Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 912773-24-1, name is 6-Bromoimidazo[1,2-a]pyrazine, 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 912773-24-1, SDS of cas: 912773-24-1

To a solution of 6-bromoimidazo[1,2-a]pyrimidine (2.4 g, 12.1 mmol) in DMF, were sequentially added (4-methylpiperazin-1-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanone (80% of 4.1 g, 12.1 mmol), a solution of NaHCO3 (3.1 g, 36.3 mmol) in water (30 mL), water (3 mL) and (A-Phos)2PdCl2 (400 mg, 0.60 mmol). The reaction mixture was heated at 90 C. for 4 h, then was diluted with water (100 mL) and extracted with EtOAc (3*100 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, eluent CHCl3/MeOH 95:5 to 85:15) to afford of (4-(imidazo[1,2-a]pyrazin-6-yl)phenyl)(4-methylpiperazin-1-yl)methanone (1.5 g, 65%). 1H NMR (400 MHz, CDCl3) delta 8.60 (d, J=2.0 Hz, 1H), 8.10 (d, J=4.0, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.58 (m, 4H) 7.39 (d, J=8.0, 1 H), 3.84 (br s, 2H), 3.50 (br s, 2H), 2.40 (br s, 4H), 2.35 (s, 3H); MS (ESI) m/z 322 [M+1]

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, 6-Bromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 312736-49-5, 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. 312736-49-5, name is 3,5-Dichloropyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

a) Synthesis of 3,5-dichloro-pyrazine-2-carboxylic acid methyl ester To a solution of 3,5-dichloro-pyrazine-2-carboxylic acid (0.50 g, 2.60 mmol) in dimethylformamide (8 ml) is added potassium carbonate (0.54 g, 3.90 mmol) at RT followed by the addition of methyl iodide (0.8 ml, 13.0 mmol). The resulting mixture is stirred at RT for 1 h. After completion of the reaction, the mixture is diluted with water (15 ml) and extracted with EtOAc (3*20 ml). The combined organic layers are washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get 3,5-dichloro-pyrazine-2-carboxylic acid methyl ester (0.45 g, 2.18 mmol, 84%), which is used in the next step without further purification.

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; GRUeNENTHAL GMBH; LUCAS, Simon; Kuehnert, Sven; Bahrenberg, Gregor; Schroeder, Wolfgang; US2014/148454; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1209459-10-8, name is 2-Bromo-5-fluoropyrazine, 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. Formula: C4H2BrFN2

Zinc dust (Aldrich, 325 mesh, 263 mg, 4.05 mmol) was stirred and heated in tetrahydrofuran (5 mL) with 1,2-dibromoethane (Aldrich, 68 mg, 0.364 mmol) at 65 C. under N2 for approximately 5 min. The mixture was cooled to ambient temperature. Chlorotrimethylsilane (Aldrich, 39 mg, 0.364 mmol) was then added. This mixture was allowed to stir under N2 at ambient temperature for approximately 30 min. The iodide from Part E (1.36 g, 3.0 mmol) was added, and the resulting mixture was stirred at 40 C. under N2 for approximately 3 hr. The product from Part C (0.7 g, 2.28 mmol), N,N-Dimethylacetamide (14 mL), and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (Aldrich, 93 mg, 0.114 mmol) were added to the mixture. It was stirred overnight at 80 C. under N2. The mixture was cooled to ambient temperature. Saturated aqueous NH4Cl (10 mL) was then added. The resulting mixture was diluted further with dH2O (50 mL) and ethyl acetate (100 mL), and then filtered through a bed of Celite . The layers were separated, and the aqueous layer was back-extracted with ethyl acetate (50 mL). The combined organic layers were washed with 1/1 dH2O/saturated aqueous NaCl and saturated aqueous NaCl (50 mL each), dried over MgSO4, filtered, and concentrated in vacuo to produce an oil that was purified by chromatography (silica, ethyl acetate/hexanes) to produce 90 mg (7%) of product.

The synthetic route of 2-Bromo-5-fluoropyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 27398-39-6 as follows. name: 3-Chloropyrazine-2-carboxylic acid

Example 10 (4-Oxo-3,4-dihydro-pteridin-2-ylmethyl)-carbamic acid benzyl ester10.1 {2-[(3-Chloro-pyrazine-2-carbonyl)-amino]-2-imino-ethyl}-carbamic acid benzyl ester; Under an atmosphere of nitrogen, 3-chloro-2-pyrazinecarboxylic acid (76 mg), TBTU (168 mg), and diisopropylethylamine (310 mg) were added to a solution of carbamimidoylmethyl-carbamic acid benzyl ester [77390-81-9] (99 mg) in DMF (6 ml). The reaction mixture was stirred for 2 h at ambient temperature, diluted with dichloromethane and washed with water. The organic layer was dried (Na2SO4), filtered, and the solvent was evaporated. The obtained, crude title compound (220 mg) was used without further purification in the next step.

According to the analysis of related databases, 27398-39-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Conte, Aurelia; Dehmlow, Henrietta; Grether, Uwe; Kratochwil, Nicole A.; Kuehne, Holger; Narquizian, Robert; Panousis, Constantinos G.; Peters, Jens-Uwe; Ricklin, Fabienne; US2008/234277; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

To a solution of (E)-methyl 4-((benzhydrylimino)methyl)benzoate (67 g, 204 mmol) in THF (700 mL) was cooled to 0 C and added dropwise NaHMDS (244 mL, 244 mmol). The mixture was stirred at this temperature for 30 minutes, and added a solution of 2,3-dichloropyrazine (33.2 g, 224 mmol) in THF (40 mL). The reaction mixture was stirred at 0 C for 20 minutes and RT for 40 minutes. After the reaction was completed, the reaction mixture was extracted with EA and water. The organic layer was treated with 3M HCl (500 mL) for 10 minutes. The phases were separated and the organic layer was extracted with 3M HCl. The aqueous was washed with EA and then alkalified with Na2CO3 to pH = 9. The aqueous solution was extracted with EA and the combined organics were dried and concentrated to give methyl 4-(amino(3-chloropyrazin-2- yl)methyl)benzoate (46 g, yield 81 %). MS-ESI (m/z): 278 (M+1) + (Acq Method: 10-80AB_2min; Rt: 0.75 min).

The synthetic route of 4858-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald, M.; LIU, Jian; LIU, Shilan; YANG, Chundao; ZHENG, Shuling; WO2014/116504; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6924-68-1, name is Ethyl pyrazine-2-carboxylate, 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 6924-68-1, Formula: C7H8N2O2

Ethyl pyrazine carboxylate (4.0 g, 13.14 mmol) in 200 mL of DCM was treated at O0C with meta-chloroperbenzoic acid (57- 80%, 5.67 g). The mixture was allowed to warm to ambient temperature and stirred for 72 h, when an additional 4.28 g of meta-chloroperbenzoic acid was added. After an additional 4 d, 6 mL of acetone was added and stored for 2.5 d. Then 2.2 g of sodium metabisulfite in 5 mL of water was added and stirred for 2 h. Ethyl acetate was added and the mixture was washed with brine, dried over sodium sulfate, filtered and concentrated to leave a solid which was purified by chromatography (silica gel, elution with ethyl acetate/pentane), affording 3.35 g of the N-oxide. The N-oxide thus prepared (2.0 g, 11.89 mmol) in 10.53 mL of phosphorous oxychloride and 18 mL of toluene was heated at 100C for 1.5 h. The mixture was carefully treated with ice and then with saturated aqueous sodium carbonate solution. The product was extracted into ethyl acetate, and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (elution with ethyl acetate/pentane) to give 1.27 g of 6-chloro-pyrazine-2- carboxylic acid ethyl ester. .

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; AVENTIS PHARMACEUTICALS INC.; WO2006/86705; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 89123-58-0,Some common heterocyclic compound, 89123-58-0, name is 5-Bromopyrazine-2,3-diamine, molecular formula is C4H5BrN4, 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: Zn(OAc)2·2H2O (5.0 mol%) was transferred to a 100 mL autoclavereactor equipped with an overhead stirrer and an automatic temperature-control system. The appropriate benzene-1,2-diamine 1 (2 mmol), DMF (10.0 mmol), and PMHS (5.0 mmol)were successively introduced. The reactor was sealed, flushedthree times with N2 (10 atm), and heated to the required temperature with vigorous stirring (600 rpm). During the course ofthe reaction, an increase of pressure was observed, due to thegeneration of Me2NH and HCHO at 120 C.15 (For this reason, the protocol needs to be performed in a sealed high-pressurereactor.) When the reaction was complete, the autoclave wascooled to r.t., and the pressure generated during the reactionwas carefully released. Basic hydrolysis was then carried out atr.t. for 30 min to remove unreacted PMHS from the mixture.13aThe mixture was then extracted with EtOAc (3 × 20 mL). Thecombined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude products were further purified bycolumn chromatography [silica gel (100-200 mesh), PE-EtOAc(20:4 to 10:2)]. The spectroscopic data for the products wereconsistent with those reported in the literature.

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

Reference:
Article; Nale, Deepak B.; Bhanage, Bhalchandra M.; Synlett; vol. 26; 20; (2015); p. 2835 – 2842;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-29-5, 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. 33332-29-5, name is 2-Amino-5-chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows.

REFERENTIAL EXAMPLE 398 Methyl 2-[(5-chloropyrazin-2-yl)amino]-2-oxoacetate: The title compound was obtained from 2-amino-5-chloropyrazine synthesised in accordance with literature (Sato, Nobuhiro et al., J. Heterocycl. Chem., 1982, 19(3), 673-4) and methyl chlorooxoacetate in a similar manner to the process described in Referential Example 242. 1H-NMR (CDCl3) delta: 4.02(3H,s), 8.35(1H,d,J=1.5 Hz), 9.37(1H,d,J=1.5 Hz), 9.41(1H,br.s). MS (FAB) m/z: 216(M+H)+.

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

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; US2005/20645; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 19745-07-4, 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 19745-07-4 as follows.

Example 4(S)- 1 -( 1 -(5 -chloropyrazin-2-yl)piperidin-4-yl)-3 -(2-fluoro-4- (methylsulfonyl) henylamino)pyrrolidin-2-one[00396] To a solution of (S)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)-l-(piperidin-4-yl)pyrrolidin-2-one (Preparation E; 3 g, 8.44 mmol) and DIEA (7.35 mL, 42.2 mmol) in DMF (30mL) was added 2,5-dichloropyrazine (2.51 g, 16.9 mmol). This mixture was degassed with nitrogen for 30 minutes then stirred at 100 °C for 4 hours under nitrogen. The mixture was poured into brine (500 mL) and extracted into ethyl acetate (3 x 100 mL). The combined organic layers were dried over MgS04, filtered and concentrated in vacuo to give an oil. Diethyl ether (200 mL) was added and a precipitate formed overnight. The ether was decanted and the solid was triturated using ethanol (100 mL) at reflux with stirring for 5 minutes. The suspension was filtered and the solid was washed using ethanol to give a solid crystal. This solid was dried over the weekend under high vacuum to provide the title compound (2.9 g, 73percent yield). Mass spectrum (apci) m/z = 468.1 (M+H). 397

According to the analysis of related databases, 19745-07-4, the application of this compound in the production field has become more and more popular.

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

Related Products of 875781-43-4, 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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 2-Bromo-5H-pyrrolo[3,2-b]pyrazine(4; 0.471 g,2.39 mmol), 4-pyridylboronic acid (0.58 g, 4.72 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloromethane adduct (0.097 g, 0.12 mmol), acetonitrile(3 mL) and 1M sodium carbonate (3 mL) were placed in a 10 mL CEM microwavevial. The vial was capped and irradiated in a CEM microwave reactor for 30minutes at 150 C.Water (3 mL) and ethyl acetate (9 mL) were added the layers were partitioned. Theaqueous layer was extracted with ethyl acetate (2 x 10 mL). The combined organicextracts were washed with saturated sodium chloride (5 mL), dried over MgSO4and concentrated under reduced pressure. The residue was purified by preparativereverse phase HPLC to give 2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine(14; 0.28 g,60%) as an off white solid: 1H NMR (400 MHz, DMSO-d6) delta 12.24 (s, 1H), 9.00(s, 1H), 8.69 (dd, J = 4.5, 1.6 Hz, 2H), 8.12 (dd, J = 4.5, 1.6Hz, 2H), 7.98 (d, J = 3.6 Hz, 1H), 6.74 (d, J = 3.6 Hz, 1H); ESMSm/z 197.1 (M+1).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5H-pyrrolo[2,3-b]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Burdick, Daniel J.; Wang, Shumei; Heise, Christopher; Pan, Borlan; Drummond, Jake; Yin, Jianping; Goeser, Lauren; Magnuson, Steven; Blaney, Jeff; Moffat, John; Wang, Weiru; Chen, Huifen; Bioorganic and Medicinal Chemistry Letters; vol. 25; 21; (2015); p. 4728 – 4732;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem