Month: June 2021

Related Products of 4774-14-5, A common heterocyclic compound, 4774-14-5, name is 2,6-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.

Step 1 (0850) To a solution of tert-butyl azetidin-3-ylcarbamate hydrochloride (LXIII) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXIV) (1.428 g, 9.58 mmol) and the reaction was stirred at 95 C. for 3 hours. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes-hexanes:EtOAc 1:1) to yield tert-butyl (1-(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXV) (2.2882 g, 8.04 mmol, 84% yield) as a white solid. ESIMS found for C12H17ClN4O2 m/z 285.1 (M+H).

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; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (254 pag.)US2016/68548; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 24241-18-7, 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 24241-18-7 as follows.

To an aqueous (10 kg) solution of 3,5-dibromopyrazine-2-amine (1018 g, 4.03 mol), 2-bromo-1,1-dimethoxyethane (1.79 kg, 4.14 mol) was added at room temperature and stirred for 2 hours while heating under reflux. To the reaction solution, water (15.3 kg) and sodium hydrogen carbonate (744 g) were added and further stirred for 15 minutes. The resultant solid substance was obtained by filtration to obtain the titled compound (1106 g, 3.99 mmol, 99%) as a brown solid substance.1H-NMR (400 MHz, DMSO-d6) delta 7.90 (s, 1H), 8.23 (s, 1H), 9.02 (s, 1H).

According to the analysis of related databases, 24241-18-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Oncotherapy Science, Inc.; US2012/59162; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 54608-52-5, name is 2-Hydrazinopyrazine, 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 54608-52-5, SDS of cas: 54608-52-5

A mixture of 2-hydrazinopyrazine (820 mg, 7.45 mmol), prepared from 2- chloropyrazine and hydrazine using a procedure analogous to that described in the literature (P. J. Nelson and K. T. Potts, J. Org. Chem. 1962, 27, 3243, except that the crude product was extracted into 10% methanol/dichloromethane and filtered, and the filtrate was concentrated and purified by flash chromatography on silica gel, eluting with 100% ethyl acetate followed by 10% methanol in dichloromethane), TFA (2.55 g, 22.4 mmol), and polyphosphoric acid (10 mL) was heated to 140 C with stirring for 18 h. The solution was added to ice and neutralized by the addition of ammonium hydroxide. The aqueous solution was extracted with ethyl acetate (3X), washed with brine, and dried over anhydrous magnesium sulfate. Concentration followed by flash chromatography (silica gel, 1: 1 hexane: ethyl acetate, then 100% ethyl acetate) afforded the title compound as a SOLID. 1H NMR (500 MHz, CDC13) 8 8. 17-8. 20 (m, 2H), 9.54 (s, 1H). LC/MS (M+1) 189.

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; MERCK & CO., INC.; WO2004/58266; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 55557-52-3, A common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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.

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 %).

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; MSD Oss B.V.; Man, de, Adrianus, Petrus, Antonius; Sterrenburg, Jan-Gerard; Raaijmakers, Hans C.A.; Kaptein, Allard; Oubrie, Arthur A.; Rewinkel, Johannes, Bernardus, Maria; Jans, Christiaan, Gerardus, Johannes, Maria; Wijkmans, Jacobus C.H.M.; Barf, Tjeerd A.; Gao, Xiaolei; Boga, Sobhana Babu; Yao, Xin; Zhu, Hugh Y.; Cooper, Allen B.; Kim, Ronald M.; EP2548877; (2013); 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloropyrazine-2-carbonitrile

The starting compound 3-chloropyrazine-2-carbonitrile (35.8 mmol) was dispersed in a 10percentsolution of sodium hydroxide (125 mmol, 3.5 equiv.) in a round bottom flask. The reaction mixturewas stirred and heated under reflux in an oil bath for 7 h. The progress of the reaction was monitoredby TLC in the system butanol/acetic acid/water (4:1:5). The reaction mixture was acidified by 10percentsolution of hydrochloric acid to pH 3. Resulting crystals of 3-chloropyrazine-2-carboxylic acid weresuctioned. The melting point and 1H-NMR corresponded with the literature [17].

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:
Article; Semelkova, Lucia; Jand’ourek, Ond?ej; Kone?na, Klara; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Franti?ek; Kubi?ek, Vladimir; Kune?, Ji?i; Dole?al, Martin; Zitko, Jan; McPhee, Derek J.; Molecules; vol. 22; 3; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 486424-37-7, The chemical industry reduces the impact on the environment during synthesis 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

Step 1: 3-Amino-6-bromo-N-methoxy-N-methyl pyrazi ne-2-carboxamideTo a stirred suspension of 3-amino-6-bromopyrazine-2-carboxylic acid (45 g, 206 mmol) andO,N-dimethylhydroxylamine hydrochloride (20.13 g, 206 mmol) in DMF (295 mL) at RT wasadded triethylamine (115 mL, 826 mmol) under N2 supply. The resulting mixture was cooledto 0C and to this yellow suspension T3P (50 % in EtOAc) (151 g, 237 mmol) was added dropwise over 5 mm (keeping T below 10C – exotherm). The mixture was allowed to warm to RT and stirred for 2-3 hours. During the reaction the contents had set solid into a gel. The flask was diluted with a further 200 ml of DMF and was warmed to 40 C and was leftovernight. Further triethylamine (50 mL, 0.4 equiv), O,N-dimethylhydroxylamine hydrochloride (10 g, 0.5 equiv) and T3P (80 g, 0.5 equiv) were added and the reaction mixture was warmed to 4000 and was allowed to stir for 2-3 hours. The mixture was allowed to cool to RT and then stirred for three days. The mixture was worked up by the addition of 2M HCI (100 mL) and was diluted with ethyl acetate (1 L) and water (500 mL). The biphasic mixture was separated. The aqueous layer was basified with 2M NaOH (- 150 mL), organicextract was added back and the biphasic mixture was shaken. The organic was extracted, washed with brine, dried over MgSO4, filtered and dried under vacuum to give a yellow oil. The crude yellow oil was loaded directly onto a 750 g column (in DCM 20 mL) and was eluted with iso-Hex / EtOAc (0- 70 % gradient). The fractions containing pure product were combined and evaporated to give a yellow oil. Diethyl ether (50 mL) was added and this wasevaporated under vacuum to give a pale yellow solid;LC-MS: Rt 0.88 mins; MS m/z 263.1 MH+; Method 2minLC_v003

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-Amino-6-bromopyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 136866-30-3,Some common heterocyclic compound, 136866-30-3, name is 3,5-Dichloro-2-iodopyrazine, molecular formula is C4HCl2IN2, 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.

Preparation Example 372 A mixture of 3,5-dichloro-2-iodopyrazine (2 g), cyclopropylboronic acid (750 mg), tetrakistriphenylphosphine palladium (0) (1.68 g), potassium phosphate (3.09 g), toluene (40 mL), and water (4 mL) was stirred at 110 C. overnight. After leaving to be cooled, the insoluble matter was removed by decantation, followed liquid separation by the addition of ethyl acetate and water. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=98:2) to obtain 3,5-dichloro-2-cyclopropylpyrazine (784 mg) as a colorless oily material.

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

Reference:
Patent; ASTELLAS PHARMA INC.; Matsuya, Takahiro; Kondoh, Yutaka; Shimada, Itsuro; Kikuchi, Shigetoshi; Iida, Maiko; Onda, Kenichi; Fukudome, Hiroki; Takemoto, Yukihiro; Shindou, Nobuaki; Sakagami, Hideki; Hamaguchi, Hisao; US2014/323463; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 723286-80-4, 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. 723286-80-4, name is tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A solution of tert-butyl 3-bromo-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylate (1 g, 3.30 mmol, 1 equiv.) in CH3NH2 (in EtOH) (7 mL) was stirred for 20 h at 100 degree Celsius. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The resulting mixture was concentrated under reduced pressure. The residue was purified by reverse phase flash with the following conditions (Column: C18 Column 120 g; Mobile Phase A: Water(10 mmol/L AcOH), Mobile Phase B: ACN; Flow rate: 50 mL/min; Gradient: 20% B to 50% B in 40 min; 254/220 nm) to afford tert-butyl 3-(methylamino)- 5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carboxylate(550 mg, 65.82%) as a off-white solid.

The synthetic route of tert-Butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 27825-21-4, name is Methyl 3-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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. name: Methyl 3-chloropyrazine-2-carboxylate

Example 15. Production of methyl 3-trifluoromethyl-pyrazine-2-carboxylate (compound No. 3-4) Methyl 3-chloropyrazine-2-carboxylate (2 g, 11.6 mmol), cuprous iodide (3.3 g, 17.3 mmol), potassium fluoride (1.34 g, 23 mmol) and methyl chlorodifluoroacetate (3.36 g, 18.2 mmol) were dissolved in DMF (20 ml) and stirred at 115C for 5 hours under argon atmosphere. The reaction solution was filtered with celite, followed by dilution of the filtrate with ethyl acetate, and washing four times with water. The filtrate was dried over magnesium sulfate, and concentrated under reduced pressure, and then the residue was purified by using silica gel chromatography (hexane:ethyl acetate=3:1) to obtain 700 mg of the desired compound as paste state. Yield: 29% Property: 1H-NMR [CDCl3/TMS, delta (ppm)] 8.85 (d, 1H), 8.83(d, 1H), 4.05(s,3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27825-21-4, its application will become more common.

Reference:
Patent; NIHON NOHYAKU CO., LTD.; EP1757595; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19847-12-2, name is Pyrazinecarbonitrile, 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 19847-12-2, SDS of cas: 19847-12-2

The synthesis of 6 was similar to that of 5, but with H2pma (50.8 mg, 0.2 mmol) in place of H2pna. The resultant solution was allowed to evaporate slowly in darkness at room temperature for several days to afford the product as plate-shaped clear yellow crystals of 6. (Yield: 75%, based on silver). Anal. Calc. (found) for AgC10H10N3O7: C, 30.64 (30.75); H, 2.57 (2.62); N, 10.72 (10.95)%. IR (KBr): nu (cm-1) = 3275 (s), 3020 (s), 1650 (s), 1568 (s), 1479 (s), 1415 (s), 1371 (s), 1313 (s), 1180 (m), 1135 (m), 1053 (m), 1015 (m), 918 (w), 780 (w), 855 (m), 804 (m), 759 (m), 689 (w), 625 (w), 568 (w), 530 (m), 434 (w).

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:
Article; Huang, Hua-Qi; Wang, Dan-Feng; Zhang, Ting; Huang, Rong-Bin; Journal of Molecular Structure; vol. 1086; (2015); p. 99 – 108;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem