Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 56423-63-3, name is 2-Bromopyrazine, belongs to pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 56423-63-3, COA of Formula: C4H3BrN2

To a solution of N-(2-nitro-5-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)phenyl)pyrrolidine- 1 -carboxamide (0.20 g, 0.55 mmol) was added at room temperature sodium bicarbonate (0.09 g, 0.80 mmol, 1.45 equiv.), 2-bromopyrazine(0.14 g, 0.89 mmol, 1.6 equiv.) and palladium (0.07 g, 0.06 mmol, 0.1 equiv). The reaction was refluxed for fourteen hours. The crude reaction was filtered and concentrated. The residue was diluted into water and washed with ethyl acetate, the concentrated. The obtained was purified through column chromatography by eluting ethyl acetate and hexane to allow N-(2-nitro-5-(pyrazin-2-yl)phenyl)pyrrolidine-1 -carboxamide (0.12 g, 70% yield)

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-Bromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Broad Institute, Inc.; The General Hospital Corporation; Massachusetts Institute of Technology; Holson, Edward; Wagner, Florence Fevrier; Weiwer, Michel; Tsai, Li-Huei; Haggarty, Stephen; Zhang, Yan-Ling; (148 pag.)US9365498; (2016); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 58138-79-7, These common heterocyclic compound, 58138-79-7, name is 2,6-Diiodopyrazine, 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.

An oven-dried sealed tube was charged with 2-bromo-4-methyl-thiazole- 5-carboxylic acid benzylamide (800 mg, 2.57 mmol, 1.0 equiv). The sealed tube was purged with nitrogen and Rieke zinc (10 mL, 10 g of zinc in 100 mL of tetrahydrofuran) was added. The reaction was heated in the microwave oven for 15 min at 100 0C. Stirring was stopped and the remaining zinc was allowed to settle. The supernatant containing the zinc reagent was transferred via syringe to a solution of 2,6-diiodopyrazine (680 mg, 2.1 mmol, 0.8 equiv), Pd(PPh3)4 (236 mg, 0.2 mmol, 7 mol%) in tetrahydrofuran (5 mL) and52 50352dimethyl formamide (0.2 mL). The reaction mixture was purged with nitrogen for 10 min, then stirred at 160 0C for 16 hr. After cooling, the solvent was removed in vacuo and the crude product was purified by column chromatography [SiO2, ethyl acetate/heptane, 10:90 to 40:60, v/v] to afford 2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazoIe- 5-carboxylic acid benzylamide ( 140 mg, 13%). MS (M+H)+ = 436, R, = 1.51 min.

The synthetic route of 58138-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; XENON PHARMACEUTICALS INC; WO2008/24390; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

57948-41-1, name is 3-Bromoimidazo[1,2-a]pyrazine, 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 3-Bromoimidazo[1,2-a]pyrazine

3-Bromoimidazo[1,2-a]pyrazine (610 mg, 3.08 mmol) was dissolved in dry N,N-dimethylformamide(2mL),Trimethylsilylacetylene (0.68 mL, 6.16 mmol) was added under argonAnd N,N-diisopropylethylamine (1 mL, 6.16 mmol),Thereafter, tetrakistriphenylphosphine palladium (356 mg, 10 mol%) and cuprous iodide (117 mg, 20 mmol%) were added.This mixture was heated to 60 C and allowed to react overnight.After the reaction was completed, the mixture was cooled to EtOAc.To this was added tetra-n-butylammonium fluoride trihydrate (1.262 g, 4 mmol), and the mixture was reacted at room temperature for 1 h.After adding water, ethyl acetate extraction, drying the organic phase with anhydrous sodium sulfate, filtering, and evaporation of solvent.The residue was purified by silica gel column chromatography to give a yellow solid,151mg

The synthetic route of 57948-41-1 has been constantly updated, and we look forward to future research findings.

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

Some common heterocyclic compound, 56423-63-3, name is 2-Bromopyrazine, molecular formula is C4H3BrN2, 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-Bromopyrazine

General procedure: A vial was charged with an aqueous solution of sodium carbonate (1.1 mL, 2 M, 2.2 mmol), toluene (7 mL), 6-(dimethylamino)naphthyl-2-boronic acid (23; 215 mg, 1.0 mmol) and halogenated heteroaromatic compound (1.0 mmol). The reaction mixture was purged with argon, sealed and heated overnight at 110 C with stirring. Upon cooling, the product was extracted with EtOAc, the organic phase was washed with an aqueous solution of NaHCO3, dried over anhydrous sodium sulfate, and the solvent was removed under vacuum. The crude product was purified by column chromatography, followed by crystallization.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 56423-63-3, its application will become more common.

Reference:
Article; ?arlah, David; Juranovi?, Amadej; Ko?ar, Boris; Rejc, Luka; Golobi?, Amalija; Petri?, Andrej; Molecules; vol. 21; 3; (2016);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 59303-10-5, name is 2-Chloro-5-methylpyrazine, molecular formula is C5H5ClN2, 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. Application In Synthesis of 2-Chloro-5-methylpyrazine

A pressure tube was charged with benzophenone hydrazine (1.07 g, 5.4 mmol), 2-chloro-5-methylpyrazine (500 mg, 3.9 mmol), sodium tert-butoxide (523 mg, 5.4 mmol), JohnPhos (34.8 mg, 0.12 mmol), Pd2(dba)3 (35.6 mg, 0.04 mmol) and degassed toluene (6 mL). The suspension was degassed further with N2 and sealed. The reaction was heated at 90 oC for 5 h. The reaction was allowed to cool to room temperature and was quenched with water (20 mL). The reaction was neutralized with 1M HCl(aq). The mixture was extracted with EtOAc (3 x 20 mL). The combined organic extracts were washed with brine (40 mL), dried (Na2SO4), filtered and concentrated. The crude product was purified by Biotage Isolera chromatography (silica gel, eluting with 0-16% EtOAc in heptane) to give 950 mg (85% yield) of the title compound as a white solid.1H NMR (500 MHz, CDCl3) d 8.81 (d, J = 1.1 Hz, 1H), 8.02 (s, 1H), 7.85 (s, 1H), 7.62- 7.55 (m, 4H), 7.54- 7.50 (m, 1H), 7.38- 7.33 (m, 4H), 7.33- 7.30 (m, 1H), 2.46 (s, 3H). LCMS (Analytical Method D) Rt= 1.30 min, MS (ESIpos): m/z= 288.90 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59303-10-5, its application will become more common.

Reference:
Patent; BLACKTHORN THERAPEUTICS, INC.; JONES, Robert M.; BRANDT, Gary; (506 pag.)WO2020/97609; (2020); 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. 56423-63-3, name is 2-Bromopyrazine, A new synthetic method of this compound is introduced below., category: Pyrazines

A mixture of R-tert-butyl 4-(am inomethyl)-3,3-difluoropiperidine-1-carboxylate (200 mg, 0.80mmol), 2-bromopyrazine (140 mg, 0.88 mmol) and DIPEA (0.42 mL, 2.40 mmol ) in NMP (6 mL) was heated with stirring overnight at 130 C. The mixture was allowed to cool to rt, and diluted with ethylacetate. The organic phase was washed with water and brine, dried over Na2SO4 and concentrated under vacuum. The concentrate was purified by column chromatography over silica gel (hexane/ethyl acetate = 1/1) to afford the title compound as a yellow oil (196 mg, 50%). MS (ESI) calcd for C15H22F2N402: 328.2 ; found: 329.2[M+H]. 1H NMR (400 MHz, CDCI3) 6 7.98 (dd, J = 2.8 and 1.2 Hz, 1H), 7.89 (d, J = 1.2 Hz, 1H), 7.81 (d, J = 2.8 Hz, 1H), 4.80-4.70 (m, 1H), 4.45-4.10 (m, 2H), 3.76-3.69 (m, 1H), 3.57-3.49 (m, 1H), 3.04-2.70 (m, 2H), 2.31-2.16 (m, 1H), 1.87-1.79 (m, 1H), 1.63-1.53 (m, 1H),1.47 (s, 9H).

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; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (246 pag.)WO2016/196513; (2016); 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 33332-25-1 as follows. name: Methyl 5-chloropyrazine-2-carboxylate

To a solution of methyl-5-chloropyrazine-2-carboxylate (120 mg, 0.70 mmol) in a mixture of acetonitrile (2 ml) and DMF (1 ml) was added lithium chloride (295 mg, 6.95 mmol). The suspension was heated to 1600C for 5 mins in a Smith creator microwave after which time the reaction was diluted with water (10 ml). Saturated sodium bicarbonate solution (20 ml) was added and the aqueous layered extracted twice with ethyl acetate (30 ml). The combined organics were discarded and the aqueous layer adjusted to pH 4 with IN hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate (20 ml) and the combined organics washed with water (2 x 20 mlL), brine (10 ml) and dried (MgSO4). The volatiles were removed to give the title compound as a colourless solid (68 mg), 1H NMR delta (CDCl3): 7.20 (IH, br s), 8.72 (IH, s), 9.21 – 9.21 (IH, m); m/z 157 (M-H)+.

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125958; (2006); 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 50866-30-3 as follows. Safety of 5-Methylpyrazine-2-carbaldehyde

b) 6-{(3S.4S)-4-ethyl-1-f(5-methylpyrazin-2-vnmethyllpyrrolidin-3-yl>-1- (tetrahvdro-2H-pyran-4-yl)-1.5-dihvdro-4H-pyrazolof3.4-dipyrimidin-4-oneTo a solution -3-yl]-1-(tetrahydro-2H- pyran-4-yl)-1H-pyrazolo[3,4-d]pynmidin-4(5H)-one (4.4g) in dimethylformamide (62 mL) was added acetic acid (2 4 ml_), 5- methylpyrazine-2-carbaldehyde (2g) and sodium tnacetoxyborohydnde (5 27g) The reaction mixture stirred for 2h at ambient temperature and was carefully quenched with saturated sodium bicarbonate solution, extracted 3x with methylene chloride, dried with magnesium sulfate, filtered and concentrated Purification via Biotage MPLC chromatography eluting with 1 – 4% methanol/methylene chlonde/0 5 % saturated ammonium hydroxide provided the title compound (3 9g) 400 MHz 1H NMR (CDCI3) delta 8 52-8 48 (m, 1 H), 8 38 (s, 1 H), 8 02 (s, 1 H), 4 81-4 75 (m, 1 H), 4 1 1 -4 01 (m, 3H), 3 79-3 75 (m, 1 H) , 3 60-3 53 (m, 2H), 3 40-3 32 (m, 1 H), 3 10-3 08 (m, 1 H), 2 94 (m, 1 H), 2 63-2 57 (m, 1 H), 2 53 (d, J = 7 5 Hz, 1 H), 2 37-2 18 (m, 4H), 1 90-1 83 (m, 2H), 1 67-1 60 (m, 1 H), 1 54-1 47 (m, 1 H), 0 95-0 92 (m, 3H) MS (M+H m/z 424 2)

According to the analysis of related databases, 50866-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; WO2008/139293; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application 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.

1.5 equivalents of N-iodosuccinimide are added at room temperature to 5 g (32.7 mmol) of a methyl 3-aminopyrazine-2-carboxylate solution in 25 ml of dimethylformamide. The reaction medium is heated at 65°C for 1 hour, added together with 0.5 equivalents of N-iodosuccinimide and maintained at 65°C for 24 hours. After returning to room temperature, the solvent is evaporated and then the product is extracted several times with dichloromethane. The organic phases are combined, washed with 10percent sodium bisulfite solution, dried on magnesium sulfate and concentrated to yield 8 g (88percent) of methyl 3-amino-6-iodopyrazine-2-carboxylate in the form of a yellow solid.LCMS (EI, m/z): (M+l) 2801H NMR: 6H ppm (400 MHz, DMSO): 8.50 (1H, s, CHarom), 7.50 (2H, bs, NH2), 3.20 (3H, s, CH3).

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; PIERRE FABRE MEDICAMENT; KALOUN, El Bachir; BEDJEGUELAL, Karim; RABOT, Remi; KRUCZYNSKI, Anna; SCHMITT, Philippe; PEREZ, Michel; RAHIER, Nicolas; WO2012/101239; (2012); 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 312736-49-5 as follows. HPLC of Formula: C5H2Cl2N2O2

3,5-dichloropyrazine-2-carboxylic acid (2.68 g, 13.9 mmol) and sodium bicarbonate (1.4 g,16.6 mmol) in DMF (20 mL) at 230C was added iodomethane (5.21 mL, 83 mmol). The reaction mixture was diluted with 10% aquous citric acid solution and extracted with EtOAc. The combined organic layer was washed with water and brine, dried over MgSO4 and concentrated under reduced pressure to give a brown solid (2.83 g, 13.6 mmol, 98% yield); IH NMR (400 MHz, DMSO-c/6) delta ppm 3.95 (s, 3 H) 8.94 (s, 1 H).

According to the analysis of related databases, 312736-49-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem