Tag: M.W=100-200

19745-07-4, A common heterocyclic compound, 19745-07-4, name is 2,5-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

Into a 250 ml 3-necked round bottom flask, was placed 45percent hydriodic acid (60 ml). To this was added sodium iodide (25 g, 0.17 mol). To the mixture was added XV-B-86 (10.5 g, 0.07 mol). The resulting solution was allowed to react at room temperature. Adjustment of the pH to >8 was accomplished by the addition of 20 g NaOH in 50 g ice to afford XV-C-86.

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

Reference:
Patent; Kalypsys, Inc.; US2005/234046; (2005); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 912773-21-8, name is 2-Bromo-5-chloropyrazine, 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 912773-21-8, COA of Formula: C4H2BrClN2

A mixture of 2-bromo-5-chloro-pyrazine (229.4 mg, 1.19 mmol), [5-fluoro-6-(2,2,2- trifluoro-1-methyl-ethoxy)-3-pyridyl]boronic acid (300 mg, 1.19 mmol), Pd(dppf)Cl2 (130.16 mg, 0.18 mmol) and CS2CO3 (772.77 mg, 2.37 mmol) in 1,4-dioxane (10 mL) and water (1 mL) was stirred at 60 C for 5 hours under N2. After cooling to r.t., the mixture was diluted with _0 (30 mL), and the mixture was extracted with EtOAc (50 mL x 2). The combined organic phase was washed with water (20 mL x 2) and brine (20 mL), dried over Na2S04, filtered and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 1% to 3% ) to give the product (210 mg, 0.64 mmol) as a solid. The product was analyzed by SFC to show two peaks (Peak 1: Rt = 2.02 min, Peak 2: Rt = 2.28 min). Method: Column: Chiralpak AD-3 150 x 4.6mm I.D, 3_ Mobile phase: A: C02 B:ethanol (0.05% DEA), Gradient: from 5% to 40% of B in 5 min and hold 40% for 2.5 min, then 5% of B for 2.5 min Flow rate: 2.5mL/min Column temp.: 35 C. 1H NMR (400MHz CDC13) _ = 8.77 (d, 1H), 8.65 (d, 1H), 8.53 (d, 1H), 8.08 (dd, 1H), 5.95 – 5.85 (m, 1H), 1.63 -1.48 (m, 3H). LCMS Rt = 0.92 min in 1.5 min chromatography, 5-95AB, purity 98.54%, MS ESI calcd. for Ci2H9ClF4N30 [M+H]+ 322.0, found 321.9

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Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (364 pag.)WO2018/98499; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4745-93-1, 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 4745-93-1 as follows.

1.1 A solution of 2.57 g (11.0 mmol) of iodine in 15 ml of DMF is added dropwise to a mixture of 1.25 g (10.0 mmol) of 5H-pyrrolo[2,3-b]pyrazine and 1.65 g (25.0 mmol) of solid potassium hydroxide in 15 ml of DMF, and the mixture is subsequently stirred at room temperature for 45 minutes. The reaction mixture is poured into 200 ml of ice-water (containing 0.5% by weight of ammonia and 0.1% by weight of sodium disulfite) and left at 5 C. for 12 hours. The resultant precipitate is filtered off with suction, washed with 100 ml of ice-water and dried in vacuo: 7-iodo-5H-pyrrolo[2,3-b]pyrazine as yellow solid.

According to the analysis of related databases, 4745-93-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; Dorsch, Dieter; Wucherer-Plietker, Margarita; Mueller, Thomas J.J.; Merkul, Eugen; US2013/217951; (2013); 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. 912773-24-1, name is 6-Bromoimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 912773-24-1

A 20 mL Biotage microwave vial loaded with 6-bromoimidazo[1,2-a]pyrazine (1.188 g, 6 mmol) was dissolved in DCM (15 mL), and N-chlorosuccinimide (881 mg, 6.60 mmol) was added in portions, and the mixture was sealed and stirred at 50 C. for 18 h. The vial was diluted with DCM and 10% NaOH, then extracted multiple times with DCM, washed with 10% NaOH, H2O, brine, and the organic layer was dried over Na2SO4, concentrated, dryloaded onto silica gel and purified on a 12 g silica gel column (hexanes/EtOAc, 0-25%), affording 6-bromo-3-chloroimidazo[1,2-a]pyrazine 67-A as a white solid (916 mg, 3.94 mmol, 66% yield, 25% EtOAc in hexanes). 1H NMR (DMSO) delta: 8.98 (d, J=1.3 Hz, 1H), 8.77 (d, J=1.3 Hz, 1H), 8.01 (s, 1H). 13C NMR (DMSO) delta: 143.03, 139.15, 134.20, 123.70, 117.92, 112.33.

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 912773-24-1.

Reference:
Patent; Arizona Board of Regents on Behalf of the University of Arizona; Hulme, Christopher; Foley, Christopher; (166 pag.)US2020/39989; (2020); 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. 274-79-3, name is Imidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., name: Imidazo[1,2-a]pyrazine

Imidazo[1,2-a]pyrazine (7.2 g, 60.44 mmol) was dissolved in 2-methoxyethanol (100 ml). Platinum(IV) oxide (1.2 g, 5.13 mmol) was added, and the mixture was stirred overnight at room temperature, under a hydrogen atmosphere of 4 bar, in an autoclave. The reaction mixture was flooded with nitrogen, filtered over Celite, concentrated and coevaporated with toluene. Purification was carried out by column chromatography dichloromethane/7 N ammonia in methanol 95:5). Yield: 5.7 g (76%)

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 274-79-3.

Reference:
Patent; Gruenenthal GmbH; US2008/153843; (2008); 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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 5-chloropyrazine-2-carboxylate

Preparative Example 1. EPO A round bottomed flask was charged with methyl 2-chloropyrazine-5-carboxylate (Lonza, 25.9 g, 145 mmol), 2-S-ethyl piperazine (prepared as per Williams et al J. Med. Chem 1996, 39, 1345, 85% active, 28.0 g, 208 mmol), cesium carbonate (Aldrich, 11O g, 338 mmol) and 1 ,4 dioxane (400 ml). The resulting suspension was stirred at room temperature for 18 hours and then filtered. The solid was washed with ethyl acetate (3X400 ml). The combined organic solutions were concentrated on a rotary evaporator to remove the solvent. The residue was purified by flash chromatography on silica gel using 5% to 10% methanol in dichloromethane as an eluent to provide A3 as a white solid (28.0 g, 77%).

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 33332-25-1.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2006/88837; (2006); A2;,
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. 6863-73-6, name is 3-Chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6863-73-6

Example A3 8-Chloro-imidazo[1,2-a]pyrazine Bromoacetaldehyde diethyl acetal (17.4 ml, 115.8 mmol) was added dropwise to a 48% aqueous solution of hydrobromic acid (4.45 ml, 38.6 mmol) at RT. The mixture was stirred at reflux temperature for 2 h. and then poured onto a suspension of sodium hydrogen carbonate (74.5 g, 0.88 mol) in isopropanol (220 ml). The mixture was stirred for a further 30 min. and then filtered off. 3-Chloro-pyrazin-2-ylamine (5 g, 38.6 mmol) was added to the filtrate and the mixture was stirred at 85 C. for 4 h. The solvent was evaporated in vacuo and the crude product suspended in a saturated solution of sodium hydrogen carbonate and extracted with DCM. The organic layer was dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was precipitated from Et2O to yield intermediate 3 (4.1 g, 70%) as a brown solid which was used in the next step without further purification.

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 6863-73-6.

Reference:
Patent; Janssen Pharmaceutica NV; US2012/329792; (2012); 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., name: 2-Bromopyrazine

n-BuLi (25.4 ml_, 63.5 mmol, 2.5 M in hexane) was added drop wise to a -78 C solution of 2-bromopyrazine (10.1 g, 63.5 mmol) in toluene (150 ml_) under N2. After 10 min at -78 C, a solution of N-cyclobutylidene-2-methylpropane-2-sulfinamide (Preparation 50, 10.0 g, 57.71 mmol) in toluene (50 ml_) was added slowly. The resulting dark red solution was stirred for 1 hr at -78 C. The reaction was quenched by the addition of sat. NH4CI solution (10 ml_) and the reaction mixture dried (MgS04), filtered and concentrated in vacuo to give a brown oil. The crude product was purified by column chromatography on silica gel eluting with pet. Ether: EtOAc (100:0 to 0: 100) to MeOH: EtOAc (9:91 ) to afford the title compound as a yellow oil, 4.0 g, 27%. 1H NMR (400 MHz, CDCI3): delta 1 .21 (s, 9H), 1.86-1 .96 (m, 1 H), 2.08-2.19 (m, 1 H), 2.58-2.78 (m, 4H), 3.62-3.75 (br s, 1 H), 8.49 (d, 1 H), 8.56 (dd, 1 H), 8.80 (d, 1 H). LCMS m/z = 254 [M+H]+

The synthetic route of 56423-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; CASIMIRO-GARCIA, Agustin; STROHBACH, Joseph Walter; HEPWORTH, David; LOVERING, Frank Eldridge; CHOI, Chulho; ALLAIS, Christophe Philippe; WRIGHT, Stephen Wayne; (213 pag.)WO2018/11681; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. Computed Properties of C6H6N2O2

A solution of the product of Example 83A (6.91 g, 50 mmol) in THF (Aldrich, anhydrous, 150 mL) was cooled down to -78° C. and a solution of LiAlH4 (Aldrich, 1.898 g, 50.0 mmol) in THF (50 mL) was added slowly via an additional funnel. The mixture was stirred at -78° C. under N2 for 1 hour, and then it was then carefully and slowly quenched with HOAc (Aldrich, 10 mL) at -70° C. The mixture was slowly warmed up to ambient temperature and stirred for 10 hours. After being concentrated, the residue was stirred with HCl (2N, 15 mL) in CH2Cl2 (300 mL) for 20 minutes and then filtered through diatomaceous earth to remove solid inorganic salt. The organic filtrate solution was concentrated and the residue was dissolved in EtOAc (100 mL) and filtered through diatomaceous earth again. The organic filtrate solution was concentrated to give the titled compound. 1H NMR (300 MHz, DMSO-d6) delta 8.91 (dd, 1H), 8.94 (d, 1H), 9.12 (d, J=1.6 Hz, 1H), 10.08 (s, 1H) ppm; MS (DCI/NH3) m/z 109 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; US2009/306096; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 122-05-4, name is Pyrazine-2,5-dicarboxylic 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. name: Pyrazine-2,5-dicarboxylic acid

Dimethyl Pyrazine-2,5-dicarboxylate (83). Hydrogen chloride gas was bubbled (approx. 5 min) into a stirred suspension of 82 (0.5 g, 2.97 mmol) in methanol (25 ml) and the mixture refluxed for 4 hours. Solvent was evaporated under reduced pressure and the residual solid dissolved in chloroform. The chloroform solution was washed with 10% sodium carbonate solution and water, dried (MgSO4) and evaporated under reduced pressure. Solid obtained was recrystallized from methanol to afford 0.42 g (72.2%) of colorless needles mp 167-169 C. [lit. Spoerri, P. E. and Erickson, A. J. Amer. Chem. Soc. 1938, 60, 400-402, mp 168-169 C. (sealed capillary)]; IR (KBr) cm-1 1720 (ester); NMR (CDCl3, 90 MHz) delta 4.09 (s, 6H, CO2 CH3), 9.40 (s, 2H, aromatic). Anal. calcd. for C8 H8 N2 O4: C, 48.98; H, 4.11; N, 14.28. Found: C, 48.89; H, 4.33; N, 14.12.

The synthetic route of Pyrazine-2,5-dicarboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Ohio State University; US4871736; (1989); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem