Tag: M.W=200-300

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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6966-01-4

Step 1: S-amino–bromopyrazine-l-carbohydrazide[00541] A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (5 g, 21.55 mmol) and hydrazine hydrate (5.397 g, 5.245 niL, 107.8 mmol) were heated to 100 0C for 1.5 hours. Water was added and the product collected by filtration, washed with methanol and dried to give 3- amino-6-bromo-pyrazine-2-carbohydrazide as a yellow solid (5.02g, 100.4% Yield). MS (ES+)

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-damien; DURRANT, Steven; KAY, David; O’DONNELL, Michael; KNEGTEL, Ronald; MACCORMICK, Somhairle; PINDER, Joanne; VIRANI, Anisa; YOUNG, Stephen; BINCH, Hayley; CLEVELAND, Thomas; FANNING, Lev, T.d.; HURLEY, Dennis; JOSHI, Pramod; SHETH, Urvi; SILINA, Alina; WO2010/54398; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-01-1,Some common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, molecular formula is C6H7ClN4O2, 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.

Preparation Example AA-1. 3,5-Diamino-pyrazine-2-carboxylic acid methyl ester To a solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid methyl ester (8.00g, 39.5mmol) in tetrahydrofuran (150mL) were added tetrakis(triphenylphosphine)palladium(0) (2.28g, 1.98mmol), formic acid (2.24mL, 59.3mmol) and triethylamine (16.5mL, 119mmol) at 0¡ãC under nitrogen atmosphere, then, the solution was stirred at 125¡ãC for 12 hours. The reaction solution was cooled to room temperature, and a solid precipitated. This solid was collected by filtration, and the title compound (10.7g, quantitatively) was obtained as a crude product of a white solid. 1H-NMR Spectrum (DMSO-d6) delta (ppm) : 3.70(3H, s), 6.95(2H, brs), 7.21 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1053656-22-6, The chemical industry reduces the impact on the environment during synthesis 1053656-22-6, name is 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, I believe this compound will play a more active role in future production and life.

Stage 2: A solution of 7-tert-butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate (300 mg, 1.02 mmol) in THF (15 ml) was cooled to -78 C., and DIBAL-H (1 M in hexane, 2.0 ml, 2.0 mmol) was added slowly under an N2 atmosphere. The reaction mixture was stirred for 1 hour at that temperature and then Na2SO4¡Á10H2O was added until no further evolution of gas was observed. Further sodium sulfate was added, the solution was filtered, and the residue was washed with DCM (25 ml). The filtrate was concentrated and the resulting crude product (450 mg) was used in the next stage without further purification.

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, 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUENENTHAL GmbH; US2010/173889; (2010); 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. 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C5H4BrN3O2

HATU (47.6 g) was added to a stirred solution of 1 ,2-phenylenediamine (13.54 g), 3-amino-6-bromopyrazine-2-carboxylic acid (26.0 g) and triethylamine (24.93 ml) in DMF (250 mL). The resulting solution was stirred at ambient temperature for 12 hours before the reaction mixture was added to water (250 ml). The resulting precipitate was collected by filtration, washed with water (250 ml) and dried in vacuo. This material was dissolved in acetic acid (200 ml) and heated to 9O0C for 4 hours. The reaction mixture was concentrated in vacuo, washed with diethylether. The ether washings were evaporated and triturated in hexane. There was thus obtained 3-(lH-benzimidazol-2-yl)-5-bromopyrazin-2-amine (5.Og); Mass Spectrum: M-H+ 290; RT 2.46 min. NMR Spectrum: (DMSOd6) 7.32 (m, 2H), 7.60 (d, IH), 7.78 (d, IH), 8.31 (s, IH), 13.2 (s, IH).

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; AstraZeneca AB; AstraZeneca UK Limited; WO2009/24825; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 762240-92-6 as follows. Product Details of 762240-92-6

The (R) – 3 – (tert-butoxycarbonylamino) – 4 – (2, 4, 5-trifluorophenyl) butanoic acid (26.6g), 2,6-dimethyl pyridine (18g) and 3 – (trifluoromethyl) – 5, 6, 7, 8-tetrahydro-[ 1, 2, 4] triazolo [4,3-a] pyrazine hydrochloride (17.3g) are sequentially added dichloromethane (300 ml) in, cooling to 0-5C, stirring, add TBTU (28.2g), natural recovery to the room temperature, to continue reaction 8-10 hours. After the reaction, the organic phase for sequentially 1NHCl (200 ml), water (200 ml), 5% sodium carbonate aqueous solution (200 ml), saturated aqueous sodium chloride solution (200 ml) washing, dry anhydrous sodium sulfate, filtered, concentrated under reduced pressure, to obtain white foam solid 36g, yield 90%. 1 HNMR (400MHz, CDCl 3) delta 1.39 (s, 9H), 2.59-2.72 (m, 2H), 2.79-2.96 (m, 2H), 3.96-4.38 (m, 5H), 4.95 (s, 1H), 4.98-5.10 (m, 1H), 5.31 (b, 1H), 6.89-6.93 (m, 1H), 6.97-7.06 (m, 1H).

According to the analysis of related databases, 762240-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Aobo Pharmtech, Inc., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd; Zhu, Wei; Fan, Qianyong; Ruan, Hongliang; (12 pag.)CN102757431; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference 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.

3,5-Dibromopyrazin-2-amine (10.0 g, 39.5 mmol) was suspended in 200 ml concentrated (32%) aqueous ammonia and the mixture was stirred at 130 00 in a pressure tube for 5 days. The mixture was allowed to cool, forming a precipitate. Thesolid was collected by filtration, washed with water and dried in vacuo to give 5.10 g(27.0 mmol, 68% yield) of the title compound as a pale brown solid. Purity 100%.1H NMR (300 MHz, DMSO-d6) oe ppm 7.20 (s, 1 H), 6.40 (br s, 2H), 6.05 (br s, 2H).UPLC/MS (3 mm) retention time 0.69 mm.LRMS: mlz 189, 191 (M+1, lxBr).

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; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; CONNOLLY, Stephen; EASTWOOD, Paul Robert; ROBERTS, Richard Spurring; SEVILLA GOMEZ, Sara; CATURLA JAVALOYES, Juan Francisco; (110 pag.)WO2017/64068; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6966-01-4, The chemical industry reduces the impact on the environment during synthesis 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

A mixture of Pd(OAc)2 (146 mg, 0.7 mmol) and 1,1-bis(diphenylphosphino)ferrocene (478 mg, 0.9 mmol) in DMF (65 ml) under an argon atmosphere was stirred at 50 for 15 min and cooled to rt. The reaction mixture was evacuated, then flushed with argon. 3-Amino-6-bromopyrazine-2-carboxylic acid methyl ester (5.0 g, 21.5 mmol), 2-furanboronic acid (2.65 g, 23.7 mmol) and triethylamine (4.3 ml) were added. The reaction mixture was again evacuated, then flushed with argon. The mixture was heated at 90 overnight. After cooling to rt, the black mixture was concentrated to dryness. The residue was dissolved in dichloromethane (800 ml), washed with water, dried over MgSO4, filtered and evaporated. The crude product was purified by silica gel chromatography using a n-heptane /EtOAc gradient for elution, providing the title compound as yellow solid (2.84 g, 60%).MS: M=220.3 (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, Methyl 3-amino-6-bromopyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bleicher, Konrad; Flohr, Alexander; Groebke Zbinden, Katrin; Gruber, Felix; Koerner, Matthias; Kuhn, Bernd; Peters, Jens-Uwe; Sarmiento, Rosa Maria Rodriguez; US2011/306589; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 23229-26-7 as follows. Computed Properties of C4H2Br2N2

(107d) 2-Bromo-5-(methylsulfonyl)pyrazine 2,5-Dibromopyrazine (270 mg, 1.14 mmol) was dissolved in tetrahydrofuran (10 mL), and sodium thiomethoxide (320 mg, 4.57 mmol) was added at room temperature, followed by stirring at room temperature for 2.5 hours under nitrogen atmosphere. To this reaction solution, water (10 mL) was added, and extraction was carried out with diethyl ether (10 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=5%-10%) to afford a yellow solid. This was dissolved in methylene chloride (10 mL), and m-chloroperbenzoic acid (approximately 65%, 580 mg, approximately 2.2 mmol) was added at room temperature, followed by stirring at room temperature for 1 hour under nitrogen atmosphere. To this reaction solution, a saturated aqueous sodium hydrogencarbonate solution (10 mL) was added, and extraction was carried out with methylene chloride (10 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=15%-25%) to afford the desired compound (190 mg, yield 70%) as a white solid. 1H-NMR (CDCl3, 400 MHz): delta 3.26 (3H, s), 8.80 (1H, d, J=1.2 Hz), 9.06 (1H, d, J=1.2 Hz).

According to the analysis of related databases, 23229-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2239253; (2010); 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. 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H3Cl2N3

(A) (S)-terf-butyl 3-((7-chloropyrido[4,3-ib]pyrazi n-5-ylami no)methyl)piperidi ne- 1 -carboxylate.[0123] A solution of (S)-teri-butyl 3-(aminomethyl)piperidine-1 -carboxylate (100 mg, 0.5 mmol), 5,7-dichloropyrido[4,3-¡ê>]pyrazine (100 mg, 0.5 mmol) and DIPEA (77 mg, 0.6 mmol) in THF (5 ml_) was stirred at room temperature for 4 hours. The volatiles were removed under reduced pressure, and the residue was treated with ethyl acetate, with brine, and concentrated to give the crude title compound.

According to the analysis of related databases, 1379338-74-5, the application of this compound in the production field has become more and more popular.

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

Synthetic Route of 622392-04-5, 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. 622392-04-5, name is 2-Bromo-5-iodopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Description 66: 2-bromo-5-(trifluoromethyl)pyrazine (D66); Potassium fluoride (238 mg, 4.09 mmol) and copper(I) iodide (779 mg, 4.09 mmol) were mixed and heated under vacuum using heat gun (temperature 360 0C, on display of heating gun) for 20 minutes (until a greenish colour of the mixture appeared). After cooling at room temperature, DMF (4 ml) and NMP (4.00 ml) were added followed by (trifluoromethyl)trimethylsilane (0.603 ml, 3.77 mmol) and 2-bromo-5-iodopyrazine D65 (896 mg). The resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was poured in 200 ml of 6N NH3 water solution and was extracted twice with Et2O(3 x 50 ml). Gathered Et2O layers were dried over Na2SO4.Diethyl ether was distilled by Claisen apparatus. It was recovered the title compound D66(586 mg).1H NMR (400 MHz, CHLOROFORM- d) delta ppm 8.73 – 8.81 (m, 1 H) 8.84 (s, 1 H)

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

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem