Category: 14508-49-7

Adding a certain compound to certain chemical reactions, such as: 14508-49-7, name is 2-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 14508-49-7, category: Pyrazines

The product of preparation 16 (83mg, 0.32mmol), 2-chloropyrazine (36mg, 0.31 mmol), sodium tert-butoxide, (36mg, 0.37mmol), Pd2(dba)3 (7mg, 8mumol) and BINAP (22mg, 35mumol) were suspended in tert-butanol (2mL) and the mixture was heated at 110C in the microwave for 3 hours. The mixture was replenished with further amounts of 2-chloropyrazine (36mg, 0.31 mmol), sodium tert-butoxide (36mg, 0.37mmol), Pd2(dba)3 (7mg, 8mumol) and BINAP (22mg, 30mumol) at hourly intervals. The reaction mixture was then azeotroped with methanol and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate:methanol: 0.88 ammonia, 100:0:0 to 90:10:1. This was followed by further purification by column chromatography on Biotage amino silica gel, eluting with pentane:ethyl acetate, 100:0 to 0:100, to afford the title compound as a colourless oil in 76% yield, 80mg. 1HNMR(CDCl3, 400MHz) delta: 1.70-1.90(m, 4H), 1.91-2.04(m, 2H), 2.47-2.63(m, 6H), 2.93-3.02(m, 2H), 3.90-3.98(m, 2H) 4.28-4.35(m, 2H), 4.63(s, 2H), 6.60(d, 1H), 7.37(d, 1H), 7.85(m, 1H), 8.10(m, 1H), 8.21(m,1H) MS APCI+ m/z 340 [MH]+ Micro analysis found (%); C(67.21), H(7.46), N(20.60); C19H25N5NO requires (%); C(67.31), H(7.42), N(20.63)

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

Reference:
Patent; Pfizer Limited; EP1595881; (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 14508-49-7 as follows. Quality Control of 2-Chloropyrazine

In a sealed tube, 30 mL of dry toluene was degazed with Argon during 15 minutes, palladium acetate (114 mg, 0.17 mmol, 0.04 eq.) and racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (106 mg, 0.17 mmol, 0.04 eq.) were added and the mixture was degazed with Argon for 10 minutes. Then 2-chloropyrazine (500 mg, 4.37 mmol, 1.0 eq.), 4-amino-1-Boc-piperidine (1.05 g, 5.24 mmol, 1.2 eq.) and sodium tert-butoxide (587 mg, 6.11 mmol, 1.4 eq.) were added and the mixture was stirred at 70 C. overnight. The reaction was concentrated in vacuum. The resulting crude product was purified by flash chromatography on silica gel, eluting with 100% ethyl acetate to afford 106a (1.0 g, 82%).

According to the analysis of related databases, 14508-49-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vetoquinol SA; US2009/221565; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 14508-49-7, A common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a-k, and4m are known compounds [6,9] except for 4l and 4n.

The synthetic route of 14508-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Chen; Li, Hong-Mei; Wang, Zhi-Qiang; Fu, Wei-Jun; Inorganica Chimica Acta; PA; (2014); p. 11 – 15;,
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. 14508-49-7, name is 2-Chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H3ClN2

General procedure: (0.1mole) of 2-halo nitrogen heterocycle and (0.5 mole) of hydrazine hydrate were mixed together in a 250mL round bottom flask equipped with reflux condenser and wereheated at 100oC, progress of the reaction was monitored byTLC. After completion of the reaction the reaction mixture was cooled to (-5-0oC) for 14hr and the precipitated solid was filtered and washed with two 5ml portions of ice coldwater and dried to give the compound 1 in good yield.

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 14508-49-7.

Reference:
Article; Nitlikar, Lakshmikant H.; Darandale, Sunil N.; Shinde, Devanand B.; Letters in Organic Chemistry; vol. 10; 5; (2013); p. 348 – 352;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 14508-49-7, A common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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.

Intermediate 741 ,1 -Dimethylethyl (2-{4-r(2S,4/?)-1 -acetyl-2-methyl-4-(2-pyrazinylamino)-1 , 2,3,4- tetrahvdro-6-quinolinyll-1 /-/-pyrazol-1 -yl)ethyl)methylcarbamateA flask was charged with 2-chloropyrazine (138 mg, 1 .209 mmol) and treated at room temperature under nitrogen with a solution of 1 ,1-dimethylethyl [2-(4-{(2S,4/?)-1 -acetyl-2- methyl-4-amino-1 ,2,3,4-tetrahydro-6-quinolinyl}-1 H-pyrazol-1 -yl)ethyl]methylcarbamate (for a preparation see intermediate 55) (250 mg, 0.605 mmol) in 1 ,4-dioxane (5 mL). 2′- (dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (DavePhos) (47.6 mg, 0.121 mmol), sodium tert-butoxide (1 16 mg, 1 .209 mmol) and tris(dibenzylideneacetone)dipalladium(0) (55.4 mg, 0.060 mmol) were added and the resulting mixture was stirred under nitrogen at 1 10C for 16 h then cooled to room temperature and partitioned between EtOAc (25 mL) and water (25 mL). The layers were separated and the aqueous phase was extracted with EtOAc (25 mL). The combined organic phases were washed with brine (50 mL), dried over Na2S04 and concentrated in vacuo. Purification of this residue on SP4 using a 25 G silica cartridge (gradient: 1 to 5% MeOH in DCM) gave 1 ,1 -dimethylethyl (2-{4-[(2S,4R)-1 -acetyl-2-methyl-4-(2- pyrazinylamino)-1 ,2,3,4-tetrahydro-6-quinolinyl]-1 H-pyrazol-1 -yl}ethyl)methylcarbamate (204.6 mg, 0.344 mmol, 56.9 % yield) as an orange oil.LCMS (Method B): Retention time 0.89 min, [M+H]+ = 506.23

The synthetic route of 14508-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GOSMINI, Romain, Luc, Marie; WO2011/54848; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 14508-49-7,Some common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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.

Step 1: 2-hydrazinylpyrazine [0204] 2-Chloropyrazine (2.0 g, 17.5 mmol) was added dropwise to a 35% aqueous solution of hydrazine hydrate (25.8 g, 97.8 mmol) at 63-65 C, the addition rate was carefully monitored to ensure that the reaction temperature did not exceed 65 C. Following the addition, the mixture was heated to 65 C. After stirring overnight, the reaction was cooled to room temperature. The solvent was evaporated to afford the title compound as a yellow powder (1.5 g, 75%). MS (ESI) calcd for C4H6N4: 110.1; found: 111.4 [M+H]. *H NMR (400 MHz, CD3OD) delta 8.10 (d, J = 1.6 Hz, 1H), 8.00 (dd, J = 3.2, 1.6 Hz, 1H), 7.73(d, J = 3.2 Hz, 1H).

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

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (239 pag.)WO2016/100349; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 14508-49-7,Some common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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.

A mixture of 2-chloropyrazine (4.00 g) and hydrazine hydrate was heated at 110 C. for 1 h, and then cooled to room temperature. The mixture was filtered to give the title compound as a solid (2.30 g, 60.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 111.0 (M+1).

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Jiancun; Zhang, Yingjun; Zhang, Weihong; Liu, Bing; Zhang, Jiquan; Liu, Jinlei; Zhang, Lu; US2014/228361; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14508-49-7, name is 2-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 14508-49-7, Recommanded Product: 2-Chloropyrazine

Preparation 1; 4-Methyi-3,4,5,6-tetrahydro-2H-[1,2’lbip(at)rrazinyl-3′-carbaldehyde; n-BuLi (56 mmol, 22.4 mL, 2.5 M in hexanes) was added to tetrahydrofuran (300 mL) cooled to-78 C followed by the addition of 2,2-6,6-tetramethylpiperidine (52 mmol, 8.71 mL). The solution was removed from the cooling bath and stirred for 30 minutes and then cooled back to -78C. 2-chloropyrazine (40 mmol, 3.65 mL) was added dropwise, and the solution turned a reddish-brown color. After stirring 30 minutes, methylformate (60 mmol, 3.7 mL) was added and the reaction mixture was stirred for 2.25 hrs at -78C. Acetic acid (8 mL) was added and the mixture was warmed to 0C, was washed 3 times with 1: 1 brine-water, dried over sodium sulfate, and then concentrated in vacuo. The residue was dissolved in 1,4- dioxane (250 mL) and 1-methylpiperazine (60 mmol, 6.6mL) and potassium carbonate solution (8.28g in 60 mL of water) were added and the mixture was heated at 100C for 1.5 hours. After cooling to room temperature, the mixture was filtered through a Celite pad which was then washed with chloroform. The filtrate was concentrated in vacuo and purified by silica gel chromatography (100: 1:1 chloroform-methanol-ammonium hydroxide) to yield 3.3 g (40% yield for two steps) of 4-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-carbaldehyde; ¹3C NMR (100 MHz, CDC13) d 191.7,154.3, 145.3,134.5, 133.2, 55.1, 48.7, 46.3; MS (AP/CI) 207.2 (M+H)+.

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

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/113535; (2005); A2;,
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 14508-49-7 as follows. Safety of 2-Chloropyrazine

General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a-k, and4m are known compounds [6,9] except for 4l and 4n.

According to the analysis of related databases, 14508-49-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xu, Chen; Li, Hong-Mei; Wang, Zhi-Qiang; Fu, Wei-Jun; Inorganica Chimica Acta; vol. 423; 1; (2014); p. 11 – 15;,
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. 14508-49-7, name is 2-Chloropyrazine, A new synthetic method of this compound is introduced below., Formula: C4H3ClN2

Example 189a tert-Butyl 4-(Pyrazin-2-yl)piperazine-1-carboxylate 189a A 500-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with DMSO (250 mL), tert-butyl piperazine-1-carboxylate (15.8 g, 85.0 mmol), 2-chloropyrazine (9.7 g, 85.0 mmol), and Cs2CO3 (55.3 g, 170 mmol). The mixture was heated at 60C for 3 days. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 5:1 petroleum ether/ethyl acetate to afford 189a (13.3 g, 60 %) as a yellow solid. MS: [M+H]+ 265.3

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; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem