Month: June 2021

Reference of 173253-42-4, 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. 173253-42-4, name is 2-Amino-5-bromo-6-chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Copper iodine (190 mg, 1 mmol), triethylamine (16.7 ml, 120 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1.3 g, 1.6 mmol), and tetrahydrofuran (100 ml) were added to 5-bromo-6-chloropyrazin-2-amine (4.2 g, 20 mmol) obtained from Step 1, and the resultant was bubbled using nitrogen gas. Trimethylsilylacetylene (3.6 ml, 26 mmol) was added to the mixture, and the resultant was reacted at 80C for 2 hours. The reactant was concentrated under reduced pressure, followed by adding water. Thereafter, the resultant was extracted 3 times with ethyl acetate. The organic layer was collected, dried over magnesium sulfate, and then concentrated under reduced pressure. Thereafter, the residue was purified on a silica gel column using chromatography. The title compound (3.16 g, 70%) was obtained by eluting as a mixed solvent (5:1 v/v) of hexane and ethyl acetate. 1H NMR (500 MHz, CDCl3) delta 7.84 (s, 1H), 4.85 (s, 2H), 0.28 (s, 9H).

The synthetic route of 2-Amino-5-bromo-6-chloropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dongguk University Industry-Academic Cooperation Foundation; GONG, Young Dae; KWAK, Se Hun; LEE, Eun Sil; (32 pag.)EP3231800; (2017); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 91476-80-1, 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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Example 547 A solution of (S)-3-(2-((S)-1-(4-(chloromethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (75 mg, 0.2 mmol) and 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (25 mg, 0.2 mmol) in DMSO (2 mL) was heated at 80 C. for 16 h. The reaction mixture was diluted with EtOAc (20 mL) and washed with water (20 mL). After separation, the aqueous phase was washed with EtOAc (2*15 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (MeOH in CH2Cl2 0 to 10%) provided (S)-3-(2-((S)-1-(4-((5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (58 mg, white solid) in 62.8% yield. 1H NMR (400 MHz, MeOD) delta 8.12 (d, J=6.0 Hz, 1H), 7.34 (d, J=5.9 Hz, 1H), 7.33 (s, 4H), 6.99 (d, J=1.3 Hz, 1H), 6.89 (d, J=1.4 Hz, 1H), 5.07 (q, J=7.0 Hz, 1H), 4.68 (br s, 1H), 4.37-4.25 (m, 2H), 4.02 (t, J=5.5 Hz, 2H), 3.72 (s, 2H), 3.63 (s, 2H), 2.90 (td, J=5.4, 2.6 Hz, 2H), 1.84 (br s, 1H), 1.51 (d, J=7.0 Hz, 3H), 0.72 (br s, 3H), 0.57 (br s, 3H); HRMS m/z 462.2606 (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; NOVARTIS AG; Caferro, Thomas Raymond; Cho, Young Shin; Costales, Abran Q.; Lei, Huangshu; Lenoir, Francois; Levell, Julian Roy; Liu, Gang; Palermo, Mark G.; Pfister, Keith Bruce; Sendzik, Martin; Shafer, Cynthia; Shultz, Michael David; Smith, Troy; Sutton, James Clifford; Toure, Bakary-Barry; Yang, Fan; Zhao, Qian; US2014/235620; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 313339-92-3, The chemical industry reduces the impact on the environment during synthesis 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, I believe this compound will play a more active role in future production and life.

Example 6 5-(1-amino-4,4,4-trifluoro-1-oxobutan-2-ylamino)-3-(quinolin-6-ylamino)pyrazine-2-carboxamide A solution of 3,5-dichloropyrazine-2-carbonitrile (50 mg, 0.287 mmol), 2-amino-4,4,4-trifluorobutanamide hydrochloride (50 mg, 0.259 mmol) and DIEA (0.150 mL, 0.862 mmol) in NMP (1 mL) was stirred at room temperature for 20 h. Water and EtOAc were added. Organic phase was separated, dried over Na2SO4, concentrated in vacuo to give 2-(6-chloro-5-cyanopyrazin-2-ylamino)-4,4,4-trifluorobutanamide (67 mg).

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

Reference:
Patent; Portola Pharmaceuticals, Inc.; Song, Yonghong; Xu, Qing; Jia, Zhaozhong J.; Kane, Brian; Bauer, Shawn M.; Pandey, Anjali; US2013/131040; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-Dichloropyrazine, 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 19745-07-4, COA of Formula: C4H2Cl2N2

Into a 250 ml 3-necked round bottom flask, was placed 45% hydriodic acid (60 ml). To this was added sodium iodide (25 g, 0.17 mol). To the mixture was added XV-B-86 (10.5 g, 0.07 mol). The resulting solution was allowed to react at room temperature. Adjustment of the pH to >8 was accomplished by the addition of 20 g NaOH in 50 g ice to afford XV-C-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; Kalypsys, Inc.; US2005/234046; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1458-01-1,Some common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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.

Intermediate A.1 3,5-Diamino-6-chloropyrazine-2-carboxylic acid A mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 I) and NaOH (6 mol/l in water; 240 ml; 1.44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 ml_). Water (200 ml) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60°C. C5H5CIN402 ESI Mass spectrum: m/z = 189 [M+H]+; m/z = 187 [M-H]”

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-diamino-6-chloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; KLEY, Joerg; FRATTINI, Sara; HAMPRECHT, Dieter; WO2015/7517; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Methyl 2-aminopyrazine-3-carboxylate

Step 1: synthesis of methyl 3-bromopyrazine-2-carboxylate (99)To a solution of methyl 3-amino-2-pyrazinecarboxylate (13.06 mmol, 2 g) in hydrobromic acid (13.06 mmol, 7.4 ml, 1.057 g) at 0°C was added bromine (38.9 mmol, 2 mL, 6.22 g) drop wise and then a solution of sodium nitrite (33.3 mmol, 2.3 g) in water (4 mL). The reaction was stirred for 2h at 0°C and the reaction mixture was extracted with CH2CI2. Organic layer was dried and evaporated to give crude methyl 3- bromopyrazine-2-carboxylate 101 (1.2gr, 43percent). (m/z) = 217 and 219 (M+H)+.

The synthetic route of 16298-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; FOLMER, Brigitte, Johanna, Bernita; MAN, de, Adrianus, Petrus, Antonius; GERNETTE, Elisabeth, Sophia; CORTE REAL GONCALVES AZEVEDO, Rita; IBRAHIM, Hemen; WO2011/147764; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 19745-07-4,Some common heterocyclic compound, 19745-07-4, name is 2,5-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

Example 164(S)- -(5-chloropyrazin-2-yl)-3-(2.5-difluoro-4-(methylsulfonyl)phenoxy)-ri.4′-bipiperidinl- -one[00580] A stirred solution of (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-[l,4′- bipiperidin]-2-one (Preparation G; 40 mg, 0.103 mmol), DIEA (90 mu, 0.515 mmol), and 2,5-dichloropyrazine (30.7 mg, 0.206 mmol) in DMF (1 mL) was heated atl00° C in a sealed tube for 2 hours. The mixture was cooled, diluted with EtOAc (25 mL), washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by preparative TLC (EtOAc/ DCM 4: 1) to afford (S)-l’-(5-chloropyrazin-2-yl)-3-(2,5-difluoro-4- (methylsulfonyl)phenoxy)-[l,4′-bipiperidin]-2-one (2 mg, 0.004 mmol, 4percent yield) as a white solid. Mass spectrum (apci) m/z = 501.1 (M+H).

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-Dichloropyrazine, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; AICHER, Thomas Daniel; BENCSIK, Josef Roland; BOYD, Steven Armen; CONDROSKI, Kevin Ronald; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald Jay; PRATT, Scott Alan; SINGH, Ajay; TURNER, Timothy M.; WO2011/146335; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33332-29-5, name is 2-Amino-5-chloropyrazine, 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 33332-29-5, Safety of 2-Amino-5-chloropyrazine

Preparation of intermediate BA A mixture of 2-Amino-5-chloropyrazine (CAS [33332-29-5], 6 g, 46.31 mmol) and intermediate J (14.52 g, 69.47 mmol) in EtOH (10 mL) was stirred at 100 C for 12 h. The solvent was removed in vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=5/l). The product fractions were collected and the solvent was evaporated to give intermediate BA, 0.81 g, 7%.

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:
Patent; JANSSEN SCIENCES IRELAND UC; GUILLEMONT, Jerome, Emile, Georges; MOTTE, Magali, Madeleine, Simone; RABOISSON, Pierre, Jean-Marie, Bernard; TAHRI, Abdellah; (194 pag.)WO2017/1660; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 55557-52-3, 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 55557-52-3 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 %).

According to the analysis of related databases, 55557-52-3, the application of this compound in the production field has become more and more popular.

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;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 50866-30-3, 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. 50866-30-3 name is 5-Methylpyrazine-2-carbaldehyde, 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.

[011761 (1R,2R)-1-hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methylpyrazin- 2-yl)propane-2-sulfonamide and (1S,2R)- 1-hydroxy-N,N-bis(4-methoxybenzyl)-1-(5- methylpyrazin-2-yl)propane-2-sulfonamide and (1 S,2S)-1-hydroxy-N,N-bis(4- methoxybenzyl)- 1-(5-methylpyrazin-2-yl)propane-2-sulfonamide and (1R,2S)-1- hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methylpyrazin-2-yl)propane-2-sulfonamide and Example 564.1. At -78 C, an- butyllithium solution (2.5 M in hexanes, 10.2525.6 mmol) was added to a 2-methyltetrahydrofuran (107 mL) solution containing N,Nbis(4-methoxybenzyl)ethanesulfonamide (7.46 g, 21.36 mmol). The resulting mixture was stirred for 15 mm at -78 C. Next, a 2-methyltetrahydrofuran solution containingmethyl-2-pyrazinecarbaldehyde (2.66 mL, 25.6 mmol) was added at -78 C and thenreaction was allowed to slowly warm to RT and stirred overnight. The reaction was quenched with a saturated ammonium chloride solution and partitioned. The remaining residue was purified on silica eluting with a DCM/EtOAc gradient (0-50%). Desired fractions were then combined and concentrated in vacuo. MS ESI (pos.) mlz: 472.2 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methylpyrazine-2-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem