Month: April 2021

Reference of 123-32-0,Some common heterocyclic compound, 123-32-0, name is 2,5-Dimethylpyrazine, molecular formula is C6H8N2, 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.

2, 5-dimethylpyrazine (6 g, 55.6 mmol), carbon tetrachloride (50 mL) were added in a three-necked flask,After stirring, N-chlorosuccinimide (NCS) (7. 4 g, 55.6 mmol) and benzoyl peroxide(0. 05 g, 0.21 mmol),The reaction mixture was irradiated under incandescent light,Stir,Reflux reaction about 18h,TLC [V (ethyl acetate): V (petroleum ether) = 1: 2 as developing solvent] After the detection reaction is substantially complete,The reaction solution was cooled to 0 C,After standing for 1 hour,filter,The filter cake is washed with cold carbon tetrachloride,Combined filtrate and wash solution,Vacuum distillation of carbon tetrachloride,Get a light brown oil,Methylene chloride dissolved,After decolorization of activated carbon,Pale yellow oil,Without further direct reaction to the next step.

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

Reference:
Patent; Anhui University of Chinese Medicine; Hefei Industrial Pharmaceutical Institute Co., Ltd.; Li, JiaMing; He, GuangWei; Hu, MinHua; Huang, WeiJun; Zhu, Xiaoyu; Wang, Jie; Ye, WenFeng; Zhang, EnLi; (10 pag.)CN103664804; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 32974-92-8, These common heterocyclic compound, 32974-92-8, name is 1-(3-Ethylpyrazin-2-yl)ethanone, 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.

General procedure: Previous method was used for preparing Ligands (L1-L7). Ethanol(10 mL, 1 mM) solution of piperidylthiosemicarbazide was added to corresponding aldehyde or ketone (one mole equivalent) and 5 drops of acetic acid glacial, with stirred and refluxed for 4 h. The precipitate was filtered with filter paper and rinsed with Cold ethanol. A vacuum desiccator was applied to dry the precipitate.

Statistics shows that 1-(3-Ethylpyrazin-2-yl)ethanone is playing an increasingly important role. we look forward to future research findings about 32974-92-8.

Reference:
Article; Qi, Jinxu; Yao, Qian; Qian, Kun; Tian, Liang; Cheng, Zhen; Wang, Yihong; Journal of Inorganic Biochemistry; vol. 186; (2018); p. 42 – 50;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 233278-56-3, 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. 233278-56-3, name is 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-bromo-N-[1-(1 H-indol-3-ylmethyl)pentyl]thiazole-5- carboxamide (0.20 g, 0.49 mmol) and 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[1 ,5- a]pyrazine (0.07 g, 0.59 mmol) in dioxane (5 ml_), CS2CO3 (0.24 g, 0.73 mmol) and RuPhos (0.05 g, 0.10 mmol) was added. The reaction mixture was purged with argon for 20 min followed by addition of Pd2(dba)3 (0.05 g, 0.05 mmol) and again purged with argon for 20 min. The reaction mixture was heated at 100C for 3h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was filtered through Celite, washed with 5% MeOH in DCM (30 ml_). The organic layer was separated, washed with H2O15 ml_), brine (15 ml_), dried over anhydrous Na2SC>4 and concentrated in vacuo. The crude residue obtained was purified by column chromatography (silica, 100-200 mesh, 1 to 4% MeOH in DCM) and prep HPLC to afford 2-(6,8- dihydro-5H-[1 ,2,4]triazolo[1 ,5-a]pyrazin-7-yl)-N-[1-(1 H-indol-3- ylmethyl)pentyl]thiazole-5-carboxamide (0.04 g, 18%) as off-white solid.HPLC Purity: 99.4%MS (ESI) m/e [M+H]7Rt/%: 450.00/2.58/97.4% 1H NMR (400 MHz, DMSO-d6) delta 0.82 (t, J=6.85 Hz, 3H) 1.12 – 1.36 (m, 4H) 1.42 – 1.65 (m, 2H) 2.82-2.94 (m, 2H) 3.99 – 4.18 (m, 3H) 4.30 (t, J=5.14 Hz, 2H) 4.81 (s, 2H) 6.93 – 6.99 (m, 1 H) 7.04 (t, J=7.58 Hz, 1 H) 7.10 (s, 1 H) 7.31 (d, J=8.31 Hz, 1 H) 7.57 (d, J=7.82 Hz, 1 H) 7.88 (s, 1 H) 8.01 (s, 1 H) 8.06 (d, J=8.80 Hz, 1 H) 10.76 (brs, 1 H).

The synthetic route of 5,6,7,8-Tetrahydro[1,2,4]triazolo[1,5-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; HALL, Adrian; PROVINS, Laurent; MACCOSS, Malcolm; (72 pag.)WO2018/138088; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 4744-50-7, 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. 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, This compound has unique chemical properties. The synthetic route is as follows.

In a 100 mL flask, 110 2,3-pyrazinedicarboxylic anhydride 12 (0.7505 g, 5 mmol) was reacted with 13 2 (1.0511 g, 5 mmol) in dry 67 THF (10 mL) stirred overnight at rt. The mixture was transferred to a separatory funnel and extracted with CH2Cl2 (3¡Á10 mL) and NaOH (1N) (10 mL). The organic phase was separated and 74 HCl (1N) (10 mL) was added to the aqueous phase until a pH=2 was reached and a 111 precipitate formed. The solid was filtered and washed with water (20 mL), and concentrated under reduced pressure to provide 13 (1.73 g, 4.8 mmol, 96%), as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 1.33 (3H, t, J=7.02 Hz), 2.51 (4H, d, J=1.59 Hz), 4.46 (2H, q, J=7.01 Hz), 7.21 (1H, t, J=7.52 Hz), 7.47 (1H, t, J=7.66), 7.59 (1H, d, J=4.10 Hz), 7.61 (1H, d, J=3.48 Hz), 7.73 (1H, d, J=7.27 Hz), 8.58 (1H, s), 8.63 (2H, s); 13C NMR (100 MHz, DMSO-d6) delta 14.2, 37.5, 109.4, 109.7, 110.95, 119.1, 119.7, 120.6, 122.3, 122.6, 126.2, 131.8, 136.8, 140.5, 141.8, 144.8, 145.8, 164.3.

The chemical industry reduces the impact on the environment during synthesis 2,3-Pyrazinecarboxylic anhydride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITY OF PUERTO RICO; HERNANDEZ-O’FARRILL, Eliud; VLAAR, Cornelis P.; DHARMAWARDHANE FLANAGAN, Suranganie; CASTILLO-PICHARDO, Linette; (52 pag.)US2019/125746; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 36070-84-5, name is 5-Bromopyrazine-2-carboxamide, molecular formula is C5H4BrN3O, 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. Safety of 5-Bromopyrazine-2-carboxamide

Step 2: [6-(5-Carbamoyl-pyrazin-2-yloxy)-l-hydroxy-4-methyl-l, 3-dhydro- benzo[c] [ 1 ,2] oxaborol-3-yl] -acetic acid ethyl ester[0615] A suspension of (1 ,6-dihydroxy-4-methoxymethyl-l ,3-dihydro- benzo[c][l,2]oxaborol-3-yl)-acetic acid ethyl ester (150 mg, 0.600 mmol) and CS2CO3 (430 mg, 1.32 mmol) in DMF (4 mL) was treated with 5-bromo-pyrazine-2- carboxylic acid amide (158 mg, 0.780 mmol) at room temperature and the reaction was heated to 80 0C for 2 h. The reaction mixture was concentrated to dryness. The residue was diluted with water and adjusted to pH 2 with IN HCl. The aqueous phase was extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate = 1 :2 to DCM/MeOH = 10: 1) to afford the title compound as a white solid (110 mg). 1H NMR (300 MHz, CD3OD) delta 8.90 (s, IH), 8.34 (s, IH), 7.48 (s, IH), 7.35 (s, IH), 7.08 (s, IH), 5.70 (s, IH), 5.69-5.66 (m, IH), 4.21 (q, 2H), 3.14-3.12 (m, IH), 2.49-2.41 (m, IH), 2.37 (s, 3H), 1.26 (t, IH). MS found: (M+H)+ : 372.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36070-84-5, its application will become more common.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; GLAXOSMITHKINE LLC; XIA, Yi; ALLEY, Michael, Richard Kevin; ZHOU, Yasheen; SINGH, Rajeshwar; DING, Charles; CAO, Kathy; PLATTNER, Jacob, J.; OU, Ligong; JIA, Guofeng; SARASWAT, Neerja; RAMACHANDRAN, Sreekanth; ZHOU, Ding; WO2011/17125; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, 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 486424-37-7, name: 3-Amino-6-bromopyrazine-2-carboxylic acid

Example 5 : 3-Amino-6-(3-hydroxy-3-methyl-but-l-ynyl)-N-phenyl-pyrazine-2- carboxamide (Compound 11-81)SCHEME VSteps 1 to 2Compound 11-81METHOD E:Step 1: 3-Amino-6-bromo-N-phenylpyrazine-2-carboxamide[00151] A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (3.5 g, 16.05 mmol), l,l’-carbonyldiimidazole (5.205 g, 32.10 mmol), DIPEA (2.282 g, 3.075 mL, 17.66 mmol) and DMAP (98.04 mg, 0.8025 mmol) were combined in DMSO (131 mL) and stirred for 30 min. Aniline (1.495 g, 1.463 mL, 16.05 mmol) was then added and the resulting solution stirred at ambient tempaerture for 18 hours. After this time water was added and the product collected by filtration to give a brown powder (3.5 g, 74% Yield).1H NMR (400.0MHz, DMSO) delta 7.04 (1H, m), 7.29 (2H, m), 7.72 (4H, m), 8.36 (1H, s), 10.22 (NH2) ppm; MS (ES+) 295.

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; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus, Alphonsus; O’DONNELL, Michael; REAPER, Philip, Michael; WO2011/143419; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 25911-65-3, name is 3-Aminopyrazine-2-carbonitrile, 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 25911-65-3, SDS of cas: 25911-65-3

Compound 1d (1 mmol, 120 mg), [HDBN+][TFE-] (6 mmol, 1.35 g)was added to a 10 ml round-bottomed flask.in CO2 Under the environment, the reaction was heated to 90C for 20 hours, and the reaction was stopped. After the temperature was cooled to room temperature, saturated NH was added.4Aqueous Cl solution to adjust the pH to neutral, respectively 20ml CH2Cl2Extract three times and collect CH2Cl2The solution was dried over anhydrous sodium sulfate, filtered, and the solution was evaporated under reduced pressure. The solid was isolated by silica gel column chromatography (eluent CH2Cl2_CH3OH=15:1) 141 mg of pale yellow solid compound 2d was obtained with a yield of 86%.

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; Guizhou Medical University; Li Chun; Zhang Lin; Yang Yuanyong; (11 pag.)CN107698587; (2018); 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. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, A new synthetic method of this compound is introduced below., COA of Formula: C5H3ClN4

After dissolution compound obtained in Step 2 (8.10 g) and platinum oxide (IV) and 10% palladium / carbon (2g, 50% water content) in methanol (8 mL), under an atmosphere of hydrogen 50psi (Parr) 34 time and stirred. After filtering the reaction solution at Hyflo Super Cel, the oil obtained by concentrating the solvent was dissolved in dichloromethane (200 mL), N, N-diisopropylethylamine (10 mL) and di-tert-butylcarbonate (11 .4g) was added was stirred for 3 hours at room temperature. The reaction solution was extracted three times with chloroform after adding a saturated aqueous sodium hydrogen carbonate solution, and the organic layer was concentrated after dried over sodium sulfate. The resulting residue to give the title compound purified by silica gel column chromatography (2.55g, 22%).

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; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 119165-68-3, 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. 119165-68-3, name is 2-(1H-Imidazol-2-yl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

A methanolic solution containing 0.5 mmol of impz in 5 mL was slowly added to a solution of 0.5 mmol of CuCl2-2H2O in 5 mL of methanol under stirring for 4 h and at room temperature.A green solid precipitated and the powder was collected by filtration, washed with a small amount of cold methanol and dried under vacuum. The yield was 38%. This complex is soluble in water, DMSO and DMF and slightly soluble in methanol and ethanol. Anal. Calc. for CuCl2C7H6N4 (%): C 30.0; H 2.16; N 20.0.Found: C 30.2; H 2.46; N 19.8. Molar conductivity in deionized water (Scm2mol1): 206.9.

The chemical industry reduces the impact on the environment during synthesis 2-(1H-Imidazol-2-yl)pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nakahata, Douglas H.; Ribeiro, Marcos A.; Corbi, Pedro P.; Machado, Daisy; Lancellotti, Marcelo; Lustri, Wilton R.; da Costa Ferreira, Ana M.; Formiga, Andre L.B.; Inorganica Chimica Acta; vol. 458; (2017); p. 224 – 232;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 875781-43-4, 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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step 4: Preparation of 3-((1H-pyrrolo[2,3-b]pyrazin-5-yl)ethynyl)-4-methyl-N-[4-((4-methylpiperazin-1-yl)methyl)-3-trifluoromethylphenyl]benzamide The product (126 mg, 0.3 mmol) obtained from Step 3, 5-bromo-1H-pyrrolo[2,3-b]pyrazine (59 mg, 0.3 mmol), Pd(PPh3)2Cl2 (63 mg, 0.006 mmol), CuI (18 mg, 0.09 mmol), 1 ml Et3N and 5 ml DMF were added into a 10 ml sealed tube, and reacted with stirring at 80C for 8 hours under the protection of an inert gas atmosphere. After completion of the reaction, the mixture was extracted with ethyl acetate and water. The organic layers were combined, washed with a saturated NaCl solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, to give a white solid. 1H NMR (500 MHz, CDCl3) delta: 8.91 (br, 1H, -NH), 8.46 (s, 1H, Ar-H), 8.02 (d, 1H, Ar-H), 7.98 (s, 1H, Ar-H), 7.87 (s, 1H, Ar-H), 7.85(s, -NH, 1H), 7.78-7.80 (m, 1H, Ar-H), 7.69-7.70 (d, 1H, Ar-H), 7.60-7.62 (m, 1H, Ar-H), 7.35 (d, 1H, Ar-H), 6.72-6.73 (m, 1H, Ar-H), 3.61 (s, 2H,-CH2), 2.60 (s, 3H, -CH3), 2.54 (b, 8H, -CH2), 2.33 (s, 3H, -CH3). ESI-MS m/z: [M+H]+ = 533.1, calculated: 533.2.

The synthetic route of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Sanhome Pharmaceutical Co., Ltd.; WANG, Yong; ZHAO, Liwen; ZHANG, Di; WU, Feng; BI, Sheng; GAO, Yiping; CHEN, Hongbin; CHEN, Hongyan; ZHANG, Cang; NAN, Yang; LIU, Yang; EP2927232; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem