Month: May 2021

Related Products of 5780-66-5, The chemical industry reduces the impact on the environment during synthesis 5780-66-5, name is Pyrazine-2-carbaldehyde, I believe this compound will play a more active role in future production and life.

The compound (99 mg) obtained in Example 47-3 and the compound (51.0 mg) obtained in Example 84-1 were dissolved in anhydrous methanol (5.0 ml). The solution was added with sodium cyanoborohydride (35.6 mg) and further added with acetic acid (1.0 ml) to adjust the solution to pH 5, followed by stirring for 5 minutes and then stirring at room temperature for 17 hours. After completion of the reaction, methanol was distilled off and the solution was then added with 1 mol/l sodium hydroxide to adjust the solution to pH 11, followed by extraction with chloroform. The organic layer was washed with saturated saline solution and dried with anhydrous magnesium sulfate. After that, the solvent was distilled off. Then, the residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (16.8 mg) of the subject compound as a white solid. MS(FAB,Pos.):m/z=512[M+H]+1H-NMR(500MHz,DMSO-d6+D2O):delta=0.82(6H,t,J=7.3Hz),1.42(4H,sext.,J=7.3Hz),2.32(4H,t ,J=7.5Hz),3.48(2H,s),3.71(2H,s),3.73(2H,s),3.77(2H,s),6.85(1 H,s),7.11(1H,s),7.27(2H,d,J=8.5Hz),7.56(2H,d,J=8.3Hz),7.67(2 H,J=8.5Hz),7.89(2H,d,J=8.3Hz),8.51(1H,s),8.55(1H,s),8.84(1H, s).

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, Pyrazine-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 87486-34-8, A common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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.

A 100-mL three-neck round-bottomed flask equipped with a mechanical stirrer and reflux condenser was charged with Ik (780 mg, 3.56 mmol), 11 (998 mg, 3.73 mmol), cesium carbonate (2.36 g, 7.26 mmol) and 1,4-dioxane (40 mL). After bubbling nitrogen through the resulting solution for 30 minutes, Xantphos (.162 g, 0.281 mmol) and tris(dibenzylideneacetone)dipalladium(0) (.15 g, .165 mmol) were added, and the reaction mixture was heated at reflux for 16 h. After this time the reaction was cooled to room temperature and concentrated under reduced pressure. The resulting residue was absorbed onto silica gel and purified by flash chromatography to afford a 57percent yield (818 mg) of Im as an orange solid: mp 206- 207 0C; 1U NMR (500 MHz, CDCl3) delta 8.27 (bs, IH), 7.72 (dd, IH, J = 2.0, 8.5 Hz), 7.36 (dd, 2H, J = 2.0, 8.5 Hz), 6.73 (s, IH), 3.71 (m, IH), 3.69 (s, IH), 3.52 (s, 3H), 3.21 (m, IH), 3.01 (m, IH), 2.97 (s, 3H), 2.67 (m, IH), 2.19 (s, 3H); MS (ESI+) m/z 406 (M+H).

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CGI PHARMACEUTICALS, INC.; GENENTECH, INC.; WO2009/137596; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 27398-39-6, name is 3-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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. category: Pyrazines

To a solution of 3-.chioropyrazine-.2-carboxyiic acid (100 mg, 0.63 mmoi) in DCM/MeOFI (2 mL : ().2 mL) was added TMSCHN2 (0.47 mL, 0.95 mmoi) at RT and the resulting mixture stirred at RT for 2 h. Acetic acid (0.2 mL) was added and the mixture diluted with water (2 mL) and extracted with DCM (4 mL x 3). The combined organic layers werewashed with brine, dried over Na2 SO4, filtered and concentrated in vacuo to give the title compound (100 mg) as a colorless oil. LRMS mIz (M+H) 173.0 found, 173.0 required. Step 2: Methyl 3-.pyridin-.2-.yl)pyrazine-2–carboxyiate (M2)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27398-39-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference 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.

The compound prepared in Example 1 (1.26 mg, 0.3 mm), 5-bromo-1 H-pyrrolo [2,3-b] pyrazine (5 9 (63 mg ‘0.006m m o 1), C u I (1 8 mg, 0.09 mm omicron 1), m m L Epsilon13 Nu and 5 m LD Mu F The reaction was stirred at 80 C for 8 hours under inert atmosphere. The end of the reaction was extracted with ethyl acetate and water. The combined organic layers were washed with a saturated NaC1 solution and dried over anhydrous N ^ SOi. Concentrated under reduced pressure, and the residue was purified on a silica gel column to give the compound as an off-white solid. & Lt; 1 & gt; H NMR (500 MHz, CDC13) delta: 8_91 Page 27 of 53

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; NANJING SHENGHE PHARMACEUTICAL CO., LTD.; WANG, YONG; ZHAO, LIWEN; LIU, YANG; ZHANG, JINGZHONG; WANG, DEZHONG; GAO, YIPING; CHEN, HONGYAN; ZHANG, CANG; ZHANG, DI; (68 pag.)TWI523856; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 912773-21-8, name is 2-Bromo-5-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 912773-21-8, name: 2-Bromo-5-chloropyrazine

To a suspension of copper(O) powder (244 g, 3877 mmol) in DMSO (5 L) was added ethyl 2-bromo-2,2-difluoroacetate (394 g, 1939 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 hour and 2-bromo-5-chloropyrazine (Shanghai Fchemicals Technology Co., Ltd., Shanghai, China) (250 g, 1292 mmol) was added in a portion-wise manner. The reaction mixture was stirred at room temperature for 3 hours then quenched with sat’d aqueous ammonia chloride (2.0 L). The mixture was filtered through a celite pad and the filtrate was extracted with ethyl acetate (2 x 2 L). The combined organic layers were dried over Na2SC>4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0 to 2% ethyl acetate in hexanes) to afford 3a (215 g, 70% yield) as a viscous colorless liquid. NMR (400 MHz, DMSO-t/6) delta 9.05 (d, J= 1.4 Hz, 1H), 8.98 (dd, J= 1.4, 0.7 Hz, 1H), 4.39 – 4.34 (m, 2H), 1.24 (t, J = 7.1 Hz, 3H).

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

Reference:
Patent; AMGEN INC.; BOURBEAU, Matthew P.; HARRINGTON, Paul E.; LIU, Qingyian; (85 pag.)WO2018/112083; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 41110-29-6, name is Methyl 3-methylpyrazine-2-carboxylate, molecular formula is C7H8N2O2, 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. Quality Control of Methyl 3-methylpyrazine-2-carboxylate

Example 9. Production of methyl 3-chloromethyl-pyrazine-2-carboxylate (compound No. 3-1) Methyl 3-methylpyrazine-2-carboxylate (2.44 g, 16 mmol) was dissolved in chloroform (100 ml) and N-chlorosuccinimde (2.14 g, 16 mmol) was added thereto. Then, benzoyl peroxide (110 mg, 70%, 0.32 mmol) was added and refluxed under heating for 30 hours. The reaction solution was cooled, followed by removing undissolved substance by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by using silica gel chromatography (hexane:ethyl acetate=1:1)to obtain 1.55 g of the desired compound. Yield: 52% Property: 1H-NMR [CDCl3/TMS, delta (ppm)] 8.75(d,1H), 8.68(d,1H), 5.14(s,2H), 4.06 (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 41110-29-6, its application will become more common.

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

Application of 1458-18-0, A common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, 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.

PREPARATIVE EXAMPLES Preparative Exam ple1.A round bottomed flask was charged with methyl 6-amino 2,3-dichloro pyrazine 5-carboxylate (Aldrich, 25 g, 112.6 mmol), 2-S-ethyl piperazine (prepared as per Williams et al J. Med. Chem. 1996, 39, 1345, 83% active, 15.7 g, 112.7 mmol), cesium carbonate (100 g, 300 mmol) and 1 ,4 dioxane (400 ml). The flask was equipped with a reflux condenser and heated to8O0C. After 12 hours, the reaction was cooled, diluted with methylene chloride (~ 200 ml), and filtered through celite. The filtrate was washed once with water and then concentrated to an oil. The crude product was purified by silica gel chromatography using a methanol/ methylene chloride eluent (3% to 10% MeOH) to afford 30.8 g (91 %) of compound A3. MS, M+H = 300.

The synthetic route of 1458-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/91428; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, 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 69214-33-1, COA of Formula: C6H4ClN3

To a stirred solution of the product from step 5 (51 .3 mg, 0.1 7 mmol) in THF (5 mL) was added NaH (20.4 tug, 0.51 mmol, 6() wt% in oil) at 0 C. The mixture was stirred at 0 C for0.5 hour, then 8chioroin:iidazo[i,2a]pyrazine (78.() mg, 0.51 mmoi) was added. The resulting mixture was stirred at RT for 2 hours arid then quenched with water (2 n:iL), extracted with EtOAc (3 x 5 mL). The combined organic layer was wished with brine, dried over Na2SO4, filtered and concentrated in vacuo, and the residue was purified by PrepHPLC to give title compound (28.6 mg) as colorless oil. LRIVIS mlz (M+H) 420.2 found, 420.2 required.

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 SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 24241-18-7, 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Step A: Preparation of ethyl 6,8-dibromoimidazo[ 1 , 2-a]pyrazine-2-carboxylateTo a stirred solution of 2-amino-3, 5-dibrompyrazine (20 g, 79mmol) in dimethyicarbonate (1 33 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10 C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na2(S04) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 %) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz, CDC ): delta =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.

The synthetic route of 2-Amino-3,5-dibromopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80228; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 89123-58-0, 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. 89123-58-0, name is 5-Bromopyrazine-2,3-diamine, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : 6-Bromo-2-(2-cyclopropylpyrimidin-4-yl)-1 /-/-imidazo[4,5-b]pyrazine A mixture of 5-bromopyrazine-2,3-diamine (50 mg, 0.3 mmol) and ethyl 2- cyclopropylpyrimidine-4-carbimidate (Intermediate 19, 50.7 mg, 0.3 mmol), triethylamine (73.8 muIota_, 0.5 mmol), acetic acid (244 muIota_, 4.2 mmol) and ethanol (0.8 mL) was heated to 100C for 30 min. The mixture was concentrated and diluted with water. Then a saturated aqueous solution of sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The organics were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude material was purified via flash chromatography (0-5% methanol in dichloromethane) to afford 6-bromo-2-(2- cyclopropylpyrimidin-4-yl)-1 H-imidazo[4,5-b]pyrazine (21 mg, 25%).

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

Reference:
Patent; PFIZER INC.; AHN, Kay; BOEHM, Markus; CABRAL, Shawn; CARPINO, Philip A.; FUTATSUGI, Kentaro; HEPWORTH, David; KUNG, Daniel W.; ORR, Suvi; WANG, Jian; WO2013/150416; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem