Boc-4-hydroxypiperidine (CAS: 109384-19-2) in DMF which was stirred for 1 h at room temperature was added, and the reaction mixture was stirred at 80 C for another 16 h. The mixture was diluted with water and extracted with DCM. The organic layer was dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 80:20). The desired fractions were collected and concentrated in vacuo to afford intermediate 151 (320 mg, 47%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5-methylpyrazine, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana Isabel; DELGADO-JIMENEZ, Francisca; CONDE-CEIDE, Susana; VEGA RAMIRO, Juan, Antonio; (245 pag.)WO2019/243530; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

59303-10-5, name is 2-Chloro-5-methylpyrazine, 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. Recommanded Product: 59303-10-5

a reaction vessel 4-bromo-N-methylbenzamide (53.1 mg, 0.248 mmol), rac-1-((2S,3R,4R)-4- amino-2,3-dimethyl-6-(tetrahyd ro-2H-pyran-4-yl)-3,4-dihyd roquinolin- I (2H)-yl)ethanone (for apreparation see Intermediate 152, 37.5 mg, 0.124 mmol), sodium tert-butoxide (35.8 mg, 0.372 mmol), in 1,4-Dioxane (5 mL) were added. The solution was treated with Pd2(dba)3 (17.03 mg, 0.019 mmol) and DavePhos (9.76 mg, 0.025 mmol) and left to stir at 100 C for 2 h under N2. The reaction mixture was allowed to cool to rt and then filtered through celite and the celite washed with ethyl acetate. The combined filtrates were concentrated in vacuo to a crude orange/brown gum. This gumwas purified by MDAP (Formic) to give asolid. This solid was eluted through a NH2 SPE (5 g) with MeOH, the eluent was concentrated to give the product (17 mg, 0.039 mmol, 31.5%) as an off-white solid. LCMS (2 mm Formic): Rt = 0.83 mi [MH] = 436.

The synthetic route of 59303-10-5 has been constantly updated, and we look forward to future research findings.

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

Electric Literature of 59303-10-5, 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. 59303-10-5, name is 2-Chloro-5-methylpyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-((lr,4r)-4-(4-(methylsulfonyl)phenoxy)cyclohexyloxy)piperidine hydrochloride (24.2 mg, 0.062 mmol), 2-chloro-5-methylpyrazine (90 mg, 0.700 mmol), and triethylamine (40 mu, 0.287 mmol) in iPrOH (1 mL) was heated under microwave irradiation at 200 C for 5 h. The mixture was concentrated and the residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (8.7 mg) as a white solid. LCMS m/z = 446.2 [M+H]+; .H NMR (400 MHz, CDC13) delta 1.46-1.68 (m, 6H), 1.89-1.96 (m, 2H), 1.99- 2.04 (m, 2H), 2.10-2.15 (m, 2H), 2.39 (s, 3H), 3.03 (s, 3H), 3.21-3.27 (m, 2H), 3.55-3.59 (m, IH), 3.63-3.67 (m, IH), 3.91-3.97 (m, 2H), 4.39-4.44 (m, IH), 6.98-7.01 (m, 2H), 7.83-7.86 (m, 2H), 7.94 (s, IH), 8.07 (s, IH).

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; BUZARD, Daniel J.; LEHMANN, Juerg; NARAYANAN, Sanju; YUE, Dawei; WO2011/127051; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 59303-10-5, These common heterocyclic compound, 59303-10-5, name is 2-Chloro-5-methylpyrazine, 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: . Following GP2, t-BuOK (0.1 g, 1 eq., 0.88 mmol) was added to a solution of tert-butyl (1R,3r,5S)-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (0.2 g, 1 eq., 0.88 mmol), and 2-chloro-5-methylpyrazine (0.11 g, 1 eq., 0.88 mmol) in dry THF (7 mL). The reaction mixture was refluxed for 16 h. Then, the mixture was quenched with water (15 mL) and extracted with DCM (210 mL). The organic extracts were washed with brine (15 mL), dried over Na2SO4 and concentrated in vacuo to furnish the crude product, which was purified by flash chromatography eluting with cyclohexane/EtOAc (0 to 80%) to give the pure title compound as colourless oil (0.07 g, 25%). UPLC-MS (method A): Rt. 2.58 min (TIC); ionization ES+320 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 8.17 (d, J=1.3 Hz, 1H), 8.06 (s, 1H), 5.26 (t, J=5.0 Hz, 1H), 4.18-4.03 (m, 2H), 2.39 (s, 3H), 2.17-1.97 (m, 4H), 1.96-1.77 (m, 4H), 1.42 (s, 9H).

Statistics shows that 2-Chloro-5-methylpyrazine is playing an increasingly important role. we look forward to future research findings about 59303-10-5.

Reference:
Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; BERTOZZI, Fabio; BANDIERA, Tiziano; PONTIS, Silvia; REGGIANI, Angelo; GIACOMINA, Francesca; DI FRUSCIA, Paolo; US2019/135778; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 59303-10-5, name is 2-Chloro-5-methylpyrazine, 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 59303-10-5, COA of Formula: C5H5ClN2

To a solution of 2-chloro-5-methylpyrazine (2.00 g, 15.56 mmol) in DMF (50 mL) was added 1H-pyrazole-4-carbaldehyde (2.24 g, 23.34 mmol) followed by Cs2CO3 (10.14 g, 31.10 mmol) and the resulting reaction mixture was heated at 100C for 6 h. The reaction mixture was cooled to ambient temperature, concentrated to dryness under reduced pressure, diluted with water (50 mL) and extracted with ethyl acetate (2 x 75 mL). The combined organic layers was washed with brine (30 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Redisep – 80 g, 0-100% EtOAc/n-hexane) to obtain Intermediate 125 (1.10 g, 37.10%) as a pale yellow solid.1H NMR (300 MHz, DMSO-d6) G ppm 2.58 (s, 3 H), 8.36 (s, 1 H), 8.54 (s, 1 H), 9.14 (s, 1 H), 9.31 (s, 1 H), 9.98 (s, 1 H). LCMS (Method- D): retention time 1.25 min, [M+H] 189.2.

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-Chloro-5-methylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem