Pyrazines

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. 126069-70-3, name is 2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8F3N3

2-Fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoic acid 1a (500 mg, 1.68 mmol) was dissolved in 10 mL of N,N-dimethylformamide, followed by addition of O-(1-benzotriazolyl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (830 mg, 2.52 mmol), 2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-c]pyrazine 12c (384 mg, 2 mmol) and N,N-diisopropylethylamine (1 mL, 5 mmol). After stirring for 12 hours, the resulting residue was purified by silica gel column chromatography with elution system A to obtain 4-[[4-fluoro-3-[2-(trifluoromethyl)-6,8-dihydro-5H-imidazo[1,2-c]pyrazine-7-carbonyl]phenyl]methyl]-2H-phthalazin-1-one 12 (200 mg, yield 25.0%) as a white solid. MS m/z (ESI): 472.1[M+1] 1H NMR (400 MHz, CDCl3): delta 10.29 (br. s, 1H), 8.47 (m, 1H), 7.80 (m, 3H), 7.37 (m, 2H), 7.25 (m, 1H), 6.50 (m, 1H), 4.67 (s, 2H), 4.28 (m, 2H), 4.14 (m, 2H), 3.73 (m, 2H)

According to the analysis of related databases, 126069-70-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JIANGSU HANSOH PHARMACEUTICAL CO., LTD.; Tang, Peng Cho; Li, Xin; Li, Xiangqin; Chen, Yang; Wang, Bin; Zhu, Zhe; US2013/131068; (2013); A1;,
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Synthetic Route of 369638-68-6, A common heterocyclic compound, 369638-68-6, name is tert-Butyl (5-methylpyrazin-2-yl)carbamate, molecular formula is C10H15N3O2, 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.

Step 2: To a solution of (5-methyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (from above and from example 21, step 1, 12.9 g, 61.6 mmol) and AIBN (10.1 g, 61 mmol) in CCl4 (100 mL) was added NBS (11 g, 61.6 mmol) and the reaction mixture was stirred at 100 C. for 4 h. The reaction mixture was filtered, washed with CH2Cl2 and concentrated in vacuo. Purification by chromatography (silica, 4:5:1 CH2Cl2:hexanes:ethyl acetate) with repurification of mixed fractions by chromatography (silica, 4:5:1 CH2Cl2:hexanes:ethyl acetate) afforded a total of (5-bromomethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (13.6 g, 77%): 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.57 (s, 9H) 4.55 (s, 2H) 8.15 (s, 1H) 8.34 (d, J=1.51 Hz, 1H) 9.28 (d, J=1.51 Hz, 1H).

The synthetic route of 369638-68-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brotherton-Pleiss, Christine E.; Walker, Keith A. M.; US2012/149718; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 22047-25-2, name is Acetylpyrazine, molecular formula is C6H6N2O, 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. COA of Formula: C6H6N2O

General procedure: Catalyst (0.1mol %) and KOH (1mmol) were dissolved in 2-propanol (4mL). To this solution, substrate (1mmol) was added and the mixture was refluxed (82C). The progress of the reaction was monitored by GC at regular intervals. After the completion of the reaction, the reaction mixture was cooled to room temperature and filtered through silica gel or alumina bed, and eluted using 50% ethyl acetate-hexane mixture. The eluted solution was reduced and analyzed by GC and/or GCMS.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22047-25-2, its application will become more common.

Reference:
Article; Sathishkumar, Pushpanathan N.; Raveendran, Neethi; Bhuvanesh, Nattamai S.P.; Karvembu, Ramasamy; Journal of Organometallic Chemistry; vol. 876; (2018); p. 57 – 65;,
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Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, 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. Recommanded Product: 5521-55-1

A boron trifluoride-diethyl ether complex (91.7 IL) was added dropwise to a suspension of 2-methylpyrazine-5-carboxylic acid (1 g) and tert-butyl 2,2,2-trichloroacetimidate (4.75 g) in tetrahydrofuran (20 mL) under ice-cooling. The reaction solution was heated to room temperature and stirred for two hours. A saturated sodium chloride solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the insoluble matter was separated by filtration. The filtrate was concentrated and purified by silica gel column chromatography to obtain the title compound (1.4 g).1H-NMR (CDCl3) delta (ppm): 1.65 (s, 9H), 2.65 (s, 3H), 8.57 (d, J=1.2 Hz, 1H), 9.10 (d, J=1.6 Hz, 1H).

The synthetic route of 5-Methylpyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; US2010/93999; (2010); A1;,
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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. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C6H6N2O2

General procedure: To the dipeptide salt (7 or 11, 1 mmol) in Schemes 2 and 3 wasadded a solution of 7 N NH3 in CH3OH (10 mL) and reaction mixturewas stirred for 10 min at 0 C. The solvent was evaporatedunder reduced pressure to afford free peptides, which was dissolvedin DMF (4 mL) and cooled to 4 C. To this reaction mixturerequisite carboxylic acid (1 mmol), DIC (1.1 mmol) and HOBt(1.1 mmol) was added and stirring continued at 4 C for 36 h. Thesolvent was removed under reduced pressure and the resultingresidue purified by column chromatography over neutral alumina using CHCl3/CH3OH (4:1) as eluant to afford desired peptides.The peptides were checked for their homogeneity on aShimadzu SPD-M20A HPLC system using a Supelcosil LC-8(25 cm 4.6 mm ID) column. The peptides were analyzed by usingan isocratic solvent system of CH3CN-H2O-TFA (70:30:0.8%) usinga SUPELCOSIL C-18 column with a flow rate of 1 mL/min

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:
Article; Meena, Chhuttan L.; Thakur, Avinash; Nandekar, Prajwal P.; Sangamwar, Abhay T.; Sharma, Shyam S.; Jain, Rahul; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5641 – 5653;,
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Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, 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. Recommanded Product: 2-Bromo-5-iodopyrazine

2-Bromo-5-iodopyrazine [CAS RN: 622392-04-5] (3.50 g, 12.3 mmol, 1.0 eq),4,4,5,5-tetramethyl-2-(prop-1 -en-2-yl)-1 ,3,2-dioxaborolane [CAS RN: 126726-62-3] (3.10 g, 18.4 mmo[, 1.5 eq), Pd(dppf)C[2.CH2C[2 (502 mg, 0.61 mmo[, 0.05 eq) and cesium carbonate (12.0 g, 36.9 mmo[, 3.0 eq) were dissolved in 130 mL dioxane/water (5/1). The reaction mixture was heated to 90C for 2 h. On cooling, the reaction mixture was partitioned between water anddichloromethane. The organic phase was washed with brine and the phases were separated by the use of a Whatman filter. The volatile components were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 100 g SNAP cartridge: hexane -> hexane/ethyl acetate 9/1) to give 600 mg (25% yield of theory) of the title compound in a round 50% purity(UPLC-area%). The impurity was identified as 2,5-di(prop-1-en-2-yl)pyrazine, that was not expected to interfere in the subsequent reaction step. The material obtained was used without further purification.UPLC-MS (Method 4): R = 1.18 mm; MS (ESI0): m/z = 199 [M].

The synthetic route of 2-Bromo-5-iodopyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
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Pyrazine | C4H4N2 – PubChem

Reference of 274-79-3, 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 274-79-3 as follows.

Imidazo[1,2-a]pyrazine (420 mg, 3.53 mmol) was dissolved in acetonitrile (10 mL).N-bromosuccinimide (691 mg, 3.88 mmol) was added thereto, and the mixture was reacted at room temperature overnight.After the reaction is completed, a saturated sodium hydrogencarbonate solution is added thereto.Extract with dichloromethane, dry the organic phase with anhydrous sodium sulfate, filter, and then dry the solvent.The residue was purified by silica gel column chromatography to give a yellow solid,619mg.

According to the analysis of related databases, 274-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Pharmaceutical Group Co., Ltd.; Wan Huixin; Li Chunli; Shi Chen; Liu Haiyan; Li Ping; Shen Jingkang; (50 pag.)CN104341425; (2018); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 186534-02-1, A common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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.

10052] In 10 mL of methanol was dissolved 2,4-dimeth- ylphenylhydrazide hydrochloride (1.72 g, 10 mmol). To the solution, 3,5,6-trimethylpyrazine-2-carbaldehyde (1.50 g, 12 mmol) was added with an ice-bath under the protection of N2. After the mixture was stirred for 10 mm, a lot of brick red precipitate showed and the reaction was then complete. The mixture was filtered through a suction funnel, and the brick red solid was transferred to a vacuum oven to be dried for using directly in the next reaction step of the reaction. The red brick intermediate (3.04 g, 10 mmol) was dissolved in 25 mL of methanol, and 1.68 ml of anhydrous triethylamine and 1.7 ml of trifluoroacetic anhydride were added respectively with an ice-bath under the protection of N2, and the reaction was run for 30 minutes. The reaction was monitored by TLC till completion. The resulting material was extracted with Ethyl acetate, dried over anhydrous Na2504, separated by a silica gel colunm (ethyl acetate:petroleum ether=1 :3) to get T-006 as a light yellow solid (3.25 g, 89.3%). ESI-MS: [M+H] mlz 365.1. ?H-NMR (CDC13, 300 MHz) oe: 2.1 (s, 3H), 2.42 (s, 3H), 2.46 (s, 3H), 2.54 (s, 3H), 2.85 (s, 3H), 7.08 (d, j=7.05 Hz, 1H), 7.24 (d, J=7.21 Hz, 1H), 7.25 (s, 1H), 7.55 (s, 1H); Anal.

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GUANGZHOU MAGPIE PHARMACEUTICALS CO., LTD.; WANG, Yuqiang; CHEN, Haiyun; ZHANG, Zaijun; ZHANG, Gaoxiao; YU, Pei; SUN, Yewei; SHAN, Luchen; TAO, Liang; US2018/346430; (2018); A1;,
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Application of 109838-85-9, The chemical industry reduces the impact on the environment during synthesis 109838-85-9, name is (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, I believe this compound will play a more active role in future production and life.

Preparation 13: [(lS2RV3-arnino-l-(315-Muoro-bemyl)-2-hydroxy-propyl]-carbarnic acid t-butyl ester Step A: (2S,5RV2,5-dihvdro-3,6-dimethoxy-5-isopropyl-2-(3,5-dMuoro)benzylpyrazine(TR.)-2,5-dihydro-3,6-dirnethoxy-2-isopropylpyrazine (9.2 g, 50 mmol) was dissolved in THF (100 mL), to which n-BuLi (4M in THF, 15 mL) was then added at -78 °C, followed by addition of difluorobenzyl chloride (9.72 g, 60 mmol). After the reaction was complete, NH4Cl was added to the reaction mixture which was then extracted with EtOAc. The organic extract was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc: n-Hex = 1/1) to afford the title compound (12.4 g, 80percent).

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, (R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LG LIFE SCIENCES, LTD.; WO2009/38411; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 221136-66-9,Some common heterocyclic compound, 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, molecular formula is C9H11BrN2O3, 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.

Example 8 r3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-vn- acetic acid ethyl ester(3-Bromo-6-methyl-2-oxo-2H-pyrazin-1 -yl)-acetic acid ethyl ester was reacted with 2,2-difluoro-2-phenyl-ethylamine in the presence of a base, at elevated temperature, to yield the title compound as shown in the Scheme above. Table 5 below lists the reagent amounts, base and temperature combinations applied to this reaction, as well as yield.

The synthetic route of 221136-66-9 has been constantly updated, and we look forward to future research findings.

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