Tag: M.W=200-300

Application of 1379338-74-5,Some common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, molecular formula is C7H3Cl2N3, 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.

A solution of 6-(aminomethyl)morpholin-3-one (130 mg, 1 mmol), 5,7-dichloropyrido[4,3-b]pyrazine (200 mg, 1 mmol) and DIEA (260 mg, 2 mmol) in THF (20 mL) was stirred at reflux overnight. After concentration, the residue was purified by column chromatography to give product as yellow solid (100 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,7-Dichloropyrido[3,4-b]pyrazine, its application will become more common.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6966-01-4, These common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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.

Preparation of methyl 3,6-dibromopyrazine-2-carboxylate A mixture of 3 – amino – 6 – bromopyrazine – 2 – carboxylic acid methyl ester (4 ? 6 2 g ’20 mmol), aqueous hydrobromic acid (48%, 24 ml) and acetic acid (3.2 ml) was added to the reactor, -5 C. The solution (20 ml) of the solution of acetic acid (5 ml) and sodium nitrite (4.8 g, 70 ml) was slowly added successively -5 C stirring reaction lh. The reaction was terminated, washed with saturated sodium sulfite solution, extracted with ethyl acetate and water, washed with saturated NaCl solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as an off-white solid.

Statistics shows that Methyl 3-amino-6-bromopyrazine-2-carboxylate is playing an increasingly important role. we look forward to future research findings about 6966-01-4.

Reference:
Patent; NANJING SHENGHE PHARMACEUTICAL CO., LTD.; WANG, YONG; ZHAO, LIWEN; LIU, YANG; ZHANG, JINGZHONG; WANG, DEZHONG; GAO, YIPING; CHEN, HONGYAN; ZHANG, CANG; ZHANG, DI; (68 pag.)TWI523856; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 41270-66-0, 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 41270-66-0 as follows.

30 g of 2-chloro-5,6-diphenylpyrazine and 131.22 g of 4-(isopropylamino)-1-butanol were mixed and then heated with stirring at 190C for 10 hours.. The reaction solution was air-cooled, poured into water, extracted with diethyl ether, dried over anhydrous magnesium sulfate and then concentrated.. The residue was purified by silica gel column chromatography to obtain 22.96 g of the desired compound as a colorless crystal having a melting point of 102 to 103C.

According to the analysis of related databases, 41270-66-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1400518; (2004); 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H3Br2N3

Step 1: synthesis of 3-amino-6-bromopyrazine-2-carbonitrile (14)A solution of copper(i) cyanide (1.20 g, 13.42 mmol) and sodium cyanide (0.658 g, 13.42 mmol) in DMF (10 mL) was heated to 125C. 2-amino-3,5-dibromo pyrazine (2.61 g, 10.32 mmol) was added in portions. The reaction was stirred at 125C, and after 5h quenched in ice cold NaHC03 solution. The black precipitate was filtrated off and the filtrate was extracted (3x) with EtOAc. The organic layer was washed with brine, dried and evaporated. Purification by chromatography (CH2CI2) gave pure 3- amino-6-bromopyrazine-2-carbonitrile 14 (1.38 g, 67.2 %). 1H-NMR (400 MHz, CDC13) 5.29 (br s, 2H), 8.30 (s, 1H). (m/z) = 199 and 201 (M+H)+.

According to the analysis of related databases, 24241-18-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; FOLMER, Brigitte, Johanna, Bernita; MAN, de, Adrianus, Petrus, Antonius; GERNETTE, Elisabeth, Sophia; CORTE REAL GONCALVES AZEVEDO, Rita; IBRAHIM, Hemen; WO2011/147764; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 1062608-42-7, name is 5-Bromo-3-iodopyrazin-2-amine, molecular formula is C4H3BrIN3, 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. Quality Control of 5-Bromo-3-iodopyrazin-2-amine

To a solution of 2b (4.0 g, 13.33 mmol) in 1,4-dioxane (55 mL) was added 3- (trifluoromethyl)phenyl boronic acid (6) (2.79 g, 14.67 mmol) followed by 1M aqueous solution of potassium carbonate (26.6 mL, 26.67 mmol) at RT. Reaction mixture was purged with N2 gas for 30 minutes. Bis(triphenylphosphine)palladium(II)chloride (0.65 g, 0.93 mmol) was added to the reaction mixture and was heated to reflux for 4 h, cooled to RT, filtered through celite. Filtrate was concentrated under vacuum to remove dioxane. 50 mL of water was added and extracted with dichloromethane. Organic layer combined and washed with water, dried over sodium sulfate and concentrated under vacuum. Crude product purified by flash chromatography using 30% ethyl acetate in petroleum ether to afford compound 3b (3.5 g, 83.3%) as pale yellow solid. 1H NMR (400 MHz, DMSO-d6): delta 8.14 (s, 1H), 7.90 (d, J = 8.40 Hz, 2H), 7.84 (d, J = 8.40 Hz, 2H), 6.63 (s, 2H). LC-MS APCI: Calculated for C11H7BrF3N3: 318.10; Observed m/z [M+H]+: 318.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1062608-42-7, its application will become more common.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; UNIVERSITY OF CAPE TOWN; WATERSON, David; WITTY, Michael John; CHIBALE, Kelly; STREET, Leslie; GONZALEZ CABRERA, Diego; PAQUET, Tanya; (36 pag.)WO2017/9773; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, 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 313340-08-8, Application In Synthesis of 3,5-Dichloro-6-ethylpyrazine-2-carboxamide

General procedure: To a solution of compound6(0.4 mmol) and anappropriateaniline derivatives(0.2 mmol) in 1,4-dioxane, was added DIPEA (0.4 mmol). The mixture was stirred at 100oC for 12 h. The solution was diluted withwater, andfiltered. The residue was washed with water twice and dried to give the crude product as yellow solid in 42-74% yield.

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:
Article; Wang, Yueliang; Xing, Li; Ji, Yinchun; Ye, Jiqing; Dai, Yang; Gu, Wangting; Ai, Jing; Song, Zilan; Bioorganic and Medicinal Chemistry Letters; vol. 29; 6; (2019); p. 836 – 838;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 1458-01-1, A common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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.

3,5-Diamino-6-chloropyrazine-2-carboxylic acid Methyl-3,5-diamino-6-chloropyrazine-2-carboxylate (8.5 g, 41.9 mmol) is dissolved in dioxane (200 mL), sodium hydroxide (1 M in water, 125 mL, 125 mmol) added and the mixture stirred overnight at room temperature. The reaction mixture is acidified to pH 5 with 4 M hydrochloric acid and concentrated to one third of the initial volume. The resulting solid is collected by filtration, washed with water and dried under vacuum at 50¡ã C. Yield: 7.4 g ESI mass spectrum: [M+H]+=189

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WIEDENMAYER, Dieter; HECKEL, Armin; HAMPRECHT, Dieter; US2015/45326; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 36070-83-4, 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. 36070-83-4 name is Ethyl 5-bromopyrazine-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.

Embodiment 66 ethyl 5-((4,4-dimethylthiochroman-6-yl)ethynyl)pyrazin-2-carboxylate ethyl 5-bromopyridazin-2-carboxylate (600mg, 2.61mmol) and 6-ethynyl-4,4-dimethylbenzothiopyran (635mg, 3.13mmol) were added to a flask, followed by addition of Pd(PPh3)2Cl2 (66mg, 0.094mmol) and CuI (36mg, 0.188mmol). After the flask was purged with argon for 3 times to remove oxygen, 6mL dry DMF and 0.4mL dry Et3N were added via syringe. Then the reaction was continued at 80C for 8 h and monitored by TLC. After completion of the reaction, the reaction was quenched with saturated ammonium chloride solution. The mixture was diluted with ethyl acetate, washed with saturated ammonium chloride solution and saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash column chromatography (PE:EtOAc = 50:1) to give WYC-322 (656mg, 71.5%). 1H NMR (500 MHz, CDCl3) delta 9.20 (d, J = 1.4 Hz, 1H), 8.76 (d, J = 1.4 Hz, 1H), 7.58 (d, J = 1.7 Hz, 1H), 7.23 (dd, J = 8.2, 1.8 Hz, 1H), 7.04 (d, J = 8.2 Hz, 1H), 4.46 (q, J = 7.1 Hz, 2H), 3.02 – 2.97 (m, 2H), 1.92 – 1.87 (m, 2H), 1.41 (t, J = 7.1 Hz, 3H), 1.29 (s, 6H). 13C NMR (126 MHz,CDCl3) delta 163.65, 146.68, 145.70, 143.08, 142.31, 140.30, 136.14, 130.54, 129.51, 126.74, 116.00, 97.55, 85.68, 62.37, 36.91, 32.99, 29.89, 23.27, 14.31. ESI(+)-MS: 353.5 [M+1]+.

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

Reference:
Patent; Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences; Huazhong University of Science and Technology; CAO, Xin; YU, Biao; WANG, Ning; CHEN, Junwei; (88 pag.)EP3428155; (2019); 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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromo-5-iodopyrazine

A mixture of 2-bromo-5-iodopyrazine (200mg, 0.704mmol), cesium carbonate (400mg, 1.23mmol) and 2R methyl piperazine (85mg, 0.85mmol) in DMF (1 OmI) was stirred at 1000C overnight. The reaction was cooled and solvent evaporated.Water (100ml) was added and insoluble solid was filtered, then dissolved in MeCb (100ml), dried over Na2SO4, filtered and solvent evaporated yielding product (205mg, 95%)

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 622392-04-5.

Reference:
Patent; SCHERING CORPORATION; WO2008/153858; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 87486-34-8,Some common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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 2a-j (10 mmol, 1.0 eq) , 3,5-dibromo-1-methylpyrazin-2(1H)-one (2.95 g, 11 mmol, 1.1 eq) and DIEA (3.3 mL,20 mmol, 2.0 eq) in MeCN (20mL) was stirred at 80 ¡ãC for 5 hours. After cooling to room temperature, thesolvent was removed in vacuo, and the residue was purified using silica gelchromatography to give the title compounds, yield 72-85percent.

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Jianhong; Du, Jiatian; Huang, Chong; Wang, Tianqi; Huang, Luyi; Yang, Shengyong; Li, Linli; Bioorganic and Medicinal Chemistry Letters; vol. 29; 13; (2019); p. 1609 – 1613;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem