Month: July 2021

Reference of 486424-37-7, These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-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.

Example 11 : 3-(lH-Benzimidazol-2-yl)-5-(3-pyridyloxy)pyrazin-2-amine (Compound 11-12)SCompound 11-12 METHOD K:Step 1: 3-Amino-iV-(2-aminophenyl)-6-bromopyrazine-2-carboxamide[00169] To a solution of 3-amino-6-bromopyrazine-2-carboxylic acid (140 g, 0.64 mol), o- phenylenediamine (70 g, 0.65 mol) and TBTU (247 g, 0.77 mol) in DMF (1.5 L) at 0 C was added drop wise DIPEA (166 g, 1.29 mol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water and the resultant precipitate isolated by filtration and washed with water. The precipitate was dried at 50C to give the sub-title compound as a brown solid that wasused in the next step without further purification product (140 g, 70 % Yield). XH NMR (400 MHz, DMSO) delta 4.95 (br s, 2H), 6.59 (m, 1H), 6.79 (d, 1H), 6.95 (m, 1H), 7.30 (d, 1H), 7.70 (bs, 2H), 8.40 (s, 1H) and 9.65 (s, 1H) ppm; MS (ES+) 307.8.

Statistics shows that 3-Amino-6-bromopyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 486424-37-7.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus, Alphonsus; O’DONNELL, Michael; REAPER, Philip, Michael; WO2011/143419; (2011); 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. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 68774-77-6

Add p-aminophenol (0.78 g, 7.2 mmol) and potassium tert-butoxide (1.46 g, 13.0 mmol) to the flask, use tetrahydrofuran as a solvent, and stir under an ice bath for 1 h under the protection of nitrogen; intermediate c (1 g, 6.5 mmol) and potassium iodide (0.12 g, 0.72 mmol) were added to the flask, tetrahydrofuran was used as a solvent, and the temperature was raised to 80 C., and the p-aminophenol after the reaction was added thereto, and reacted under the protection of nitrogen. After the reaction is completed, suction filtration is performed. The filtrate is spin-evaporated. After evaporation to dryness, a small amount of NaOH aqueous solution is added to sonicate, solids are precipitated, suction-filtered, and the filter cake is dried to obtain 0.45 g of a gray solid with a yield of 30.6%.

The synthetic route of 68774-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Xu Shan; Liu Xiaobo; Zhang Qian; Zhou Lingjia; Han Haoyun; Yu Li; Zhou Hualan; Qiu Yufeng; (25 pag.)CN110467616; (2019); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 14508-49-7,Some common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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: 2,6-dichloropyrazine (10.49 g, 70.38 mmol) was dissolved in 150 mL of ethanol. After stirring for 5 min, 80% hydrazine hydrate (7.05 g, 0.147 mol) was added. The reaction was heated to 80 C and refluxed for 10 h until the solution became clear. The resulting mixture was cooled to room temperature, and a yellow solid was precipitated. The suspension was filtered, and the filtrate was concentrated under reduced pressure to afford a yellow solid 9.1 g.

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

Reference:
Article; Liu, Weijie; Li, Jiao; He, Kai; Huang, Fangfang; Ma, Yi; Li, Yuxin; Li, Qingshan; Xu, Fengbo; Chinese Chemical Letters; (2019); p. 417 – 420;,
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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 3-amino-6-bromopyrazine-2-carboxylate

Methyl 3-AMINO-6-BROMO-2-PYRAZINE-CARBOXYLATE (14.3 g9 61.6 mmol; see Example 16 (a) above) was suspended in 40 % aqueous METHYLAMINE (350 mL) and the resulting mixture was stirred vigorously for 7 hours at room temperature. The precipitate was collected, washed with water, and dried to afford 3-amino-6-bromo- pyrazine-2-carboxylic acid methylamide as a yellow solid (12.7 g, 90 %). H NMR (300 MHz, DMSO-D6) S2. 77 (d, J= 3 Hz, 3 H), 7.70 (br s, 2 H), 8. 33 (s, 1 H), 8. 56 (q, J= 3 Hz, 1 H); 13C NMR (100 MHz, DMSO-d6) #27.84, 123.49, 127.69, 150.43, 156.04, 167.18.

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; BIOGEN IDEC MA INC.; WO2004/92177; (2004); 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (3-Chloropyrazin-2-yl)methanamine hydrochloride

2-Aminomethyl-3-chloropyrazine hydrochloride (content 77%; 34.7 mmol, 6.47 g), trans-4- hydroxycyclohexanecarboxylic acid (34.7 mmol, 5 g), N,N-diisopropylethylamine (104 mmol, 18.12 ml, 13.45 g), 4-dimethylaminopyridine (3.47 mmol, 0.424 g) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide) hydrochloride (45.1 mmol, 8.64 g) in dichloromethane (100 ml) were stirred at room temperature. After 16 hours the reaction mixture was diluted with 2N hydrochloric acid and extracted with dichloromethane three times. The organic layer was dried (sodium sulfate) and concentrated in vacuo. The crude product was triturated with dichloromethane to give 2 g of solid (trans)-N-((3-chloropyrazin-2- yl)methyl)-4-hydroxycyclohexanecarboxamide. The mother liquor was dissolved in ethyl acetate and washed with aqueous sodium hydrogencarbonate solution, dried (sodium sulfate) and concentrated to give an additional crop of 0.7 g of (trans)-N-((3-chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide.

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 939412-86-9.

Reference:
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 19847-12-2, 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 19847-12-2 as follows.

General procedure: A screw capped vial was charged with nitrile (2 mmol), NaN3(2.4 mmol, 1.2 equiv.) and tetrabutylammonium bromide (2.4 mmol,1.2 equiv.). The resulting mixture was stirred at 105 C and monitoredby TLC. After completion of the reaction, the reaction mixture wascooled to room temperature and dissolved with water (5 mL). Then, theaqueous solution was acidified with 1M HCl to pH = 3. If a precipitatewas formed, the suspension was filtered and the filter cake was washedwith water to afford the pure product. Otherwise, the aqueous solutionwas extracted with EtOAc (3 × 4 mL). The organic phase was washedwith 1M HCl (3 × 4 mL), dried with anhydrous Na2SO4, filtered andevaporated under vacuum to afford the pure product.

According to the analysis of related databases, 19847-12-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xie, Aming; Cao, Meiping; Feng, Liandong; Dong, Wei; Journal of Chemical Research; vol. 37; 11; (2013); p. 665 – 667;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 59489-71-3,Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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 5-bromo-pyrazine-2-amine according to formula (ii) (2.3 g, 13.21 mmol) in 1,4-dioxane (15 ml) was added a boronic acid of formula (vi) such as 4- methylsulfonylphenylboronic acid (CombiBlocks) (2.77 g, 13.87 mmol) at RT and the resulting mixture was purged with N2 gas for 30 minutes. Bis(triphenylphosphine)palladium(II)chloride (463 mg, 0.66 mmol) and 1 M aqueous solution of potassium carbonate (15.84 ml, pre-purged with N2 gas) were added to the reaction mixture. The reaction mixture was heated to reflux for 16 h, cooled to RT and concentrated under vacuum. 10 ml of water was added to the reaction mixture and extracted with ethyl acetate (15 ml X 4). Combined organic layers were washed with brine solution (10 ml), dried over anhydrous Na2S04 and concentrated under vacuum. The crude material was purified by column chromatography over silica gel 230-400 mesh by using 2-3% of MeOH in DCM as an eluent to yield to a 5-substituted pyrazine- 2-amine of formula (vii) (2.5g, 75.91%) as white solid.

The synthetic route of 59489-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF CAPE TOWN; MMV MEDICINES FOR MALARIA VENTURE; YOUNIS, Yassir; CHIBALE, Kelly; WITTY, Michael, John; WATERSON, David; WO2013/121387; (2013); 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 54608-52-5 as follows. Quality Control of 2-Hydrazinopyrazine

General procedure: To a vigorously stirred mixture of alpha-bromonitroalkane (0.50 mmol), heteroaryl hydrazine (0.60 mmol, 1.2 equiv), potassium iodide (1.0 mmol, 2.0 equiv) and potassium carbonate (1.0 mmol, 2.0 equiv) in 1,2-dimethoxyethane (5.0 mL) was added a solution of urea hydrogen peroxide in 1,2-dimethoxyethane/water (4:1) (0.50 M solution, 1.0 mL, 0.50 mmol, 1.0 equiv) over 2 h via syringe pump at r.t. After the addition was complete, the mixture was stirred for an additional 4 h. Aqueous sodium thiosulfate was then added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography to give pure fused triazole.

According to the analysis of related databases, 54608-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tokumaru, Kazuyuki; Bera, Kalisankar; Johnston, Jeffrey N.; Synthesis; vol. 49; 20; (2017); p. 4670 – 4675;,
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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 939412-86-9

(3-Chloropyrazin-2-yl)methanamine hydrochloride (157 mg, 0.873 mmol), 2-chloro-4- methoxyphenylboronic acid (325 mg, 1.75 mmol), potassium carbonate (482 mg, 3.49 mmol) and tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.043 mmol) in water (1.5 mL) and DME (4.5 mL) was microwave irradiated at 110 C for 30 min. After organic solvent was removed in vacuo, the residue was extracted with EtOAc and washed successively with water and brine. The organic layer was dried over Na2S04and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (MeOH/DCM) to obtain 64 mg of [3-(2-chloro-4-methoxy- phenyl)-pyrazin-2-yl]-methylamine.

According to the analysis of related databases, 939412-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF WASHINGTON; FAN, Erkang; ZHANG, Zhongsheng; HUANG, Wenlin; BUCKNER, Frederick S.; (180 pag.)WO2018/237349; (2018); 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. 71257-38-0, name is 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazine

Step 3 4-[[3-(3,4-dihydro-1H-pyrrolo[1,2-c]pyrazine-2-carbonyl)-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 2-Fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoic acid 1a (300 mg, 1 mmol) was dissolved in 3 mL of N,N-dimethylformamide, followed by addition of O-(1-benzotriazolyl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (568 mg, 1.50 mmol), 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine 2c (210 mg, 1.50 mmol) and N, N-diisopropylethylamine (350 muL, 2 mmol). After stirring for 12 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by thin layer chromatography with elution system A to obtain 4-[[3-(3,4-dihydro-1H-pyrrolo[1,2-c]pyrazine-2-carbonyl)-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 2 (15 mg, yield 3.7%) as a white solid. MS m/z (ESI): 403.1 [M+1] 1H NMR (400 MHz, CDCl3): delta 10.19 (br. s, 1H), 8.51 (d, 1H), 7.82 (m, 3H), 7.41 (m, 2H), 7.13 (m, 1H), 6.65 (m, 1H), 6.24 (m, 1H), 5.81 (m, 1H), 4.97 (s, 1H), 4.59 (s, 1H), 4.33 (s, 2H), 4.13 (m, 1H), 4.00 (m, 1H), 3.71 (m, 1H), 2.85 (m, 1H)

According to the analysis of related databases, 71257-38-0, 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;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem