Author: Jessica.F

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

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. 19745-07-4, name is 2,5-Dichloropyrazine, A new synthetic method of this compound is introduced below., SDS of cas: 19745-07-4

Step C: (S)-3-(2-Fluoro-5-methyl-4-(methylsulfonyl)phenylamino)-l-(piperidin-4-yl)pyrrolidin-2-one (420 mg, 1.14 mmol) was dissolved in DMSO (10 mL) and 2,5-dichloropyrazine (203 mg, 1.36 mmol) and N-ethyl-N-isopropylpropan-2-amine (297 mu, 1.71 mmol) were added and the reaction heated to 110 ¡ãC overnight. The reaction was cooled to ambient temperature, water (60 mL) was added and the solids filtered. The solids were dissolved in CH2CI2, washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified over silica gel (70 to 100percent EtOAc in hexanes) to afford (S)-l-(l-(5- chloropyrazin-2-yl)piperidin-4-yl)-3-(2-fluoro-5-methyl-4-(methylsulfonyl)phenylamino)pyrrolidin-2-one (330 mg, 0.685 mmol, 60.2percent yield) as a pale yellow solid. Mass spectrum (apci) m/z = 482.2 (M+H).

The synthetic route of 19745-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; AICHER, Thomas Daniel; BENCSIK, Josef Roland; BOYD, Steven Armen; CONDROSKI, Kevin Ronald; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald Jay; PRATT, Scott Alan; SINGH, Ajay; TURNER, Timothy M.; WO2011/146335; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 957230-70-5, 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. 957230-70-5, name is 3,6-Dibromopyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of compound D as desc?bed in the general reaction scheme; 5,8-DiotabromoiotamiotadazofJ ,2- ajpyrazine.[00250] Bromoacetaldehyde diethyl acetal (49mL, 326mmol) and 48% hydrobromic acid is heated to reflux for 1 5h, then poured into propan-2-ol (60OmL) and quenched with NaHCO3. After filtering, 2,5-dibromo-3-aminopyrazme (41.34g, 163mmol) is added to the solution and heated at reflux overnight. The reaction is cooled and solvents removed in vacuo, followed by addition of aq NaHCO3 and extraction with EtOAc. The organic phase is dried over MgSO4, filtered, and concentrated in vacuo to afford a brown solid. 1H NMR (250MHz, CDCl3) delta(ppm)7.86 (IH, s), 7 93-7.94 (IH, d), 7.98-7.99 (IH, d), m/z (APCI) 278 (M+H)+; m.p 132-135C

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

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 118853-60-4, 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 118853-60-4 as follows.

Into a 50-mL round-bottom flask was placed pyridine (25 mL), methyl 6- aminopyrazine-2-carboxylate (1 g, 6.53 mmol, 1.00 equiv) and 1-methyl-1H-pyrazole-4- carbonyl chloride (1.13 g, 7.82 mmol, 1.20 equiv). The resulting solution was stirred for 2 h at 25 oC in an oil bath. The resulting mixture was concentrated under vacuum at 55 oC for 1 h. This resulted in 1.72 g (93% purity) of methyl 6-(1-methyl-1H-pyrazole-4-amido)pyrazine-2- carboxylate as a yellow solid.

According to the analysis of related databases, 118853-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; PADILLA, Fernando; TOOGOOD, Peter, L.; CHEN, Shoujun; (331 pag.)WO2016/138335; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 89180-45-0, 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 89180-45-0 as follows.

A mixture of 2-hydroxy-5-chloropyrazine in POCl3 (21 equiv.) was heated at 1200C for 2 h. The reaction mixture was cooled and poured on ice and extracted with dichloromethane. The organic solvent was collected, dried over Na2SO4 and filtered. The solvent was filtered over silica gel followed by ethyl acetate. The solvents were evaporated to provide the title compound

According to the analysis of related databases, 89180-45-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2008/46226; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 6164-79-0, 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 6164-79-0 as follows.

To methyl pyrazine-2-carboxylate (3.35 g, 24.3 mmol) in EtOH (60 mL) was added calcium chloride (4.03 g, 36.4 mmol) followed by sodium borohydride (1.38 g, 36.4 mmol). The reaction mixture was stirred at 23C for 5 h. The mixture was quenched with a mixture of acetic acid (4.20 mL, 72.8 mmol) and water (1.31 mL, 72.8 mmol), and stirred for 30 min. The mixture was filtered through a pad a silica gel, and the pad was washed with 5-10% MeOH/DCM containing 0.3% conc. NH3 (aq). The combined filtrates were concentrated in vacuo, and the crude residue was purified by FCC (SiO2, elution with 0-10% MeOH/DCM)to provide 2.01 g (75%) of pyrazin-2-ylmethanol. 1H NMR (400 MHz, d6-DMSO): d ppm 8.71 (m, 1H), 8.56 (dd, 1H), 8.54 (d, 1H), 5.61 (t, 1H), 4.63 (d, 2H); LCMS (Method E): tR= 0.56 min, m/z 111.3 (M+H)+. Step 3: 2-(Chloromethyl)pyrazine

According to the analysis of related databases, 6164-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VENENUM BIODESIGN LLC; LETOURNEAU, Jeffrey J; COLE, Andrew G; MARINELLI, Brett A; QUINTERO, Jorge G; (329 pag.)WO2017/214359; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 939412-86-9, 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(2R,5R)-tert-butyl 5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-(hydroxymethyl) morpholine-4-carboxylate (2g, 4.12 mmol) was dissolved in 100 mL CH2Cl2and cooled to 0 C. TEMPO(0.13 g, 0.82 mmol) was added, followed by (diacetoxyiodo)benzene (2.65 g, 8.24 mmol). The ice bath was removed, and the reaction was allowed to warm to room temperature and stirred overnight. The mixture was diluted with 200 mL ethyl acetate and washed with 10% Na2S203, aq. satd. NaHC03, and brine. The organic phase was dried with Na2S04, filtered and concentrated to give (2R,5R)-4-(tert- butoxycarbonyl)-5 -(((tert-butyl diphenylsilyl)oxy)methyl)morpholine-2-carboxylic acid (1.36g, 66%). LCMS: [M-H]+:498.23 Ret. time= 1.33 min, LC-MS method E). Used as such for the next step without any further purification. (2R,5R)-4-(tert-butoxycarbonyl)-5-(((tert- butyldiphenylsilyl)oxy)methyl)morpholine-2-carboxylic acid (1.5g, 3.0 mmol) and (3- chloropyrazin-2-yl)methanamine. HC1 salt (0.54g, 3.0 mmol) were dissolved in DMF 100 mL. To the reaction mixture was added Et3N (0.76g, 6.0 mmol) followed by slow addition of HATU (1.37g, 3.6 mmol) at 0 C. The reaction was stirred at rt for 1 day under a stream of nitrogen and then quenched with sat. NaHC03 (100 mL) and extracted with EtOAc(2xl50 mL). The combined organic layer was washed with water(200 mL) , brine(200mL), dried over anhydrous Na2S04, filtered, and evaporated. The crude residue was subjected to column purification using 20-50%) EtO Ac/Hex. to give (2R,5R)-tert-butyl 5-(((tert-butyldiphenylsilyl)oxy) methyl)-2-(((3-chloropyrazin- 2-yl)methyl)carbamoyl)morpholine-4-carboxylate (0.86g, 46%). LCMS: [M-Boc +H]+:525.25 Ret. time= 2.74 min, LC-MS method E).

The synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 16298-03-6, 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 16298-03-6 as follows.

Bromine (3.91 g, 24.46 mmol) was added dropwise to a stirred mixture of 3- aminopyrazine-2-carboxylic acid methyl ester (1.27 g, 8.29 mmol) and hydrobromic acid (4.70 mL, 41.5 mmol) at 00C. A solution of sodium nitrite (1.44 g, 20.9 mmol) in water (6 mL) was then added dropwise. The reaction mixture was stirred for 15 min, brought to pH 8 with NaHCO3 (saturated, aqueous), and extracted with ethyl acetate (80 mL) and chloroform (50 mL). The combined organics were dried over MgSO4 and concentrated in vacuo to give 1.13 g (63percent) of an orange oil which solidified on standing. LC-MS m/z 217 (M+H+); RT 1.15 mm.

According to the analysis of related databases, 16298-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/49681; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 36070-80-1, 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 36070-80-1 as follows.

5-(Oxetan-2-ylmethoxy)pyrazine-2-carboxylic acid In a microwave vial 5-chloropyrazine-2-carboxylic acid (100.0 mg, 0.631 mmol), dimethylformamide (5 mL), oxetan-2-ylmethanol (83.4 mg, 0.946 mmol) and potassium tert-butoxide (176.9 mg, 1.58 mmol) are added. A small exotherm is observed. After 1 minute at room temperature the vial is sealed and the mixture heated at 120 C. for 30 minutes in the microwave. The reaction mixture is then quenched with aqueous NH4Cl and the solvent evaporated under reduced pressure. The resultant residue is triturated in 2-propanol. The filtrate is concentrated under reduced pressure to give the title compound as a cream solid (0.294 g, 99%) and is used without further purification. ES/MS (m/e): 211.0 (M+1), 208.8 (M-H).

According to the analysis of related databases, 36070-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GREEN, Steven James; HEMBRE, Erik James; MERGOTT, Dustin James; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR., Leonard Larry; US2014/371212; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 6164-79-0, These common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, 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.

General procedure: To a mixture of NaH (60% in mineral oil, 0.68 g, 28.2 mmol),methyl pyrazine-2-carboxylate (3 g, 21.7 mmol) and dry DMF(30 mL), methyl acetate (2.09 g, 28.2 mmol) was added dropwiseunder N2 atmosphere. After being stirred at rt for 5 h, the reactionmixture was concentrated in vacuo, and the residue treated withsaturated aqueous NaHCO3 solution followed by extraction withEtOAc. The combined organic phase were dried with MgSO4,filtered, and concentrated in vacuo. Column chromatographicpurification (n-hexane/EtOAc = 8:1) yielded 5a as white solid

The synthetic route of 6164-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lee, Young Hun; Lee, Jung Min; Kim, Sang Geon; Lee, Yong Sup; Bioorganic and Medicinal Chemistry; vol. 24; 12; (2016); p. 2843 – 2851;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem