Month: May 2021

These common heterocyclic compound, 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, 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. Computed Properties of C6H9N3

Example 97 A mixture of 2-chloro-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (prepared in Example 95) 285 mg, 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine 197 mg, triethylamine 0.22 ml and chloroform 3 ml is stirred at room temperature for 2.5 hours, followed by stirring at 60 C. for 2.5 hours. The mixture is diluted with ethyl acetate, and washed with water. The water layer is extracted with ethyl acetate, and the organic layer is washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is purified with silica gel chromatography (silica gel 10 g, solvent; chloroform_methanol=50:1) and concentrated in vacuo and triturated with isopropyl ether to give 2-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-7-yl)-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine as a colorless crystalline powder, 290 mg. mp 179-182 C., MS(m/z): 443(M+H)+

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

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

Synthetic Route of 36070-80-1, 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

5-(2,2-difluoroethoxy)pyrazine-2-carboxylic acid Potassium tert-butoxide (4.25 g, 37.84 mmol) is added to a solution of 5-chloropyrazine-2-carboxylic acid (1.00 g, 6.31 mmol) and difluoroethanol (2.59 g, 31.54 mmol) in DMF (20 mL) and the mixture is heated at 100 C. for 2 hours. The reaction is cooled to room temperature and stirred overnight under nitrogen. The reaction is quenched with 1M HCl (30 mL) and extracted with ethyl acetate (3 times). The combined organic layers are dried over sodium sulfate, filtered, and concentrated to give the crude product. The crude product is purified by silica gel flash chromatography, eluting with a gradient of 0.5% to 10% methanol in dichloromethane and azeotroped with xylenes to remove residual DMF to give the title product (1.18 g, 91%). ES/MS (m/e): 205.0 (M+1). The following compounds in Table 1 are prepared in a manner essentially analogous to the method set forth in Preparation 21 using the appropriate alcohol.

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-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GREEN, Steven James; HEMBRE, Erik James; MERGOTT, Dustin James; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR., Leonard Larry; US2014/371212; (2014); 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. 54608-52-5, name is 2-Hydrazinopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. name: 2-Hydrazinopyrazine

Step B: Preparation of (la/?,5a/?)-2-(Pyrazin-2-yl)-la,2,5,5a-tetrahydro-lH-2,3- diaza-cyclopropa[a]pentalene-4-carboxylic Acid Ethyl Ester. Method CTo a stirred suspension of 2-ethoxy-2-oxo-l-((lR,5R)-2-oxobicyclo[3.1.0]hexan-3- ylidene)ethanolate (300 mg, 1.28 mmol) in ethanol (5 mL) was added 2-hydrazinylpyrazine (141 mg, 1.28 mmol) followed by 6 N HQ (0.5 mL, 3.0 mmol). The reaction was stirred overnight at room temperature. The reaction was diluted with H20 and extracted with DCM. The combined organic phases were washed with H20, dried over MgS04, and concentrated. Purification by silica gel flash chromatography gave the title compound (150 mg). LCMS m/z = 271.2 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 0.47 (td, = 4.7 and 3.4 Hz, 1H), 1.22-1.28 (m, 1H), 1.39 (t, = 7.1 Hz, 3H), 2.26-2.30 (m, 1H), 2.77-2.82 (m, 1H), 2.87 (d, = 16.6 Hz, 1H), 2.98 (dd, / = 16.6 and 6.3 Hz, 1H), 4.40 (q, = 7.1 Hz, 2H), 8.40 (dd, / = 2.6 and 1.5 Hz, 1H), 8.51 (d, = 2.5 Hz, 1H), 9.39 (d, = 1.3 Hz, 1H).

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; THATTE, Jayant; BLACKBURN, Anthony C.; HAN, Sangdon; JONES, Robert M.; JUNG, Jae-Kyu; MONTALBAN, Anthony Garrido; PAL, Biman B.; RUETER, Jaimie Karyn; STRAH-PLEYNET, Sonja; THORESEN, Lars; XIONG, Yifeng; YUE, Dawei; ZHU, Xiuwen; WO2012/116279; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36070-75-4, name is 5-Chloropyrazine-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 36070-75-4, Application In Synthesis of 5-Chloropyrazine-2-carbonitrile

To a mixture of 5-chloropyrazine-2-carbonitnle (140mg, l.Olmmol) and [(3R,45)-4- (2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid rerf-butyl ester (Preparation 48, 300mg, l.Olmmol) in DMSO (ImL) was added DBU (150muL, l.Olmmol). The mixture was bubbled with argon for 5 min and then heated to 700C for 3 h. After cooling to r.t. the crude reaction mixture was partitioned between EtOAc (20OmL) and water (75mL), then the organic phase was separated, washed with brine, dried (MgSO.4), and the solvent removed in vacuo Purification by column chromatography (IH:EtOAc, 60:40) afforded the title compound: RT = 3.93 mm; m/z (ES+) = 402 1 [M + H]+.

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; PROSIDION LIMITED; BARBA, Oscar; DAVIS, Susan, Helen; FYFE, Matthew, Colin, Thor; JEEVARATNAM, Revathy, Perpetua; SCHOFIELD, Karen, Lesley; STAROSKE, Thomas; STEWART, Alan, John, William; SWAIN, Simon, Andrew; WITHALL, David, Matthew; WO2010/103335; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 89464-87-9, 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 89464-87-9 as follows.

(i) 4-Dimethylaminopyridine (0.1 g) was added to a solution of 2-chloropyridine-3-sulphonyl chloride (1.06 g), 2-amino-3-methoxy-5-methylpyrazine (0.695 g) and pyridine (0.424 ml) in dichloromethane (5 ml) and the mixture was stirred at ambient temperature for 18 hours. The solution was then transferred to a silica gel Mega Bond Elut column. Elution with 0-40% ethyl acetate/hexane gave 2-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.47 g) as an oil; 1 H NMR (d6 -DMSO): 2.3 (s, 3 H), 3.9 (s, 3 H), 7.5 (s, 1 H), 7.65 (dd, 1 H), 8.45 (dd, 1 H), 8.7 (dd, 1 H); mass spectrum (+ve CI): 315 (M+H)+.

According to the analysis of related databases, 89464-87-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zeneca Limited; US5866568; (1999); A;,
Pyrazine – Wikipedia,
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. 5049-61-6, name is Pyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., Safety of Pyrazin-2-amine

A solution of Z-1 (10.0 g, 105 mmol) in DME (100 mL) is treated dropwise with the Z-2 (16.3 mL, 129 mmol) over lh at rt. After 3h, the mixture is cooled to 0C and filtered. The solid is washed with ether (50 mL) and dried under vacuum. The solid is heated in refluxing EtOH (100 mL) for 3h. The mixture is concentrated, the residue is dissolved in CHC13 (100 mL), and basified to pH 9 with sat. NaHC03 (100 mL). The suspension is filtered through a pad of Diatomaceous earth, which is washed with water (100 mL) and CHCI3 (3 x 100 mL). The phases are separated, and the aqueous layer extracted with CHCI3 (100 mL). The combined organic extracts are dried over MgS04, filtered and concentrated. The residue is crystallized from EtOH (100 mL) to give Z-3

According to the analysis of related databases, 5049-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRUNETTE, Steven, Richard; ABEYWARDANE, Asitha; BURKE, Michael, J.; KAPADIA, Suresh, R.; KIRRANE, Thomas, Martin, Jr.; NETHERTON, Matthew, Russell; RAZAVI, Hossein; RODRIGUEZ, Sonia; SAHA, Anjan; SIBLEY, Robert; SMITH KEENAN, Lana, Louise; TAKAHASHI, Hidenori; TURNER, Michael, Robert; WU, Jiang-Ping; YOUNG, Erick, Richard, Roush; ZHANG, Qiang; ZHANG, Qing; ZINDELL, Renee, M.; WO2013/134226; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, 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. Safety of 5-Methylpyrazine-2-carboxylic acid

To a stirred suspension of 5-methyl-pyrazine-2-carboxylic acid (25 gm, 181 mmol) in 540mL THF at room temperature under nitrogen was addedDIEA (31.7 mL, 181 mmol) resulting in a brown solu- tion. Diphenyl phosphoryl azide (39.2 mL, 181 mmol)then was added dropwise as a solution in 50 mL THFover 1 hour behind a blast shield. The reaction wasallowed to stir overnight. The reaction then wasrotoevaporated to a small volume at room temperatureand partitioned between Et2O (1 L) and H20 (1 L) .The H2O layer was back extracted with 2 x 250 mLEt2O, and the combined organics washed 2 x 1 L withsaturated sodium bicarbonate. The organics weredried (MgSO4) , filtered and concentrated to a solidmass which was triturated with Et20 to give theproduct as a yellow solid (15 gm, 50%). Purercompound could be isolated by taking 1 gm of thecrude product in 20 mL of Et2O and treating with 1-2gm of decolorizing carbon at room temperature for afew minutes. After filtration and concentration,this material was homogeneous by TLC in EtOAc andpure white. The recovery was typically 65%.

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICOS CORPORATION; WO2006/12308; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4858-85-9, These common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, 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 stirred solution of 2,3-dichloropyrazine (500 mg, 3.35 mmol), 4-chlorophenyl boronic acid (472 mg, 3.02 mmol) and sodium carbonate monohydrate (1.2 g, 10.05 mmol) in a mixture of DMSO and water (10 mL, 3 : 1) was added [1,1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium (II) (122 mg, 0.16 mmol) at RT. The reaction mixture was degassed and bubbled with nitrogen thrice before heating at 80 C for 16 h. The mixture was cooled to RT and diluted with ethyl acetate (30 mL). The organic solution was washed with water (30 mL) and brine (30 mL). The solvent was removed under reduced pressure and the residue obtained was purified by silica gel column chromatography to obtain 320 mg of the desired product; 1H NMR (300 MHz, CDC13) delta 7.47 (d, J = 12 Hz, 2H), 7.76 (d, = 7.2 Hz, 2H), 8.35 (d, = 1.8 Hz, 1H), 8.58 (d, = 1.8 Hz, 1H).

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

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; GHARAT, Laxmikant Atmaram; HARDE, Rajendra Laxman; SHELKE, Sandeep Yadunath; PARDESHI, Shailesh Ramesh; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; (181 pag.)WO2017/21879; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 63286-28-2, A common heterocyclic compound, 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, molecular formula is C4H5ClN4, 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.

[00145] To a solution of l-(4-chlorophenyl)cyclopropanecarboxylic acid (6300 mg, 32.0 mmol) and 4-methylmorpholine (3.87 mL, 35.2 mmol) in THF (100 mL) at 0 0C was added isobutyl chloroformate (4.21 mL, 32.0 mmol). After completion of addition, the reaction mixture was stirred for 25 min, and then a solution of 2-chloro- 3-hydrazinylpyrazine (5095 mg, 35.2 mmol) in THF (60 mL) was added. The resulting mixture was stirred for 45 min. After that time, the reaction mixture was quenched with saturated aq. NaHCtheta3 and then extracted with EtOAc (25 mL). The organic layer was collected, washed with saturated aq. NH4Cl followed by aq. NaCL, dried over Na2SO4 and then concentrated by rotary evaporation to yield compound 35A (10 g, 97 % yield) as a yellow solid. The crude product was utilized in the next step without further purification. LC/MS (m/z) = 323.1 [M+ 1] +.

The synthetic route of 63286-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/130951; (2008); A1;,
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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Product Details of 313339-92-3

3,5-Dichloropyrazine-2-carbonitrile (585 mg, 3.36 mmol), tert-butyl N-(5-methylpiperidin-3- yl)carbamate (655 mg, 3.06 mmol) and DIEA (1.07 mL, 6.12 mmol) were dissolved in EtOH (20 mL) and stirred at 40 C for 50 minutes. The reaction was concentrated and water was added to the residue. The product was extracted with ethyl acetate (twice). The collected organic layers were dried over Na2SO4, filtered and concentrated under high vacuum to give crude tert-butyl N- [1-(6-chloro-5-cyanopyrazin-2-yl)-5-methylpiperidin-3-yl]carbamate (1.18 g, 90% yield) as diastereoisomeric mixture (d.r. = 4/11). MS found for C16H22ClN5O2 as (M+H)+ 352.0.

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; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem