Tag: M.W=200-300

Related Products of 76537-18-3, 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. 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3-bromo-5-chloro-pyrazin-2-amine (600 mg, 2.88 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (397.48 mg, 3.17 mmol), Cs2C03 (1.88 g, 5.76 mmol) and Pd(dppf)Cl2 (210.62 mg, 0.29 mmol) in 1,4-Dioxane (5 mL) and Water (0.50 mL) was stirred at 70 C for 16 hours. After cooling to r.t., the mixture was concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 20% to 40% to 60% to 80%) to give the product (200 mg) as a solid. *H NMR (400MHz, CDC13) _ = 7.90 (s, 1H), 4.55 (br s, 2H), 2.40 (s, 3H).

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, 3-Bromo-5-chloropyrazin-2-amine, other downstream synthetic routes, hurry up and to see.

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

Reference of 957230-68-1, 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. 957230-68-1, name is 3,6-Dibromo-2-pyrazinecarboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Synthesis of Intermediate 1a as described in the general reaction scheme; 3,6-Dibromo-pyrazin-2-ylamine Diphenylphosphorylazide (2.59 mL, 12 mmol) and triethylamine (1.67 mL, 12 mmol) are added to a solution of 3,6-dibromo-pyrazin-2-carboxylic acid (3.52 g, 12 mmol) in t-butanol (90 mL). The reaction is heated at reflux for 18 hours. The reaction is quenched with water, then concentrated in vacuo and taken up in DCM. The organic solution is washed with water and 1N NaOH, dried over anhydrous MgSO4 and concentrated in vacuo. The resultant solid is filtered through a pad of silica using EtOAc, then concentrated and TFA:DCM (4:1, 12 mL) is added to the solid and stirred for 30 min. The solution is concentrated in vacuo then neutralised with 1N NaOH and extracted with DCM. The organic layer is dried over anhydrous MgSO4 and concentrated in vacuo to give the product. 1H NMR (250 MHz, DMSO-d6) ppm 7.25 (br s, 2H), 7.68 (s, 1H); m/z (APCI) 254 (M+H)+; m.p 135-139 C.

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

Reference:
Patent; WIGERINCK, Piet Tom Bert Paul; ANDREWS, Martin James Inglis; De WEER, Marc Maurice Germain; SABOURAULT, Nicholas Luc; KLUGE, Stefan Christian; US2011/118269; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 173253-42-4,Some common heterocyclic compound, 173253-42-4, name is 2-Amino-5-bromo-6-chloropyrazine, molecular formula is C4H3BrClN3, 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.

In a pressure tube were mixed 5-bromo-6-chloropyrazin-2-amine (4.32 g, 20.73 mmol), phenylboronic acid (2.78 g, 22.80 mmol, 1 .1 equiv.) and Na2003 (4.39 g, 41 .45 mmol, 2 equiv.) in a4:1 mixture of 1 ,4-dioxane : water (50 mL). The reaction mixture was sparged with argon andPd(PPh3)4 (1 .20 g, 1 .04 mmol, 5 mol%) was then added. The pressure tube was capped andthe reaction mixture was heated at 10000 overnight. After that time, the reaction mixture wascooled down to r.t., filtered and concentrated under reduced pressure. The obtained crude ma-terial was purified by flash chromatography on silica eluting with hexane: EtOAc = 1:0 – 1:1 to lead to the title product as a white solid (2.11 g, 50%). ESI-MS: 206.05 [M+H]+. 1 H NMR (300 MHz, DMSO-d6) 6 7.93 (s, 1 H), 7.66 – 7.59 (m, 2H), 7.47 – 7.32 (m, 3H), 7.00 (br s, 2H).

The synthetic route of 173253-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SELVITA S.A.; BOBOWSKA (NEE WITKOWSKA), Aneta; GALEZOWSKI, Michal; NOWAK, Mateusz; COMMANDEUR, Claude; SZEREMETA-SPISAK, Joanna; NOWOGRODZKI, Marcin; OBARA, Alicja; DZIELAK, Anna; LOZINSKA, Iwona; DUDEK (NEE SEDLAK), Marcelina; JANIGA, Anita; REUS, Jacek; WRONOWSKI, Marek; ZASTAWNA, Magdalena; RADZIMIERSKI, Adam; SWIRSKI, Mateusz; ZACHMANN, Julian; FABRITIUS, Charles-Henry; PORTER, Rod; FOGT, Joanna; (276 pag.)WO2019/2606; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, 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 143591-61-1, Formula: C6H3BrClN3

A 33% (w/v) ethanol solution of methylamine (5.4 mL,130.55 mmol)was added to a solution of 3-bromo-8-chloroimidazo[1,2-a]pyrazine (500 mg, 2.15 mmol) in ethanol in a microwaveadaptedvial. The reaction was submitted to microwave irradiationsduring 20 min at 140 C. The solvent was removed underreduced pressure. The crude mixture was dissolved in ethyl acetateand successively washed with saturated aqueous chloride ammonium,distilled water and finally brine. The organic phase was driedon sodium sulphate, filtered and concentrated under reducedpressure. The compound is obtained as a white solid (92% yield). C7H7BrN4. Mw: 227.06 g/mol. Mp 145-146 C. 1H-RMN delta (ppm,400 MHz, DMSO-d6) 2.94 (d, 3H, NHCH3, J 6 Hz), 7.42 (d, 1H, CH 6,J 8 Hz), 7.52 (d, 1H, CH 7, J 8 Hz), 7.65 (m, 2H, NH, CH 2). 13CRMNdelta (ppm, 100 MHz, DMSO-d6) 22.77 (NHCH3), 97.83 (Cq 1),107.34 (CH 7),130.04 (CH 6),132.10 (CH 2),133.81 (Cq 3′),150.72 (Cq4). MS (ESI+ , QTof, m/z): 227.1 [M+H]+. HRMS calculated forC7H8BrN4 226.9932, found 226.9935.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Article; Patinote, Cindy; Bou Karroum, Nour; Moarbess, Georges; Deleuze-Masquefa, Carine; Hadj-Kaddour, Kamel; Cuq, Pierre; Diab-Assaf, Mona; Kassab, Issam; Bonnet, Pierre-Antoine; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 909 – 919;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1416740-16-3, 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. 1416740-16-3 name is 2-Bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine, 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.

Example 3; 2-hydroxy-N-(2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazin-7- yl)benzamide (Compound 1-14)METHOD C:Step 1: 2-bromo-7-nitro-5-trityl-pyrrolo[2,3-b]pyrazine [00203] 2-bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine (5 g, 20.57 mmol) was dissolved in DMF (100 mL) under N2. Solution was cooled in an ice bath and sodium hydride (867.1 mg, 22.63 mmol) added portionwise. After 30 minutes (effervescence completed) trityl chloride (6.022 g, 21.60 mmol) was added in one portion and the mixture allowed to warm to ambient temperature (Precipitate observed after around 15 mins). Reaction mixture was poured into water and mixture stirred for 1 hour then filtered. Solid was washed with copious water then dried in a vacuum oven over 48 hours at 80 C. Taken on to the next step as is. (9.7 g, 97.3%) XH NMR (400.0 MHz, DMSO) delta 8.46 (s, 1H), 8.40 (s, 1H), 7.38 – 7.36 (m, H), 7.23 – 7.20 (m, 8H) and 3.32 (s, 7H) ppm

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; MACCORMICK, Somhairle; STORCK, Pierre-henri; MORTIMORE, Michael, Paul; CHARRIER, Jean-damien; KNEGTEL, Ronald; YOUNG, Stephen, Clinton; PINDER, Joanne; DURRANT, Steven, John; WO2012/178123; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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 6966-01-4, Application In Synthesis of Methyl 3-amino-6-bromopyrazine-2-carboxylate

Methyl 3-amino-6-bromo-pyrazine-2-carboxylate (334 mg), tert-butyl 4-[3-methyl-4- (4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)pyrazol- 1 -yl]piperidine- 1 -carboxylate (563 mg) and bis(triphenylphosphine) palladium (II) chloride (101 mg) and cesium fluoride (656 mg) in MeOH (11 mL) were degassed under vacuum and argon , stirred at 130 0C for 20mn under microwave conditions. The mixture wac concentrated and the residue was dissolved in dichloromethane and filtered. The filtrate was purified by flash chromatography on silica gel eluting with 50 to 100% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford methyl 3-amino-6-[l-(l-tert-butoxycarbonyl-4- piperidyl)-3-methyl-pyrazol-4-yl]pyrazine-2-carboxylate (421 mg). Mass spectrum: M+H+ 417. Retention time: 3.47min

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, Methyl 3-amino-6-bromopyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; AstraZeneca UK Limited; WO2009/24825; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1208082-91-0, 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. 1208082-91-0, name is 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-(2-methyl-oxazol-5-yl)-phenylamine (615 mg, 3.53 mmol), intermediate 101 (933 mg, 3.21 mmol), and DIPEA (1.24 g, 9.62 mmol) in CH3CN (10 ml) were heated at 200 0C under microwave irradiation for 1.5 h. The volatiles were evaporated under reduced pressure and the residue was partitioned between DCM and H2O. The organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by flash chromatography over silica gel (eluent: DCM/ MeOH(NH3) 95/5). The fractions containing product were collected and the solvent was evaporated. The residue was purified further by preparative HPLC [RP Shandon Hyperprep Cl 8 BDS (8 mum, 250 g, LD. 5 cm); mobile phase: (0.25 % NH4CO3 sol. in water, MeOH)]. The product fractions were collected and concentrated under reduced pressure. Yield: 0.031 g of compound 179 (3 %).

The chemical industry reduces the impact on the environment during synthesis 6,8-Dibromo-2-methylimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; VELTER, Adriana, Ingrid; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; WU, Tongfei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; PIETERS, Serge, Maria, Aloysius; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; OEHLRICH, Daniel; WO2010/89292; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, 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. HPLC of Formula: C6H8ClF3N4

General procedure: To the stirred reaction mixture of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyrazine hydrochloride(11) (300 mg, 1.32 mmol), TEA (0.55 mL, 3.95 mmol)and toluene (10 mL), substituted cyanates 12(a-e)/isocyanates12(f-j) (1.32 mmol) were added at ambient temperature.The reaction mass was agitated at 75-80 C until thecompletion of the reaction that was monitored by TLC. Thereaction mass was allowed to cool at ambient temperatureand it was washed sequentially with 3% aqueous HCl(5.0 mL) and then water (5.0 mL). The organic fraction wasconcentrated under vacuum at 50-55 C to obtain crudeproduct. It was purified by column chromatography using10-50% of EtOAc:hexane mixture as a mobile phase.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 762240-92-6, its application will become more common.

Reference:
Article; Mannam, Madhava Rao; Devineni, Subba Rao; Pavuluri, Chandra Mouli; Chamarthi, Naga Raju; Kottapalli, Raja Sekhara P.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 9; (2019); p. 922 – 932;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 143591-61-1, 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. 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

In a 2000ml three-necked flask, with mechanical stirring, Ar gas protection. Join4.62 g of 3-bromo-8-chloroimidazo [1,2-a] pyrazine (molecular weight 231, 0.02 mol)5.6 g (molecular weight 254.2, 0.022 mol) of bis (pinacolato) diboron, 23.2 g (0.0044 mol) of Pd (dppf) Cl, 36 g (molecular weight 138,1,4-dioxane 500ml. Start mechanical stirring,After 3 times of evacuation under reduced pressure to maintain Ar gas protection,The reaction was monitored by TLC (thin layer chromatography)Until the complete disappearance of raw materials, reflux for 3 hours, the reaction was complete. Let cool, the reaction system divided into two layers, the organic layer was separated and evaporated to dryness to give 5.04g product, yield 90.2%.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-8-chloroimidazo[1,2-a]pyrazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Li Yinkui; Tang Jinming; Fan Hongtao; (34 pag.)CN104650116; (2017); B;,
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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromo-5-(trifluoromethyl)pyrazine

Example 44k (300 mg, 0.8 mmol), 2-Chloro-5-(trifluoromethyl)pyrimidine (199 mg, 1.09 mmol) and N,N-diisopropylethylamine (287 mul, 1.67 mmol) are dissolved in 4 ml of anhydrous DMSO and heated in a microwave reactor during 30 minutes at 150C. The crude is partitioned between EtOAc and water, the organic layer is dried over anhydrous Na2S04 then concentrated under reduced pressure to obtain 360 mg of the title product. HPLC-MS (Method 10): Rt = 3. MS (ES+): m/z = 505 [M+H]+ . The enantiomers are obtained by HPLC using a chiral stationary phase. Method for separation: HPLC apparatus type: Waters 600 Pump; column: Daicel Chiralpack AD-H, 5.0 muiotaeta, 250 mm x 20 mm; method: eluent hexane/ IPA 70:30; flow rate: 15 mL/min, Temperature: 25 C; UV Detection: 254 nm Example of separation by chiral HPLC: Submitted to separation: 665 mg of Example 1 prepared as described above; Obtained: 157 mg of enantiomer 1 (Exp. 2) and 40 mg of enantiomer 2 (Exp. 3). Example 110 is synthesized as described for example 1 starting from example 44b (60 mg of the corresponding hydrochloride, 0.15 mmol) instead of example 44k, 2-Bromo-5- (trifluoromethyl)pyrazine (42 mg, 0.19 mmol) instead 2-Chloro-5- (trifluoromethyl)pyrimidine, N,N-diisopropylethylamine (107 mu, 0.62 mmol) and 1 ml of anhydrous DMSO; the reaction mixture is heated during 30 minutes at 120C in a microwave reactor. The crude is purified by preparative HPLC-MS to obtain the title compound (24 mg, 32% yield) HPLC-MS (Method 10): Rt = 3.48 min. MS (ES+): m/z = 487 [M+H]+

According to the analysis of related databases, 1196152-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem