Tag: M.W=100-200

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. 33332-28-4, name is 2-Amino-6-chloropyrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Amino-6-chloropyrazine

A. 6-Methylpyrazine-2-ylamine. To a solution containing 6-chloro-2- pyrazineamine (5.0 g, 38.75 mmol) in 1,4-dioxane (70 mL) was added [1,3- bis(diphenylphosphino]Ni(II)Cl2 (2.10 g, 38.76 mmol), followed by drop-wise addition of dimethylzinc in toluene (38.75 mL, 2.0 M, 77.50 mmol), over 15 min. The solution was allowed stir at 105 °C for 16 hours. The solution was then condensed under reduced pressure, diluted with ethyl acetate and filtered through celite to remove the nickel salts. The resultant slurry was purified via Biotage silica gel chromatography (0-8percent methanol in dichloromethane) to afford the title compound as an orange solid (1.18 g, 28percent yield). MS (ESI) m/z 1 10.3 [M+ 1]+.

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; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4774-14-5, The chemical industry reduces the impact on the environment during synthesis 4774-14-5, name is 2,6-Dichloropyrazine, I believe this compound will play a more active role in future production and life.

To a solution of fert-butyl azetidin-3-ylcarbamate hydrochloride (LXXX) (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 (LXXXI) (1.428 g, 9.58 mmol) and the reaction was stirred at 95C for 3 h. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous NaaSO/t, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes?hexanes:EtOAc 1 : 1) to yield fert-butyl (l-(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXXXII) (2.2882 g, 8.04 mmol, 84 % yield) as a white solid. ESIMS found for C12H17CIN4O2 mlz 285.1 (M+H).

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, 2,6-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (265 pag.)WO2017/24010; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 875781-43-4, 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. 875781-43-4 name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, 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.

Step 1To a 500 ml three necked round bottom flask, 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.0 g,0.0252 mole) was taken in CH2C12 (150 ml). The reaction mixture was cooled to 0 C and diethylaluminiumchloride (1M solution in hexanes) (9.11 g, 0.0756 mole) was added drop wise at the same temperature under nitrogen atmosphere. The reaction mixture was stirred for 30 min at 0 C followed by slow addition of pivoloyl chloride (29.45 g, 0.2444 mole) over 15min at the same temperature. After completion of the addition, the reaction mixture was warmed up to RT Attorney Docket No. 11913-1008 and then up to 40 C and stirred for 16 hrs. The completion of the reaction was monitored on TLC using hexanes: ethyl acetate (5:5) as a mobile phase. After completion of the reaction, the reaction mixture was poured in saturated NaHC03 solution with stirring at 10 C, diluted with CH2C12 and filtered through high flow. The filtrate was collected and washed with brine solution. Layers were separated and the aq. Layer was extracted with CH2C12. The combined organic layer was dried over Na2S04, filtered and concentrated to afford crude product which was subjected for the column purification. The crude compound was purified using column purification by eluting the compound with 10 -25% ethyl acetate in hexanes to yield 5.3g of l-(2- bromo-5H-pyrrolo[2,3-b] pyrazine-7-yl)- 2,2-dimethyl propan-l-one

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; VERNER, Erik; WO2012/158785; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 4774-14-5, The chemical industry reduces the impact on the environment during synthesis 4774-14-5, name is 2,6-Dichloropyrazine, I believe this compound will play a more active role in future production and life.

Svnthesis 2-1-A 6-Chloropyrazin-2-amine 2,6-Dichloropyrazine (2.89 g, 19.4 mmol) was stirred in aqueous ammonia (28%, 10 mL) and heated to 100C overnight in a sealed tube. The reaction mixture was cooled and the resultant precipitate was filtered. Trituration with water and then ether gave the title compound as a white solid (2.28 g, 17.6 mmol, 91%). 1H NMR (d6-DMSO, 400 MHz) delta 7.80 (d, 1 H1 J = 0.4 Hz), 7.70 (d, 1 H, J = 0.4 Hz), 6.9 (br s, 2H). LC-MS (2) rt 1.05 min; m/z (ESI+) 130/132.

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, 2,6-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/103966; (2009); 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.

2-Chloro-3-hydrazinylpyrazine C-1 (15.6 g; 108 mmol) is slurried up in (300 ml) THF and cooled down in an ice bath to -5 C. Trifluoroacetic anhydride (17 ml; 118 mmol) is also dissolved in 300 ml THF and dropped slowly to the first solution. After 1 h most of the THF is evaporated, than a small amount of water is added and the mixture is extracted with DCM. The organic phase is dried over MgSO4 and evaporated to dryness. Yield: 100%. HPLC-MS: (M+H)+=241/243; tRet=1.31 min; method FSUN2.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; GIANNI, Davide; SMETHURST, Christian; US2014/142098; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, 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 75907-74-3, name: (3,5,6-Trimethylpyrazin-2-yl)methanol

To a solution of (3,5,6-trimethylpyrazin-2-yl)methanol(4) (15.50 g, 102 mmol) in anhydrous CH2Cl2 (300 mL),thionyl chloride (7.41 mL, 102 mmol) was added drop bydrop at 0 C. After finishing dropping, the mixture wasstirred at room temperature for 2.5 h. The solvent was evaporatedin vacuo and the product 2-chloromethyl-3,5,6-trimethylpyrazine hydrochloride (5) was obtained as yellowsolid (21.11 g, 100%), mp: 102-105 C [11].

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; Li, Zhenyu; Yu, Fang; Cui, Lei; Chen, Wenmin; Wang, Shouxun; Zhan, Peng; Shen, Yuemao; Liu, Xinyong; Medicinal Chemistry; vol. 10; 1; (2014); p. 81 – 89;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4774-15-6, These common heterocyclic compound, 4774-15-6, name is 2,6-Dimethoxypyrazine, 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.

20 ml of 30% hydrogen peroxide was slowly added to 20 ml of acetic acid at room temperature, and then 4 g of 2,6-dimethoxypyrazine was added to the above oxidizing agent solution.After it is dissolved, the reaction system is heated to 55 C, and reacted for 4 hours; after the reaction is completed, the reaction system is cooled to room temperature and poured into ice water;The mixture was extracted 9 times with ethyl acetate.After the solid was filtered off, the filtrate was evaporated under reduced pressure to remove solvent.The white solid product 2,6-dimethoxypyrazine-4-oxide was obtained in a yield of 68%.

The synthetic route of 4774-15-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Engineering Physics Institute Chemical Materials Institute; Huang Qi; Li Hongzhen; Nie Fude; (11 pag.)CN107266376; (2017); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 59489-71-3, The chemical industry reduces the impact on the environment during synthesis 59489-71-3, name is 2-Amino-5-bromopyrazine, I believe this compound will play a more active role in future production and life.

5-Bromopyrazin-2-amine (2.0 g, 11.49 mmol), (4-methylsulfonylphenyl)boronic acid (2.758 g, 13.79 mmol) and K3P04 (4.878 g, 22.98 mmol) were combined in MeCN (40 niL) / Water (10 mL) and Pd[P(tBu)3]2 (216 mg, 0.4227 mmol) was added. The reaction was heated at 60 C for 1 hour. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was triturated with water, then Et20 then dried in vacuo to give the sub-title compound as a beige solid which was used without further purification (2.53 g, 88% Yield). 3H NMR (400.0 MHz, DMSO) delta 3.20 (s, 3H), 6.80 (br s, 2H), 7.94 (d, 2H), 8.00 (d, 1H), 8.17 (d, 2H) and 8.64 (d, 1H) ppm.

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-Amino-5-bromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; YOUNG, Stephen, Clinton; STORCK, Pierre-Henri; VIRANI, Aniza, Nizarali; REAPER, Philip, Michael; PINDER, Joanne; WO2011/143423; (2011); A2;,
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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., Product Details of 91476-80-1

A mixture of (2-chloropyrimidin-4-yl)-(l -isopropyl-1 H-imidazo[4,5-c]pyridin-6-yl)amine (Example 12, step 4) (70 mg, 0.24 mmol), 5,6,7,8-tetrahydroimidazo[l,2-a]pyrazine (44 mg, 0.36 mmol), triethylamine (0.15 mL) in isopropyl alcohol (0.5 mL) was heated at 150 C under microwave irradiation on high absorbance for 2.5 h. The cooled reaction mixture was poured onto an SCX cartridge; the cartridge was washed with MeOH followed by elution of the product with 2M NH3 in MeOH. The product containing fractions were concentrated in vacuo and the resulting residue was crystallised from MeOH/EtOAc to afford the title compound as a white solid (55 mg, 62%). LCMS (ESI): RT 1.72 min, [M+H]+ 376.0, Method = E. lH NMR (400 MHz, CDC13): delta 8.75 (1H, d, J = 1.0 Hz), 8.29 (1H, s), 8.06 (1H, d, J = 5.7 Hz), 7.95 (1H, s), 7.66 (1H, s), 7.02 (1H, d, J = 1.3 Hz), 6.86 (1H, d, J = 1.3 Hz), 6.22 (1H, d, J = 5.7 Hz), 5.08 (2H, s), 4.79-4.67 (1H, m), 4.30 (2H, t, J = 5.4 Hz), 4.07 (2H, t, J = 5.4 Hz), 1.70 (6H, d, J = 6.7 Hz).

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; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 870787-06-7,Some common heterocyclic compound, 870787-06-7, name is 3-(Trifluoromethyl)pyrazine-2-carboxylic acid, molecular formula is C6H3F3N2O2, 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 100 mL round bottom flask was charged with the compound represented by the formula (II-1) (2 mmol), EDCI (2.4 mmol), HOBt (2.4 mmol) and 10 mL of DMF, and reacted at 25 C. for 1 h. Then, the compound (2.4 mmol) represented by the formula (II-2) was added to the above solution and reacted at 25C for 24 hours. After the solvent was removed, the target product was obtained by column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Trifluoromethyl)pyrazine-2-carboxylic acid, its application will become more common.

Reference:
Patent; Central China Normal University; Yang Guangfu; Li Hua; Xiong Li; (34 pag.)CN108069915; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem