Tag: M.W=200-300

Application of 63744-22-9, 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. 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

[0293] (R)-(4-(4-((6-Bromoimidazo[1,2-a]pyrazin-8- yl)amino)phenyl)morpholin-2-yl)methanol XVII: In a 250 mL round bottom flask equipped with a condenser was placed 6,8-dibromoimidazo[1,2-a]pyrazine (2000 mg, 7.22 mmol) and added 30 mL isopropanol followed by N,N-diisopropylethylamine (2.52 ml, 14.44 mmol) and (R)-(4-(4-aminophenyl)morpholin-2-yl)methanol (1504.12 mg, 7.22 mmol). The reaction was heated to reflux (oil bath 95 C) overnight. The reaction was cooled and precipitates were collected by filtration and washed with isopropanol followed by hexanes to give the desired compound XVII, 2.92 g, 95% yield.

The synthetic route of 6,8-Dibromoimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter, A.; CLARKE, Astrid; CURRIE, Kevin, S.; DI PAOLO, Julie; KROPF, Jeffrey, E.; LEE, Seung, H.; LO, Jennifer, R.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; SWAMINATHAN, Sundaramoorthi; XIONG, Jin-Ming; XU, Jianjun; ZHAO, Zhongdong; (169 pag.)WO2016/10809; (2016); A1;,
Pyrazine – Wikipedia,
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Synthetic Route of 6966-01-4, These common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, 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.

A mixture of Pd(OAc)2 (146 mg, 0.7 mmol) and l,l-bis(diphenylphosphino)ferrocene (478 mg, 0.9 mmol) in DMF (65 ml) under an argon atmosphere was stirred at 50 for 15 min and cooled to rt. The reaction mixture was evacuated, then flushed with argon. 3-Amino-6-bromopyrazine- 2-carboxylic acid methyl ester (5.0 g, 21.5 mmol), 2-furanboronic acid (2.65 g, 23.7 mmol) and triethylamine (4.3 ml) were added. The reaction mixture was again evacuated, then flushed with argon. The mixture was heated at 90 overnight. After cooling to rt, the black mixture was concentrated to dryness. The residue was dissolved in dichloromethane (800 ml), washed with water, dried over MgS04, filtered and evaporated. The crude product was purified by silica gel chromatography using a n-heptane/EtOAc gradient for elution, providing the title compound as yellow solid (2.84 g, 60%).MS: M = 220.3 (M+H)+

The synthetic route of 6966-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; GRUBER, Felix; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; WO2011/154327; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 5900-13-0, 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 5900-13-0 as follows.

General procedure: Toa solution of 5-bromo-3-methoxypyrazin-2-amine (500 mg, 2.45 mmol) in pyridine(5 mL) at room temperature was added 3-chlorophenyl)methanesulfonyl chloride(552 mg, 2.45 mol) over 5 min. The mixture was stirred 10 mins, the pyridineevaporated, then DCM (60 mL) and water (10 mL) was added. The phases wereseparated and the organic phase was washed with brine (5 mL), dried (Na2SC>4),the mixture filtered and the filtrate evaporated to dryness to afford an orangeoil which was chromatographed on silica (Heptane: EtOAc 1 :1) to afford thetitle compound as a light brown solid (483 mg, 48%); The procedure to prepare N-(5-bromo-3-methoxypyrazin-2-yl)-1-(3-chlorophenyl)- methanesulfonamide was used except that methyl 3 -(chlorosulfonyl)benzoate was substituted for 3-chlorophenyl)methanesulfonyl chloride. In addition, the reaction was carned out at 60C rather than at room temperature (15%); mlz=40 1.9, 403.9 (MH).

According to the analysis of related databases, 5900-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1422772-78-8, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic 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. Formula: C7H4BrN3O2

To a suspension of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (Example 83 Step 1, 145 g, 602 mmol) in MeOH (1.5 L) at 0C was added thionyl chloride (93 g, 781 mmol) dropwise over 40 minutes. The reaction was heated to reflux for 4 hours before cooling and concentrating in vacuo. The resulting solid was triturated with TBME to afford the title compound as a yellow solid (109 g, 71%) that was taken directly on to the next step.

The synthetic route of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; THORARENSEN, Atli; BROWN, Matthew Frank; CASIMIRO-GARCIA, Agustin; CHE, Ye; FLANAGAN, Mark Edward; GILBERT, Adam Matthew; HAYWARD, Matthew Merrill; TELLIEZ, Jean-Baptiste; UNWALLA, Rayomand Jal; TRUJILLO, John I.; LIANG, Sidney Xi; (212 pag.)WO2016/178110; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1458-01-1, 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. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Intermediate A.13,5-Diamino-6-chloropyrazine-2-carboxylic acidA mixture of methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (100 g; 494 mmol), methanol (1 I) and NaOH (6 mol/l in water; 240 ml; 1 .44 mol) is refluxed for 3 h. The mixture is allowed to cool to r.t. and then neutralized by addition of hydrochloric acid (6 mol/l in water; approx. 240 ml_). Water (200 ml) is added. The precipitate formed is filtered off with suction, washed with water and dried at 60°C.C5H5CIN402 ESI Mass spectrum: m/z = 189 [M+H]+; m/z = 187 [M-H]-

The synthetic route of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; KLEY, Joerg; FRATTINI, Sara; HAMPRECHT, Dieter; HECKEL, Armin; WO2015/7516; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1379338-74-5, The chemical industry reduces the impact on the environment during synthesis 1379338-74-5, name is 5,7-Dichloropyrido[3,4-b]pyrazine, I believe this compound will play a more active role in future production and life.

Intermediate 22: 1,1-Dimethylethyl (2R)-2-{[(7-chloropyrido[3,4-b]pyrazin-5-yl)amino]methyl}-4-morpholinecarboxylate 1,1-dimethylethyl (2R)-2-(aminomethyl)-4-morpholinecarboxylate (for preparation see: J. Medicinal Chemistry, 2009, 52 (15), 4810-4819) (6 g, 27.7 mmol) was dissolved in N-methyl-2-pyrrolidinone (NMP) (60 mL) and to this was added DIPEA (7.27 mL, 41.6 mmol) and 5,7-dichloropyrido[3,4-b]pyrazine (5.55 g, 27.7 mmol). This was split between 4 large microwave vials and each was heated at 130 C. for 30 min. They were monitored by LCMS and were given a further 10 min at 130 C. The reaction mixtures were partitioned between ethyl acetate (700 ml) and diluted aqueous ammonium chloride (1 litre). The aqueous was reextracted with ethyl acetate (300 ml) and the combined organics were washed with aqueous ammonium chloride (500 ml), dried over sodium sulfate and concentrated in vacuo to yield a crude brown oil. It was dissolved in DCM and passed through silica (70 g) eluting with DCM (6*40 ml) then 5% ethyl acetate in DCM (2*40 ml), 10% ethyl acetate in DCM (5*40 ml) then 15% ethyl acetate in DCM (2*40 ml) then 20% ethyl acetate in DCM (2*40 ml). Appropriate fractions were combined and concentrated in vacuo to yield: N8231-100-2, orange-yellow slightly gummy solid, 7.7 g LCMS (Method B): Rt=1.17 min, MH+ 380

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, 5,7-Dichloropyrido[3,4-b]pyrazine, other downstream synthetic routes, hurry up and to see.

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

117719-17-2, name is 5-Bromo-3-morpholinopyrazin-2-amine, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 5-Bromo-3-morpholinopyrazin-2-amine

Chloroacetaldehyde (4.4 g) was mixed with isopropanol (15 mL) and a portion of the mixture (10 mL) was added to a round bottom flask containing compound 2 (1.7 g). Then the temperature was raised to 45 C and stirring was continued. After 1 h, the remaining solution was added and thetemperature raised to 65 C with continuous stirring. After TLC indicated the reaction was finished, the reaction was stopped and cooled to room temperature. Then the solution was added into a beaker containing ice water (300 mL) with continuous stirring. The brown-yellow solid that precipitated was filtered and dried to give the product in a yield of 26.8%. 1H-NMR (DMSO-d6) delta 7.93 (s, 1H),7.25 (d, J = 7.3 Hz, 1H), 7.01 (d, J = 7.3 Hz, 1H), 3.45 (s, 4H), 3.77 (d, J = 4.3 Hz, 4H).

The synthetic route of 117719-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Shan; Sun, Chengyu; Chen, Chen; Zheng, Pengwu; Zhou, Yong; Zhou, Hongying; Zhu, Wufu; Molecules; vol. 22; 2; (2017);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route 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.

Intermediate Example 7-1 : Preparation of 3-bromo-N-(2- methylpropyl)imidazo[ 1 ,2-a]pyrazin-8-amineTo a stirred solution of 3-bromo-8-chloro-imidazo[1 ,2-a]pyrazine which was prepared according to intermediate example 2-1 (4 g, 17.2 mmol) in THF (54 mL) was added 4.9 mL isobutylamine (3.77 g, 51.6 mmol, 3 eq) and 7.2 mL TEA (5.22 g, 51.6 mmol, 3 eq) in one portion at rt and the mixture was heated at 140C in a microwave tube. Purification by flash chromatography yielded 4.45 g (91 %) of the title compound. 1H-NMR (300 MHz, d6-DMSO): delta = 7.64 (d, 1 H), 7.61 (s, 1 H), 7.48 (d, 1 H), 7.36 (d, 1 H), 3.24 (dd, 2H), 1.96 (m, 1 H), 0.85 (d, 6H) ppm. UPLC-MS: RT = 0.84 min; m/z 270.2 [MH+]; required MW = 269.2.

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; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; KLAR, Ulrich; JAUTELAT, Rolf; KOSEMUND, Dirk; BOHLMANN, Rolf; BADER, Benjamin; LIENAU, Philip; SIEMEISTER, Gerhard; WO2012/80229; (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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H3Br2N3

3,5-Dibromopyrazin-2-amine (200 mg, 0.79 mmol) and chloroacetaldehyde (200 mul, 1.58 mmol) were dissolved in DMF (5 ml). The mixture was stirred at 100 C. overnight. LC/MS showed 6,8-dibromoimidazo[1,2-a]pyrazine plus the mass with one bromine displaced by chlorine. The crude material was used for the next step without further purification. 1H NMR (400 MHz, CDCl3) delta 8.28 (s, 1H) 7.88 (s, 1H) 7.80 (s, 1H). [M+H] calc’d for C6H3Br2N3, 276; found, 276.

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; Dong, Qing; Hosfield, David J.; Paraselli, Bheema R.; Scorah, Nicholas; Stafford, Jeffrey A.; Wallace, Michael B.; Zhang, Zhiyuan; US2006/84650; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 76537-18-3, These common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-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.

First, into a three-neck flask equipped with a reflux pipe were put 5.01 g of 60 3-bromo-5-chloropyrazin-2-amine, 6.04 g of 5 2-methoxynaphthalene-1-boronic acid, 5.32 g of 6 potassium fluoride, and 86 mL of dehydrated tetrahydrofuran, and the air in the flask was replaced with nitrogen. The mixture in the flask was degassed by being stirred under reduced pressure, and then 0.44 g of 7 tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3) and 3.4 mL of 8 tri-tert-butylphosphine (abbreviation: P(tBu)3) were added thereto. The mixture was stirred at 80 C. for 22 hours to be reacted. After a predetermined time elapsed, the obtained mixture was subjected to suction filtration and the filtrate was concentrated. Then, purification by silica gel column chromatography using a developing solvent (toluene:ethyl acetate=10:1) was performed, so that 5.69 g of a target pyrazine derivative (yellowish white 61 powder) was obtained in a yield of 83%. A synthesis scheme of Step 1 is shown in (e-1) below

Statistics shows that 3-Bromo-5-chloropyrazin-2-amine is playing an increasingly important role. we look forward to future research findings about 76537-18-3.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Yamaguchi, Tomoya; Yoshizumi, Hideko; Kido, Hiromitsu; Seo, Satoshi; Sasaki, Toshiki; (180 pag.)US2019/31673; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem