Month: July 2021

Reference of 24241-18-7, The chemical industry reduces the impact on the environment during synthesis 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, I believe this compound will play a more active role in future production and life.

(a) Add 2-amino-3,5-dibromopyrazine (10 g, 39.54 mmol, 1 eq) to a 100 mL autoclaveAnd ammonia (50 mL, commercially available),Raise the temperature to 130 C under nitrogen protection conditions and carry out the reaction overnight (10 to 12 hours);Cooling, suction filtration,The obtained solid was vacuum dried to give 5.0 g of Compound II.

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, 2-Amino-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Suzhou Derivative Biological Technology Co., Ltd.; Liu Ke; (6 pag.)CN108395436; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5049-61-6, 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 5049-61-6 as follows.

To a solution of 2-aminopyrazine (2.0 g, 21.03 mmol) in ethanol (40 mL) was added 2-bromo-1,1-dimethoxyethane (2.5 mL, 21.03 mmol) followed by 5 drops of concentrated hydrochloric acid. After refluxing for 14 hours, the solvent was evaporated. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate (3×). The combined organic phase was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by flash chromatography (100% ethyl acetate, 10% methanol in ethyl acetate, then 10% methanol in dichloromethane) to give 536 mg of the title compound as a solid. 1H NMR (500 MHz, CDCl3) delta 7.70 (bs, 1H), 7.82 (bs, 1H), 7.89 (d, 1H, J=4.4 Hz), 8.10 (d, 1H, J=4.6 Hz), 9.12 (s, 1H)

According to the analysis of related databases, 5049-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Corp.; Edmondson, Scott D.; Fisher, Michael H.; Kim, Dooseop; Maccoss, Malcolm; Parmee, Emma R.; Weber, Ann E.; Xu, Jinyou; US2015/359793; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 23688-89-3, A common heterocyclic compound, 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

6-Chloro-N-cyclobutylpyrazine-2-carboxamide: To a suspension of 6-chloropyrazine-2-carboxylic acid (100 mg, 0.631 mmol), HATU (288 mg, 0.757 mmol), and cyclobutanamine (49 mg, 0.69 mmol) in DMF (1.26 mL) at 0 C was added DIEA (220 pi, 1.26 mmol) and the resulting mixture was stirred at rt for 2 h. The volatiles were removed under reduced pressure. The residue was purified via silica gel chromatography (0 – 100 % EtOAc in hexanes) to give the title compound (84 mg, 63%) as an off-white solid. MS (ES+) C9H,0C1N30 requires: 211, found: 212 [M+Hf?. ?H NMR (600 MI-Tz, Chloroform-d) oe 9.28 (s, 1H), 8.75 (s, 1H), 7.72 (s, 1H), 4.66 – 4.53 (m, 1H), 2.50 – 2.38 (m, 2H), 2.13 – 1.98 (m, 2H), 1.87- 1.73 (m, 2H)

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; TESARO, INC.; JONES, Philip; CZAKO, Barbara; BURKE, Jason P.; CROSS, Jason; LEONARD, Paul Graham; (208 pag.)WO2018/81276; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1174321-06-2, 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. 1174321-06-2, name is 5-(Difluoromethyl)pyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General Procedure A: the coupling of anilines prepared in Preparation Examples 25- (14) and 26-Q2) with aryl carboxylic acidsThe aniline (100 mg) was dissolved in DCM (2 mL) and the aryl carboxylic acid (1.2 – 1.6 equiv.), N,N-diisopropylethylamine (3 equiv.) and (lH-benzotriazol-1- yloxy)tripyrrolidin-l-yl)phosphonium hexafluorophophate (1.2 – 1.6 equiv.) were added. The reaction mixture was stirred at RT for 16 h – 3 days, and sodium bicarbonate (sat., aq., 25 mL) was added. The mixture was extracted with EtOAc (2 x40 mL), the combined organic portions were dried over MgSO4, evaporated and purified by silica gel chromatography (EtOAc/hexanes gradient) to afford the amide as a white solid. The amide was dissolved in DCM (2 mL) and TFA (1 mL) was added. After stirring at RT for 1-3 h, the reaction mixture was evaporated and sodium bicarbonate (sat., aq., 25 mL) was added. The mixture was extracted with EtOAc (2 x 40 mL), and the combined organic portions dried over MgSO4 and evaporated to afford the desired compound as a white solid. On occasions where the product was not pure, purification was effected by silica gel chromatography (MeOH/EtOAc/DCM gradients). Example 1 : N-(3-((‘4aR,5S,7aS)-2-amino-5-(‘fluoromethyl)-4a,5,7,7a-tetrahvdro-4H- furor3,4-diri,31oxazin-7a-yl)-4-fluorophenyl)-5-(difluoromethyl)pyrazine-2- carboxamideSynthesized from tert-butyl [(4aR,5S,7aS)-7a-(5-amino-2-fluorophenyl)-5- fluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][l,3]oxazin-2-yl]carbamate 25-(14) and 5-difluoromethyl-pyrazine-2-carboxylic acid according to General Procedure A. 1H NMR (400 MHz, CDCl3) delta (ppm): 2.94 (d, /=7.8 Hz, IH), 3.79 (dd, /=8.6, 2.5 Hz, IH), 3.89 – 4.05 (m, 2H), 4.28 – 4.66 (m, 4H), 6.72 (t, J 54.3 Hz, IH), 7.05 (dd, /=11.6, 8.8 Hz, IH), 7.67 (dd, /=7.1, 2.8 Hz, IH), 7.91 – 8.03 (m, IH), 8.85 (s, IH), 9.45 (s, IH), 9.61 (br s, IH)

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, 5-(Difluoromethyl)pyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD; ELLARD, John Mark; FARTHING, Christopher Neil; HALL, Adrian; WO2011/9898; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 27398-39-6, 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. 27398-39-6 name is 3-Chloropyrazine-2-carboxylic acid, 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.

To a solution of 3-chloropyrazine-2-carboxylic acid (100 mg, 0.63 mmol) in DCM/MeOH (2 mL : 0.2 mL) was added TMSCH1?2 (0.47 mL, 0.95 mmol) at RT and the resulting mixture was stirred at RT for 2 h. Acetic acid (0.2 mL) was added and the mixture was diluted with water (2 mL) and extracted with DCM (4 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. LRMS m/z (M+H) 173.0 found, 173.0 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloropyrazine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (97 pag.)WO2016/100157; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 5521-58-4, These common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, 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.

Examples (2R)-2-(3-Chloro-4-cyclopropanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid (Preparation 9) was coupled with amines selected from 2-amino-5-methylpyrazine, 3- amino-5-methylisoxazole, 3-aminoisoxazole, 2-amino-5-methylthiazole, 3-amino-6- methylpyridazine, l-methyl-3-aminopyrazole, 2-aminopyrazine and 4-aminopyrimidine using the following procedure to provide Examples 1-8.CH2Cl2 (6OmL) and DMF (0.08mL, 1.064mmol, 1.2 eq) were cooled to -100C and oxalylchloride slowly added (0.09mL, 0.465mol, 1.2 eq). After stirring for 15 min the reaction mixture was cooled to -300C and (2R)-2-(4-cyclopropanesulfonylphenyl)-3- (tetrahydropyran-4-yl)propionic acid (Preparation 8, 0.300g, 0.886mmol, 1.0 eq) was added.The reaction was stirred at -300C for 45min then pyridine (1.395mol, 0.3ImL in ImL CH2Cl2, 4.5eq) and the amine (4.43mmol, 5.0eq) were slowly added in parallel at -400C. The reaction mixture was stirred for 15min then the ice bath removed. The reaction mixture was stirred for 2h until it reached rt. The solvent was removed under partial vacuum and the crude mixture dissolved in EtOAc (1OmL) and aqueous HCl (1.5mL). The layers were separated and the aqueous phase extracted with EtOAc (5mL). The organic fractions were combined and washed with H2O (1OmL), saturated aqueous NaHCO3 (2 x 1OmL), water (5mL) and brine (5mL) and dried (MgSOzi). Purification was by flash chromatography (EtOAc :heptane, 2:1) and/or recrystallisation.

Statistics shows that 5-Methylpyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 5521-58-4.

Reference:
Patent; PROSIDION LTD; WO2007/51846; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 160252-31-3, 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. 160252-31-3, name is 1-(5-Chloropyrazin-2-yl)ethanone belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A stirred solution of 2-chloro-4-acetylpyrazine B.I (500 mg, 3.2 mmol) in EtOH (3 ml) was treated with 4-trifluoromethylaniline (619 mg, 3.8 mmol) at room temperature, followed by the addition of 4N HCl in Dioxane (0.32ml). The resulting reaction mixture was stirred at 100 C for 16 hr in a sealed tube. After consumption of the starting material (by TLC), the reaction mixture was concentrated under reduced pressure, and the resulting crude was purified by column chromatography (20% ethyl acetate/ hexane) using silica gel (60-120 mesh) to afford 430 mg (47%) of l-(5-(4-(trifluoromethyl)phenylamino)pyrazin-2-yl)ethanone B.2. 1H-NMR (DMSO- D6, 200 MHz) delta 10.51 (s, INH), 8.73 (d, J = 2 Hz, 1H), 8.31 (d, J = 2 Hz, 1H),7.99 (d, J = IO Hz, 2H), 7.72 (d, J = 8 Hz, 2H), 2.49 (s, 3H). LCMS m/z = 281.9 [M+l].

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, 1-(5-Chloropyrazin-2-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; CHUAQUI, Claudio; COSSROW, Jennifer; DOWLING, James; GUAN, Bing; HOEMANN, Michael; ISHCHENKO, Alexey; JONES, John, Howard; KABIGTING, Lori; KUMARAVEL, Gnanasambandam; PENG, Hairuo; POWELL, Noel; RAIMUNDO, Brian; TANAKA, Hiroko; VAN VLOTEN, Kurt; VESSELS, Jeffrey; XIN, Zhili; WO2010/78408; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, 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: 4744-50-7

General procedure: A solution of substituted benzyl amine (10 mmol) and an acid anhydride (10 mmol) in glacial acetic acid (15mL) was heated under reflux for 4h. After the evaporation of the reaction mixture to dryness under reduced pressure, the residue was neutralised by a solution of sodium bicarbonate (4%) until effervescence ceased. The precipitate obtained was washed with water, dried and re-crystallised from an appropriate solvent.

The synthetic route of 2,3-Pyrazinecarboxylic anhydride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alanazi, Amer M.; El-Azab, Adel S.; Al-Suwaidan, Ibrahim A.; Eltahir, Kamal Eldin H.; Asiri, Yousif A.; Abdel-Aziz, Naglaa I.; Abdel-Aziz, Alaa A.-M.; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 115 – 123;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 19745-07-4,Some common heterocyclic compound, 19745-07-4, name is 2,5-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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 stirred solution of (4-methyl-4-((3-(trifluoromethyl)phenyl)sulfonyl)tetrahydro-2H-pyran-2-yl)methanol (1 g, 2.9 mmol, 1 eq) in toluene (20 mL) was added 2,5-dichloro-pyrazine (0.3 mL, 2.9 mmol, 1 eq), Cs2CO3 (1.8 g, 5.9 mmol, 2 eq) and the mixture was heated to reflux for 48 h. Then the reaction mass was cooled to RT, diluted with H20 (15 mL), extracted with EtOAc (2×30 mL), washed with brine (20 mL),dried over Na2SO4 and concentrated. The crude product was purified by CC to afford 2-chloro-5-((4- methyl-4-((3-(trifluoromethyl)phenyl)sulfonyl)tetrahydro-2H-pyran-2-yl)methoxy)pyrazine (0.7 g, 53percent) as yellow gum.

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

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 54608-52-5, A common heterocyclic compound, 54608-52-5, name is 2-Hydrazinopyrazine, molecular formula is C4H6N4, 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 stirred solution of2-hydrazinopyridines 1a-k or 2-hydrazinopyrazines 2a-f (1equiv.) and aldehyde 3a-k (1equiv.) in polyethyleneglycol (PEG) (10 mL) were added p-TsOH (5 mol%)) and DDQ (2 equiv.). The mixture was stirred at reflux untilthe starting material was completely consumed (monitored by TLC, 1h) and then cooled down to roomtemperature. After filtration and evaporation of solvent from the filtrate, the resulting residue was purified bysilica gel column chromatography (EtOAc/Hexane, 3:7 v/v), affording the pure N-fused 1,2,4-triazolederivative, [1,2,4]triazolo[4,3-a]pyridines 4a-k & [1,2,4]triazolo[4,3-a]pyrazines 5a-f.

The synthetic route of 54608-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bhatt, Ashish; Singh, Rajesh K.; Kant, Ravi; Arkivoc; vol. 2018; 7; (2018); p. 236 – 247;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem