Month: February 2021

Related Products of 768-05-8,Some common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, molecular formula is C5H6N4O, 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: The desired compounds 1a-g and 2a-f were prepared by reaction between pyridoxal hydrochloride (0.15 g, 0.74mmol) and the appropriate aromatic or heteroaromatic hydrazine or N-acylhydrazine (1.1 eq., 0.81mmol) in ethanol (10.0 mL). The reaction mixture was stirred for 1-48 hours at room temperature. After that, product was purified by wash-ing with cold ethanol (3.0 mL) and cold diethyl ether (3.0 mL), leading to the pure derivatives 1a-g and 2a-f as solid in 42-86% yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Pyrazinoic acid hydrazide, its application will become more common.

Reference:
Article; Nogueira, Thais Cristina Mendonca; Cruz, Lucas Dos Santos; Lourenco, Maria Cristina; de Souza, Marcus Vinicius Nora; Letters in drug design and discovery; vol. 16; 7; (2019); p. 792 – 798;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4745-93-1, 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 4745-93-1 as follows.

1.1 A solution of 2.57 g (11.0 mmol) of iodine in 15 ml of DMF is added dropwise to a mixture of 1.25 g (10.0 mmol) of 5H-pyrrolo[2,3-b]pyrazine and 1.65 g (25.0 mmol) of solid potassium hydroxide in 15 ml of DMF, and the mixture is subsequently stirred at room temperature for 45 minutes. The reaction mixture is poured into 200 ml of ice-water (containing 0.5% by weight of ammonia and 0.1% by weight of sodium disulfite) and left at 5 C. for 12 hours. The resultant precipitate is filtered off with suction, washed with 100 ml of ice-water and dried in vacuo: 7-iodo-5H-pyrrolo[2,3-b]pyrazine as yellow solid.

According to the analysis of related databases, 4745-93-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; Dorsch, Dieter; Wucherer-Plietker, Margarita; Mueller, Thomas J.J.; Merkul, Eugen; US2013/217951; (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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Product Details of 939412-86-9

To a solution of 3-(l -methoxy-2-methyl-l -oxopropan-2-yl)cyclohexanecarboxylic acid (1500 mg, 6.57 mmol) in THF (20 ml) was added HATU (3748 mg, 9.86 mmol), DIEA (3.44 ml, 19.71 mmol) and(3-chloropyrazin-2-yl)methanamine hydrochloride (1538 mg, 8.54 mmol) in one portion. After the addition was completed, the mixture was stirred at 25 C for 12h. The The reaction was quenched by addtion of water. The mixture was extracted with ethyl acetate several times. The combined organics was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residure was purified by column chromagrophy on silica gel (PE/THF=4) to afford methyl 2-(3-(((3-chloropyrazin-2- yl)methyl)carbamoyl)cyclohexyl)-2-methylpropanoate as a light solid. XH NMR (400 MHz, METHANOL-^) delta ppm 1.01 – 1.07 (m, 1 H) 1.12 (s, 6 H) 1.26 (d, J=12.13 Hz, 1 H) 1.32 – 1.38 (m, 2 H) 1.57 – 1.62 (m, 1 H) 1.69 – 1.77 (m, 2 H) 1.86 (br. s., 2 H) 2.30 – 2.36 (m, 1 H) 3.65 (s, 3 H) 4.60 (s, 2 H) 8.31 – 8.34 (m, 1 H) 8.50 – 8.52 (m, 1 H) ppm.

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.; LIU, Jian; KOZLOWSKI, Joseph, A.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; LIU, Shilan; (85 pag.)WO2016/109219; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, 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. HPLC of Formula: C6H8ClF3N4

General procedure: To the stirred reaction mixture of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyrazine hydrochloride(11) (300 mg, 1.32 mmol), TEA (0.55 mL, 3.95 mmol)and toluene (10 mL), substituted cyanates 12(a-e)/isocyanates12(f-j) (1.32 mmol) were added at ambient temperature.The reaction mass was agitated at 75-80 C until thecompletion of the reaction that was monitored by TLC. Thereaction mass was allowed to cool at ambient temperatureand it was washed sequentially with 3% aqueous HCl(5.0 mL) and then water (5.0 mL). The organic fraction wasconcentrated under vacuum at 50-55 C to obtain crudeproduct. It was purified by column chromatography using10-50% of EtOAc:hexane mixture as a mobile phase.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 762240-92-6, its application will become more common.

Reference:
Article; Mannam, Madhava Rao; Devineni, Subba Rao; Pavuluri, Chandra Mouli; Chamarthi, Naga Raju; Kottapalli, Raja Sekhara P.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 9; (2019); p. 922 – 932;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 21279-62-9, 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 21279-62-9 as follows.

General procedure: The starting compound (1.27 mmol) was treated with 18 aliphatic amines, alicyclic amines or saturated heterocycles containing at least one nitrogen atom (2.54 mmol). Four reactions were completed by conventional heating methods. The conditions were 110 C, toluene as a solvent and pyridine (1.27 mmol) as a base. The reaction time was set to one hour. Then the reactions were completed using the microwave reactor with focused field and conditions used for syntheses were 140 C, 30 min,120 W, methanol used as a solvent and pyridine (1.27 mmol) as a base. They were set experimentally with respect to prior experience. The progress of reaction was monitored with TLC in system hexane/ethyl acetate (1:1). Then the mixture was separated by flash column chromatograph using gradient elution. Mobile phases were hexane and ethyl acetate again.

According to the analysis of related databases, 21279-62-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jandourek, Ondrej; Dolezal, Martin; Kunes, Jiri; Kubicek, Vladimir; Paterova, Pavla; Pesko, Matus; Buchta, Vladimir; Kralova, Katarina; Zitko, Jan; Molecules; vol. 19; 7; (2014); p. 9318 – 9338;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 939412-86-9, These common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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.

(S)-benzyl 2-((3-chloropyrazin-2-yl)methylcarbamoyl)piperidine-1-carboxylate To a solution of (3-chloropyrazin-2-yl)methanamine.HCI (3.60 g, 19.98 mmol, 40% wt) and (S)- 1-N-Cbz-pipecolinic acid (2.63 g, 9.99 mmol) in dichloromethane (40 mL) was added triethylamine (2.78 mL, 19.98 mmol) and the reaction mixture was cooled to 0C. After 15 min stirring at 0C, HATU (4.18 g, 10.99 mmol) was added. The mixture was stirred for 1 hour at 0C and then overnight at room temperature. The mixture was washed with 0.1 M HCI-solution, 5% NaHC03, water and brine, dried over sodium sulfate and concentrated in vacuo. The product was purified using silica gel chromatography (dichloromethane/methanol = 99/1 to 97/3 v/v% + triethylamine) to give 2.12 g of (S)-benzyl 2-((3-chloropyrazin-2- yl)methylcarbamoyl)piperidine-1-carboxylate (54.6%).

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSD OSS B.V.; MAN, de Adrianus, Petrus, Antonius; WIJKMANS, Jacobus C.H.M.; STERRENBURG, Jan-Gerard; RAAIJMAKERS, Hans C.A.; BARF, Tjeerd A.; BUIJSMAN, Rogier, Christian; OUBRIE, Arthur A.; REWINKEL, Johannes, Bernardus, Maria; JANS, Christiaan, Gerardus, Johannes, Maria; STOCK, Herman, Thijs; WO2013/10869; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 313339-92-3,Some common heterocyclic compound, 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, molecular formula is C5HCl2N3, 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.

The (4-tert-butoxy-carbonyl-aminophenyl) boric acid pinacone ester (8.26g) is added to include the magnetic stirring rod and 3,5-di-chloro-pyrazine-2-carbonitrile (5.0g), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (1.68g) and cesium carbonate (28.1g) in the reaction container, subsequently joined 100 ml dioxane and 10 ml of water, the mixture is heated under stirring to 100 C. 1h reaction mixture after cooling to the room temperature and with the saturated aqueous solution of sodium bicarbonate (100 ml) for quenching and EtOAc (3¡Á200 ml) extraction. The combined organic phase is dried with sodium sulfate, filtered and evaporation to obtain brown oily crude product, the fast by silica gel chromatography using EtOAc and heptane mixture of purification as an eluent. The obtained product is used methyl tert butyl ether recrystallization and in the vacuum drying to obtain light yellow solid [4 – (6-chloro-5-cyano-pyrazine-2-yl)-phenyl]-amino- formic acid tert-butyl ester. Yield: 6.92g (73%).

The synthetic route of 313339-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sanofi; Nazare, M; HALLAND, N; SCHMIDT, F; WEISS, T; Dietz, U; Hofmeister, A; (76 pag.)CN103012407; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6164-79-0, 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. 6164-79-0, name is Methyl 2-pyrazinecarboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A stirred solution of methyl 2-pyrazinecarboxylate(4.94 g, 35.8 mmol) in methanol (350 mL)was slowly added sodium borohydride (5.410 g, 143 mmol)in 1 g portions over 10 min. Caution: The solution becameyellow and evolved heat and gas, add the sodium borohydridecautiously. The solution was stirred overnightat room temperature. H2O (20 mL) was added and thereaction was shaken vigorously. The suspension was thenevaporated to dryness under reduced pressure to an oilyyellow powder. Ethyl acetate (350 mL) was then added andthe resulting suspension was stirred vigorously overnight.The suspension was filtered and evaporated to drynessunder vacuum to give the crude product as a yellow oilwhich was used without further purification (2.80 g, ca.71%). 1H NMR (300 MHz, CDCl3): delta (ppm) 8.64 (br, 1H, H-3),8.53 (m, 1H, H-2), 8.50 (m, 1H, H-1), 4.84 (s, 2H, CH2).

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

Reference:
Article; Feltham, Humphrey L. C.; Cowan, Matthew G.; Kitchen, Jonathan A.; Jameson, Guy N. L.; Brooker, Sally; Supramolecular Chemistry; vol. 30; 4; (2018); p. 296 – 304;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1208082-91-0, 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. 1208082-91-0, name is 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-(2-methyl-oxazol-5-yl)-phenylamine (615 mg, 3.53 mmol), intermediate 101 (933 mg, 3.21 mmol), and DIPEA (1.24 g, 9.62 mmol) in CH3CN (10 ml) were heated at 200 0C under microwave irradiation for 1.5 h. The volatiles were evaporated under reduced pressure and the residue was partitioned between DCM and H2O. The organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by flash chromatography over silica gel (eluent: DCM/ MeOH(NH3) 95/5). The fractions containing product were collected and the solvent was evaporated. The residue was purified further by preparative HPLC [RP Shandon Hyperprep Cl 8 BDS (8 mum, 250 g, LD. 5 cm); mobile phase: (0.25 % NH4CO3 sol. in water, MeOH)]. The product fractions were collected and concentrated under reduced pressure. Yield: 0.031 g of compound 179 (3 %).

The chemical industry reduces the impact on the environment during synthesis 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; VELTER, Adriana, Ingrid; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; WU, Tongfei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; PIETERS, Serge, Maria, Aloysius; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; OEHLRICH, Daniel; WO2010/89292; (2010); 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. 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 63286-28-2

Step 1 : To a solution of tetrahydrofuran-3-carboxylic acid (1 .0 g, 8.6 mmol) in DMF (15 ml) was added HATU (3.60 g, 9.47 mmol), DIPEA (1 .22 g, 1 .66 ml, 9.47 mmol) and finally 2-chloro-3-hydrazinylpyrazine (1 .37 g, 9.47 mmol). The mixture was stirred for 3 hours at RT. The reaction mixture was poured into sat. aq. Na2CO3 (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic phases were washed with brine (3×25 mL), dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography using a gradient of ethyl acetate and heptane to yield 1 .1 g (53%) A/’-(3-chloropyrazin-2-yl)tetrahydrofuran-3- carbohydrazide.

According to the analysis of related databases, 63286-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; JESSING, Mikkel; (126 pag.)WO2016/55618; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem