Tag: M.W=200-300

Application of 313340-08-8,Some common heterocyclic compound, 313340-08-8, name is 3,5-Dichloro-6-ethylpyrazine-2-carboxamide, molecular formula is C7H7Cl2N3O, 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.

Compound D1Sa (46 mg, 0.21 mmol), B2Rb (40 mg, 0.14 mmol) and DIPEA (36 mg, 0.28 mmol) were dissolved in 1,4-dioxane (2 mL), the reaction solution was heated to 130 C. and stirred for 16 hours in seal. The LCMS indicated the reaction was complete, the reaction mixture was concentrated in vacuo; the residue was poured into water, filtrated. The residue was washed by DCM to afford yellow solid D7Rb (36 mg, yield 55%). MS m/z 473.2 [M+H]+, 475.2 [M+H]+.

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-Dichloro-6-ethylpyrazine-2-carboxamide, its application will become more common.

Reference:
Patent; Hangzhou Innogate Pharma Co., Ltd.; ZHANG, Hancheng; LIU, Shifeng; YE, Xiangyang; (92 pag.)US2019/308993; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 937669-80-2,Some common heterocyclic compound, 937669-80-2, name is 3-Bromopyrazine-2-carboxylic acid, molecular formula is C5H3BrN2O2, 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 mixture of 6-(4,6-dimethylpyrimidin-2-yl)-3 ,6-diazabicyclo [3.2.1 ]octane 10-2 (150 mg, 0.69 mmol), 3-bromopyrazine-2-carboxylic acid (167 mg, 0.83 mmol), EDC (198 mg, 1.03mmol), HOAt (140 mg, 1.03 mmol), and N,N-diisopropylethylamine (0.36 mL, 2.06 mmol) in acetonitrile (1 mL) was stirred at room temperature for 24 h. The reaction was concentrated in vacuo and the crude residue was purified by silica gel chromatography (0-100% EtOAc/hexanes, 20 mm) to give 48-1 as an oil. MS (ESI) mlz: 403.3 (M+H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; ROECKER, Anthony, J.; (0 pag.)WO2016/85783; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 91775-62-1, name is 3-Bromo-8-methoxyimidazo[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 91775-62-1, Product Details of 91775-62-1

To a well stined solution of silver(I)fluoride (3.4g, 26.5 mmol) in DMF (20 ml), wasadded trifluoromethyltrimethylsilane and stined at room temperature for 0.5h. To the reactionmixture, was added copper (2.4g, 39.0 mmol) and stined at room temperature for 4h. Then added 3-bromo-8-methoxyimidazo[1,2-a]pyrazine (5.5g, 24.1 mmol) and stined at 90C for 5h. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated underreduced pressure to get the crude product. The crude product was purified by column chromatography (60-120 mesh silica gel and 10- 20% EtOAc in hexane) to obtain 8-methoxy-3- (trifluoromethyl)imidazo[ 1 ,2-a]pyrazine (1 .5g, 29%). LC-MS: 218.3 [M+Hf.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-8-methoxyimidazo[1,2-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; KOTRABASAIAH UJJINAMATADA, Ravi; PANDIT, Chetan; (152 pag.)WO2016/185342; (2016); 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. 1422772-78-8, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

To a solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1.4 g,5.22 mmol) in ethanol (20 mL) was added sulfuric acid (0.5 mL) at 0 C. and the mixture was stirred at 80 C. for 1 hour. After cooling the reaction mixture was quenched with ice and extracted with ethyl acetate. The organic layer was washed with water,brine,dried over anhydrous sodium sulfate,filtered and concentrated in vacuo. The crude material was purified using flash chromatography (10% ethyl acetate/hexane) to provide ethyl 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate as a brown liquid (1.4 g,80% yield): MS (ES) m/z 272 (M+H).

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; ACLARIS THERAPEUTICS, INC.; JACOBSEN, Eric Jon; ANDERSON, David Randolph; BLINN, James Robert; HOCKERMAN, Susan Landis; HEIER, Richard; MUKHERJEE, Paramita; (196 pag.)US2020/48262; (2020); 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. 1458-16-8, name is Methyl 3-amino-6-iodopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., Formula: C6H6IN3O2

Tetrakis(triphenylphosphine)palladium(0) (176 mg, 0.152 mmol) was added to a solution of methyl 3-amino-6-iodopyrazine-2-carboxylate (350 mg, 1.25 mmol) and Cul (167 mg, 0.878 mmol) in DMF (8 ml) in a pressure tube. The reaction tube was flushed with nitrogen then CuCN (225 mg, 2.51 mmol) was added. The tube was sealed then heated at 80 C for 4 h. The reaction mixture was allowed to cool to RT, then added onto saturated aq. NaHC03 solution (25 ml) and extracted with EtOAc (3 x 25 ml). The combined organic extracts were washed with brine (25 ml) then dried over MgS04, filtered, then concentrated in vacuo to a pale yellow oil. The crude material was transferred onto a C18 Samplet, dried under vacuum, and then purified by flash column chromatography on silica (25 g). The column was eluted with EtOAc: heptane, increasing the gradient linearly from 12:88 to 100:0 over 10 column volumes. The desired fractions were combined and evaporated to afford the product as a white solid (23 mg, 10%). 1H NMR (250 MHz, CDCI3) delta 8.48 (s, 1 H), 8.1 1 (s, 1 H), 5.85 (s, 1 H), 4.02 (s, 3H). LC/MS (System A): m/z (ESI+) = 179 [MH+], Rt = 0.75 min, UV purity = 100%.

The synthetic route of 1458-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan David; HAY, Duncan Alexander; SCHOFIELD, Thomas Beauregard; WENT, Naomi; (111 pag.)WO2017/221008; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 762240-92-6, A common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, 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 the acid (VII?) (1.00 g, 2.62 mmol) in THF (5 mL) at 0 C is added carbonyldiimidazole (510 mg, 3.15 mmol) and 10 minutes later triethylamine (0.4 mL, 2.62 mmol), previously solubilised in THF (5 mL), and triazolopiperazine hydrochloride (VIII) (599 mg, 2.62 mmol). The mixture, under an inert atmosphere of N2, is magnetically stirred under reflux for 16 hours until completion, then the mixture is cooled to room temperature, water added and the mixture extracted with toluene. The combined organic phases are dried and evaporated under reduced pressure. 1H NMR (300 MHz, d6-dmso, 100 C.) delta 7.4-7.2 (m, 7H), 6.90 (bs, 1H) 4.97 & 4.90 (AB system, J=12.9 Hz, 2×1H), 4.92 (s, 2H), 4.26-4.14 (m, 3H), 3.97 (t, J=5.5 Hz, 2H), 2.92 & 2.67 (2×dd, J=14.1, 4.9 Hz, 2×1H), 2.83-2.72 (m, 2H).

The synthetic route of 762240-92-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMO IBERICA S.A.; Rasparini, Marcello; Tufaro, Roberto Rocco; Minelli, Cosima; US2014/81026; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 486424-37-7, 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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

3-amino-6-bromopyrazine-2-carboxylic acid (500 mg, 2.29 mmol), HOBT (464 mg, 3.44 mmol) and EDCI (660 mg, 3.44 mmol) were dissolved in dry DMF (20 mL), and the resulting solution was stirred for 6 hours. Then 3-fluoroaniline (305 mg, 2.75 mmol) and Et3N (0.43 mL) was added to the mixture. After being stirred overnight, the mixture was diluted with water and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2S04, filtered and evaporated. The crude product was purified by prep-TLC (PE : EtOAc = 6 : 1) to give the pure product of 3-amino-6-bromo-N-(3-fluorophenyl)pyrazine-2- carboxamide (500 mg, yield: 68%). XH-NMR (CDC13, 400 MHz) delta 9.44 (s, 1H), 8.22 (s, 1H), 7.59 (d, J= 11.2 Hz, 1H), 7.24-7.27 (m, 2H), 6.79-6.82 (m, 1H), 3.21 (s, 2H). MS (M+H)+: 311/ 313.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-6-bromopyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

To a solution of methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (0.444 g, 2.0 mmol) in tetrahydrofuran (5 mL)/water (10 mL)/toluene (20 mL) was added phenyl boronic acid (0.536 g, 4.4 mmol), sodium carbonate (0.699 g, 6.6 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.116 g, 0.10 mmol). The reaction was evacuated and purged with nitrogen several times before being refluxed for 6 h. The organic layer was separated and the aqueous layer extracted with toluene (3 x 20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and evaporated under reduced pressure to give methyl 3-amino-6-chloro-5-phenyl-2-pyrazinecarboxylate as a yellow solid (0.43 g, 82%).

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

Reference:
Patent; Biotron Limited; Gage, Peter William; Ewart, Gary Dinneen; Wilson, Lauren Elizabeth; Best, Wayne; Premkumar, Anita; US2015/313909; (2015); A1;,
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. 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1458-18-0

a) 3-Amino-6-bromo-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl esterTo a mixture of 3-amino-5,6-dichloro-pyrazine-2-carboxylic acid methyl ester [CAS 1458-18-0] and 3-amino-6-bromo-5-chloro-pyrazine-2-carboxylic acid methyl ester [CAS 14340-25-1] (799 mg, 3 mmol) in DMF was added 2-methoxy-ethylamine (0.31 ml, 3.6 mmol) and NEt3 (2.09 ml, 15 mmol) and the mixture was stirred at r.t. for 3.5 h. The reaction mixture was poured into water (150 ml) and extracted with toluene (2×150 ml). The organic layers were washed with half-saturated aq. sodium chloride, combined, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane/EtOAc 100:0 to 0:100%) to provide the title compound together with 3-amino-6-chloro-5-(2-methoxy-ethylamino)-pyrazine-2-carboxylic acid methyl ester (about 1:1) as colorless solid. This mixture was used for the next step.HPLC: RtH4=0.77 min; ESIMS [M+H]+=305.1; (Cl-pyrazine: HPLC: RtH4=0.73 min; ESIMS [M+H]+=261.1).

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 1458-18-0.

Reference:
Patent; BADIGER, Sangamesh; CHEBROLU, Murali; HURTH, Konstanze; JACQUIER, Sebastien; LUEOEND, Rainer Martin; MACHAUER, Rainer; RUEEGER, Heinrich; TINTELNOT-BLOMLEY, Marina; VEENSTRA, Siem Jacob; VOEGTLE, Markus; US2012/184539; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 58139-04-1, name is 2-Iodo-3-methoxypyrazine, 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 58139-04-1, COA of Formula: C5H5IN2O

Step 1: tert-Butyl (1-(4-((3-methoxypyrazin-2-yl)ethynyl)phenyl)cyclobutyl)carbamate: To a degassed solution of 2-iodo-3-methoxypyrazine (163 mg, 0.69 mmol) intriethylamine (1.5 mL) at 0 C was added Pd(P’Bu3)2 (14.1 mg, 6 mol%), Cul (1.8 mg, 2 mol%) and fert-butyl (1 -(4-ethynylphenyl)cyclobutyl)carbamate (125 mg, 0.46 mmol). The brown suspension was stirred for 6 hours at room temperature before the reaction mixture was suspended in dichloromethane and washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (gradient 0 to 25% EtOAc in hexane) to give the title compound as a white solid (124 mg, 47%). 1H-NMR (500 MHz, CDCI3) delta 8.15 (s, 1 H), 8.04 (s, 1 H), 7.60 (d, 2H), 7.44 (d, 1 H), 5.30 (bs, 1 H), 4.1 1 (s, 3H), 2.51 -2.56 (m, 4H), 2.09-2.14 (m, 1 H), 1.84-1.91 (m, 1 H), 1.37 (bs, 9H).

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-Iodo-3-methoxypyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark, Peter; O’DOWD, Colin, Roderick; ROUNTREE, James, Samuel, Shane; TREVITT, Graham, Peter; HARRISON, Timothy; MCFARLAND, Mary, Melissa; WO2011/55115; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem