Tag: M.W=100-200

Related Products of 14508-49-7, The chemical industry reduces the impact on the environment during synthesis 14508-49-7, name is 2-Chloropyrazine, I believe this compound will play a more active role in future production and life.

The reaction was run under nitrogen atmosphere. 2-chloropyrazine (96 mL, 1073 mmol) was added dropwise to 35 wt aqueous hydrazine (544 mL, 6009 mmol) at 65 C over 1 h. After the addition, stirring was continued at 63-67 C for 16 h then let stand at room temperature for two days. The mixture was filtered to remove a small amount of precipitate, then extracted with 10% iPrOH/dichloromethane (5 x 250 mL). The combined organic extracts were dried (MgS04), filtered, then concentrated under reduced pressure. The resulting solid was triturated with isopropyl acetate (600 mL). The solid was collected by filtration, rinsed with isopropyl acetate and dried under vacuum to give 2-hydrazinylpyrazine (60 g, 51 %) as a pale yellow solid. LCMS m/z = 111.2 [M+H]+. lU NMR (400 MHz, DMSO-i ) delta 4.21 (s, 2H), 7.70 (d, = 2.8 Hz, 1H), 7.89 (s, 1H), 7.93 (dd, = 2.8, 1.5 Hz, 1H), 8.10 (d, = 1.5 Hz, 1H).

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; BLACKBURN, Anthony C.; HAN, Sangdon; JONES, Robert M.; MONTALBAN, Anthony Garrido; PAL, Biman B.; RUETER, Jaimie Karyn; WO2012/116276; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 914452-71-4, name is 2-Bromo-6-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 914452-71-4, category: Pyrazines

General procedure: To a solution of Example 4A (50 mg, 0.176 mmol) in dioxane (0.8 mL) were added tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 8.0 mg, 8.78 mumol), xantphos (10.2 mg, 0.018 mmol) and 2-chloro-3-methylpyrazine (24.8 mg, 0.193 mmol). Then potassium carbonate (72.8 mg, 0.527 mmol) was added. The reaction mixture was stirred overnight at 80 C. The reaction mixture was filtered, and the solids were washed with acetonitrile (3 ¡Á 2 mL). The filtrate and washes were concentrated under reduced pressure, and the residue was purified by preparative HPLC (Phenomenex Luna C8(2) 5 mum 100A AXIA column (30 mm ¡Á 75 mm); a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/minute (0-1.0 minute 5% A, 1.0-8.5 minutes linear gradient 5-100% A, 8.5- 11.5 minutes 100% A, 11.5-12.0 minutes linear gradient 95-5% A) to give the title compound (50 mg, 0.13 mmol, 76% yield). The reaction and purification conditions described in Example 579 substituting 2- bromo-6-methylpyrazine (33.4 mg, 0.193 mmol) for 2-chloro-3-methylpyrazine (24.8 mg, 0.193 mmol) gave the title compound. 1H NMR (501 MHz, DMSO-d6) delta ppm 8.73 (s, 1H), 7.72 (s, 1H), 7.63 (s, 1H), 7.60 (s, 1H), 7.50 (t, J = 8.9 Hz, 1H), 7.08 (dd, J = 11.4, 2.8 Hz, 1H), 6.86 (ddd, J = 8.9, 2.9, 1.2 Hz, 1H), 4.50 (s, 2H), 2.33 (s, 6H), 2.27 (s, 3H); MS (ESI+) m/z 377 (M+H)+.

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; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); 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. 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, A new synthetic method of this compound is introduced below., name: (3,5,6-Trimethylpyrazin-2-yl)methanol

Step (1): in 50mL flask it contained QR01006-IN-01 (500mg, 3.29mmol), dichloromethane (10mL), and chloromethyl chloroformate (460mg, 3.6mmol), at -2 degrees and pyridine (0.32mL) was added dropwise to control the temperature not exceeding 3C. The reaction was warmed to room temperature overnight. TLC (petroleum ether/ethyl acetate=1/3) was done to monitor the completion of the reaction. The reaction was filtered and the filtrated was dried to give 1.1g yellow oil which was purified by preparative plate to give 620mg of yellow solid, yield: 77.3%. LCMS and HNMR spectra were used to confirm the structure.

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; Wuhan Langlai Science and Technology Development Co., Ltd.; Wuhan Qirui Pharmaceuticals Co., Ltd.; Ge, Jian; Ma, Jianyi; Xiang, Guangya; Wang, Wei; Wang, Chaodong; (44 pag.)CN105237527; (2016); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 56423-63-3, 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 56423-63-3 as follows.

A mixture of ethyl 2-((diphenylmethylene)amino)acetate (6.0 g, 22.47 mmol), 2-bromopyrazine (7.1 g, 44.90 mmol), potassium carbonate (9.30 g, 67.40 mmol) and tetrabutyl ammonium iodide (8.10 g, 22.40 mmol) in N-methyl-2-pyrrolidone (25 mL) was heated in a sealed tube at 110 C. for 16 hours. The mixture was poured into water (100 mL) and extracted with ethyl acetate (3¡Á50 mL). The organic layers were washed with brine (25 mL) and dried over sodium sulfate. Removal of solvent under vacuum afforded crude product which was purified in Combi-Flash instrument using a gradient of methanol in chloroform. Yield: 4.90 g (63%). 1H NMR (300 MHz, DMSO-d6) delta: 1.16 (t, 3H), 4.07 (q, 2H), 5.26 (s, 1H), 7.18 (dd, 2H), 7.38-7.61 (m, 8H), 8.56 (d, 1H), 8.57 (d, 1H), 8.60 (s, 1H). MS (ES) MH+: 346.3 for C21H19N3O2.

According to the analysis of related databases, 56423-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; BASARAB, Gregory Steven; GOWRAVARAM, Madhusudhan Reddy; HAUCK, Sheila Irene; ZHOU, Fei; US2014/206677; (2014); 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. 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 72788-94-4

Triethylamine (4.17 mL, 3.0 mmol) and mesyl chloride (1.57 mL, 2.00 mmol) were added to a solution of (5-chloro-2-pyrazinyl)methanol (1.44 g, 10.0 mmol) in anhydrous THF (20 mL) at 00C. The mixture was stirred at 00C for 0.5 h then partitioned between EtO Ac/water. The organic fraction was dried (MgSO4) and the solvent was removed under reduced pressure to give the crude mesylate. The mesylate was dissolved in acetone (40 mL), sodium iodide (7.5 g, 50 mmol) was added and the mixture was refluxed for Ih. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc/water. The residue was chromatographed on silica gel (DCM) to give 2- chloro-5-(iodomethyl)pyrazine. Sodium hydride (60% w/w, 0.36 g, 9.0 mmol) was added to a solution of(S)-2-nitro-6,7-dihydro-5H-imidazo[2,l-b][l,3]oxa-zin-6-ol (0.93 g, 5.02 mmol) and 2-chloro-5-(iodomethyl)pyrazine (1.54 g, 6.05 mmol) in DMF (10 mL) at -78C. The mixture was stirred at 00C for 1 h and then quenched with ice. EtOAc (200 mL) was added, the organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with a gradient (0-5%) MeOH/EtOAc to give the title compound (1.015 g, 65%) as a white solid. APCI MS m/z 312.6 (M + H). 1H NMR (400 MHz, (CD3)2SO) delta 8.76 (d, J= 1.4 Hz, IH), 8.50 (d, J= 1.4 Hz, IH), 8.02 (s, IH), 4.85 (d, J = 13.7 Hz, IH), 4.81 (d, J= 13.7 Hz, IH), 4.70 (td, J= 12.1, 2.6 Hz, IH), 4.49 (bd, J= 12.0 Hz, IH), 4.29-4.38 (m, 2H), 4.25 (dd, J= 13.5, 3.3 Hz, IH).

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 72788-94-4.

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; WO2009/120789; (2009); 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., SDS of cas: 36070-80-1

To a 0 C mixture of 5-chloropyrazine-2-carboxylic acid (1.0 g, 6.31 mmol) in DCM (6.3 mL) was added oxalyl chloride (6.3 mL, 12.6 mmol) and several drops of (0965) DMF. The mixture was stirred at RT overnight, then was concentrated in vacuo to provide the title compound, which was used in the next step without further purification.

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; BRISTOL-MYERS SQUIBB COMPANY; CHENG, Peter Tai Wah; SHI, Yan; KALTENBACH, Robert F. III; WANG, Ying; ZHANG, Hao; (160 pag.)WO2019/126099; (2019); 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. 118853-60-4, name is Methyl 6-aminopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 6-aminopyrazine-2-carboxylate

A solution of methyl 6-amino-2-pyrazinecarboxylate (17 kg, 111 mmol, 1.00 equiv) in N,N-dimethylformamide (100 L) was placed in a 200 L reactor. NBromosuccinimide (56 kg, 333 mol, 3.3 equiv) was added in several portions to above thesolution while maintaining the temperature at 0C. The reaction progress was monitored by TLC (EA: PE = 1: 1) until the starting material was consumed completely. The reaction was quenched with 300 L water/ice. The solids were collected by filtration and dried. The crude product was re-crystallized in a solvent of MeOH (Svol: 1 g). The product (17 kg, purity = 98 %, 54%) was obtained as a yellow solid.1H-NIVIR (300 MHz, DMSO-d6) : 7.36(2H, b), 3.87(3H, s).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CUI, Haifeng; HENNESSY, Alan; JIN, Qi; MILES, Timothy James; MOSS, Stephen Frederick; PEARSON, Neil David; (173 pag.)WO2017/29602; (2017); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 50866-30-3, These common heterocyclic compound, 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde, 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.

To a solution of N,Nbis(4-methoxybenzyl)ethanesulfonamide (Example 12.0, 73.13 g, 0.209 mol, 1.2 equiv.) in anhydrous THF (600 mL) at -78 C was added n-butyl lithium (83.71 mL, 0.209 mol, 2.5 M solution in hexanes, 1.2 equiv.) via additional funnel slowly, and the resulting mixture was stirred for 10 mm. Then a solution of 5-methylpyrazine-2-carbaldehyde (Example 33.1, 21.3 g, 0.174 mol, 1.0 equiv.) in anhydrous THF (150 mL) was added, and the resulting mixture was stirred at the same temperature for 45 mm and then allowed to warm to RT for 2 h. The reaction mixture was quenched by the addition of aqueous ammonium chloride (200 mL) and extracted with EtOAc (2 x 2 L). The combined organic layers were washed with brine (2 x 500 mL) (Note: no productwas observed in the ammonium chloride or brine layer). After drying over anhydrous Na2SO4, the filtrate was concentrated in vacuo, to afford an oil. The oil was purified by flash column chromatography (silica gel, 23 0-400 mesh) to afford the two isomers. The faster moving isomer (32 g as a white solid) was obtained from the column with a gradient of 10 % to 30 % EtOAc in petroleum ether. 1H NMR (400 MHz, DMSO-d6) 0 8.61 (d, J 1.5 Hz, 1H), 8.51 (d, J= 1.5 Hz, 1H), 7.22-7.11 (m, 4H), 6.90-6.80 (m, 4H), 6.10 (d, J= 5.9 Hz, 1H), 5.29 (dd,J= 5.9, 2.2 Hz, 1H), 4.36-4.16 (m, 4H), 3.73 (m, 6H), 3.70-3.66(m, 1H) 2.50 (merged with solvent peak, 3H) and 1.10 (d,J= 7.0 Hz, 3H). LCMS-ESI (pos.) m/z:472.4 (M+H)t; Further elution of themixture with a gradient of 30 % to 35 % EtOAc in petroleum ether yielded Example 33.3 (16 g, pale yellow gummy liquid). 1H NMR (400 MHz, CDC13) oe 8.62 (d, J= 1.6 Hz, 1H), 8.44 (d,J= 1.5 Hz, 1H), 7.25-7.12 (m, 4H), 6.93-6.82 (m, 4H), 5.17 (d,J= 7.1 Hz, 1H), 4.47 (d, J= 15.2 Hz, 3H), 4.14 (d, J 15.4 Hz, 2H), 3.82 (d, J 1.8 Hz, 6H), 3.66-3.61 (m, 1H), 2.60 (d, J = 2.0 Hz, 3H), and 1.08 (dd, J = 7.2, 2.1 Hz, 3H). LCMSESI (pos.) m/z:472.4 (M+H)t

Statistics shows that 5-Methylpyrazine-2-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 50866-30-3.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; (434 pag.)WO2018/93577; (2018); 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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H7N3O2

(Step 6-i) To a solution of methyl 3-aminopyrazine-2-carboxylate (5 g, 32.65 mmol) in 20 mL warm acetic acid was added to 2.8 mL of bromine dropwise. The reaction mixture was allowed to stand for 10 min, then added to 150 mL of water. The precipitate was collected and washed with water. After drying in vacuo, the resulting orange solid, methyl 3-amino-6-bromopyrazine-2-carboxylate, can be used directly without further purification.

According to the analysis of related databases, 16298-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/36272; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 55557-52-3, 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 55557-52-3 as follows.

Step 7: synthesis of Ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate (7)A mixture of 3-chloropyrazine-2-carbonitrile (17.9 g, 128 mmol), sodium carbonate (17.7 g, 167 mmol) and ethyl-2-mercaptoacetate (18.4 mL, 167 mmol) in ethanol (120 mL) was heated to reflux for 4.5h. Quenched with water (1.5 L) and stirred for 30 min. The resulting precipitate was collected and washed with water. The residue was dissolved in diethyl ether and a black precipitate was filtrated off. Ether was evaporated to give pure compound ethyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate 7 (19.6 g, 68.5 %). 1H-NMR (400 MHz, CDC13) 1.42 (t, J= 7.2 Hz, 3H), 4.40 (q, J= 7.2 Hz, 2H), 6.19 (br s, 1H), 8.58 (d, J= 2.2 Hz, 1H), 8.63 (d, J= 2.2 Hz, 1H).

According to the analysis of related databases, 55557-52-3, 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