Tag: M.W=200-300

Synthetic Route of 87486-34-8, 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.

3,5-Dibromo-l-methyl-lH-pyrazin-2-one (1.Og, 3.73 mmol) and 4- amino-2-nitrobenzoic acid (0.68g, 3.73 mmol) are dissolved in isopropanol (20 mL) and heated at 9O0C for 4 hours. The reaction is cooled to room temperature and the resulting suspension is filtered. The filter cake is then washed with ethyl ether (3 x 10OmL) and air dried to give 4-(6-bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2- ylamino)-2-nitro-benzoic acid (3) as a tan solid (1.17g).

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CGI PHARMACEUTICALS, INC.; WHITNEY, James A.; DI PAOLO, Julie; VALLECA, Mark A.; BRITELLI, David R.; CURRIE, Kevin S.; DARROW, James W.; KROPF, Jeffrey E.; LEE, Tony; GALLION, Steven L.; MITCHELL, Scott A.; PIPPEN, Douglas A.I.; BLOMGREN, Peter A.; STAFFORD, Douglas Gregory; WO2008/33858; (2008); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 486424-37-7, 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 486424-37-7 as follows.

HATU (3.54 g, 9.36 mmol) was added to a solution containing 1.64 g (7.5 mmol) of 3- amino-6-bromopyrazine-2-carboxylic acid in 25 mL of DMF. The reaction was stirred for 5 minutes before adding 2.5 mL (22.5 mmol) of N-methylmorpholine and 1.68 g (9.36 mmol) of 4- morpholinopyridin-3-amine. The reaction mixture was stirred for 16 h then quenched with 10 mL of saturated NH4C1 solution and then 10 mL of water. The mixture was extracted with EtOAc three times; the combined organics were washed with brine and then dried over a2S04. The solvent was then evaporated and the residue was chromatographed (0% to 20% CH3OH / dichloromethane) to afford compound Int lB-1 as a yellow solid

According to the analysis of related databases, 486424-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SILVERBACK THERAPEUTICS, INC.; THOMPSON, Peter Armstrong; EDRIS, Badreddin; COBURN, Craig Alan; BAUM, Peter Robert; (372 pag.)WO2018/227023; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 63744-22-9,Some common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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.

To a solution of 4-(4-(oxetan-3-yl)piperazin-1-yl)-3-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)aniline XXIV (619 mg, 2.17 mmol) and 6,8-dibromoimidazo[1,2-a]pyrazine (601 mg, 2.2 mmol) in IPA (15 mL) was added N,N-Diisopropylethylamine (0.95 ml, 5.43 mmol). The mixture was stirred at 110 C. for 16 h. After this time, DCM (10 mL) and sat aqueous NaHCO3 (15 mL) were added. The aqueous layer was separated and extracted with DCM (2*10 mL). The combined organic extracts were washed with brine (10 mL) and dried over sodium sulfate. The resulting residue was purified by column chromatography ISCO Rf (24 g column) eluting with a gradient of 100% DCM-60:35:5 DCM:Et2O:MeOH to provide 6-bromo-N-(4-(4-(oxetan-3-yl)piperazin-1-yl)-3-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl)imidazo[1,2-a]pyrazin-8-amine XXV.

The synthetic route of 63744-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Lo, Jennifer R.; Mitchell, Scott A.; Schmitt, Aaron C.; Xiong, Jin-Ming; Xu, Jianjun; Zhao, Zhongdong; US2015/175616; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 24241-18-7,Some common heterocyclic compound, 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, molecular formula is C4H3Br2N3, 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.

Intermediate Example 1 -1 : Preparation of 6,8-dibromo-imidazo[ 1 ,2-a]pyrazineTo a stirred suspension of 2-amino-3,5-dibrompyrazine (427 g, 1688mmol) in water (6.4 L) / THF (482 mL), at rt was added bromacetaldehyde-diethylacetal (998 g, 5065 mmol) in one portion. After stirring under reflux for 4 h, the clear orange solution was stirred for an additional 15 h at rt. The suspension was filtered, and the remaining solid was washed with MeOH (2 L) and dried in vaccuo at 60 C to yield 6,8-dibromo-imidazo[1 ,2-a]pyrazine as an off-white solid (500 g, 107% with residual MeOH): 1 H-NMR (300 MHz, d6-DMSO): delta =9.02 (s, 1 H), 8.23 (d, 1 H), 7.89 (d, 1 H) ppm. UPLC-MS: RT = 0.80 min; m/z 277.9 [MH+]; required MW = 276.9.

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80236; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, molecular formula is C7H3Cl2N3, 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: 5,7-Dichloropyrido[3,4-b]pyrazine

Intermediate 29: 1,1-Dimethylethyl 3-{[(7-chloropyrido[3,4-b]pyrazin-5-yl)oxy]methyl}-4,4-difluoro-1-piperidinecarboxylate 1,1-Dimethylethyl 4,4-difluoro-3-(hydroxymethyl)-1-piperidinecarboxylate (207 mg, 0.825 mmol) was dissolved in dry N,N-dimethylformamide (DMF) (5 ml) and sodium hydride (45.0 mg, 1.125 mmol) was added under nitrogen at room temperature. After 60 min, 5,7-dichloropyrido[3,4-b]pyrazine (150 mg, 0.750 mmol) was added and the reaction was stirred at room temperature under nitrogen for 2 h. The reaction was quenched by the addition of sat. ammonium chloride solution and extracted with ethyl acetate. The aqueous layer was extracted further with ethyl acetate. The combined organics were washed with water, dried using a hydrophobic frit and evaporated in vacuo to give an orange oil (369 mg). The residue was loaded in dichloromethane and purified on silica (50 g) column using a 0-100% ethyl acetate/cyclohexane gradient. Appropriate fractions were combined and evaporated to give the title compound as an orange oil (163 mg). LCMS (Method B): Rt=1.25 min, MH+=415

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1379338-74-5, its application will become more common.

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.; US2014/5188; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 25710-18-3, name is 2,3-Dichloropyrido[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. Quality Control of 2,3-Dichloropyrido[2,3-b]pyrazine

[0445] Example 14 [0446] Synthesis of 3 -(4-(3 -chlorobenzyl)piperazin- 1 -yl)-N-phenylpyrido [2,3 -b]pyrazin-2- amine, 2,2,2-trifluoroacetic acid salt [0447] To a solution of 2,3-dichloropyrido[2,3-b]pyrazine (20 mg, 0.100 mmol) in dioxane (0.3 mL) was added aniline (9.78 mg, 0.105 mmol) and -ethyl-N-isopropylpropan-2-amine (38.8 mg, 0.30 mmol). The reaction mixture was heated at 150 °C overnight, then l-(3- chlorobenzyl)piperazine (31.6 mg, 0.150 mmol) was added. The resulting solution was heated at 150 °C overnight. HPLC purification afforded the title compound as a yellow solid. MS (ESI, pos. ion) m/z: 431.2 (M+l)

The synthetic route of 2,3-Dichloropyrido[2,3-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVOY THERAPEUTICS, INC.; HITCHCOCK, Stephen; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; KIKUCHI, Shota; MACKLIN, Todd; HOPKINS, Maria; WO2014/28479; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 63744-22-9, The chemical industry reduces the impact on the environment during synthesis 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

Intermediate Example15-1 Preparation of 6,8-dibromo-3-iodo-imidazo[ 1 ,2-a]pyrazinTo a stirred solution of intermediate example 1-1 (8.7 g g, 31.4 mmol) in DMF (210 mL) was added NIS (7.42 g, 33 mmol, 1.05 eq) in one portion at rt. After 18 h stirring at 60C, the solvent was removed in vaccuo and the residue was taken up in DCM and washed with water and saturated sodium thiosulfate solution. The organic phase was dried over sodium sulphate, filtered and the solvent was evaporated to yield 9.46 g (74.8 ¾) 6,8-Dibromo-3-iodo-imidazo[1 ,2-a]pyrazine: 1H-NMR (300 MHz, CDCb): delta = 8.22 (1 H, s), 7.91 (1 H, s) ppm.

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, 6,8-Dibromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80236; (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 1458-18-0 as follows. Safety of Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate

a) 3-Amino-6-chloro-5-(1 -ethoxy-vinyl)-pyrazine-2-carboxylic acid methyl ester A mixture of 3-amino-5,6-dichloro-pyrazine-2-carboxylic acid methyl ester [1458-18-0] (600 mg, 2.62 mmol), lithium chloride (389 mg, 9.17 mmol), Pd(PPh3)2CI2 (184 mg, 0.262 mmol) and tributyl-(1-ethoxy-vinyl)-stannane [97674-02-7] (1.6 ml, 4.50 mmol) in DMF (27 ml) under argon was heated at 80 C bath temperature for 3 h and 50 min. Saturated aq. NH4CI was added and the mixture was extracted with MTBE (3x). The combined organic layers were washed with brine, dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 7:3) to provide the title compound as yellow solid (433 mg). HPLC: RtH2= 0.94 min; ESIMS [M+H]+ = 258.1 ; 1H-NMR (400 MHz, DMSO-c/6): delta 7.59 (br. s, 2H), 4.64 (d, 1 H), 4.58 (d, 1 H), 3.91 (q, 3H), 3.86 (s, 3H), 1.31 (t, 2H).

According to the analysis of related databases, 1458-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; LUEOEND, Rainer Martin; MACHAUER, Rainer; RUEEGER, Heinrich; VEENSTRA, Siem Jacob; WO2013/27188; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 87486-34-8, A common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, molecular formula is C5H4Br2N2O, 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-(iii): Synthesis of 5 -bromo- 1 -methyl-3-((3-(4-methylpiperazin- 1 -yl)phenyl)amino) pyrazin-2( 1H)-one:To a stirred solution of Intermediate-i (1 g, 3.75 mmol) in DMA (6 mL) was added compound-32b (0.78 g 4.13 mmol) and stirred at 110°C for 16h. After the reaction wascompleted, the reaction mixture was cooled to RT, poured into crushed ice; the solid formed was filtered and dried under vacuum to get the desired product (800 mg, 52percent); MS (ES) m/z 378 (M+1).

The synthetic route of 87486-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125410; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 24241-18-7, The chemical industry reduces the impact on the environment during synthesis 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, I believe this compound will play a more active role in future production and life.

To a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79 mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 110 C. for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na2(SO4) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6%) ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz,

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; BAYER INTELLECTUAL PROPERTY GMBH; Koppitz, Marcus; Klar, Ulrich; Jautelat, Rolf; Kosemund, Dirk; Bohlmann, Rolf; Bader, Benjamin; Lienau, Philip; Siemeister, Gerhard; US2013/281460; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem