Tag: M.W=100-200

312736-49-5, A common compound: 312736-49-5, name is 3,5-Dichloropyrazine-2-carboxylic acid, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Step 2: methyl 3,5-dichloropyrazine-2-carboxylate To a solution of 3,5-dichloropyrazine-2-carboxylic acid (0.304 g, 1.58 mmol) in MeOH (5 mL) and diethyl ether (5 mL) at RT was added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, 4.00 mL, 8.00 mmol). The reaction mixture was stirred at RT for 30 min and then concentrated. Purification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes) gave methyl 3,5-dichloropyrazine-2-carboxylate (0.312 g, 1.51 mmol, 96% yield) as a white solid.

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, 3,5-Dichloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
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122-05-4, 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. 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

5 mmol of (2FPpy)2Ir(Cl)2Ir(2FPpy)2, 25 mmol of pyrazine-2,5-dicarboxylic acid (Py2CA), and 50 mmol of potassium carbonate were mixed in 100 mL of 1,2-dichloroethane, and refluxed for 24 hours under a nitrogen atmosphere. After the reaction was complete, the solution was cooled down to about 50 C., and filtrated. The filtrated solution was purified by using column chromatography to thereby produce (2FPpy)2Ir(Py2CA)Ir(2FPpy)2 at a yield of 86%.

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Reference:
Patent; SAMSUNG ELECTRONICS CO., LTD.,; US2008/269484; (2008); A1;,
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These common heterocyclic compound, 21279-62-9, name is 3-Chloropyrazine-2-carboxamide, 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. 21279-62-9

General procedure: Compounds 1-6 were prepared according to conventional organic synthesis methods. 3-Chloropyrazine-2-carboxamide (1.27 mmol) was dissolved in THF (20 mL) in a round bottom flask and after that treated with two equivalents of the corresponding benzylamine and an equimolar amount of triethylamine. The reaction was conducted with continuous stirring and heating (70 C) under reflux in an oil bath for 15 h. Compounds 7-15 were synthesised using a microwave reactor with a focused field. 3-Chloropyrazine-2-carboxamide (1.27 mmol) was put into a thick-walled tube together with the corresponding benzylamine (2.54 mmol), pyridine (1.27 mmol), methanol (approx. 5 mL) and a magnetic stir bar and then sealed with a special cap. The reaction parameters were set according to the previously published paper as follows-140 C, 30 min, 200 W [29]. Reaction progress was checked by TLC (hexane:ethyl acetate-1:1). Regardless of the synthesis method used,all reaction mixtures were adsorbed on silica and subjected to preparative flash chromatography (hexane and ethyl acetate, gradient elution, detection wavelengths 260 nm and 280 nm). Products were recrystallized from ethanol or ethanol and water if necessary. All final substances were chemically characterized (1H-NMR, 13C-NMR, IR, melting point and elemental analysis).

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 21279-62-9.

Reference:
Article; Jandourek, Ondrej; Tauchman, Marek; Paterova, Pavla; Konecna, Klara; Navratilova, Lucie; Kubicek, Vladimir; Holas, Ondrej; Zitko, Jan; Dolezal, Martin; Molecules; vol. 22; 2; (2017);,
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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. 56423-63-3, name is 2-Bromopyrazine, This compound has unique chemical properties. The synthetic route is as follows., 56423-63-3

Preparation 133 2-Chloro-4-(pyrazin-2-yl)aniline To a mixture of 4-amino-3-chlorophenylboronic acid pinacol ester (0.110 g, 0.434 mmol), 2-bromopyrazine (0.090 g, 0.56 mmol), 1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) DCM complex (24 mg, 0.029 mmol) was added anhydrous DME (3.0 mL) followed by 2M aqueous sodium carbonate (0.53 mL, 1.06 mmol). The microwave vial was heated at 75 C. for 40 minutes under microwave irradiation. Further catalyst (0.012 g) was added and the vial was heated at 90 C. for 25 minutes under microwave irradiation. Further 2-bromopyrazine (0.060 g), catalyst (12 mg) and 2M aqueous sodium carbonate (0.25 mL) were added and the reaction mixture was heated at 90 C. for an additional 30 minutes under microwave irradiation. The reaction was partitioned between ethyl acetate (60 mL) and a saturated aqueous NaHCO3 solution (15 mL). The organic layer was washed with a saturated aqueous NaHCO3 solution (2*15 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified using preparative TLC eluting with 7% ethyl acetate in CH2Cl2. The product band was recovered and stirred with 2% MeOH in ethyl acetate/CH2Cl2 (v/v; 1:10) (20 mL). The silica was removed by filtration, washed with ethyl acetate/CH2Cl2 (v/v; 1:5) (2*5 mL) and acetone (3*4 mL) to give the title compound as an off-white solid (0.039 g, 44%). 1H-NMR (500 MHz, DMSO-d6) 5.86 (s, 2H), 6.89 (d, J=8.5, 1H), 7.85 (dd, J=2.1, 8.5 Hz, 1H), 8.02 (d, J=2.1 Hz, 1H), 8.44 (d, J=2.5 Hz, 1H), 8.57 (dd, J=1.6, 2.5 Hz, 1H), 9.12 (d, J=1.5 Hz, 1H).

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Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; Bavetsias, Vassilios; Atrash, Butrus; Naud, Sebastien Gaston Andre; Sheldrake, Peter William; Blagg, Julian; US2013/345181; (2013); A1;,
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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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 313339-92-3

Preparation of compound 2Od: terf-butyl (3/?)-3-[(6-chloro-5-cyanopyrazin-2- yl)amino]piperidine-1-carboxylateTo a solution of 20c (0.6 g, 3.46 mmol) and te/f-butyl (3R)-3-aminopipehdine-1 – carboxylate (0.41 g, 2 mmol) in n-BuOH (20 ml_) was added DIPEA (1.2 ml_, 6.9 mmol) at room temperature. The resulting mixture was stirred at 50 0C for 5 h. The mixture was concentrated to dryness. The residue was purified by column chromatography (CH2CI2: CH3OH from 500:1 to 100:1 ) which gave the title compound 2Od as yellow solid (0.7 g, 60%). 1H NMR (400 MHz, CDCI3) delta ppm 1.37 (s, 9H), 1.56 (m, 1 H), 1.70 (m, 2H), 1.86 (s, 1 H), 3.36 (s, 3H), 3.57 (s, 1 H), 3.96 (s, 1 H), 5.78 (br, 1 H), 7.76 (s, 1 H).

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

Reference:
Patent; PFIZER INC.; NINKOVIC, Sacha; BRAGANZA, John Frederick; COLLINS, Michael Raymond; KATH, John Charles; LI, Hui; RICHTER, Daniel Tyler; WO2010/16005; (2010); A1;,
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55557-52-3, Name is 3-Chloropyrazine-2-carbonitrile, 55557-52-3, 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.

(a). (3-Chloropyrazin-2-yl)methanamine hydrochloride was prepared as follows. To a solution of 3-chloropyrazine-2-carbonitrile (160 g, 1 .147 mol) in acetic acid (1.5 L) was added Raney Nickel (50% slurry in water, 70 g, 409 mmol). The resulting mixture was stirred under 4 bar hydrogen at room temperature overnight. Raney Nickel was removed by filtration over decalite and the filtrate was concentrated under reduced pressure and co-evaporated with toluene. The remaining brown solid was dissolved in ethyl acetate at 50C and cooled on an ice-bath. 2M hydrogen chloride solution in diethyl ether (1 .14 L) was added in 30 min. The mixture was allowed to stir at room temperature over weekend. The crystals were collected by filtration, washed with diethyl ether and dried under reduced pressure at 40C. The product brown solid obtained was dissolved in methanol at 60C. The mixture was filtered and partially concentrated, cooled to room temperature and diethyl ether (1000 ml) was added. The mixture was allowed to stir at room temperature overnight. The solids formed were collected by filtration, washed with diethyl ether and dried under reduced pressure at 40C to give 153.5 g of (3-chloropyrazin-2- yl)methanamine.hydrochloride as a brown solid (74.4 %, content 77 %).

Statistics shows that 3-Chloropyrazine-2-carbonitrile is playing an increasingly important role. we look forward to future research findings about 55557-52-3.

Reference:
Patent; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (268 pag.)WO2016/24227; (2016); A1;,
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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. 74803-32-0, name is 8-Chloro[1,2,4]triazolo[1,5-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., 74803-32-0

A mixture of the above 8-chloro-[1,2,4]triazolo[1,5-a]pyrazine (50 mg, 0.32 mmol) and (S)-tert-butyl pyrrolidin-3-yl carbamate (100 mg, 0.53 mmol) in diethylisopropylamine (2 mL) was heated to 120 C. for 2 h. After coolingto room temperature, the mixture was diluted with 10%MeOH in EtOAc and washed with saturated aqueous solutionsof KH2PO4 and NaHCO3, followed by brine. The organic layer was concentrated in vacuo and the residue purified by flash chromatography (Si02, 2 to 5% MeOH in CH2C12 as eluent) to give the desired compound as a foam (80mg, 82% yield, which was used directly for the next step). MS: (ES) m/z 305.2 (M+H+).

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Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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.

General procedure: Pyrazine-2,3-dicarboxylic anhydride (1.0 g, 6.7 mmol) was dissolved in tetrahydrofuran (40 mL)in an Erlenmeyer flask and the corresponding substituted aniline (6.7 mmol, 1 equiv.) was added in one dose. The reaction mixture was stirred for 1 hour at laboratory temperature. Water (30 mL) was added into the mixture followed by the saturated aqueous solution of NaHCO3 until pH 6 to form thecorresponding 3-(phenylcarbamoyl)pyrazine-2-carboxylic acid 1-18. Obtained crystals were filtered off and washed with water. The progress of the procedure was monitored by TLC eluted with thesystem water/butanol/acetic acid 5:4:1.

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Reference:
Article; Semelkova, Lucia; Jano?cova, Petra; Fernandes, Carlos; Bouz, Ghada; Jand?Ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; Molecules; vol. 22; 9; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

91476-80-1, A common compound: 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

(5) A mixture of 4-benzylthio-5-methoxycarbonyl-6-(4-hydroxypiperidine-1-yl)-2-chloropyrimidine (prepared in the above (4)) 120 mg, 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine 70 mg, triethylamine 57 mg and N,N-dimethylacetamide 3 ml is stirred at 10 C. for 3 hours. The reaction mixture is diluted with an aqueous citric acid solution and extracted with ethyl acetate. The water layer is made basic with an aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo to give 4-benzylthio-5-methoxycarbonyl-6-(4-hydroxypiperidin-1-yl)-2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)pyrimidine as a colorless foam, 105 mg. IR (Neat+CHCl3)cm-1: 3050-3600,1695,1533,1503, 1433 APCI-MS(m/z): 481 (M+H)+

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, 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yamada, Koichiro; Matsuki, Kenji; Omori, Kenji; Kikkawa, Kohei; US2004/142930; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

16298-03-6, The chemical industry reduces the impact on the environment during synthesis 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, I believe this compound will play a more active role in future production and life.

A solution of methyl 3-aminopyrazine-2-carboxylate (3.0 g, 19.6 mmol) and NBS(3.5 g, 23.5 mol) in MeCN (70 mL) was stirred at 70¡ãC for 5 h. Then the mixture was concentrated and extracted with EtOAc. The organic layer was washed with Na2503 (a.q.) and brine, dried over Na2504 and concentrated in vacuo. The crude product of methyl 3-amino-6-bromopyrazine-2-carboxylate (3.0 g, yield: 92percent) was used for next step without further purification. ?H-NMR(CDC13, 400 MHz) 8.18 (s, 1H), 6.546.93 (m, 2H), 3.86 (s, 3H). MS (M+H): 232 / 234.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem