Month: April 2021

Electric Literature of 13535-07-4, 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. 13535-07-4, name is 2-Amino-5-ethylpyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Pyridine (1.051 mL, 12.99 mmol) was added dropwise to a stirred solution of phenyl carbonochloridate (1.324 mL, 10.56 mmol) in dichloromethane (DCM) (20 ml) at room temperature and stirred for 30 minutes. Then 5-ethylpyrazin-2-amine (1 g, 8.12 mmol) dissolved in dichloromethane (DCM) (10 ml) was added dropwise at room temperature and stirred at 50 C for 16 h. Allowed the reaction mixture to room temperature, diluted with DCM (3X50 mL), washed with water (2X30 mL) and brine (30 mL). Separated the organic layer and dried over sodium sulfate, filtered and concentrated. Residue was purified by column chromatography using silica gel (100-200 mesh) by 10% ethyl acetate in pet ether as eluent to get desired product as off white fluffy solid (1.6 g, 6.58 mmol, 81%), LCMS (m/z) 244.2 (M+H)+.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, 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. COA of Formula: C6H6N2O2

A solution of the product of Example 83A (6.91 g, 50 mmol) in THF (Aldrich, anhydrous, 150 mL) was cooled down to -78¡ã C. and a solution of LiAlH4 (Aldrich, 1.898 g, 50.0 mmol) in THF (50 mL) was added slowly via an additional funnel. The mixture was stirred at -78¡ã C. under N2 for 1 hour, and then it was then carefully and slowly quenched with HOAc (Aldrich, 10 mL) at -70¡ã C. The mixture was slowly warmed up to ambient temperature and stirred for 10 hours. After being concentrated, the residue was stirred with HCl (2N, 15 mL) in CH2Cl2 (300 mL) for 20 minutes and then filtered through diatomaceous earth to remove solid inorganic salt. The organic filtrate solution was concentrated and the residue was dissolved in EtOAc (100 mL) and filtered through diatomaceous earth again. The organic filtrate solution was concentrated to give the titled compound. 1H NMR (300 MHz, DMSO-d6) delta 8.91 (dd, 1H), 8.94 (d, 1H), 9.12 (d, J=1.6 Hz, 1H), 10.08 (s, 1H) ppm; MS (DCI/NH3) m/z 109 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; US2009/306096; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 330786-09-9,Some common heterocyclic compound, 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, molecular formula is C6H4Cl2N2O2, 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 mixture of methyl 3,5-dichloropyrazine-2-carboxylate (2.0 g, 9.7 mmol, synthesized via Step a of Intermediate A), trimethyl-l,3,5,2,4,6-trioxatriborinane (2.4 g, 19.3 mmol), Pd(PPh3)4 (558 mg, 483 pmol) and Cs2C03 (6.3 g, 19.3 mmol) in dioxane (70 mL) was stirred at 110 C for 12 hours under N2 atmosphere. The reaction mixture was concentrated in vacuo to give a residue, which was purified by silica gel chromatography (ethyl acetate in petroleum ether = 0% to 50% ) to afford methyl 3-chloro-5-methylpyrazine- 2-carboxylate (250 mg, 14% yield) as a yellow solid. LCMS m/z [M+H]+ = 187.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,5-dichloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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 24241-18-7, name: 2-Amino-3,5-dibromopyrazine

Intermediate Example 1 -2: Preparation of (6,8-dibromoimidazo[1 ,2-a]pyrazin-2- yl)methanolStep A: Preparation of ethyl 6,8-dibromoimidazo[1 , 2-a]pyrazi’ne-2-carboxylateTo a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10 C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over a2(S04) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 %) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz, CDCI3): delta =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.

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-Amino-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80234; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 56423-63-3, name is 2-Bromopyrazine, molecular formula is C4H3BrN2, 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. SDS of cas: 56423-63-3

5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3,6-dihydropyridine-1 (2H) -carboxylic acid Tert-butyl ester (200mg, 0.65mmol)And 3-bromopyridine (51.1mg, 0.323mmol) into a bottle,Add 1,2-dimethoxyethane (4 mL)And 2M aq. Na2CO3 (1.5 mL).After removing oxygen from the reaction system, Pd (dppf) Cl2-CH2Cl2 (26.4 mg, 0.032 mmol) was added.The reaction was heated at 95 C overnight, diluted with water and extracted with ethyl acetate.Dry and concentrated,Purification by column gave the target compound YB119.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 56423-63-3, its application will become more common.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Jia; Wang Zengtao; Zhang Shiyan; Zang Yi; Wang Peipei; Sun Dandan; Zhang Hanyan; (155 pag.)CN110818683; (2020); A;,
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. 33332-28-4, name is 2-Amino-6-chloropyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Amino-6-chloropyrazine

6-Pyridin-2-ylpyrazin-2-amine An oven dried resealable Schlenk tube was charged with 2-amino-6-chloropyrazine (1.00 g, 7.72 mmol), 2-(tributylstannyl)pyridine (3.55 g, 7.72 mmol) and xylene (40 ml_). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tetrakis(triphenylphosphine)palladium (446 mg, 0.38 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 15O0C oil bath. After 2Oh, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase was extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Silica gel flash chromatography (dichloromethane/methanol 98:2 to dichloromethane/methanol 90:10) provided the title compound as a light brown solid (950 mg, 71percent). delta 1H-NMR (CDCI3): 8.90 (s, 1H), 8.70 (d, 1H), 8.20 (d, 1H), 8.00 (s, 1H), 7.80 (dd, 1 H). 7.30 (m, 1 H), 4.65 (s, 2H).ESI/MS m/e: 173 ([M+H]+, C9H8N4)

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; ALMIRALL PRODESFARMA, S.A.; WO2007/17096; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 33332-29-5, The chemical industry reduces the impact on the environment during synthesis 33332-29-5, name is 2-Amino-5-chloropyrazine, I believe this compound will play a more active role in future production and life.

General procedure: Method B is a modification of Method A and was performed under nitrogen atmosphere andwith extended work-up. Substituted benzoyl chloride (1.5 mmol, 1.2 equiv) was placed into the askunder nitrogen, diluted with dry DCM (5 mL) and dry pyridine (400 mg, 5 mmol, 4 equiv) was added.The mixture was mixed for 5 min under nitrogen. Then, 5-chloropyrazin-2-amine (162 mg, 1.25 mmol,1 equiv) dissolved in DCM (10 mL) was added dropwise over 10 min under nitrogen ow. The askwas closed by septum and stirred for additional 6 h. After reaction, the mixture was diluted with DCMto the final volume of 40 mL and washed with water (1 30 mL), 5% (m/m) aqueous NaHCO3 solution(1 30 mL), and brine (1 30 mL). The organic layer was dried over anhydrous Na2SO4 and adsorbedon silica (4 g) by evaporating the solvents under reduced pressure. Automated flash chromatographywas run using same conditions as described in Method A. If needed, the products were recrystallizedfrom hot EtOH (crystallization initiated by cooling and dropwise addition of cold water).

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

Reference:
Article; Zitko, Jan; Mindlova, Al?b?ta; Vala?ek, Ond?ej; Jand’ourek, Ond?ej; Paterova, Pavla; Janou?ek, Ji?i; Kone?na, Klara; Dole?al, Martin; Molecules; vol. 23; 9; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 89283-32-9, 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. 89283-32-9, name is (3-Chloropyrazin-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows.

To (3-chloropyrazin-2-yl)methanol of step 1 was dropwise added a solution of SOCI2 (700mg, 5.89mmol) in DMF (10ml) at 0C. Stirring at 0C for 30 min was followed by extraction with ethyl acetate. The organic layer was washed with a saturated NaHC03 solution, dried over anhydrous magnesium sulfate, filtered, and concentrated in a vacuum. The residue was used in a subsequent step without further purification.

The chemical industry reduces the impact on the environment during synthesis (3-Chloropyrazin-2-yl)methanol. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DONG-A ST CO.,LTD; PARK, Jang Hyun; SONG, Seung Hyun; CHUNG, Han Kook; KIM, Heung Jae; LEE, Ji Hye; JANG, Byeong Jun; KIM, Eun Jung; JUNG, Hae Hum; RYU, Chae Lim; HWANG, Jae-Sung; LEE, Hyung Ki; KANG, Kyung Koo; KIM, Soon Hoe; WO2014/157994; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

19847-12-2, name is Pyrazinecarbonitrile, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C5H3N3

2-cyano-pyrazol 1g (10.5 g, 100 mmol) was dissolved in 150 mL 1,4- dioxane was added 1.0 g Raney nickel in 250 mL autoclave at 60 , 40 atm of hydrogen the reaction was stirred for 8 hours. Filtered, and the filtrate was concentrated under reduced pressure, to give C- pyridin-2-yl – methylamine 1h (10.7 g, brown oil). Yield: 98%.

The synthetic route of 19847-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JIANGSU HENGRUI MEDICINE CO., LTD.; SHANGHAI HENGRUI PHARMACEUTICAL CO., LTD.; TANG, PENG CHO; SUN, PIAOYANG; YANG, FANGLONG; LIANG, JINDONG; SHEN, GUANGYUAN; WANG, YANG; FAN, JIANG; (44 pag.)TWI522358; (2016); B;,
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. 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 113305-94-5

Preparation 15; -32-(E)-5-(3 -(2-Methoxy-6-(4-methoxybenzyloxy)phenyl)- 1 -(methylthio)-3 -oxoprop- 1 – enylamino)pyrazine-2-carbonitrile; To a dry, inert 22 L flask are added sodium hydride (159.2 g, 3.98 mol) and tetrahydrofuran (10.4 L). The mixture is cooled to 5 – 15 0C. 5-Isocyanopyrazin-2- amine (382.2 g, 3.18 mol) is added in four portions over 30 min to control the release of hydrogen, allowing foaming to subside between additions and maintaining the temperature at 10 0C. The mixture is stirred for 15 – 90 min while allowing the temperature to increase to 15 0C. To the reaction mixture is charged with l-(2-methoxy- 6-(4-methoxybenzyloxy)phenyl)-3,3-bis(methylthio)prop-2-en-l-one (1036 g, 2.65 mol) in portions to control foaming. The resulting slurry is stirred for 15 min. The mixture is heated to a gentle reflux at 66 0C. The reaction conversion is monitored by HPLC. The reaction mixture is quenched into chilled water (14.2 L) followed by extractive work up with ethyl acetate. The organic portion is concentrated to form a slurry which is filtered to provide 957 g (78%) of the title compound, mp 128 – 135 0C; ES/MS m/z 463.2

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; ELI LILLY AND COMPANY; FAROUZ, Francine, S.; HOLCOMB, Ryan, Coatsworth; KASAR, Ramesh; MYERS, Steven, Scott; WO2010/77758; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem