Tag: M.W=100-200

Synthetic Route 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: In a Schlenk tube, a mixture of the required amount of catalyst, plus the aryl chloride (1.0 mmol), aryl boronic acid (1.5 mmol) and the selected base (2.0 mmol) in water was evacuated and charged with nitrogen. The reaction mixture was heated at 100C for 12 h. After cooling, the mixture was extracted with CH2Cl2 and the extract was evaporated. The resulting residue was purified by flash chromatography on silica gel using a mixture of CH2Cl2/ethyl acetate (5/1) as eluent. The known products 5, 6a [17,18], 6b [22], 6c [23], 6e [24], 6g [19], 6h [25] and 7a [26] were characterized by comparison of data with those in the literature. The products 6d, 6f and 7b-h were new compounds and characterized by elemental analysis, MS, 1H and 13C NMR.

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; Han, Xin; Li, Hong-Mei; Xu, Chen; Xiao, Zhi-Qiang; Wang, Zhi-Qiang; Fu, Wei-Jun; Hao, Xin-Qi; Song, Mao-Ping; Transition Metal Chemistry; vol. 41; 4; (2016); p. 403 – 411;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 19847-12-2, 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. 19847-12-2, name is Pyrazinecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 53; C-Pyrazin-2-yl-methylamine; In a Parr bottle, charge pyrazine-2-carbonitrile (1 g) in absolute ethanol (10mol). Add 10% Pd-C (w/w, 0.4g) and place on a Parr Hydrogenation Apparatus under 50 psig hydrogen at ambient temperature for sixteen hours. Filter the mixture through a pad of Celite. Purify material on SCX column. Use crude basic material in next step without further purification.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/66126; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 54608-52-5, 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. 54608-52-5, name is 2-Hydrazinopyrazine, This compound has unique chemical properties. The synthetic route is as follows.

Step 1:; To a suspension of hydrazinopyrazine (400 mg, 3.57 mmol) in 50 ml Toluene was added 2(4-fluorphenyl)-1-(pyridin-4y1)ethanone (770 mg, 3.57 mmol) (J. Med Chem. 2003, 46, 4702) and p-toluenesulfonic acid (50 mg). The reaction mixture was refluxed with azeotropic removal of water. After 16 h, the reaction mixture was concentrated in vacuo to give the crude pyrazinylhydrazone (1.35 g) which was used in the next step without further purification.

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

Reference:
Patent; Bayer CropScience AG; EP2338890; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 33332-25-1, 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Example 29 5- [2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-PROPIONYLAMINO]- PYRAZINE-2-CARBOXYLIC acid HYDROXYAMIDE [000197] A solution of methyl 5-chloropyrazine-2-carboxylate (30.00 g, 0.17 mol) in tetrahydrofuran (87 mL) was treated with a solution of potassium carbonate (72.08 g, 0.52 mol) in water (261 mL). The resulting reaction mixture stirred at 25C for 42 h. The reaction mixture was then acidified to a pH of about 2 with concentrated hydrochloric acid, diluted with a saturated aqueous sodium chloride solution (300 mL), and was continuously extracted with ethyl acetate (4L total) until no product was present in the aqueous layer. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 5-chloro-pyrazine-2-carboxylic acid (26.54 g, 96%) as an off-white solid: mp 150-151C ; EI-HRMS m/e calcd for CSH3CIN202 (M 157.9883, found 157.9877.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/52869; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4774-14-5, These common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, 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 1 To a solution of tert-butyl azetidin-3-ylcarbamate hydrochloride (LXIV) (2 g, 9.58 mmol) in dry DMF (19.2 mL) was added DIPEA (8.37 ml, 47.9 mmol). To this mixture was added 2,6-dichloropyrazine (LXV) (1.428 g, 9.58 mmol) and the reaction was stirred at 95 C. for 3 hours. The reaction was quenched with water (20 mL) and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (40 g) (100% hexanes?hexanes:EtOAc 1:1) to yield tert-butyl (1-(6-chloropyrazin-2-yl)azetidin-3-yl)carbamate (LXVI) (2.2882 g, 8.04 mmol, 83.9% yield) as a white solid. ESIMS found for C12H17ClN4O2 m/z 285.1 (M+H).

The synthetic route of 4774-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (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. 59489-71-3, name is 2-Amino-5-bromopyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C4H4BrN3

Into a 20-L 4-necked round-bottom flask was placed a solution of 5-bromopyrazin-2-amine (400 g, 2.30 mol) in ethylene glycol dimethyl ether (8 L) , iodocopper (131 g, 687.84 mmol) , diiodane (293 g, 1.15 mol) , iodopotassium (380 g, 2.29 mol) and 3-methylbutyl nitrite (1800 mL, 11.5 mol) . The resulting solution was stirred for 30 min at 60 C, then extracted with 2 x 10 L of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford the title compound.

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; MERCK SHARP & DOHME CORP.; DEBENHAM, John S.; COX, Jason M.; LAN, Ping; SUN, Zhongxiang; FENG, Zhe; SUN, Chunrui; SEGANISH, W. Michael; LAI, Zhong; ZHU, Chen; BARA, Thomas; RAJAGOPANALAN, Murali; DANG, Qun; KIM, Hyunjin M.; HU, Bin; HAO, Jinglai; (112 pag.)WO2018/107415; (2018); 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. 126069-70-3, name is 2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 126069-70-3

2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1 ,2-a]pyrazine (1.06 g, 5.55 mmol, Intermediate 4) and triethylamine (0.850 ml, 6.10 mmol) were dissolved in dichloromethane (DCM) (25 ml). 2-chloro-3-(trifluoromethyl)benzoyl chloride (1.348 g, 5.55 mmol) was added and the mixture stirred at room temperature for 24 h. The solvents were removed in vacuo and the solid partitioned between dichloromethane (100 ml) and saturated sodium bicarbonate solution (50 ml). The aqueous phase was extracted with dichloromethane (3 x 50ml), the combine organic extracts were dried over anhydrous sodium sulfate and then concentrated to afford 7-{[2-chloro-3- (trifluoromethyl)phenyl]carbonyl}-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1 ,2- a]pyrazine (2.22 g, 5.58 mmol, 101 % yield). LC/MS [M+H]+ = 398, 400, retention time = 1.04 minutes (2 minute method).

The synthetic route of 126069-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

16298-03-6, name is Methyl 2-aminopyrazine-3-carboxylate, 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. Quality Control of Methyl 2-aminopyrazine-3-carboxylate

Step 1: synthesis of methyl 3-bromopyrazine-2-carboxylate (99)To a solution of methyl 3-amino-2-pyrazinecarboxylate (13.06 mmol, 2 g) in hydrobromic acid (13.06 mmol, 7.4 ml, 1.057 g) at 0C was added bromine (38.9 mmol, 2 mL, 6.22 g) drop wise and then a solution of sodium nitrite (33.3 mmol, 2.3 g) in water (4 mL). The reaction was stirred for 2h at 0C and the reaction mixture was extracted with CH2CI2. Organic layer was dried and evaporated to give crude methyl 3- bromopyrazine-2-carboxylate 101 (1.2gr, 43%). (m/z) = 217 and 219 (M+H)+.

The synthetic route of 16298-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; FOLMER, Brigitte, Johanna, Bernita; MAN, de, Adrianus, Petrus, Antonius; GERNETTE, Elisabeth, Sophia; CORTE REAL GONCALVES AZEVEDO, Rita; IBRAHIM, Hemen; WO2011/147764; (2011); 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. 63286-28-2, name is 2-Chloro-3-hydrazinylpyrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Chloro-3-hydrazinylpyrazine

Into a 500-mL 3 -necked round-bottom flask, was added 2-chloro-3- hydrazinylpyrazine (5.0 g, 34.59 mmol, 1.00 equiv) in tetrahydrofuran (100 mL). While stirring this solution at 0 C a solution of TFAA (8.0 g, 38.09 mmol, 1.10 equiv) in tetrahydrofuran (100 mL) was added dropwise. The resulting solution was stirred for 1 h and then washed with sodium chloride(aq). The resulting solution was extracted with ethyl acetate and the organic layers were combined and concentrated under vacuum. Purification by flash chromatography (silica gel column with ethyl acetate: petroleum ether (1:5)) provided 7.3 g (88%) of 1-1 as a white solid.

According to the analysis of related databases, 63286-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; BECK, Hilary, Plake; GONZALEZ-LOPEZ, Marcos; SUTTON, James, Clifford, Jr.; (86 pag.)WO2019/156989; (2019); 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. 13484-56-5, name is 3-Chloro-6-methoxypyrazin-2-amine, A new synthetic method of this compound is introduced below., Formula: C5H6ClN3O

To a solution of 3.15 g of 3-chloro-6-methoxypyrazin-2-amine in 20 mL of triethylamine, 2.6 mL of ethyl acrylate and 0.50 g of bis(tri-tert-butylphosphine)palladium(0) were added, and the mixture was stirred at an external temperature of 120 to 130C for 2 hours in a sealed tube. Thereto was further added 5 mL of triethylamine, and the mixture was stirred at the same temperature for 4 hours 50 minutes. The reaction mixture was cooled to room temperature and left overnight, then 0.5 mL of ethyl acrylate and 0.25 g of bis(tri-tert-butylphosphine)palladium(0) were added thereto and the mixture was stirred at an external temperature of 115 to 125C for 9 hours 20 minutes in a sealed tube. The reaction mixture was cooled to room temperature, water and ethyl acetate were then added thereto, the organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of hexane:ethyl acetate = 4:1 to obtain 2.55 g of ethyl (2E)-3-(3-amino-5-methoxypyrazin-2-yl)acrylate as a yellow solid. 1H-NMR (CDCl3) delta: 1.32 (3H, t, J = 7.1 Hz), 3.91 (3H, s), 4.26 (2H, q, J = 7.1 Hz), 4.72 (2H, s), 6.73 (1H, d, J = 15.1 Hz), 7.61-7.68 (2H, m)

The synthetic route of 13484-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; Taisho Pharmaceutical Co. Ltd.; EP2022793; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem