Category: 33332-25-1

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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 5-chloropyrazine-2-carboxylate

Dissolve 5-chloro-pyrazine-2-carboxylic acid methyl ester (10.0 g, 57.9 mmol) in THF (65 mL) and MeOH (65 mL). Cool the solution to 0 0C before adding IN NaOH (63.7 mL) with stirring. Warm the mixture to room temperature and stir for 5 h. Concentrate the mixture in vacuo to 1/3 volume. Quench with IN HCl (75 mL) to form a white precipitate. Dilute with CH2Cl2 (200 mL) and filter. Wash the filter cake with water and CH2Cl2. Separate the phases, dry the organic phase over MgSO4, filter, and concentrate. Add the aqueous layer to the concentrated organic residue and concentrate. Purify by silica gel flash column chromatography, eluting with 40% ethyl acetate/n-hexane, followed by 10% MeOH, 3% acetic acid and 87% EPO CH2Ch- Collect the mixed fractions and concentrate. Take up the resulting solid with CH2CI2 (50 mL) and H2O (50 mL) and stir. Filter the solid and add it to the first filter cake. Add 5.0N NaOH to the filtrate to make the solution basic. Separate the two layers. Discard the organic layer, add 5.0N HCl to the aqueous layer until acidic. Extract with CH2Cl2 (3 x 100 mL). Dry the organic layer over Na2SO4, filter, and concentrate. Add the solid to the pure fractions from the column. Combine the pure filter cakes with the pure fractions from the column, yielding the desired product (8.46 g, 92%). mass spectrum (exact mass): 157.99.

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/66173; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-25-1, 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Methyl 5-[(oxan-4-yl)amino]pyrazine-2-carboxylat Methyl 5-chloro-2-pyrazinecarboxylate (507 mg, 2.94 mmol), Et3N (1.08 mL, 7.64 mmol) and 4-aminotetrahydropyran (0.40 mL, 3.82 mmol) were dissolved in dioxane (5 mL) and heated in a microwave reactor at 100 C. for 20 min. Water (50 mL) and brine (25 mL) were added and the reaction mixture was extracted into EtOAc (2*100 mL), dried (MgSO4) and concentrated in vacuo to give the title compound (236 mg, 33.9%) as a yellow oil. LCMS (ES+): 238.2 [MH]+.

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

Reference:
Patent; Proximagen Limited; Espensen, Max; Patient, Lee; Evans, David; Savory, Edward; Simpson, Iain; US2014/275040; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-25-1, 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Example 35-Chloropyrazine-2-carboxylic acidFehler. Es ist nicht moglich, durch die Bearbeitung von Feldfunktionen Objekte zu erstellen. Methyl 5-chloropyrazine-2-carboxylate (CAS [33332-25-1], 1 g, 5.79 mmol) was dissolved in a mixture of THF (50 ml) and water (50 ml). Lithium hydroxide monohydrate (243 mg, 5.79 mmol) was added and the reaction mixture was stirred at RT overnight. The pH was adjusted to 1 with 1M HC1 and the product was extracted with three portions of EtOAc. The combined organic layers were dried over Na2S04 and concentrated under vacuum. The crude material was purified by flash chromatography (Si02, 50 g, 0 to 20% MeOH in DCM) to yield the title compound as white solid (741 mg, 81%). MS (ISP): m/z = 159.0 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Methyl 5-chloropyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BORRONI, Edilio; GOBBI, Luca; HILPERT, Hans; HONER, Michael; MURI, Dieter; NARQUIZIAN, Robert; POLARA, Alessandra; WO2012/168175; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-25-1, 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 33332-25-1 as follows.

Example 95 [0308] [Formula 107]CI xj – ~ CI’ [0309] 1) In tetrahydrofuran (66 mL) was dissolved methyl 5-chloropyrazine-2-carboxylate (3.3 g), and 1M diisobutylaluminum hydride/hexane solution (38.3 mL) was added dropwise to the solution under nitrogen atmosphere at -70C or lower over 10 minutes, and the resulting mixture was further stirred for 10 minutes. At -60C or lower, 1M diisobutylaluminum hydride/hexane solution (31.3 mL) was added dropwise to the mixture over 20 minutes, and the mixture was further stirred at -70C or lower for 1 hour. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and after stirring at room temperature, filtered with Celite. The filtrate was extracted with ethyl acetate, washed with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=100:0 to 80:20) to obtain 5-chloropyrazine-2-carbaldehyde (970 mg). MS (m/z): 142/144 [M+H]+

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; SAKURAI, Osamu; SARUTA, Kunio; HAYASHI, Norimitsu; GOI, Takashi; MOROKUMA, Kenji; TSUJISHIMA, Hidekazu; SAWAMOTO, Hiroaki; SHITAMA, Hiroaki; IMASHIRO, Ritsuo; WO2012/81736; (2012); 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 33332-25-1 as follows. Recommanded Product: Methyl 5-chloropyrazine-2-carboxylate

Synthesis of 5′-(3-{1-[4-(2-amino-pyrimidin-5-yl)-phenyl]-1-cyclopropyl-ethyl}-[1,2,4]oxadiazol-5-yl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic Acid tert-butyl Ester A 250 ml RB flask is charged with R-7 (5.4 g, 28.99 mmol) in 100 mL of NMP. R-8 (5.00 g, 28.99 mmol) is added followed by triethylamine (4.85 ml, 34.79 mmol). The reaction is heated to 60 C. under nitrogen overnight. The reaction is cooled to room temperature, poured into ice water and the precipitated I-76 (8.60 g) is isolated by filtration; m/z 323.4 [M+H]

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/195879; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-25-1, 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(5-chloropyrazin-2-yl)methyl methanesulfonate; [00369] To a solution of 5-chloropyrazine-2-carboxylic acid (3.21 g, 20.3 mmol) in diethyl ether (20 mL) and methanol (20.0 mL) was added a 2M solution in diethyl ether of trimethylsilyldiazomethane (20.3 mL, 40.5 mmol). A vigorous bubbling was observed initially, and LCMS after 30 minutes indicated that the reaction was complete.Concentration of the reaction mixture afforded methyl 5-chloropyrazine-2-carboxylate (3.53 g, 20.5 mmol, 101% yield) as a tan solid. This material was shown to be >95% pure by NMR analysis and was used in the subsequent step without any purification. lH NMR (400 MHz, CDC13) delta (ppm): 9.09 (s, 1H), 8.70 (s, 1H), 4.04 (s, 3H).[00370] To a 0 C solution of methyl 5-chloropyrazine-2-carboxylate (3.50 g, 20.3 mmol) in tetrahydrofuran (101 mL) was added a 1M solution in tetrahydrofuran of diisobutylaluminum hydride (42.6 mL, 42.6 mmol). The reaction was stirred at 0 C for 2 hours, after which it was quenched by the addition of methanol (2 mL). To this mixture was added saturated sodium-potassium tartrate solution, and the resulting reaction mixture was extracted with ethyl acetate (3 x 100 mL), dried (sodium sulfate), filtered and concentrated to brown residue. Purification was achieved by column chromatography on silica gel (Luknova 120 g, 20 mL/min) using 30 to 100% ethyl acetate in hexanes over 60 minutes to afford (5- chloropyrazin-2-yl)methanol (1.45 g, 10.0 mmol, 50 % yield) as a tan solid. NMR (400 MHz, CDC13) a (ppm): 8.56 (s, 1H), 8.45 (s, 1H), 4.84 (s, 3H), 2.79 (br. s, 1H).[00371] To a 0 C solution of (5-chloropyrazin-2-yl)methanol (648 mg, 4.48 mmol) in dichloromethane (12 mL) was added triethylamine (1.87 mL, 13.5 mmol) followed by dropwise addition of methanesulfonyl chloride (0.699 mL, 8.97 mmol). After 20 minutes, analysis by LCMS indicated the complete conversion to the mesylate product. The reaction mixture was concentrated to afford (5-chloropyrazin-2-yl)methyl methanesulfonate (787 mg, 3.53 mmol, 79% yield) as an oil. The material was used crude in the next step without further purification.

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

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; HUDSON, Colleen; BARDEN, Timothy, C.; JIA, James; MERMERIAN, Ara; PENG, Bo; YANG, Jane; YU, Xiang, Y.; SPROTT, Kevin; WO2012/88469; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 33332-25-1, 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. 33332-25-1 name is Methyl 5-chloropyrazine-2-carboxylate, 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.

To a mixture of methyl 5-chloropyrazine-2-carboxylate (1 g, 5.79 mmol) and 2,2,2-trifluoroethanol (2.111 ml, 29.0 mmol) was added potassium carbonate (0.801 g, 5.79 mmol). The reaction was stirred at ambient temperature for 16 hrs. The reaction was partitioned between ethyl acetate and water. The organic portion was concentrated and purified in 10-60% EtOAc/Heptane to give the title compound (1.1 g, 4.66 mmol, 80%). MS m/z=237.1 (M+H).

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

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-25-1,Some common heterocyclic compound, 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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 solution of methyl-5-chloropyrazine-2-carboxylate (120 mg, 0.70 mmol) in a mixture of acetonitrile (2 ml) and DMF (1 ml) was added lithium chloride (295 mg, 6.95 mmol). The suspension was heated to 1600C for 5 mins in a Smith creator microwave after which time the reaction was diluted with water (10 ml). Saturated sodium bicarbonate solution (20 ml) was added and the aqueous layered extracted twice with ethyl acetate (30 ml). The combined organics were discarded and the aqueous layer adjusted to pH 4 with IN hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate (20 ml) and the combined organics washed with water (2 x 20 mlL), brine (10 ml) and dried (MgSO4). The volatiles were removed to give the title compound as a colourless solid (68 mg), 1H NMR delta (CDCl3): 7.20 (IH, br s), 8.72 (IH, s), 9.21 – 9.21 (IH, m); m/z 157 (M-H)+.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125958; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-25-1, 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 33332-25-1 as follows.

EXAMPLE 43A. [00211] A solution of methyl 3-hydroxy-5-isopropoxybenzoate (Bioorg. Med. Chem. Lett., 15:2103 (2005)) (609 mg, 2.90 mmol), methyl 5-chloropyrazine-2- carboxylate (500 mg, 2.90 mmol), and K2CO3 (1.20 mg, 8.69 mmol) in CH3CN (20 mL) was heated to 8O0C for 2 h under an atmosphere of Ar (g). The reaction was cooled to RT, diluted with CH2Cl2 (50 mL) and filtered. The filtrate was concentrated in vacuo, and the residue was chromatographed (SiO2; 40 g; continuous gradient from 100% hexane to 100% EtOAc over 40 min) to provide Part A compound (1.005 g, 100% yield) as a colorless oil. [M + H]+ = 347.

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/154563; (2008); 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 5-chloropyrazine-2-carboxylate

Methyl 5-(chloropyrazine)-2-carboxylate (36 7) (2g, 0.0115mmol) was dissolved in 80mL of 87 DMSO. 88 Sodium azide (3g, 0.0463mmol) and 39 triphenylphosphene (4.6g, 0.1738mmol) were added and the mixture was refluxed at 120C for 4h. 20mL of 1N 89 HCl was added and the reaction was continued at 120C for 2h. The mixture was cooled and neutralized by using 90 aqueous NaHCO3 solution and 91 product was extracted in ethyl acetate, dried using Na2SO4. The ethyl acetate fraction was evaporated and washed with n-pentane to get 0.7g (yield 39.5%) yellow solid of compound 8. 1H NMR (400MHz, DMSO-d6) delta 8.53 (d, J=1.2Hz, 1H), 7.91 (d, J=1.2Hz, 1H), 7.39 (s, 2H), 3.79 (s, 3H). C6H7N3O2 [M]: 153.14; MS (ESI) m/z: [M-H]+: 152.05.

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 33332-25-1.

Reference:
Article; Trivedi, Prakruti; Adhikari, Nilanjan; Amin, Sk. Abdul; Jha, Tarun; Ghosh, Balaram; European Journal of Pharmaceutical Sciences; vol. 124; (2018); p. 165 – 181;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem