Tag: M.W=100-200

Related Products of 75907-74-3, 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. 75907-74-3 name is (3,5,6-Trimethylpyrazin-2-yl)methanol, 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.

Weigh 2-hydroxymethyl-3,5,6-trimethylpyrazine (3.0 g, 25 mmol),Dissolved in 50mL of absolute ethanol,Manganese dioxide powder (4.34 g, 50 mmol) was added with stirring.The reaction was carried out under heating and reflux for 6 h.Cooling the reaction solution,Add diatomaceous earth and filter under reduced pressure.After the filter cake is rinsed with ethanol,Merged with the filtrate,Evaporation of the solvent gave a pale yellow solid.Is a crude product of 3,5,6-trimethylpyrazine-2-formaldehyde,Then perform rapid column chromatography separation,Light yellow solid,That is pure 3,5,6-trimethylpyrazine-2-carboxaldehyde,Yield 90%,Melting point 84-85 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (3,5,6-Trimethylpyrazin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Shandong University; Liu Xinyong; Zou Jinmi; Zhan Peng; (14 pag.)CN108484511; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 27825-20-3, 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. 27825-20-3, name is Methyl 3-Hydroxy-2-pyrazinecarboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 99 methyl 3-((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methoxy)pyrazine-2-carboxylate; [00197J l-(3-fluorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea (Intermediate XXIII,1.0 mmol) and methyl 3-hydroxypyrazine-2-carboxylate (1.0 mmol) were dissolved in N- methylpyrrolidinone (3 ml) and K2CO3 (1.1 eq) was added. The mixture was stirred overnight. 20 ml water was added and the product was extracted three times with dichloromethane. The organic was dried over Na?SCu, filtered, and concentrated. The crude was purified by column chromatography using 0-70% gradient of saturated ammonia/MeOH and dichloromethane. 1H NMR (400 MHz, DMSOd6): ¡ì 10.73 (s, IH), 7.89 (d, IH), 7.40 (d, IH), 7.35 (m, IH), 6.95-7.10 (m, 3H), 6.94 (m, 2H), 5.04 (s, 2H), 4.31 (d, 2H), 3.79 (s, 3H). MS (ES+): M/Z 418 (M+l).

The synthetic route of Methyl 3-Hydroxy-2-pyrazinecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REPLIDYNE, INC.; WO2008/11191; (2008); 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. 74290-65-6, name is 3-Bromo-5-methylpyrazin-2-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Bromo-5-methylpyrazin-2-amine

[00791] To a mixture of 3-bromo-5-methyl-pyrazin-2-amine (31 g, 164.87 mmol) in MeOH (150 mL) was added NaOMe (14 g, 263.79 mmol) in one portion at 30 C under N2. The mixture was stirred at 100 C for 6 hrs. The mixture was concentrated under reduced pressure and the resulting residue was dissolved in water (100 mL). The mixture was extracted with EtOAc and the combined organic layers were washed with brine (20 mL), dried with Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (to afford 3-methoxy-5-methyl-pyrazin-2-amine (21 g, 92% yield) as a white solid. 1H MR (400 MHz, CDCh-d) delta ppm 7.39 (s, 1H) 4.59 (br s, 2 H) 3.97 (s, 3 H) 2.29 (s, 3 H)

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; REVOLUTION MEDICINES, INC.; BLANK, Brian R.; PITZEN, Jennifer; WANG, Gang; WON, Walter S.; TZITZILONIS, Christos; LI, Jie Jack; KOLTUN, Elena S.; AAY, Naing; BUCKL, Andreas; MELLEM, Kevin; SEMKO, Christopher; JOGALEKAR, Ash; KISS, Gert; GILL, Adrian; (298 pag.)WO2018/136265; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4430-75-5, The chemical industry reduces the impact on the environment during synthesis 4430-75-5, name is Octahydro-2H-pyrido[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

General procedure: 5.1.2. General procedure 1 (GP1). The amine (1.0equiv) in ethanol (1mL per mmol amine) was added to the alkyl halide (1.1equiv) and sodium carbonate (3equiv) in ethanol (2mL per mmol amine). The reaction was heated to reflux for 2-3h then water (5mL per mmol amine) and aqueous sodium carbonate (1M, 5mL per mmol amine) were added. The product was extracted with ethyl acetate (3 times, 20mL per mmol amine) and the organic layers combined. Dowex 50WX2 hydrogen form 100-200 mesh (4g per mmol amine) was washed with methanol (10mL per gram resin). The reaction mixture was loaded onto the ion exchange resin using gravity filtration and the resin was washed with methanol (10mL per gram resin). The product was eluted off the resin with ca. 1M NH3 in methanol (10mL per gram resin) and the solution was concentrate to give the product

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, Octahydro-2H-pyrido[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kelly, Nicholas M.; Wellejus, Anja; Elbr¡ãnd-Bek, Heidi; Weidner, Morten Sloth; J¡ãrgensen, Signe Humle; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 3334 – 3347;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, 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. Formula: C5H4N4

To a stirring mixture of 5-aminopyrazine-2-carbonitrile (433 mg, 3.61 mmol) in THF (10 mL) was slowly added sodium hydride (240 mg, 6.02 mmol) below 15 C. The reaction mixture was stirred at room temperature for 1 h. To the above mixture was added compound 305-3 (1.0 g, 3.01 mmol). The resulting mixture was stirred at 60 C for 4 h. The reaction mixture was quenched with ice-water and extracted with ethyl acetate. The organic layer was dried over Na2504 and concentrated to afford the title compound 306-3 (1.5 g, crude) as a yellow oil. LCMS:405.0[M+1].

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

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 4744-50-7, 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 4744-50-7 as follows.

17a. 3-(N-(2-Methyl-2-sulfanylpropyl)carbamoyl)pyrazine-2-carboxylic acid A suspension of 2-mercapto-2-methyl-1-propylamine hydrochloride (1.14 g, 8 mmol) in dichloromethane (15 mL) was cooled to 0 C. and then treated with triethylamine (1.23 mL, 0.9 g, 8.9 mmol) followed by furano(3,4-b)pyrazine-5,7-dione (1.2 g, 8 mmol). The reaction mixture was stirred at 0 C. for 40 minutes then at room temperature for 1 hour. The solvent was removed by evaporation and the residue triturated with hexane/ether to give the title compound (1.2 g, 59%). Mp 141-144 C. 1H NMR (300 MHz, DMSO-d6) delta8.83-8.86 (m, 3H), 3.45 (d, J=6.4 Hz, 2H), 2.87 (s, 1H), 1.33 (s, 6H).

According to the analysis of related databases, 4744-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fang, Xinqin; Garvey, David S.; Gaston, Ricky D.; Lin, Chia-En; Ranatunga, Ramani R.; Richardson, Stewart K.; Wang, Tiansheng; Wang, Weiheng; Wey, Shiow-Jyi; US2003/203915; (2003); 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 54608-52-5 as follows. Application In Synthesis of 2-Hydrazinopyrazine

Example 2: Synthesis of (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-lH-l,2,4-triazol- 1 -yl)-N’-(pyrazin-2-yl)acr lohydrazide (1-3 .A 50-mL, 3-necked, round-bottomed flask was charged with a suspension of (Z)-3-(3- (3,5-bis(trifluoromethyl)phenyl)-lH-l,2,4-triazol-l-yl)acrylic acid (0.200 g) in 1 :1 CH2C12: AcOEt (25 mL). 2-Hydrazinopyrazine (0.062 g) was added at -40 C followed by T3P (50%) (0.432g) and DIPEA (0.147 g). The reaction mixture was stirred for 30 min at -40 C before being concentrated under reduced pressure (35 C, 20 mmHg). The crude oil was purified by preparative TLC using 5% MeOH in CH2C12 as mobile phase (under ammonia atmosphere) to afford 40 mg (yield: 16%) of (Z)-3-(3-(355-bis(trifluoromethyl)phenyl)-lH-l,2,4-triazol-l- yl)-N’-(pyrazin-2-yl)acrylohydrazide. 1H NMR (400 MHz, DMSO-d6) delta ,10.53 (s, 1H), 9.59 (s, 1H), 9.14 (s, 1H), 8.53 (s, 2H), 8.29 (s, 1H), 8.13 (s, 1H), 8.06-8.07 (m, 1H), 7.92-7.93 (d, J=2.8 Hz, 1H), 7.51-7.53 (d, J=10.4 Hz, 1H), 6.07-6.10 (d, J=10.4 Etazeta,IotaEta); LCMS for CnHi2F6N70 [M+H]+ predicted: 444.31, found: 444.49 (RT 2.70 min, purity: 95.78%).

According to the analysis of related databases, 54608-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SANDANAYAKA, Vincent, P.; SHACHAM, Sharon; MCCAULEY, Dilara; SHECHTER, Sharon; WO2013/19548; (2013); 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. 13924-95-3, name is Methyl 5-hydroxypyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 13924-95-3

Step 1: (0546) To 5-hydroxypyrazine-2-carboxylic acid methyl ester (2.0 g, 13 mmol) in a glass tube reaction vessel in DMF (26 mL) was added potassium carbonate (5.3 g, 39 mmol) and sodium 2-chloro-2,2-difluroacetate (4.0 g, 26 mmol). The reaction vessel was capped and warmed to 100 C. The reaction was stirred for 30 minutes and cooled to room temperature. The reaction was filtered washing with EtOAc. The filtrate was concentrated in vacuo. The residue was taken up into EtOAc and washed with brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc/hex) to give methy-5-(difluoromethoxy)pyrazine-2-carboxylate (0.09 g, 0.46 mmol) (0.40 g, 20%).

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; MERCK SHARP & DOHME CORP.; Scott, Jack D.; Stamford, Andrew W.; Gilbert, Eric J.; Cumming, Jared N.; Iserloh, Ulrich; Misiaszek, Jeffrey A.; Li, Guoqing; US2015/307465; (2015); 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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5HCl2N3

Under inert atmosphere, a mxture of 3,5dichoropyrazine2carbonitrNe (1 equiv.), 2 methylpyridine3boronic acid pinacol ester (I equiv.), cesium carbonate (3 equiv.) and PdCl2(dppf).CH2C2 (0.1 equiv.) in doxane (0.10 moLL1) and water (0.80 moLL1) was heatedat 80 C for 1 hour. The reaction mixture was hydroysed and extracted twice with ethy acetate. The organic layers were combined, washed with brine, dried over MgSO4, concentrated under vacuum and purfied by flash column chromatography on sWca gel (usng 20% to 100% ethy acetate (EtOAc) in cyclohexane as eluent) to afford the product as a brown solid in 57% yield. 1HNMR (400 MHz, DMSOD6): 9.17 (s, 1H, Ar); 8.65 (dd, J4.8, 1.7 Hz, 1H,Ar); 8.02 (dd, J 7.8, 11 Hz, 1H, Ar); 7.46 (dd, J 7.8, 4.8 Hz, 1H, Ar); 2.62 (s, 3H, CH3). M/Z (M[35Cl]+H) = 230.9.

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 313339-92-3.

Reference:
Patent; MAVALON THERAPEUTICS LIMITED; BLAYO, Anne-Laure; CATELAIN, Thomas; DORANGE, Ismet; GENET, Cedric; MANTEAU, Baptiste; MAYER, Stanislas; SCHANN, Stephan; (290 pag.)WO2018/206820; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 5521-55-1, These common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-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.

In methanol (15 ml), 5-methylpyrazine-2-carboxylic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (1.25 g) was dissolved. Then, the solution was added with WSCI hydrochloride (2.59 g) and N,N-dimethylaminopyridine (1.65 g) in this order, followed by stirring at room temperature for 3 hours. The reaction solution was added with water and then extracted with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. The solvent was distilled off and the resulting crude product was then purified through silica gel column chromatography (chloroform/methanol). The purified product was dissolved in ethanol (15 ml) and THF (8 ml) and added with calcium chloride (1.11 g). After that, the reaction solution was cooled to 0C and then gradually added with sodium borohydride (757 mg), followed by stirring at room temperature for 19 hours. The reaction solution was added with a 1 mol/l citric acid solution (40 ml), followed by extraction with ethyl acetate. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate, followed by distilling the solvent off. The residue was dissolved in chloroform (10 ml) and then added with manganese dioxide (chemically processed product) (2.2 g), followed by stirring at room temperature for 1 hour. After completion of the reaction, the catalyst was filtrated out through Celite and the solvent was then distilled off. The crude product obtained was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (35.9 mg) as a colorless oily substance.

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem