Tag: M.W=200-300

These common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, 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. Safety of 5,7-Dichloropyrido[3,4-b]pyrazine

To a solution of 4-hydroxycyclohexanone (171 mg, 1.5 mmol) in dloxane was added Cs2CO3 (488 mg, 1.5 mmol) and 5,7-dichloropyrido[4,3-b]pyrazine (200 mg, 1.0mmo) at room temperature. The mixture was stirred at 80 C for 18 hours. After that,the 5,7-dichloropyrido[4,3-b]pyrazine was consumed and the reaction was used for next step directly.

The synthetic route of 5,7-Dichloropyrido[3,4-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; WO2014/86032; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1416740-16-3, These common heterocyclic compound, 1416740-16-3, name is 2-Bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine, 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 4: 2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-amine[00200] To a solution of 2-bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine (21.76 g, 89.54 mmol) in acetic acid (108.8 mL) and concentrated hydrogen chloride (108.8 mL) was added dichlorotin dihydrate (101.0 g, 447.7 mmol). The reaction mixture was left to stir for 1 hour at ambient temperature. Reaction mixture was quenched by addition of 2M NaOH solution and the aqueous extracted with EtOAc (x3). Organic layer was dried (MgS04), filtered and concentrated in vacuo. The resulting solid was washed with saturated aHC03 solution and the solid collected, washed with water and dried to give 2-bromo-5H-pyrrolo[2,3-b]pyrazin- 7-amine. (10.4 g, 54.6%). XH NMR (400.0 MHz, DMSO) delta 1 1.50 (br s, 1H), 8.22 (s, 1H), 7.16 (s, 1H) and 4.35 (br s, 2H) ppm; MS (ES+) 214.79

The synthetic route of 1416740-16-3 has been constantly updated, and we look forward to future research findings.

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

These common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, 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 C7H3Cl2N3

Intermediate 37: 1 ,1 -dimethylethyl 3-{r(7-chloropyridor3,4-fllpyrazin-5- yl)amino1methyl)-4,4-difluoro-1 -piperidinecarboxylate (Isomer 2); 5,7-Dichloropyrido[3,4-b]pyrazine (620mg, 3.10mmol) was dissolved in N-methyl-2- pyrrolidinone (NMP) (5mL) and to this was added DIPEA (0.601 ml_, 4.65mmol) and 1 , 1-dimethylethyl 3-(aminomethyl)-4,4-difluoro-1-piperidinecarboxylate (776mg, 3.10mmol). This was heated in a microwave at 130C for 30min. The reaction mixture was partitioned between ethyl acetate and water. The aqueous was re-extracted twice with ethyl acetate and the combined organic layers washed with brine, dried over a hydrophobic frit and concentrated in vacuo to yield a brown oil. It was dissolved in DCM and passed through silica (100g) eluting with a 10-50% ethyl acetate in cyclohexane gradient. Appropriate fractions were combined and concentrated in vacuo to yield the title compound as a yellow solid, 1.0g.Chiral separation was achieved (Sample preparation: Sample dissolved in ethanol (30ml) sonicating and heating with air gun as required. 4-5ml injections were then pumped onto a preparative scale Whelk-0 (S, S) column (2 inch). Details as follows: Column – Whelk-0 (S, S) (50x250mm, l Omicron); Detection – UV DAD – 300nm (bandwidth 180nm, reference 550nm (bandwidth 100nm)); Flow Rate – 70ml/min; Mobile Phase A: Heptane; Mobile Phase B: I PA; Isocratic method (premixed) 5% B; Runtime – 60min; Number of runs – 8) to yield the title compound (second eluting peak from the chiral column) as a yellow solid (441 mg).LCMS (Method B): Rt =1.27min, MH+ =414 The following intermediate was obtained as the first eluting peak from the chiral separation above:; Intermediate 38: 1 ,1 -dimethylethyl 3-{r(7-chloropyridor3,4-fllpyrazin-5- yl)amino1methyl)-4,4-difluoro-1 -pipendinecarboxylate (Isomer 1); LCMS (Method B): Rt =1.27min, MH+ =414The following intermediate was prepared similarly:Intermediate 39: 1 ,1 -dimethylethyl 5-{r(7-chloropyridor3,4-fllpyrazin-5-LCMS (Method B): Rt =1.24min, MH+= 414

The synthetic route of 5,7-Dichloropyrido[3,4-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; ATKINSON, Stephen John; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander G; SHIPLEY, Tracy Jane; WILSON, David Matthew; WATSON, Robert J; WO2012/123312; (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. 1082843-70-6, name is 3,5-Dibromo-2-chloropyrazine, A new synthetic method of this compound is introduced below., name: 3,5-Dibromo-2-chloropyrazine

Step 2: Synthesis of Compound (B’) as Described in the General Reaction Scheme; 3-chloro-6-bromopyrazin-2-yl Amine Compound A’ described in the previous step (9.5 g, 37.55 mmol) is suspended in concentrated NH4OH (60 mL) and the resulting mixture is heated in a pressure autoclave to 80 C., typically overnight. The vessel is then allowed to cool down to room temperature slowly, and is then further cooled in an ice bath, causing the precipitation of the desired material. The solid is separated by filtration, washed with cyclohexane, to afford after drying, the title compound B’ (5 g) as a 83/17 mixture of regiosiomers. The mixture is then purified by column chromatography. M+H+, m/z=209

The synthetic route of 1082843-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andrews, Martin James Inglis; Chambers, Mark Stuart; Van De Poel, Herve; Bar, Gregory Louis Joseph; US2009/286798; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 24241-18-7, 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of Intermediate tert-butyl (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate Step A: 3,5-dibromopyrazin-2-amine to 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine [0183] To a solution of 3,5-dibromopyrazin-2-amine (125 g, 494 mmol), TEA (207.0 mL, 1483 mmol), and copper (I) iodide (0.941 g, 4.94 mmol) in THF (1255 mL) is added PdCl2(PPh3)2 (3.47 g, 4.94 mmol). The reaction mixture is cooled at about -5-0 C. and a solution of (trimethylsilyl)acetylene (65.0 mL, 470 mmol) in THF (157 mL) is added dropwise over about 15 min. The reaction mixture is stirred at about -5-0 C. for about 1.5 h and then allowed to warm to room temperature (RT) overnight. The reaction mixture is then filtered through a CELITE pad and washed with THF until no further product eluted. The filtrate is concentrated under reduced pressure to give a brown-orange solid. The solid is triturated and sonicated with warm petroleum ether (b.p. 30-60 C., 400 mL), cooled to RT, collected, washed with petroleum ether (b.p. 30-60 C.; 2×60 mL), and dried to give 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine (124 g, 93%, 93% purity) as a brown solid: LC/MS (Table 1, Method b) Rt=2.51 min; MS m/z: 270, 272 (M+H)+.

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; ABBVIE INC.; Voss, Jeffrey W.; Camp, Heidi S.; Padley, Robert J.; US2015/118229; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6966-01-4, 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. 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To the solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (10.0 g 43.1 mmol) in MeOH (70 mL) was added a solution of Li OH (9.0 g, 215 mmol) in water (70 mL). The mixture was stirred at 90 C for 3 hours. The reaction mixture was cooled to rt and acidified to PH = 4-5 with HC1 (2 M). The mixture was filtered to afford 7.4 g of 6 (79 %) as yellow solid. (0170) [0033] LC-MS (M+l): 218.0; 1H MR (400 MHz, DMSO-d6) delta 8.39 (s, 1H), 7.59 (br, 2H).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-amino-6-bromopyrazine-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERRIMACK PHARMACEUTICALS, INC.; DRUMMOND, Dary| C.; GENG, Bolin; KIRPOTIN, Dmitri B.; TIPPARAJU, Suresh, K.; KOSHKARYEV, Alexander; ALKAN, Ozan; (142 pag.)WO2017/123588; (2017); 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 6966-01-4 as follows. Product Details of 6966-01-4

To a solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (100 mg, 0.43mmol) in MeOH (5 mL) was added 2 mL of NaOH aqueous solution (5 N). After being stirred at50C for 4 h, the mixture was cooled and acidified with 1 M HC1 to a pH of 2. The precipitate was collected by filtration and washed with water to afford the product of 3-amino-6-bromopyrazine-2-carboxylic acid (90 mg, yield: 96%). ?H-NMR (DMSO-d6, 400 MHz) 8.38 (s, 1H), 7.517.56 (m, 2H). MS (M+H): 218 / 220.

According to the analysis of related databases, 6966-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, 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. Application In Synthesis of 3,5-Dibromo-1-methylpyrazin-2(1H)-one

General procedure: To a solution of 2a-j (10 mmol, 1.0 eq) , 3,5-dibromo-1-methylpyrazin-2(1H)-one (2.95 g, 11 mmol, 1.1 eq) and DIEA (3.3 mL,20 mmol, 2.0 eq) in MeCN (20mL) was stirred at 80 °C for 5 hours. After cooling to room temperature, thesolvent was removed in vacuo, and the residue was purified using silica gelchromatography to give the title compounds, yield 72-85percent.

The synthetic route of 3,5-Dibromo-1-methylpyrazin-2(1H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Jianhong; Du, Jiatian; Huang, Chong; Wang, Tianqi; Huang, Luyi; Yang, Shengyong; Li, Linli; Bioorganic and Medicinal Chemistry Letters; vol. 29; 13; (2019); p. 1609 – 1613;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 723286-79-1, name is tert-Butyl 5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-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 723286-79-1, Formula: C10H16N4O2

Procedure for step-2 :To a solution of compound A48-1 (1.29 g, 5.75 mmol) in dry THF (50 mL) was added a solution of 2.5 M ?-BuLi in hexane (2.53 mL, 6.33 mmol) at -78 C under argon. After 15 min ethyl formate (702 muL, 8.63 mmol) was added and the reaction mixture was stirred for 15 min at -78 0C. Saturated aqueous NH4Cl (150 mL) was added and the mixture was extracted with CH2CI2 (3 x 100 mL) . The combined organic layer was dried (Na2SO4) and evaporated to dryness to afford aldehyde A48-2 (1.21 g, 83%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; WO2009/90055; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 486424-37-7, The chemical industry reduces the impact on the environment during synthesis 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

To 3-amino-6-bromo-pyrazine-2-carboxylic acid (5.0g, 22.9mmol), HOBt (3.867g, 22.9mmol), EDCI (9.15g, 47.62mmol) and NEt3 (8mL, 58mmol) in DMF (80mL) was added C-((R)-1-Isopropyl-piperidin-3-yl)-methylamine (2.98g, 19.08mmol) in DMF (20mL). The reaction mixture was heated at 45oC for 18h before the volume reduced by half in vacuo and water was added. The aqueous phase was extracted with EtOAc and the combined organic phase was washed with sat. NaHCO3, brine, dried (MgSO4) and the solvent was removed in vacuo. The residue was purified by column chromatography (NEt3:THF 5:95) to give, after removal of the solvent in vacuo, the title compound: RT = 1.92 min; m/z (ES+) = 356.1, 358.1 [M+H]+.

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-Amino-6-bromopyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hanrahan, Patrick; Bell, James; Bottomley, Gillian; Bradley, Stuart; Clarke, Phillip; Curtis, Eleanor; Davis, Susan; Dawson, Graham; Horswill, James; Keily, John; Moore, Gary; Rasamison, Chrystelle; Bloxham, Jason; Bioorganic and Medicinal Chemistry Letters; vol. 22; 6; (2012); p. 2271 – 2278;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem