Tag: M.W=200-300

24241-18-7, A common compound: 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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 the reaction flask was added tetrahydrofuran (50 ml). trimethylsilylacetylene (580 mg, 5.9 mmol), triethylamine (1.2 g, 11.8 mmol), CuI (0.1 g), Pd(PPh3)4 (0.1 g) and the compound 3,5-dibromo-2-aminopyrazine 1a (1.0 g, 3.95 mmol) were reacted under nitrogen for 3 hours at room temperature.TLC showed the reaction was completed, 50ml of water was added and extracted with ethyl acetate (30mL) twice the aqueous phase, the organic phases are combined,Once, dried over anhydrous sodium sulfate washed with brine, and dried to give the crude product under reduced pressure using a rotary evaporator,Through the column to give the crude title compound 5a (0.5g, 18.5mmol), a yield of 47.1%

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-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Qiang; Qu Minkai; Zhang Linli; Song Jinqian; Liu Lei; Chen Haiji; Liu Qiang; Wang Yijin; Ge Jian; (67 pag.)CN109535164; (2019); A;,
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 13301-04-7 as follows. 13301-04-7

A solution of methyl 3,6-dibromopyrazine-2-carboxylate (500 mg, 1.690 mmol, 1 equiv), (3S,4S)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine dihydrochloride (493.05 mg, 2.028 mmol, 1.2 equiv) and DIEA (1091.88 mg, 8.448 mmol, 5.0 equiv) in DMA (10 mL) was stirred for 2 at 55 C. Di-tert-butyl dicarbonate (552.33 mg, 2.531 mmol, 1.5 equiv) was then added and the resulting mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc =1 : 1 to afford the title compound (615 mg, 2 steps yield 75%) as yellow oil.

According to the analysis of related databases, 13301-04-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIKANG THERAPEUTICS, INC.; FU, Jiping; LOU, Yan; HE, Yigang; (0 pag.)WO2020/61101; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

24241-18-7, A common compound: 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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.

A mixture of 3,5-dibromopyrazin-2-amine (214 mg, 0.83 mmol) and phenyl boronic acid (100 mg, 0.8 mmol) in toluene (8 mL) was degassed and backfilled with nitrogen 3 times. Pd(PPtLs)4 (46 mg) was added followed by 2M K3PO4 (0.8 mL) and EtOH (1 mL). The mixture was heated at reflux for 18 h. The solution was cooled to room temperature, partitioned between EtOAc (25 mL) and water (5 mL). The layers were separated and the organic layer dried over Na2SO4, filtered and concentrated to an oil which was purified via silica gel chromatography (15% EtOAc/heptane) to afford the product (187 mg, 95% yield)

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-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/155388; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

5900-13-0, The chemical industry reduces the impact on the environment during synthesis 5900-13-0, name is 5-Bromo-3-methoxypyrazin-2-amine, I believe this compound will play a more active role in future production and life.

Toa stirred suspension of sodium hydride (60%, 196 mg, 4.9 mmol) and THF (10 mL)at 0C, under N2, was added 5-bromo-3-methoxypyrazin-2-amine (1.00g, 4.9 mmol) in one portion. This was stirred at 0C for 30 min before theaddition of 3,5-dichlorobenzene-l- sulfonyl chloride (120 mg, 0.49 mmol) in oneportion. The reaction was allowed to warm to room temperature and stirred for 2hrs. The reaction was acidified to pH 2 with 2 M HC1, diluted with water (100mL) and extracted with EtOAc (100 ml x 3). The combined organic extracts werewashed with water (100 ml), brine (100 ml), dried ( a2S04), filtered andconcentrated to give the crude product as a brown oil, which was purified usingsilica chromatography (eluent 12% to 50% EtOAc in heptane) to give the titlecompound as a white solid (866 mg, 39%); m z=411.7, 413.6 (MH)+

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-3-methoxypyrazin-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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. 6966-01-4

Step 2 : 3-amino-6-bromopyrazine-2-carboxylic acid[00211] A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (3 g, 12.93 mmol) and lithium hydroxide (1.548 g, 64.65 mmol) in MeOH (11.74 mL) and H2O (11.74 mL) was heated to 90 0C for 2 hours. The reaction mixture was allowed to cool, neutralised with HCl and diluted with water, and the resultant precipitate collected by filtration (2.2 g, 78% Yield). 1H NMR (400.0 MHz, DMSO) 7.57 (br s, 2H) and 8.39 (s, IH), 13.41 (br s, IH) ppm.

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 6966-01-4.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-damien; DURRANT, Steven; KAY, David; O’DONNELL, Michael; KNEGTEL, Ronald; MACCORMICK, Somhairle; PINDER, Joanne; VIRANI, Anisa; YOUNG, Stephen; BINCH, Hayley; CLEVELAND, Thomas; FANNING, Lev, T.d.; HURLEY, Dennis; JOSHI, Pramod; SHETH, Urvi; SILINA, Alina; WO2010/54398; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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.

Step 1 A 500 ml three necked round bottom flask was charged with 3,5-dibromopyrazine-2- amine (25.0 g, 0.0988 mole) which was dissolved in acetonitrile (250 ml). The reaction mixture was cooled to 0 C and triethylamine (50.0 g, 0.4941 mole), copper (1) iodide (2.26 g, 0.0119 mole), and Pd (PPh3)4 (5.7 g, 0.0049 mole) were added under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0 C followed by slow addition of trimethylsilylacetylene (10.7g, 0.1089 mole) over 15 min at the same temperature. After completion of the addition, the reaction mixture was warmed up to RT and stirred for 90 min. The reaction mixture was diluted by ethyl acetate and filtered. The filtrate was collected and washed with water. Layers were separated and aqueous layer was re-extracted by ethyl acetate. Combined organic layer was dried over Na2S04, filtered and concentrated to afford crude product which was purified using column purification to afford 20.0 g of 5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine.

According to the analysis of related databases, 2-Amino-3,5-dibromopyrazine, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David, Michael; BRAMELD, Kenneth, Albert; OWENS, Tim; WO2014/81732; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, 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. 24241-18-7

2-chloroacetaldehyde (0.79 g, 4 mmol) was slowly added to a freshly prepared solution of 3,5-dibromopyrazin-2-amine (1) (0.51 g, 2 mmol) in 2-propanol (20 mL). The mixture was stirred at reflux under a nitrogen atmosphere for 24 h. After cooling, CH2Cl2 (25 mL) and Et3N (1 mL) were added to the reaction solution. Thereafter, the solvent was evaporated under reduced pressure, and then the residue was washed with 11 mL mixed solution (water: 2-propanol = 10:1) for 2 times, filtered and dried under vacuum to give 6,8-dibromoimidazo[1,2-a]pyrazine (2) as a brown solid, which was pure enough to be used in the next step without further purification.

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 24241-18-7.

Reference:
Article; Huang, Boshi; Liang, Xin; Li, Cuicui; Chen, Wenmin; Liu, Tao; Li, Xiao; Sun, Yueyue; Fu, Lu; Liu, Huiqing; De Clercq, Erik; Pannecouque, Christophe; Zhan, Peng; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 330 – 337;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

5900-13-0, 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. 5900-13-0, name is 5-Bromo-3-methoxypyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

3-Methoxy-5-vinylpyrazin-2-amine A mixture of 5-bromo-3-methoxypyrazin-2-amine (800 mg, 3.92 mmol, 1 eq.; Jiang, B. et al. Bioorg. Med. Chem (2001 ), 9, 1149-1 154.), trivinylboroxine pyri- dine-complex (944 mg, 3.92 mmol, 1.0 eq), tetrakis(triphenylphosphin)palladium(0) (45 mg, 0.04 mmol, 0.01 eq) and potassium carbonate (542 mg, 3.92 mmol, 1.0 eq) in 40 ml_ dimethoxyethane/water (3/1) was stirred at room temperature for 10 min and then heated to reflux temperature for 3 hours. The reaction mixture was hydrolysed with 100 ml_ of water and extracted with ethyl acetate. The resulting organic phase was washed with brine, dried with sodium sulphate and concentrated in vacuo. The crude mixture was purified via MPLC (column: Snap cartridge, eluent: hexane -> hexane/ethyl acetate 1/1) to deliver 495 mg (78%) of the title compound. UPLC-MS (Method 2): RT = 0.87 min; m/z = 152 (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; BAYER INTELLECTUAL PROPERTY GMBH; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SCOTT, William; HAeGEBARTH, Andrea; INCE, Stuart; REHWINKEL, Hartmut; POLITZ, Oliver; NEUHAUS, Roland; BOeMER, Ulf; WO2013/104610; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

41270-66-0, 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. 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, A new synthetic method of this compound is introduced below.

2-chloro-5,6-diphenylpyrazine (10 gm), 4-(isopropylamino)-1 -butanol (44 gm) and N-methylpyrrolidine (50 mL) were charged into a 250 mL round bottom flask at 30C. The reaction mass was heated to 190C and stirred for 10 hours. The reaction mass was cooled to 30C and poured into cold water, extracted with ethylacetate, dried over anhydrous magnesium sulphate and then concentrated to get 9 gm of the title compound.

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; DR. REDDY’S LABORATORIES LIMITED; ORUGANTI, Srinivas; KANDAGATLA, Bhaskar; DAHANUKAR, Vilas Hareshwar; CHINTADA, Krishnarao; SHAIKH, Latif Jafar; YARRAGUNTLA, Sesha Reddy; PEDDIREDDY, Subba Reddy; KOTTUR, Mohan Kumar; (33 pag.)WO2017/29594; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

41270-66-0, 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. 41270-66-0 name is 5-Chloro-2,3-diphenylpyrazine, 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.

6 g of the compound of the formula (1), 7 g of isopropylamine and 5 mL of dimethyl sulfoxide were placed in a sealed pressure-resistant reaction vessel, and the mixture was heated to 90 C for 48 hours, and the reaction was completed. The reaction solution was cooled to 25 C, then 18 mL of ethanol was added, and the solution was dissolved at 80 C, then 24 mL of water was added dropwise over 1 h, a large amount of solid was precipitated, and the temperature was lowered to 25 C, stirred for 0.5 hour, and suction-filtered to obtain a solid.Drying at 80 C for 24 h under vacuum gave 6 g of the compound of formula (2) as a pale yellow solid.The yield was 92.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-2,3-diphenylpyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Dongguan Dongyangguang Pharmaceutical Research And Development Co., Ltd.; Liu Yongjun; Wang Zhongqing; Liao Shouzhu; Luo Zhonghua; (5 pag.)CN109422698; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem