Tag: M.W=100-200

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, Computed Properties of C4H3BrN2

Preparation 133: 2-Chloro-4-(pyrazin-2-yl)aniline; [00303] To a mixture of 4-amino-3-chlorophenylboronic acid pinacol ester (0.1 10g, 0.434 mmol), 2-bromopyrazine (0.090 g, 0.56 mmol), 1 ,1 ‘- bis(diphenylphosphino)ferrocene)-dichloropalladium(ll) DCM complex (24 mg, 0.029 mmol) was added anhydrous DME (3.0 mL) followed by 2M aqueous sodium carbonate (0.53 mL, 1 .06 mmol). The microwave vial was heated at 75C for 40 minutes under microwave irradiation. Further catalyst (0.012 g) was added and the vial was heated at 90C for 25 minutes under microwave irradiation. Further 2-bromopyrazine (0.060g), catalyst (12 mg) and 2M aqueous sodium carbonate (0.25 mL) were added and the reaction mixture was heated at 90C for an additional 30 minutes under microwave irradiation. The reaction was partitioned between ethyl acetate (60 mL) and a saturated aqueous NaHC03 solution (15 mL). The organic layer was washed with a saturated aqueous NaHC03 solution (2 x 15 mL), dried (Na2S04) and concentrated in vacuo. The residue was purified using preparative TLC eluting with 7% ethyl acetate in CH2CI2. The product band was recovered and stirred with 2% MeOH in ethyl acetate / CH2CI2 (v/v; 1 :10) (20 mL). The silica was removed by filtration, washed with ethyl acetate / CH2CI2 (v/v; 1 :5) (2×5 mL) and acetone (3 x 4 mL) to give the title compound as an off- white solid (0.039 g, 44%). 1 H-NMR (500 MHz, DMSO-d6) 5.86 (s, 2H), 6.89 (d, J = 8.5, 1 H), 7.85 (dd, J = 2.1 , 8.5 Hz, 1 H), 8.02 (d, J = 2.1 Hz, 1 H), 8.44 (d, J = 2.5 Hz, 1 H), 8.57 (dd, J = 1 .6, 2.5 Hz, 1 H), 9.12 (d, J = 1 .5 Hz, 1 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile, 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 313339-92-3, HPLC of Formula: C5HCl2N3

A solution of compound C1-4 (1.90 g, 4.67 mmol) and TFA (6.00 mL) in DCM (20 mL) was stirred for 1H at RT. The resulting mixture was concentrated under reduced pressure. 3,5-dichloropyrazine-2-carbonitrile (818 mg, 4.70 mmol) , DMSO (8 mL) and DIPEA (6.56 g, 50.76 mmol) was added and stirred for 1H at 70 . The reaction mixture was diluted with water (50 mL) and extracted with EA (2 ¡Á 50 mL) . The combined organic layers were dried over anhydrous Na 2SO 4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting with EA : Hex = 1 : 2, v/v) to give compound 50-1 (1.81 g) . MS: 444 [M+1] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichloropyrazine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; HAN, Huifeng; GAO, Panliang; MA, Cunbo; KANG, Di; (214 pag.)WO2020/63760; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 69816-38-2, These common heterocyclic compound, 69816-38-2, name is 5-(Trifluoromethyl)pyrazin-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.

Step 2: 3-{4-Trifluoromethyl-2-[3-(5-tri-fluoromethyl-pyrazin-2-yl)-ureido]-phenoxymethyl}-piper-idine-1-carboxylic acid tert-butyl ester. 3-[2-(4-Nitro-phenoxycarbonylamino) -4-trifluoromethyl-phenoxymethyl] -piperidine-1-carboxylic acid tert-butyl ester (217 mg, 0.4 mmol) and 5-trifluoromethyl-pyrazin-2-ylamine (66 mg, 0.4 mmol) (prepared according to the method of U.S. 4,293,552) were mixed as solids in a 5 mL reaction vial, diluted with 400 uL NMP, capped and stirred as a darkyellow solution that then was immersed in an oil bath at 85C and stirred for six hours. The reaction mixture was cooled to room temperature and stirred overnight. NMP then was removed by Kugelrohr distillation at 0.5 mm and 80C. The brown residue was diluted to 30 mL with CH2C12 then washed 3 x 30 mL with 1M Na2C03 to remove p-nitro-phenol. The organics were dried (MgS04) , filtered, and concentrated to a crude solid that was triturated with EtOAc and filtered to give the desired product as a white solid.

Statistics shows that 5-(Trifluoromethyl)pyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 69816-38-2.

Reference:
Patent; ICOS CORPORATION; WO2006/21002; (2006); A2;,
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. 912773-21-8, name is 2-Bromo-5-chloropyrazine, A new synthetic method of this compound is introduced below., Computed Properties of C4H2BrClN2

Example 19 1-(5-Chloropyrazin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-tetrazol-1-yl)propan-2-ol (49) To a stirred suspension of copper powder (3.0 g, 46.51 mmol) in DMSO (10 mL) was added ethyl 2-bromo-2,2-difluoroacetate (4.7 g, 23.15 mmol) at RT, and the mixture was stirred at RT for 1 h under inert atmosphere. A solution of 2-bromo-5-chloropyrazine (3.0 g, 15.54 mmol) in DMSO (20 mL) was added to the reaction mixture, and stirring was continued for another 16 h at RT. After the consumption of starting material (by TLC), the reaction mixture was diluted with aq NH4Cl solution (40 mL), filtered through a Celite pad and washed with CH2Cl2 (3*25 mL). The collected filtrate was washed with H2O (30 mL) and brine (30 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by column chromatography (eluting with 20% EtOAc/hexane) afforded ester AS (1.12 g, 4.73 mmol, 31%) as a liquid. 1H NMR (500 MHz, CDCl3): delta 8.78 (s, 1H), 8.62 (s, 1H), 4.38 (q, J=7.0 Hz, 2H), 1.37 (t, J=7.0 Hz, 3H).

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; VIAMET PHARMACEUTICALS, INC.; US2012/329802; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 120984-76-1, name is 2-Bromo-3-methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Bromo-3-methylpyrazine

4-[3-Methyl-4-(4,4,5,5-tetramethyl-1 ,3 ,2-dioxaborolan-2-yl)phenoxy]furo[3 ,2-c]pyridine (C2) (250 mg, 0.712 mmol), 5-bromo-4,6-dimethylpyrimidine (160 mg, 0.855 mmcl), tris(dibenzylideneacetone)dipalladium(0) (95%, 26.9 mg, 0.142 mmol), tricyclohexyiphosphine (79.9 mg, 0.285 mmcl) and potassium phosphate (302 mg, 1.42 mmol) were combined in a 3:1mixture of 1 ,4-dioxane and water (12 mL), and subjected to irradiation in a microwave reactor at120 00 for 5 hours. The reaction mixture was filtered through Celite; the filtrate was concentrated under reduced pressure, taken up in ethyl acetate, filtered through silica gel (1 g), and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) afforded the product as a colorless oil. Yield: 123 mg, 0.371 mmol,52%. LCMS m/z 332.1 (M+H). 1H NMR (500 MHz, ODd3) oe 8.98 (s, 1H), 8.07 (d, J5.9 Hz, 1H),7.67 (d, J=2.2 Hz, 1H), 7.25-7.27 (m, 1H, assumed; partially obscured by solvent peak), 7.24(br d, J=2.4 Hz, 1H), 7.19 (brdd, J=8.3, 2.4 Hz, 1H), 7.08 (d, J=8.3 Hz, 1H), 6.90 (dd, J=2.2, 1.0 Hz, 1H), 2.27 (s, 6H), 2.04 (s, 3H).

The synthetic route of 120984-76-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 19745-07-4, 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 19745-07-4 as follows.

Step C: A flask was charged with (S)-3-(2,6-difluoro-4-(methylsulfonyl)phenylamino)-l,4′-bipiperidin-2-one hydrochloride (0.250 g, 0.590 mmol), 2,5-dichloropyrazine (0.105 g, 0.708 mmol), Hunig’s base (0.309 mL, 1.77 mmol), and DMF (5 mL). The reaction mixture was stirred at 100 ¡ãC overnight. The organic solvents were removed under reduced pressure. The residue was purified using silica gel column chromatography eluting with ethyl acetate to provide (S)-l’-(5-chloropyrazin-2-yl)-3-(2,6- difluoro-4-(methylsulfonyl)phenylamino)-[l,4′-bipiperidin]-2-one (0.102 g, 0.204 mmol, 34.6percent yield) as light yellow solid. Mass spectrum (apci) m/z = 500.1 (M+H).

According to the analysis of related databases, 19745-07-4, the application of this compound in the production field has become more and more popular.

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

Related Products of 36070-75-4, 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. 36070-75-4, name is 5-Chloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-1H-pyrazole (170 mg, 2.0 mmol), and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at the 100C for 4 hours. The reaction mixture was cooled to 20C, poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and purified by column chromatography (hexane: ethyl acetate = 5:1) to give 5-(4-fluoro-1H-pyrazol-1- yl)pyrazine-2-carbonitrile (310 mg, Yield 82%). The structure was confirmed by LC-MS.

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-Chloropyrazine-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; DIPIETRO, Lucian, V.; (105 pag.)WO2018/22761; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 186534-02-1,Some common heterocyclic compound, 186534-02-1, name is 3,5,6-Trimethylpyrazine-2-carbaldehyde, molecular formula is C8H10N2O, 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.

5.5 g (36.7 mmol) of compound 1a-4The sample was dissolved in 30 ml of formic acid.Weigh 3.2g (45.9mmol)Hydroxylamine hydrochloride was added, followed by 3.13 g (45.9 mmol)Sodium formate, miscible, 120 C oil bath reaction reflux overnight.The pH of the reaction mixture was adjusted to 10 with a saturated aqueous sodium hydroxide solution and extracted with dichloromethane (30 ml*5 times). 100-200 mesh silica gel sample, dry sample column chromatography:Mobile phase EA: PE (1:5), TLC monitors the fraction of the effluent fraction,The compound 1a-5 fraction was collected. Combine the same fraction and distill dry,White solidCompound 1a-5, yield 65%.

The synthetic route of 186534-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Xique Pharmaceutical Co., Ltd.; Wang Yuqiang; Yao Hui; Wu Chuanbin; Tao Liang; Sun Yewei; (27 pag.)CN103804309; (2019); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 93049-39-9, name is 7-Chloropyrido[3,4-b]pyrazine, molecular formula is C7H4ClN3, 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: C7H4ClN3

EXAMPLE 1117-[3-(Pyrrolidin-l-ylmethyl)phenyllpyrido[3,4-Z>lpyrazineA mixture of 3-(bromomethyl)phenylboronic acid (150 mg, 0.69 mmol), pyrrolidine (70 muL, 0.84 mmol) and potassium phosphate (440 mg, 2.10 mmol) in DME (3 mL) was heated at 8O0C in a sealed reaction tube for 16 h. The reaction mixture was cooled to room temperature. 7-Chloropyrido[3,4-d]pyrazine (110 mg, 0.69 mmol), Pd(PPh3)4 (40 mg, 0.035 mmol) and water (0.5 mL) were then added. The resulting mixture was purged with nitrogen for 5 minutes, sealed and heated at 850C for 16 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (5 mL) and filtered through Celite. The filtrate was concentrated to dryness and purified by preparative HPLC to give the title compound (12.0 mg, 6%) as a pale brown solid. 5H (CDCl3) 9.62 (IH, s), 9.02 (IH, d, J 1.78 Hz), 8.91 (IH, d, J 1.78 Hz), 8.37 (IH, s), 8.22 (IH, s), 8.13 (IH, dt, J 6.69, 2.04 Hz), 7.58-7.48 (2H, m), 3.96 (2H, s), 2.70-2.84 (4H, m), 2.03-1.79 (4H, m). LCMS (ES+) 291 (M+H)+, 9.83 minutes {Method 5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 93049-39-9, its application will become more common.

Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 59303-10-5, name is 2-Chloro-5-methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Chloro-5-methylpyrazine

Example 8l-((2S,4R)-6-(l-(2-methoxyethyl)-lH-pyrazol-4-yl)-2-methyl-4-((5- methylpyrazin-2-yl)amino)-3, -dihydroquinolin-l(2H)-yl)ethanonel-((2S,4R)-4-Amino-6-(l-(2-methoxyethyl)-lH-pyrazol-4-yl)-2-methyl-3,4- dihydroquinolin-l(2H)-yl)ethanone (for a preparation see Intermediate 7) (150mg, 0.457 mmol), 2-chloro-5-methylpyrazine (147mg, 1.142 mmol), Davephos (71.9mg, 0.183 mmol), Pd2(dba)3 (84mg, 0.091 mmol) and sodium tert-butoxide (132mg, 1.370 mmol) were combined in 1,4-dioxane (4ml) and the mixture heated at 120C for 25min (microwave). The reaction mixture was partitioned between water (75ml) and DCM (3x 75ml). The organics were combined, dried (hydrophobic frit) and evaporated under vacuum. The resulting brown oil was dissolved in DMSO (3x 1ml) and purified by MDAP (formate x3). The solvent was evaporated under vacuum to give l-((2S,4R)-6-(l-(2-methoxyethyl)-lH-pyrazol-4-yl)-2- methyl-4-((5-methylpyrazin-2-yl)amino)-3,4-dihydroquinolin-l(2H)-yl)ethanone (91mg, 0.216 mmol, 47 % yield) as a yellow glass. LCMS (formate), Rt 0.75min, MH+ 421.

The synthetic route of 59303-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; AMANS, Dominique; DEMONT, Emmanuel, Hubert; JONES, Katherine, Louise; SEAL, Jonathan, Thomas; WALKER, Ann, Louise; WO2012/150234; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem