Tag: M.W=200-300

Electric Literature of 1379338-74-5, The chemical industry reduces the impact on the environment during synthesis 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, I believe this compound will play a more active role in future production and life.

(A) methyl 3-(7-chloropyrido[4,3-ib]pyrazi n-5-ylamino)propanoate.[01 62] A solution of methyl 3-aminopropanoate hydrochloride (4.88 mmol), Et3N (6.50 mmol) and 5,7-dichloropyrido[4,3-£>]pyrazine (3.25 mmol) in THF (10 mL) was stirred at room temperature overnight. Volatiles were removed under reduced pressure, and the residue was treated with water and extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography to afford the title compound. MS (m/z): 267 (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, 5,7-Dichloropyrido[3,4-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; JI, Jianguo; WO2012/167423; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

13301-04-7, name is Methyl 3,6-dibromopyrazine-2-carboxylate, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 13301-04-7

To a solution of methyl 3,6-dibromopyrazine-2-carboxylate (8.4 g, 28.3 mmol) in MeCN (142 mL) was added (3Patent; REVOLUTION MEDICINES, INC.; LI, Jie Jack; KOLTUN, Elena S.; GILL, Adrian Liam; BUCKL, Andreas; WON, Walter; AAY, Naing; MELLEM, Kevin; TZITZILONIS, Christos; JOGALEKAR, Ashutosh; CREGG, James Joseph; (177 pag.)WO2019/75265; (2019); 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. 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, A new synthetic method of this compound is introduced below., Safety of 3,5-Dichloro-6-ethylpyrazine-2-carboxamide

Weighing compounds 1-3 (165 mg, 0.52 mmol), 1-4 (137 mg, 0.62 mmol) in a reaction flask, After stirring with 1,4-dioxane, N,N-diethylisopropylamine (DIPEA) (201 mg, 1.56 mmol) was added, warmed to 100 C and stirred for 12 h. After stopping the reaction, the reaction solution was cooled to room temperature, a small amount of water was added, the solid was precipitated, suction filtration, and the filter cake was rinsed with ethanol for 2 times and dried. The yellow solid product 1-5, 125 mg was obtained.

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; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Geng Meiyu; Ye Jiqing; Ai Jing; Song Zilan; (29 pag.)CN109384774; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1196152-38-1, A common heterocyclic compound, 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, molecular formula is C5H2BrF3N2, 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.

1,1 -dimethyl ethyl (lS,4S,6S)-4-ethynyl-3-azabicyclo[4.1.0]heptane-3-carboxylate D17 (150 mg), 2-bromo-5-(trifluoromethyl)pyrazine (154 mg, 0.678 mmol), DIPEA (0.592 ml, 3.39 mmol), Pd[(C6H5)3P]4 (78 mg, 0.068 mmol) and copper(I) iodide (25.8 mg, 0.136 mmol) were collected together and dissolved in DMF (5 ml).The reaction was stirred at 23 C for 3 hours.A saturated solution of NaHC03 (20 ml) was added and the aqueous layer was back extracted with Et20 (3 x 10 ml). The collected organic layers were washed with brine (3 x 5 ml), dried over Na2S04, filtered, and concentrated under vacuum to give the crude product. The crude product was purified by silica gel chromatography (SNAP KP-Sil 25g cartridge; eluted with Cy/EtOAc 5 CV from 100% Cy to 90/10, 5 CV 90/10).Evaporation of the fractions gave the title compound D18 (140 mg).UPLC (IPQC): rt = 1.38 minutes, peak observed: 312 [M+l- C(CH3)3]

The synthetic route of 1196152-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89607; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 117103-53-4, name is 2-Bromo-5-nitropyrazine, 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 117103-53-4, Safety of 2-Bromo-5-nitropyrazine

Example 72 2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-N- [5- (2-METHOXY- ethylamino)-pyrazin-2-yl]-propionamide [000336] A mixture of 2-bromo-5-nitropyrazine (500 mg, 2.45 mmol) and 2- METHOXYETHYLAMINE (276 mg, 3.67 mmol) in methanol (15 ML) was stirred at 25C for 5 h. After such time, the reaction was concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 40/60 to 20/80 hexanes/ethyl acetate) afforded (2-methoxy-ethyl)- (5-nitro-pyrazin-2-yl) -amine (291 mg, 60%) as a yellow solid: mp 116.0-117. 3C ; EI- HRMS m/e calcd for C7HLON403 (M+) 198.0753, found 198. 0751.

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; F. HOFFMANN-LA ROCHE AG; WO2004/52869; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 87486-34-8,Some common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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: To a solution of 2a-j (10 mmol, 1.0 eq) , 3,5-dibromo-1-methylpyrazin-2(1H)-one (2.95 g, 11 mmol, 1.1 eq) and DIEA (3.3 mL,20 mmol, 2.0 eq) in MeCN (20mL) was stirred at 80 °C for 5 hours. After cooling to room temperature, thesolvent was removed in vacuo, and the residue was purified using silica gelchromatography to give the title compounds, yield 72-85percent.

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-Dibromo-1-methylpyrazin-2(1H)-one, its application will become more common.

Reference:
Article; Yang, Jianhong; Du, Jiatian; Huang, Chong; Wang, Tianqi; Huang, Luyi; Yang, Shengyong; Li, Linli; Bioorganic and Medicinal Chemistry Letters; vol. 29; 13; (2019); p. 1609 – 1613;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 762240-92-6, 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. 762240-92-6 name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, 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.

General procedure: A solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro [1,2,4]triazolo[4,3-a]pyrazine hydrochloride salt 9 (1.0 eq.) in dimethylformamide (DMF, 2e3 mL) was added potassium carbonate (2.5eq.) at 5 C and stirred for 15 min at room temperature. To this,various chloride derivatives (1.0 eq.) in DMF was added to reaction mixture at same temperature. The resultant reaction mixture was allowed to stir at room temperature for 24 h. The completion of the reaction was monitored on TLC (using 10% MeOH: DCM and ammonia as a modifier as mobile phase). The reaction mixture was poured into ice-cold water and extracted with ethyl acetate(2 x 15 mL). Organic layers were combined and the combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford crude material and crystallized it from methanol to get 3-(trifluoromethyl)-5,6,7,8-tetrahydro [1,2,4]triazolo [4,3-a]pyrazine derivatives (12f-12j) in good practical yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Jethava, Divya J.; Acharya, Prachi T.; Vasava, Mahesh S.; Bhoi, Manoj N.; Bhavsar, Zeel A.; Rathwa, Sanjay K.; Rajani, Dhanji P.; Patel, Hitesh D.; Journal of Molecular Structure; vol. 1184; (2019); p. 168 – 192;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Methyl 3,5-dichloropyrazine-2-carboxylate

The mixture of methyl 3,5-dichloropyrazine-2-carboxylate (1.0 g, 4.83 mmol), (3L’)- l,3-dihydrospiro[indene-2,4′-piperidin]-3-amine dihydrochloride (1.65 g, 4.83 mmol, Intermediate I) and CsF (3.66 g, 24.1 mmol) in DMF (15 mL) was stirred at 70 C for 2 hours. BOC20 (1.57 g, 7.24 mmol) and TEA (1 mL) were added to the mixture and the mixture was stirred at 20 C for 1 hour. The mixture was diluted with H20 (50 mL), extracted with EtOAc (50 mL x 2). The organic layer was washed with brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure and the residue was purified by column chromatography (petroleum ether / ethyl acetate = 1 : 0 ~ 5 : 1) to afford methyl 5-[(3ri)-3-{[(/er/-butoxy)carbonyl]amino}-l,3-dihydrospiro[indene-2,4′-piperidin]-r- yl]-3-chloropyrazine-2-carboxylate (1.58 g, 69% yield) as a yellow solid and methyl 3-[(3L’)- 3-{[(/er/-butoxy)carbonyl]amino}-l,3-dihydrospiro[indene-2,4′-piperidin]-l’-yl]-5- chloropyrazine-2-carboxylate (320 mg, 14% yield) as a yellow solid. LCMS m/z (M+H)+ = 473.1 for both isomers.

The synthetic route of 330786-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 143591-61-1,Some common heterocyclic compound, 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, molecular formula is C6H3BrClN3, 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.

Add 3-bromo-8-chloroimidazo [1,2-a] pyrazine (1.33 g, 5.7 mmol), 1-methyl-1H-pyrazole-4-amine (0.66 g, 6.8 mmol)And triethylamine (1.15 g, 11.4 mmol) were added to 15 mL of n-butanol, and the temperature was raised to 120 C. and reacted overnight.The solvent was removed by rotary evaporation, diluted with 30 mL of water, and extracted with ethyl acetate (20 mL * 3). The organic phases were combined,It was washed with 20 mL of saturated brine, dried over anhydrous sodium sulfate, and concentrated.1.25 g of a pale yellow solid was isolated on a silica gel column with a yield of 75%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, its application will become more common.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Xing Qingfeng; Ai Yixin; (85 pag.)CN110272426; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63744-22-9, 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Intermediate Example 2-1 : Preparation of 6-bromo-8-methylsulfanyl- imidazo[1 ,2-a]pyrazineTo a stirred suspension of intermediate example 1 -1 6,8-dibromo-imidazo[1 ,2- ajpyrazine (489 g, 1766 mmol) in MeOH (2900 mL) at -20 C was dropwise added a solution of sodium methan thiolate (225 g, 3214 mmol, 1 .8 eq) in 800 mL water. After stirring overnight, the clear solution was poured on 30 L water and the yellowish precipitate was filtered, washed with 3 L water and dried in vaccuo to yield 301 g 6-bromo-8-methylsulfanyl-imidazo[1 ,2-a]pyrazine (69.8 %). 1H-NMR (300 MHz, d6-DMSO): delta = 8.64 (1 H, s), 8.00 (1 H, d), 7.66 (1 H, d2.54 (3H, s) 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, 6,8-Dibromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80234; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem