Month: June 2021

Electric Literature of 55557-52-3, 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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

2-cyano-3-chloropyrazine (0.8 g, 5.8 mmol) and Raney-Ni (0.3 g) were added to 10 mL glacial acetic acid, the atmosphere was replaced with hydrogen gas for three times, the mixture was stirred under 3 atmospheric pressure of hydrogen gas at 50 C overnight. The reaction was filtered after the reaction was complete, filtrate was concentrated, the residue was dissolved in ethyl acetate, washed with saturated solution of sodium bicarbonate, dried over anhydrous sodium sulfate, concentrated, and separated by silica gel column to afford 0.5 g of a light yellow oil, yield was 60%. LC-MS(APCI): m/z = 144(M+1)+.

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

Reference:
Patent; Shenzhen Targetrx, Inc.; WANG, Yihan; XING, Qingfeng; (51 pag.)EP3492471; (2019); 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 59489-32-6 as follows. Computed Properties of C6H7ClN2

Pd2(dba)3-CHC13 (5 mg, 0.5 mol %), ligand 1 (8 mg, 2 mol %) and 1.4 eq sodium tert- butoxide (13 mg, 0.14 mmol) were weighed in air and transferred into a microwave tube, followed by dioxane (750 muL), 1.0 eq JVrlambda/-dimethyl-l-(piperidin-4-yl)-2’/f-spiro[piperidine-4,41- quinolineJ-rp’i^O-carboxamide (36 mg, 0.10 rnmol) and 1.0 eq 5-chloro-2,3-dimethylpyrazine (14 mg). The tube was flushed with nitrogen, capped and stirred at 800C for 3 hours. The reaction was cooled to room temperature, diluted with methanol (500 muL), filtered (Whatman 0.45 mum PTFE) and subjected to reverse-phase HPLC purification (2-40% CH3CN gradient [w/ 0.1 % TFA (aq)] over / = 10 minutes, 750 muL injected, 35 mL/min) to yield compound no. 20. LC/MS (10-99% CH3CN/0.05% TFA gradient over 5 min): m/z 463.4, retention time 2.13 minutes.

According to the analysis of related databases, 59489-32-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/100670; (2007); 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. 143591-61-1, name is 3-Bromo-8-chloroimidazo[1,2-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Bromo-8-chloroimidazo[1,2-a]pyrazine

Example 7-1 : Preparation of N-cyclopropyl-4-[8-(pentylamino)imidazo[1 ,2- a]pyrazin-3-yl]benzamide3-bromo-8-chloro-imidazo[1 ,2-a]pyrazine (intermediate example 1 -1 , 0.15 mmol, 0.75 mL, 0.2M in NMP), 1 -pentanamine (1.5 eq, 0.3 mL, 0.5 M in NMP) and DIPEA (3 eq, 77 mu) were combined in a sealed vial and heated at 160 C under microwave irradiation for 60 min. After cooling, [4-[(cyclopropylamino)carbonyl]phenyl]- boronic acid (1.5 eq, 0.45 mL, 0.5 M in NMP), Pd(dppf)Cl2 (0.1 eq, 400 mu, 0.0375 M in NMP) and potassium carbonate (450 muIota_, 1M in water) were added and the mixture was heated at 160 C under microwave irradiation for 80 min. After cooling, the solution was filtered and subjected to preparative HPLC to give N- cyclopropyl-4-[8-(pentylamino)imidazo[1 ,2-a]pyrazin-3-yl]benzamide (3.8 mg, 7 %): UPLC-MS: RT = = 0.83 min; m/z (ES+) 364.5 [MH+]; required MW = 363.5

The synthetic route of 143591-61-1 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; WO2012/80229; (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. 32974-92-8, name is 1-(3-Ethylpyrazin-2-yl)ethanone belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-(3-Ethylpyrazin-2-yl)ethanone

General procedure: The ligands L1-L4 were synthesized by reflux method. Shown in Scheme 1, 5mM of 2-Acetyl-3-ethylpyrazine and thiosemicarbazides (L1), 5mM of 2-Acetyl-3-ethylpyrazine and 4-methylthiosemicarbazide (L2), 5mM of 2-Acetyl-3-ethylpyrazine and 4-phenylthiosemicarbazide (L3), and 5mM of 2-Acetyl-3-ethylpyrazine and 3-pyrrolethiosemicarbazide (L4) were stirred in CH3OH for 3 h at 65C. The ligands were precipitated and filtered. L1-L4 were characterized by infrared spectroscopy, electrospray ionization mass spectrometry (ESI-MS), 1H NMR, and 13C NMR (Supplementary Figs S4- S31).

The synthetic route of 32974-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khan, Muhammad Hamid; Cai, Meiling; Li, Shanhe; Zhang, Zhenlei; Zhang, Juzheng; Wen, Xiaoan; Sun, Hongbin; Liang, Hong; Yang, Feng; European Journal of Medicinal Chemistry; vol. 182; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 957344-74-0, The chemical industry reduces the impact on the environment during synthesis 957344-74-0, name is 5,8-Dibromoimidazo[1,2-a]pyrazine, I believe this compound will play a more active role in future production and life.

Step 1 (5-Bromo-iotamiotadazo[ 1 , 2-a]pyraziotan-8-yl)-(4-methanesulfonyl-phenyl) -amine[00270] A degassed mixture of 5,8-dibromo-imidazo[l,2-a]pyrazme (2.19g, 7.916mmol), A- methylsulfonylamlme (1 49g, 8.708mmol), Pd2dba3 (145mg, 0.15mmol) and Xantphos (183mg, 0.317mmol), m dry toluene (5OmL) is stirred at 1100C for 16 hours. After evaporation of the solvent, the residue is purified by silica gel column chromatography elutmg with 95:5 DCM:NH3 (7M in MeOH). The title compound (1.496g, 51%) is isolated containing some starting material (20%) and used in the next step 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, 5,8-Dibromoimidazo[1,2-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 33332-28-4,Some common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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.

EXAMPLE 8 N-(6-Chloro-pyrazin-2-yl)-2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 8.5 g (30 mmols) of methyl 2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 3.9 g (30 mmols) of 2-amino-6-chloro-pyrazine were reacted in 600 ml of xylene and worked up analogous to Example 1, yielding 7.3 g (64percent of theory) of N-(6-chloro-pyrazin-2-yl)-2-ethyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide. Melting point: 233°-235° C. (from xylene). C15 H13 ClN4 O4 S (380.83): Calc.: C–47.31percent; H–3.44percent; Cl–9.31percent; N–14.71percent; S–8.42percent. Found: C–47.42percent; H–3.44percent; Cl–9.50percent; N–14.62percent; S–8.51percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-chloropyrazine, its application will become more common.

Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4533664; (1985); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-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 19745-07-4, Safety of 2,5-Dichloropyrazine

Step C: (S)-3 -(6-(Methylsulfonyl)pyridin-3 -ylamino)- 1 -(piperidin-4- yl)pyrrolidin-2-one (0.076 g, 0.22 mmol) and 2,5-dichloropyrazine (0.054 g, 0.36 mmol) were dissolved in NMP (0.45 mL) and treated with DIEA (0.098 mL, 0.56 mmol). The mixture was stirred at 80 °C overnight and then cooled to ambient temperature. The reaction mixture was partitioned between EtOAc (40 mL) and FLO (20 mL). The mixture was filtered through a 0.45 muiotaeta nylon membrane and the solids were washed with EtOAc and then dried under high vacuum to provide (S)-l-(l-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(6- (methylsulfonyl)pyridin-3-ylamino)pyrrolidin-2-one (0.030 g, 0.067 mmol, 30percent).

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; 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

Reference 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.

To a 12 L threenecked RBF equipped with an overhead stirrer and reflux condenser was chargedsequentially with (-)-1,4-dimethyl-3-(4-aminophenyl)piperazin-2-one (V, 491 g, 2.24 mol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (VI, 600 g, 2.24 mol), i-PrOH (5 L) and triethylamine (350mL, 2.5 mol). The resulting suspension was heated at 82 °C for 24 h (Caution: reaction was exothermic).After the reaction mixture was cooled for 5 h, 1.25 L of 2 M Na2CO3solution was added and the suspension was stirred overnight. The orange solids were then collected on afritted funnel and washed with 2 L of fresh IPA (color was washed off). The resulting tan solids were suspended in 3L of deionized water and stirred at 25 °C for 1 h. After filtration, the solids were washed with1 L of methyl tert-butyl ether (MTBE)and dried under vacuum in the funnel at 25 °C for 1 h and in an amber glass at40 °C overnight. White solids wereobtained as compound VII (629 g, 69percent).

Statistics shows that 3,5-Dibromo-1-methylpyrazin-2(1H)-one is playing an increasingly important role. we look forward to future research findings about 87486-34-8.

Reference:
Article; Young, Wendy B.; Barbosa, James; Blomgren, Peter; Bremer, Meire C.; Crawford, James J.; Dambach, Donna; Gallion, Steve; Hymowitz, Sarah G.; Kropf, Jeffrey E.; Lee, Seung H.; Liu, Lichuan; Lubach, Joseph W.; Macaluso, Jen; Maciejewski, Pat; Maurer, Brigitte; Mitchell, Scott A.; Ortwine, Daniel F.; Di Paolo, Julie; Reif, Karin; Scheerens, Heleen; Schmitt, Aaron; Sowell, C. Gregory; Wang, Xiaojing; Wong, Harvey; Xiong, Jin-Ming; Xu, Jianjun; Zhao, Zhongdong; Currie, Kevin S.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 6; (2015); p. 1333 – 1337;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 68774-77-6

Step 1. (3S, 4 ?)-tert-butyl 4-(([l,2,4]triazolo[4,3-o]pyrazin-8-ylamino)methyl)-3- fluoropiperidine-l-carboxylate [0187] A mixture of 8-chloro-[l,2,4]triazolo[4,3-a]pyrazine (2.00 g, 12.94 mmol), (3S, 4 ?)-tert-butyl 4- (aminomethyl)-3-fluoropiperidine-l-carboxylate (2.86 g , 12.32 mmol) and DIPEA (4.07 mL, 24.64 mmol) in n-butyl alcohol (40 mL) was heated to 120 C in the sealed tube under N2 atmosphere. After stirring overnight, the mixture was cooled to rt and concentrated under reduce pressure. 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 = 1/20) to afford the title compound as a pale-yellow powder (2.91g, 67%). MS (ESI) calcd for C16H23FN602: 350.2; found: 351.7[M+H]. *H NM (400 MHz, CD3OD) delta 9.09 (s, 1H), 7.70 (d, J = 4.8 Hz, 1H), 7.31 (d, J = 4.8 Hz, 1H), 4.86-4.73 (m, 1H), 4.42-4.35 (m, 1H), 4.19-4.16 (m, 1H), 3.67-3.62 (m , 1H), 3.59-3.54 (m, 1H), 3.05-2.74 (m, 2H), 2.25 -2.10 (m, 1H), 1.67-1.53 (m, 2H), 1.46 (s, 9H).

According to the analysis of related databases, 68774-77-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (239 pag.)WO2016/100349; (2016); 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. 330786-09-9, name is Methyl 3,5-dichloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 3,5-dichloropyrazine-2-carboxylate

The mixture of methyl 3,5-dichloropyrazine-2-carboxylate (1.0 g, 4.83 mmol, CAS 330786-09-9), (3ri)-l,3-dihydrospiro[indene-2,4′-piperidin]-3-amine dihydrochloride (1.65 g, 4.83 mmol, Intermediate I) and CsF (3.66 g, 24.1 mmol) in DMF (15 mL) was stirred at 70 C for 2 hours. Boc20 (1.57 g, 7.24 mmol) and TEA (1 mL) were then added to the mixture and the mixture was stirred at 20 C for 1 hour. The mixture was diluted with H20 (50 mL), and extracted with EtOAc (50 mL x 2). The organic layer was washed with brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether / ethyl acetate = l : 0 ~ 5 : l) to afford methyl 5-[(3ri)-3-{[(/er/-butoxy)carbonyl]amino}-l,3-dihydrospiro[indene-2,4′- piperidin]-l’-yl]-3-chloropyrazine-2-carboxylate (1.58 g, 69% yield) as a yellow solid. LCMS m/z [M+H]+ = 473.1.

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; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem