Month: April 2021

These common heterocyclic compound, 5900-13-0, name is 5-Bromo-3-methoxypyrazin-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. HPLC of Formula: C5H6BrN3O

(+/-)-l-(3,5-dichlorophenyl)-2,2,2-trifiuoroethane-l-sulfonyl chloride (165 mg, 0.48 mmol) was added to a solution of 5-bromo-3-methoxypyrazin-2-amine (107 mg, 0.53 mmol) in anhydrous pyridine (5 mL) The reaction was sealed under nitrogen and stirred at room temperature for 60 min then at 60 C for 45 min. The reaction was allowed to cool to room temperature then concentrated in vacuo. The residue was purified over silica (Biotage 10 g SNAP cartridge) eluted with Heptane:EtOAc 1 :0 to 8:2 to 6:4 to 4:6 to afford the title compound (20 mg, 7%) as a light brown solid. H NMR (500 MHz, CDCls) delta 4.06 (s, 3H), 5.71 (q, 1H), 7.36 (br.s, 1H), 7.46 (d, 2H), 7.49 (m,lH), 8.03 (s, 1H).

The synthetic route of 5-Bromo-3-methoxypyrazin-2-amine has been constantly updated, and we look forward to future research findings.

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

Application of 74290-67-8,Some common heterocyclic compound, 74290-67-8, name is 2-Amino-5-bromo-3-methylpyrazine, molecular formula is C5H6BrN3, 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 suspension of 5-bromo-3-methylpyrazin-2-amine (4.63g, 24.6 mmol) in iPrOH (30 ml) was added l-bromo-2,2-dimethoxypropane (3.66 ml, 27.1 mmol), pyridinium para-toluene sulfonic acid (0.62g, 2.5 mmol) and the mixture heated to 65C in a sealed tube for 36h. The reaction was diluted with DCM, washed with saturated sodium hydrogen carbonate solution, dried (Na2S04) and concentrated. Purification by flash column chromatography on silica gel (EtOAc: Hept 1:4-1: 1) afforded the titled product as a light yellow crystalline solid (3.96 g, 71%). MS (m/e): 226.1 (M+H+, Br)

The synthetic route of 74290-67-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GREEN, Luke; PINARD, Emmanuel; RATNI, Hasane; WILLIAMSON, Patrick; (95 pag.)WO2015/197503; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 122-05-4,Some common heterocyclic compound, 122-05-4, name is Pyrazine-2,5-dicarboxylic acid, molecular formula is C6H4N2O4, 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.

270 mg (1 mmol) of FeCl3.6H2O (Alfa Aesar, 98%) and 204 mg (1 mmol) of 2,5-pyrazinedicarboxylic acid (Aldrich, 98%) are dispersed in 5 ml of DMF (Fluka, 98%) with 0.05 ml of 5M HF (SDS, 50%). The mixture is left in a 23 ml Teflon vessel inserted into a metallic PAAR type bomb for 3 days at 100 C. The solid is recovered by filtration.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Pyrazine-2,5-dicarboxylic acid, its application will become more common.

Reference:
Patent; Universite De Caen-Basse Normandie; Centre National De La Recherche Scientifique- CNRS-; US2011/172412; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4774-14-5, name is 2,6-Dichloropyrazine, 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 4774-14-5, category: Pyrazines

General procedure: To the solution of a corresponding amine (1.8 mmol) in DMF (5 mL) was added K2CO3 (2.0 mmol). The reaction mixture was stirred at room temperature for 30 min. After the addition of 2,6-dichloropyrazine (1.3 mmol) the reaction mixture was further stirred at room temperature for 15 h. After removal of solvent under reduced pressure, the precipitates formed by a treatment of residue with DCM:methanol (95:5) mixture was filtered off. Het-Cl was obtained by the removal of solvent in vaccuo and used for next reaction without further purification.

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, 2,6-Dichloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; More, Kunal N.; Hong, Victor S.; Lee, Ahyeon; Park, Jongsung; Kim, Shin; Lee, Jinho; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2513 – 2517;,
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. 144692-85-3, name is 2,3-Dichlorofuro[3,4-b]pyrazine-5,7-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 2,3-Dichlorofuro[3,4-b]pyrazine-5,7-dione

Under air, a test tube was charged with 2,3-dichlorodiazaphthalic anhydride (410mg, 1.872mmol) and 2-chloroethylamine hydrochloride (223mg, 1.919mmol). Acetic anhydride (400muL) was added and the reaction sealed and heated to 120C for 30min. The reaction was cooled to ambient temperature and diluted with H2O (2mL). The crude solid was filtered and washed with H2O (2¡Á5mL) and then purified by eluting through a plug (SiO2; CH2Cl2) to afford analytically pure 5a as a white solid. Yield=391mg (75%). (0022) 1H NMR (500MHz, CDCl3): delta 4.18 (t, 3JHH=6.1, 2H, CH2), 3.83 (t, 3JHH=6.1, 2H, CH2). 13C{1H} NMR (126MHz, CDCl3): delta 161.9, 154.1, 143.4, 40.5, 40.4. HR ESI-MS positive ion: 333.9521m/z [M+Na+MeOH]+ (calc. 333.9523). Anal. Calcd for C8H4Cl3N3O2 (280.49gmol-1): C, 34.26; H, 1.44; N, 14.98. Found: C, 34.33; H, 1.38; N, 14.96.

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:
Article; Knighton, Richard C.; Chaplin, Adrian B.; Tetrahedron; vol. 73; 31; (2017); p. 4591 – 4596;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 153800-11-4,Some common heterocyclic compound, 153800-11-4, name is 2-Ethynylpyrazine, molecular formula is C6H4N2, 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 227(100mg, 0.3O6mrnoI) and 10(63.7mg, 0.61 immol) in 2OmL of Et3N was added Pd(PPh3)2C12 (10.73mg, 0.OiSmrnoi) and CuT (5.82mg, 0.03 immol). The mixture was protected with N2 atmosphere, then was heated at 70C for 24 hours. TLC analysis showed complete conversion of starting material to a major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep-IPLC to give the target productCompound 103(18mg, yield: 1941 %).LCMS: m/z 304 (M+H)NMR (400 MHz, CDCI3): 5 8.668.65 (m, 3H), 7.67 (s, 1H), 7.60-7.57 (m, IH), 7.43.-7.40 (m, 1H), 6.55 (s, 11:1), 2.47 (s, 31:1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Ethynylpyrazine, its application will become more common.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (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 243472-70-0 as follows. Product Details of 243472-70-0

Add 3-methyl-2-bromo-quinoxaline (622 mg, 2.00 mmol) to cis-5-(isopropylamine) under nitrogen.a solution of methyl-)tetrahydrofuran-2-yl)methanol (1.04 g, 6.00 mmol) in N-methylpyrrolidone (20 mL)After refluxing at 170 C for 15 h, the reaction was monitored by LC-MS, the starting material was completely reacted, and the reaction was cooled and ice water was added to the reaction solution.The ethyl acetate (50 mL*3) was extracted, and the organic mixed phase was washed with water (50 mL) and saturated brine (50 mL*2).Filtration, decompression to solvent, purification by chromatography on silica gel column, and collected under reduced pressure.Drying in vacuo gave 673 mg of Compound VIII as a white solid.

According to the analysis of related databases, 243472-70-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Yuandong Bio-pharmaceutical Co., Ltd.; Zeng Yanqun; Yan Shengyong; Zhang Tao; Wang Ying; (17 pag.)CN108623541; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

912773-21-8, name is 2-Bromo-5-chloropyrazine, 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. COA of Formula: C4H2BrClN2

A mixture of 2-bromo-5-chloro-pyrazine (800 mg, 4.14 mmol), 3-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-[l- (trifluoromethyl)cyclobutoxy]pyridine (1642.99 mg, 4.55 mmol), CS2CO3(4042.64 mg,12.41 mmol), Pd(dppf)Cl2(60.52 mg, 0.08 mmol) in l,4-dioxane (12 mL) and H2O (4 mL) was stirred at 50 C for 8 hours. After cooling to room temperature, the reaction mixture was concentrated to remove solvent, diluted with water (20 mL), and extracted with EtOAc (20 mL x 2). The combined organic phase was washed with brine (40 mL), dried over Na2S04and concentrated to give a crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 10%) to give the product as a solid, which was confirmed by LCMS Rt= 1.01 min in 1.5 min chromatography, MS ESI calcd. for C14H11CIF4N3O [M+H]+348.1, found 347.9.

The synthetic route of 912773-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; MARTINEZ BOTELLA, Gabriel; REDDY, Kiran; WITTMANN, Marion; (0 pag.)WO2019/232209; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 63744-29-6, The chemical industry reduces the impact on the environment during synthesis 63744-29-6, name is 5-Bromo-[1,2,4]triazolo[4,3-a]pyrazine, I believe this compound will play a more active role in future production and life.

Step 1: (3S,4 ?)-tert-butyl 4-(([l,2,4]triazolo[4 -a]pyrazin-5-ylamino)methyl)-3-fluoropiperidine- 1-carboxylate [0185] A mixture of 5-bromo-[l,2,4]triazolo[4,3-a]pyrazine (102 mg, 0.51 mmol), (3S,4R)-tert-butyl 4- (aminomethyl)-3-fluoropiperidine-l-carboxylate (80 mg , 0.34 mmol) and DIPEA (1.2 mL, 1.0 mmol) in ethylene glycol (2 mL) was heated to 110 C in the sealed tube for 7 hr under N2 atmosphere. The mixture was allowed to cool to rt and concentrated. The concentrate was partitioned into DCM and water. The organic phase was washed with water, brine, dried over Na2S04 and concentrated. The concentrate was purified by column chromatography over silica gel (MeOH/DCM=50/l) to afford the title compound as an off-white powder (60 mg, 50%). MS (ESI) calcd for C16H23FN602: 350.2; found: 351.3[M+H]. 1H NMR (400 MHz, CDCI3) delta 8.72 (s, 1H), 7.41 (d, J = 4.8 Hz, 1H), 7.34 (d, J = 4.8 Hz, 1H), 6.55-6.47 (m, 1H), 4.90-4.65 (m, 1H), 4.62-4.35 (m, 1H), 4.33-4.05 (m , 1H), 3.74-3.64 (m, 2H), 2.96-2.62 (m, 2H), 2.24 -2.04 (m, 1H), 1.73-1.58 (m, 1H), 1.46 (s, 9H).

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-Bromo-[1,2,4]triazolo[4,3-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (239 pag.)WO2016/100349; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 16298-03-6, 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 16298-03-6 as follows.

Step 1: Synthesis of 3-amino-6-iodo-pyrazine-2-carboxylic acid methyl ester.[0295] Methyl 3-amino-2-pyrazinecarboxylate (10 g, 65.3 mmol) and N-iodosuccinimide(24 g, 106.7 mmol) were dissolved in anhydrous DMF (150 mL) and the mixture wasstirred at 70 ¡ãC for 15 hours under a nitrogen atmosphere. The mixture was then cooled toroom temperature and a saturated aqueous solution of sodium thiosulfate (400 mL) wasadded. The suspension was sonicated for 15 minutes, concentrated under vacuum anddispersed in water. The crude product was filtered off and washed with cold ethanol. Theresidue was crystallized from ethanol, using decolorizing charcoal to afford 3-amino-6-iodo-pyrazine-2-carboxylic acid methyl ester (11.2 g, 61 percent yield) as orange needles. 1H-NMR (d6-DMSO) 8.57 [1H] s, 7.59 [2H] s,br, 3.93 [3H] s. MS: m/z 280 [MH+].

According to the analysis of related databases, 16298-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SGX PHARMACEUTICALS, INC.; WO2006/15124; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem