Tag: M.W=200-300

Synthetic Route of 193966-70-0, 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. 193966-70-0, name is Methyl 5-(bromomethyl)pyrazine-2-carboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

[0139j To a solution of methyl 5-(bromomethyl)pyrazine-2-carboxylate (0.5 g, 2.16 mmol) in tetrahydrofuran (20 mL) was added potassium trimethylsilanolate (0.11 g, 0.80 mmol) and the reaction mixture was stirred at 70 C for 45 minutes. The reaction mixture was diluted with water (30 mL), acidified with 1.5 M hydrochloric acid (pH 2-3) and extracted with ethyl acetate (50 mL x 3). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude was purified by silica gel column chromatography using 3% methanol in dichloromethane as eluant, to afford the title compound 5-(bromomethyl)pyrazine-2-carboxylic acid (0.174 g, 37% yield) as a yellow solid. Calculated M+H: 218.02; Found M+H: 218.1.

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, Methyl 5-(bromomethyl)pyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
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. 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, A new synthetic method of this compound is introduced below., Computed Properties of C9H11BrN2O3

Example 13-(2,2-Difluoro-2-phenylethylamino)-1-(ethoxycarbonylmethyl)-6- methylpyrazinoneA 2-liter, one-neck round bottom flask (equipped with a nitrogen inlet) was charged with 3-bromo-1 -(ethoxycarbonylmethyl)-6-methylpyrazinone (51.5 g, 0.187 mol), 2,2-difluoro-2-phenylethylamine (64.78 g, 0.412 mol), and toluene (450 ml). The reaction mixture was refluxed for 2 days and concentrated to yield a solid. The solid was triturated with ethanol-water (1 :1 , 890 ml) and the resulting mixture stirred for 2 h. The solid was collected by filtration and then washed with ethanol-water (1 :3, 450 ml), filtered, dried and to yield the title compound as a tan solid. MP: 106 – 1100C

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; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 24241-18-7, 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. 24241-18-7 name is 2-Amino-3,5-dibromopyrazine, 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.

5-Bromo-3-methoxypyrazin-2-amine A mixture of 3,5-dibromo-2-aminopyrazine (750 mg, 2.9 mmol), sodium methoxide (400 mg, 7.4 mmol) and methanol (20 ml) was refluxed for 16 h. The solvent was removed and the residue was purified using column chromatography. Yield: 450 mg 1H NMR (CDCI3): 3.99 (3H, s), 4.76 (2H, s), 7.63 (1H, s)

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

Reference:
Patent; MEDEIA THERAPEUTICS LTD; GOLDSTEINS, Gundars; KOISTINAHO, Jari; KOISTINAHO, Milla; RATILAINEN, Jari; PYSTYNEN, Jarmo; WO2014/68171; (2014); 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. 446286-94-8, name is 5-Bromo-N,N-dimethylpyrazin-2-amine, A new synthetic method of this compound is introduced below., category: Pyrazines

2-dimethylamino-5-bromo-pyrazine (21) (1.37g, 6.8mmol) was dissolved in dehydrated tetrahydrofuran (THF) (50ml), it was under an argon atmosphere. The solution was cooled to -80 C. with acetone bath, 1.57 M n-butyl lithium (n-BuLi) slowly added hexane solution (10.8 ml), and stirred for 1 hour. Then it was slowly added N, N-dimethylformamide (DMF) (2.0ml, 26mmol) to this mixed solution was stirred for 1 h allowed to warm to room temperature. Then stirred for 15 minutes Water was added to the reaction mixture and extracted with ethyl acetate (2 ¡Á 200ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography [silica gel 46.9g; hexane – ethyl acetate (1: 1)] and purified by, 5-aldehyde-2-dimethyl-amino-pyrazine (22) (975mg, 6.5mmol, 95 %) as a light yellow powder solid.

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; UNIVERSITY OF ELECTRO-COMMUNICATIONS; MAKI, SHOJIRO; NIWA, HARUKI; (25 pag.)JP2015/193584; (2015); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 6966-01-4, 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Hydrazine hydrate (23.59 mL, 480.75 mmol) was added dropwise to a stirred mixture of methyl 3-amino-6-bromopyrazine-2-carboxylate (100 g, 418.04 mmol) in EtOH (2 L). The mixture was heated at 50 C. under nitrogen. The resulting thick suspension was stirred at 50 C. for 16 hours. Further hydrazine (2.5 mL) was added in one portion and the suspension was stirred at 50 C. for a further 24 hours. Ethanol (500 mL) was charged to the thick reaction mixture and the mixture was allowed to cool to room temperature. The resulting suspension was filtered and the solid washed with ethanol (1 L) and dried in vacuo to give 3-amino-6-bromopyrazine-2-carbohydrazide (98 g, quantitative) as a cream solid: 1H NMR Spectrum; (DMSO-d6) 4.52 (2H, s), 7.59 (2H, s), 8.30 (1H, s), 9.74 (1H, s); Mass Spectrum [M+H]+=232.

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

Reference:
Patent; ASTRAZENECA AB; BARLAAM, Bernard Christophe; DELOUVRIE, Benedicte; OUVRY, Gilles; LAMBERT-VAN DER BREMPT, Christine Marie, Paul,; HARRIS, Craig Steven; BERRY, David; TOMKINSON, Gary Peter; REID, Gary Patrick; US2014/206700; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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.

Intermediate Example 1 -1 :Preparation of 6,8-dibromo-imidazo[1 ,2-a]pyrazineTo a stirred suspension of 2-amino-3,5-dibrompyrazine (427 g, 1688mmol) in water (6.4 L) / THF (482 ml_), at rt was added bromacetaldehyde-diethylacetal (998 g, 5065 mmol) in one portion. After stirring under reflux for 4 h, the clear orange solution was stirred for an additional 15 h at rt. The suspension was filtered, and the remaining solid was washed with MeOH (2 L) and dried in vaccuo at 60 C to yield 6,8-dibromo-imidazo[1 ,2-a]pyrazine as an off-white solid (500 g, 107% with residual MeOH): 1H-NMR (300 MHz, d6-DMSO): delta =9.02 (s, 1 H), 8.23 (d, 1 H), 7.89 (d, 1 H) ppm. UPLC-MS: RT = 0.80 min; m/z 277.9 [MH+]; required MW = 276.9.

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; WO2012/80230; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 486424-37-7, 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 486424-37-7 as follows.

A mixture of 3-amino-6-bromopyrazine-2-carboxylic acid (3.90 mmol, 1.1 equiv), 3-(methylsulfonamido)phenylboronic acid (1.0 equiv), sodium carbonate (5.0 equiv) and Pd(PPh3)4 (10 mol %) were sequentially added in 30 mL 4:1 (v/v) degassed dioxane-water. The reddish brown mixture was stirred under Ar for 2 min at room temperature before heating to 88 C. for 2.5 hours. The mixture was slowly acidified by adding 30 mL of 10% citric acid until pH=4. The mixture was cooled to 25-30 C., diluted with 40 mL ethyl acetate, then 20 mL water and transferred to a separatory funnel. The aqueous layer was removed, extracted with ethyl acetate (3¡Á10 mL), the combined organic layers were washed with water (2¡Á20 mL) and brine (3¡Á20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to provide compound 181 as yellow solid which was washed with methylene chloride and used directly in the next step. ESI-MS m/z: 309.3 [M+H]+.

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Intellikine LLC; Infinity Pharmaceuticals, Inc.; CASTRO, Alfredo C.; CHAN, Katrina; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LI, Liansheng; LIU, Tao; LIU, Yi; REN, Pingda; SNYDER, Daniel A.; TREMBLAY, Martin R.; US2013/267521; (2013); 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. 446286-94-8, name is 5-Bromo-N,N-dimethylpyrazin-2-amine, A new synthetic method of this compound is introduced below., COA of Formula: C6H8BrN3

2-dimethylamino-5-bromo-pyrazine (21) (1.37g, 6.8mmol) was dissolved in dehydrated tetrahydrofuran (THF) (50ml), it was under an argon atmosphere. The solution was cooled to -80 C. with acetone bath, 1.57 M n-butyl lithium (n-BuLi) slowly added hexane solution (10.8 ml), and stirred for 1 hour. Then it was slowly added N, N-dimethylformamide (DMF) (2.0ml, 26mmol) to this mixed solution was stirred for 1 h allowed to warm to room temperature. Then stirred for 15 minutes Water was added to the reaction mixture and extracted with ethyl acetate (2 ¡Á 200ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography [silica gel 46.9g; hexane – ethyl acetate (1: 1)] and purified by, 5-aldehyde-2-dimethyl-amino-pyrazine (22) (975mg, 6.5mmol, 95 %) as a light yellow powder solid.

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; UNIVERSITY OF ELECTRO-COMMUNICATIONS; MAKI, SHOJIRO; NIWA, HARUKI; (25 pag.)JP2015/193584; (2015); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

Preparation-1: Preparation of (R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6- dihydro-[l,2,4]triazolo[4,3-a]pyrazin-7(8H)-yI)-l-(2,4,5-trifluorophenyl) butan-2-ylcarbamate (0089) In 2 L three necked round bottom flask equipped with mechanical stirrer, thermometer and an addition funnel, were added 400 mL DMF, 100 g (3i?)-N- (tert-butoxycarbonyl)-3-amino-4-(2,4,5-trifluorophenyl) butanoic acid and 72 g 3- (trifluoromethyl)-5,6,7,8-tetrahydro-l,2,4-triazolo-[4,3-a]pyrazine hydrochloride. The reaction mixture was cooled to 0 to 5C and 106 g TBTU was added. 116.3 g DIPEA was added to the reaction mixture and stirred for 1 hour. After the completion of reaction, 1 L water and 600 mL 1% NaHC03 was added. The reaction mixture was stirred for 1 hour at 25C to 35C. The precipitates were filtered and washed with water. The product was dried under vacuum at 60C for 4 hours to obtain 151.9 g of title compound.

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

Reference:
Patent; CADILA HEALTHCARE LIMITED; DWIVEDI, Shri Prakash Dhar; KHERA, Brij; SINGH, Kumar Kamlesh; SOLANKI, Kirtipalsinh Sajjansinh; WO2015/114657; (2015); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 41270-66-0, A common heterocyclic compound, 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, molecular formula is C16H11ClN2, 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 mixture of 5-Chloro-2,3-diphenyl-pyrazine (10.00 g, 37.5 mmol) and a 70% solution of isopropylamine in water (44.32 g, 74.9 mmol) in isopropanol (100 ml) was heated at 150 C for 24 h in a autoclave with 200-400 psi pressure. The reaction progress was monitored by HPLC and after completion of reaction; resulting mass was cooled to 25-30 C and concentrated. The residue was diluted with water and extracted with dichloromethane, after which the extract was distilled completely to obtain solid (5,6-diphenyl- pyrazin-2-yl)-isopropyl-amine (7.0g, 76%) as pale yellowish solid. [Yleld= 7g]

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; MEGAFINE PHARMA (P) LTD.; MATHAD VIJAYAVITTHAL THIPPANNACHAR; DODDAPPA PRALHAD ANEKAL; KARDILE PRITESH BHIMRAJ; PADAKI SANTHOSH AMBADAS; GAIKWAD BAPUSAHEB SHRIHARI; SHINDE GORAKSHANATH BALASAHEB; (63 pag.)WO2017/42828; (2017); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem