Category: 4858-85-9

4858-85-9, 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 4858-85-9 as follows.

A 12L 3-neck round bottom flask fitted with a magnetic stirrer under nitrogen was charged with zinc dust (745 g, pre-activated, 11.4 mol, 2 eq.) and DMA (2 L, anhydrous). 1, 2-dibromoethane (71 mL, 0.855 mol, 0.15 eq, Aldrich) was then added over 10 minutes, followed by TMSC1 (108 mL, 0.855 mol, 0.15 eq, Acros) over 20 minutes. The reaction mixture was stirred for 25 minutes at room temperature. A solution of N-Boc-3-iodoazetidine (2420 g, 8.55 mol, 1.5 eq, CNH Technologies) in DMA (5 L, anhydrous) was added via a 2L addition funnel over 2 h keeping the internal temperature below 65 C using a water bath. The suspension was stirred for 1 hour at RT at which point it was degassed with nitrogen. Stirring was stopped and the suspension was allowed to stand. A 22L 3-neck round bottom flask fitted with a mechanical stirrer was charged with 2, 3-dichloropyrazine (850 g, 5.70 mol, 1.0 eq, AK Scientific), PdCl2dppf-CH2Cl2 (140 g, 171 mmol, 0.03 eq, Aldrich), Cul (67.3 g, 353 mmol, 0.062 eq, Aldrich), and DMA (5 L, anhydrous). The solution was degassed with nitrogen. The clear zinc reagent solution above the residual solid zinc was poured into the 22L flask under nitrogen. The brown solution was degassed with nitrogen and heated to 80 C for 16 hours at which point LCMS indicated complete conversion of 2, 3-dichloropyrazine. The reaction mixture was transferred to brine (8 L) in 50L separatory funnel. Water (8 L) and EtOAc (15 L) were added and the layers were separated. The aqueous layer was extracted with EtOAc (2 x 10 L). The combined organics were washed with water (3 x 10 L) and brine (5 L), dried over sodium sulfate and evaporated. The resulting residue was purified by column chromatography (eluting with hexanes/ethyl acetate = 10: 1) to get 536 g of pure tert-butyl 3-(3-chloropyrazin-2- yl)azetidine- 1 -carboxylate and 121 g of mixed fractions. The impure material was distilled under high vacuum to remove the impurity (N-Boc-azetidine) to give 81 g of pure tert-butyl 3- (3-chloropyrazin-2-yl)azetidine- 1 -carboxylate.Total: 617g, Yield: 40%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4858-85-9, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

4858-85-9, 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. 4858-85-9, name is 2,3-Dichloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

2,3-Dichloropyrazine A-1 (15 g; 100.68 mmol) and hydrazine hydrate 65% (15.509 ml; 201.37 mmol) are dissolved in 45 ml ethanol and stirred for 1 h at 80 C. While cooling down, a precipitate is formed. It is slurred up with a small amount of water and filtered off. It is washed with water and then dried to afford the product. Yield: 93% (13.6 g; 94.07 mmol) HPLC-MS: (M+H)+=145/147; tRet=0.34 min; method FECB5

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

Reference:
Patent; ENGELHARDT, Harald; US2015/133447; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

4858-85-9, A common compound: 4858-85-9, name is 2,3-Dichloropyrazine, 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.

To a solution of (?)-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 HC1 (500 mL) for 10 minutes. The phases were separated and the organic layer was extracted with 3M HC1. The aqueous was washed with EA and then alkalified with Na2C03 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+l) + (Acq Method: 10-80AB_2min; Rt: 0.75 min).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; LIU, Shilan; YANG, Chundao; ZHENG, Shuling; WO2014/113942; (2014); A1;,
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. 4858-85-9, name is 2,3-Dichloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., 4858-85-9

A. Preparation of the intermediate compounds; Example Al; a) Preparation of intermediate compound 1; Reaction in microwave oven. A mixture of 2-phenoxyethanamine (0.010 mol), 2,3- dichloropyrazine (0.012 mol) and l,8-diazabicyclo(5.4.0.)undec-7-ene (DBU) (0.012 mol) in CH3CN (20 ml) was heated for 20 minutes at 180 0C. The solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2). The product fractions were collected and the solvent was evaporated. Yield: 2.5 g of intermediate compound 1 (quantitative yield; used in next reaction step, without further purification).

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; JANSSEN PHARMACEUTICA N.V.; WO2007/71646; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 4858-85-9

To a 1.0 M solution of LiHMDS in toluene (14.8 mL, 14.8 mmol) under nitrogen at 0 C was added 2,3-dichloropyrazine (0.699 mL, 6.71 mmol) and ethyl acetate (0.725 mL, 7.38 mmol). The mixture was stirred overnight for 18 hours, allowing the ice bath to warm to room temperature. The mixture was poured into saturated ammonium chloride (100 mL), and extracted with diethyl ether (3×100 mL). The combined ether extracts were washed with brine, dried (sodium sulphate) and evaporated. The residue was chromatographed (40 g silica cartridge, 0-25% ethyl acetate/petroleum benzine 40-60 C) to give the title compound (199) (0.414 g, 31 % yield) as a pale yellow oil; 1 H NMR (400 MHz, CDCI3) delta 8.46 (d, J = 2.5 Hz, 1 H), 8.31 (d, J = 2.5 Hz, 1 H), 4.22 (q, J = 7.1 Hz, 2H), 4.03 (s, 2H), 1.27 (t, J = 7.1 Hz, 3H). LCMS Method C: rt 5.16 min.

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 4858-85-9.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 4858-85-9, name is 2,3-Dichloropyrazine, 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 4858-85-9. 4858-85-9

2,3-Dichloropyrazine (448 mg, 3 mmol) and 1 -[2-(4-fluorophenoxy)ethyl] piperazine (CAS 77602-92-7, 2.9 mmol) were dissolved in DMSO (0.4 ml). Subsequently, NaOH pellets (1 g, 25 mmol) were added. The reaction was stirred at 150 0C under microwave irradiation for 0.5 hours. Then, 0.4 ml of NaOH (4M) and 0.4 ml of DMSO were added, heating at 150 0C in microwave for 0.5 hours more. The mixture was dissolved in AcOEt, washed with H2O and brine, dried with MgSO4 and evaporated under vacuum. The product was used without any further purification, yielding 710 mg of the desired final compound 13-1 (77 %).

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 2,3-Dichloropyrazine.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/135131; (2007); 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. 4858-85-9, name is 2,3-Dichloropyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 4858-85-9

To a solution of l-(quinolin-2-yl)piperidin-4-ol (see PREPARATION Pl . l ; 2.0 g, 8.7 mmol) in DMF (30 mL) at room temperature was added sodium hydride (60% wt in mineral oil) (0.47 g, 17.4 mmol) at 0 C. The mixture was stirred at room temperature for 60 min and then 2, 3-dichloro-pyrazine (1.2 g, 8.7 mmol) was added. The reaction mixture was heated to 90 C overnight and then diluted with water (60 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with water (40 mL) and brine (40 mL), dried over Na2S04, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (10% to 30% EtOAc in petroleum ether) to give the title product ( 2.0 g, 5.8 mmol, 70% yield ) as white solid. ESI-MS (M+l): 341 calc. for

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

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; HORNE, Daniel B.; HU, Essa; KALLER, Matthew R.; MONENSCHEIN, Holger; NGUYEN, Thomas T.; REICHELT, Andreas; RZASA, Robert M.; WO2011/143495; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 4858-85-9

To a flame dried 25 mL flask with zinc dust (217 mg, 3.31 mmol) and N,N-dimethylacetamide (2 mL) was added chlorotrimethylsilane (33.5 muL, 0.265 mmol) and 1,2- dibromoethane (22.83 muL, 0.265 mmol). The resulting slurry was stirred 15 min, then tert-butyl 3-iodoazetidine-l-carboxylate (753 mg, 2 66 mmol) was added to the above mixture (mild exotherm). The suspension was stirred at rt 30 min. [00422] The zinc solution was added via syringe to a solution of 2,3-dichloropyrazine (277 mg, 1.862 mmol), (dppf)PdCl2-CH2Cl2 (65.2 mg, 0.080 mmol), and copper(I) iodide (30.4 mg, 0.160 mmol) in N,N-dimethylacetamide (1.0 mL) that was degassed with N2 (3 x). The solution was heated to 80 0C and stirred 1 h. The reaction was quenched with NH4Cl (10 mL) and extracted with EtOAc (3 x 10 mL). The combined organic fractions were dried (MgSO4), concentrated, and purified by ISCO (40 g SiO2, 10-100% EtOAc/Hexane) to give tert-butyl 3-(3- chloropyrazin-2-yl)azetidine-l-carboxylate (262 mg, 0.971 mmol, 36.5 % yield) as a clear, colorless oil.

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 4858-85-9.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; BOURBEAU, Matthew P.; CHEN, Ning; HU, Essa; KUNZ, Roxanne; RUMFELT, Shannon; WO2010/57121; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

4858-85-9, 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. 4858-85-9 name is 2,3-Dichloropyrazine, 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.

Reference Production Example 19 A mixture of 3.73 g of 2,3-dichloropyrazine, 8.80 g of diethyl malonate, 30 ml of dimethyl sulfoxide and 17.9 g of cesium carbonate was stirred for 8 hours at 110C under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, then, to this was added ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine twice, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. 3.67 g of the resultant residue was subjected to silica gel column chromatography, to obtain 2.69 g of diethyl (3-chloro-2-pyrazinyl) malonate. 1H-NMR (CDCl3, TMS) delta (ppm): 1.27 (6 H, t, J=7.2 Hz), 4.30 (4 H, q, J=7.2 Hz), 5.20 (1 H, s), 8.36 (1 H, d, J=2.6 Hz), 8.50 (1 H, d, J=2.6 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3-Dichloropyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1958946; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

4858-85-9, 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 4858-85-9 as follows.

2,3-Dichloropyrazine A-1 (15 g; 100.68 mmol) and hydrazine hydrate 65 % (15.509 ml; 201.37 mmol) are dissolved in 45 ml ethanol and stirred for 1 h at 80 C. While cooling down, a precipitate is formed. It is slurred up with a small amount of water and filtered off. It is washed with water and then dried to afford the product. Yield: 93% (13.6 g; 94.07mmol) HPLC-MS: (M+H)+ = 145/147; tRet = 0.34 min; method FECB5

According to the analysis of related databases, 2,3-Dichloropyrazine, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; WO2015/67770; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem