Tag: M.W=100-200

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

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

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

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

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

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

Application of 98-97-5, 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. 98-97-5, name is Pyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A catalytic amount of concentrated H2SO4 wasadded to a solution of carboxylic acids 16(a-j) (1.0 mmol)in 50 mL of methanol, and the mixture was refluxed for 6 h. It was allowed to cool. The saturated solution ofNaHCO3 was added to the reaction mixture, and it wasextracted with EtOAc (2 X 50 mL). The combined organiclayer was dried Na2SO4 and concentrated to obtain puremethyl esters 17(a-j).

The chemical industry reduces the impact on the environment during synthesis Pyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Murty; Penthala, Raju; Polepalli, Sowjanya; Jain; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 627 – 643;,
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. 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6863-74-7

Step 1: [6-(6-Cyano-pyrazin-2-yloxy)-l-hydroxy-4-methyl-l,3-dihydro- benzo[c] [ 1 ,2] oxaborol-3-yl)-acetic acid ethyl ester[0592] To a solution of (1 ,6-dihydroxy-4-methyl-l ,3-dihydro- benzo[c][l,2]oxaborol-3-yl)-acetic acid ethyl ester (1.6 g, 6.4 mmol) in anhydrous DMF (15 mL) was added cesium carbonate (5.2 g, 16.0 mmol) and 6-chloro-pyrazine- 2-carbonitrile (0.89 g, 6.4 mmol). The resulting mixture was stirred at room temperature overnight then quenched with crushed ice. The pH was adjusted to 2 with 6M HCl and the mixture extracted with EtOAc (2 x 200 mL). The organic extracts were washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (0-75% EtOAc in hexane) to give 6-(6-cyano-pyrazin-2-yloxy)-l-hydroxy-4-methyl-l,3- dihydro-benzo[c][l,2]oxaborol-3-yl)-acetic acid ethyl ester (1.6 g, 71%). 1H NMR 400 MHz (DMSO-J6) delta 9.30 (s, IH), 8.93 (s, IH), 8.90 (s, IH), 7.33 (s, IH), 7.18 (s, IH), 5.58(m, IH), 4.05 (q, J = 7.2, 2H), 3.17 (m, IH), 2.40 (m, IH), 2.33 (s, 3H), 1.13 (t, J = 6.8 Hz, 3H).

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 6863-74-7.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; GLAXOSMITHKINE LLC; XIA, Yi; ALLEY, Michael, Richard Kevin; ZHOU, Yasheen; SINGH, Rajeshwar; DING, Charles; CAO, Kathy; PLATTNER, Jacob, J.; OU, Ligong; JIA, Guofeng; SARASWAT, Neerja; RAMACHANDRAN, Sreekanth; ZHOU, Ding; WO2011/17125; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 5521-55-1, 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. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

N,N-Dimethylformamide (5.0 mL), pyridine (1.0 mL, 12.36 mmol), and 1- [bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (945 mg, 2.48 mmol, HATU) were added to a mixture of 5- methylpyrazine-2-carboxylic acid (Alfa, 277 mg, 2.0 mmol) and tert-butyl (3- aminobicyclo[1.1.1]pentan-1-yl)carbamate (Pharmablock, 379 mg, 1.91 mmol) in sequential order. The reaction mixture was then stirred at ambient temperature for 1 hour and was then partitioned between dichloromethane (2 × 50 mL) and aqueous sodium carbonate (1.0 M, 100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Trifluoroacetic acid (10 mL, 130 mmol) was added to the residue, and the resulting solution was stirred at ambient temperature for 1 hour and concentrated in vacuo. The residue was directly purified by preparative HPLC [Waters XBridge C185 mum OBD column, 50 × 100 mm, flow rate 90 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1% trifluoroacetic acid)] to give the title compound ( (0.71 g, 1.59 mmol, 83% yield). MS (ESI+) m/z 219 (M+H)+.

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

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farah; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (661 pag.)WO2017/193063; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 153800-11-4, These common heterocyclic compound, 153800-11-4, name is 2-Ethynylpyrazine, 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.

To a solution of 235(100mg, 0.272mrno1) and 10(56.6mg, 0.543mrno1) in 2OmL of Et3N was added Pd(PPh3)2C12 (9.53mg, 0.Oi4mmol) and Cul (5.17mg, C.O27mmol). The mixture was protected with N2 atmosphere, then was heated at 70C for 4 hours. TLC analysis showed complete conversion of starting material to major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep-1-IPLC to give the target product Compound 134(3mg, yield: 24.59%).LCMS: m/z 345 (M+H?H M?IR (400 MHz cDCI.) oe 8 78 (s 1H), 8 58 (s 1H) 8 O (s IH) 7 53 (d, 1= 8 8 Hz, 2H),7.35 (d, J:= 8.0 Hz, 2K), 6.51 (s, 1K), 2.38 (s, 3H).

The synthetic route of 153800-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem