Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 72788-94-4, name is 2-Chloro-5-(hydroxymethyl)pyrazine, 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 72788-94-4, Product Details of 72788-94-4

Step 1: (5-chloropyrazin-2-yl)methyl methanesulfonate To a solution of (5-chloropyrazin-2-yl)methanol (750 mg, 5.2 mmol) and DIPEA (1.34 g, 10.4 mmol) in dichloromethane (10 mL) was added methanesulfonyl chloride (1.18 g, 10.4 mmol) dropwise at 0 C. The resulting mixture was stirred at r.t. for 0.5 hr. The mixture was diluted with ethyl acetate (30 mL) and washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure to give (5-chloropyrazin-2-yl)methyl methanesulfonate (800 mg). MS (ESI): m/z 223, 225 (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-Chloro-5-(hydroxymethyl)pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Arrington, Kenneth L.; Burgey, Christopher; Gilfillan, Robert; Han, Yongxin; Patel, Mehul; Li, Chun Sing; Li, Yaozong; Luo, Yunfu; Lei, Zhiyu; US2014/100231; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 110223-15-9, 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. 110223-15-9, name is 2-Amino-3-benzyloxypyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: For aromatic urea derivatives; the appropriate aromatic isocyanate(3.0 mmol) was added to a solution of the appropriate 2-amino-3-benzyloxy pyrazine derivative (2.5 mmol) in THF(10 mL). The reaction was refluxed for 3e6 h. After cooling, thereaction mixture was evaporated and the residue was purified byprecipitation in cold methanol and filtered to give the targetcompound(s). For aliphatic urea derivatives; the appropriatealiphatic isocyanate derivative (1.02 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.85 mmol) in dry THF (5 mL) in the presence of NaH (60% inmineral oil, 68 mg, 1.71 mmol). The reaction was refluxed for 5 h.After cooling, the reaction mixture was evaporated and the residuewas purified by flash column chromatography (SiO2, EA/n-Hex 1/4).

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-benzyloxypyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Elkamhawy, Ahmed; Park, Jung-eun; Hassan, Ahmed H.E.; Pae, Ae Nim; Lee, Jiyoun; Paik, Sora; Park, Beoung-Geon; Roh, Eun Joo; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 268 – 278;,
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. 14508-49-7, name is 2-Chloropyrazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H3ClN2

General procedure: (0.1mole) of 2-halo nitrogen heterocycle and (0.5 mole) of hydrazine hydrate were mixed together in a 250mL round bottom flask equipped with reflux condenser and wereheated at 100oC, progress of the reaction was monitored byTLC. After completion of the reaction the reaction mixture was cooled to (-5-0oC) for 14hr and the precipitated solid was filtered and washed with two 5ml portions of ice coldwater and dried to give the compound 1 in good yield.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 14508-49-7.

Reference:
Article; Nitlikar, Lakshmikant H.; Darandale, Sunil N.; Shinde, Devanand B.; Letters in Organic Chemistry; vol. 10; 5; (2013); p. 348 – 352;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 59489-71-3,Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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 1; iV-(2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)benza mide (Compound 1-1)METHOD A:Step 1: 5-(4-(Isopropylsulfonyl)phenyl)pyrazin-2-amine[00187] 5-Bromopyrazin-2-amine (5 g, 28.74 mmol), (4-isopropylsulfonylphenyl) boronic acid (7.866 g, 34.49 mmol) and K3P04 (12.20 g, 57.48 mmol) were combined in MeCN (100 mL) / Water (25 mL) and Pd[P(tBu)3]2 (734.4 mg, 1.437 mmol) was added. The reaction was heated at 60 C for 1 hour. The reaction mixture was cooled to ambient temperature and diluted with EtOAc and water. The layers were separated and the aqueous layer extracted with EtOAc (x 3). The combined organic layers were dried (MgS04), filtered andconcentrated in vacuo. The residue was triturated from DCM and isolated by filtration to give the sub-title compound as an orange solid (6.43 g, 76% Yield). ¾ NMR (400.0MHz, DMSO) delta 1.17 (d, 6H), 3.43 (sept, IH), 6.86 (s, 2H), 7.87 (d, 2H), 8.00 (s, IH), 8.20 (d, 2H) and 8.67 (s, IH) ppm; MS (ES+) 278.2.

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-5-bromopyrazine, its application will become more common.

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

Reference of 912773-21-8, 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. 912773-21-8, name is 2-Bromo-5-chloropyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Preparation of ethyl 2-(5-chloropyrazin-2-yl)-2,2-difluoroacetate (39A) To a suspension of copper powder (244 g, 3877 mmol) in DMSO (5000 mL) was added ethyl 2-bromo-2,2-difluoroacetate (394 g, 1939 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 1 hour. 2-Bromo-5-chloropyrazine (250 g, 1292 mmol) was added to the reaction mixture portion-wise. The reaction mixture was stirred at ambient temperature for 3 hours. After the completion of reaction (monitored by TLC), the reaction mixture was quenched with aq. NH4C1 (2.0 L), filtrate through celite pad and filtrate was extracted with ethyl acetate (2 x 2 L). The combined organic extracts were dried over sodium sulfate and concentration under reduced pressure to get crude residue, which was purified by column chromatography (60-120 silica mesh, mobile phase 0- 2% ethyl acetate in hexane) affording ethyl 2-(5-chloropyrazin-2-yl)-2,2-difluoroacetate (39A) (215 g, 70% yield) as viscous clear liquid. lH NMR (400 MHz, DMSO-t/6) delta 9.05 (d, J = 1.4 Hz, 1H), 8.98 (dd, J= 1.4, 0.7 Hz, 1H), 4.39 – 4.34 (m, 2H), 1.24 (t, J= 7.1 Hz, 3H).

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-Bromo-5-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BOURBEAU, Matthew, P.; BROWN, James, A.; CHEN, Ning; FROHN, Michael, J.; LIU, Longbin; LIU, Qingyian; PETTUS, Liping, H.; QIAN, Wenyuan; REEVES, Corey, M.; SIEGMUND, Aaron, C.; (509 pag.)WO2017/24180; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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 C5H7Cl2N3

Intermediate 20. Step 7: (6R.8aS)-N-((3-chloropyrazin-2-yl)methyl)-2.2-dimethyl-3-oxooctahydroindolizine-6- carboxamide To a solution of (6R,8aS)-2,2-dimethyl-3-oxooctahydroindolizine-6-carboxylic acid (2.9 g, 13.74 mmol) in anhydrous DCM (137 mL) was added isopropyl carbonochloridate (2.02 g, 16.48 mmol) and Epsilon Nu (1.67 g, 16.48 mmol) at 0 C. The reaction mixture was stirred for 1 hour at room temperature. Then Epsilon Nu (2.78 g, 27.47 mmol) and (3-chloropyrazin-2-yl)methanamine hydrochloride (3.2 g, 17.86 mmol) was added , the reaction was stirred for 5 hours at room temperature. The solution was quenched with water, extracted with DCM and the combined organic layer was washed with water, brine and dried over anhydrous Na2SC>4. The organic layer was concentrated in vacuo. The crude was purified by silica gel column chromatography (PE/THF = 3/1) to afford (6R,8aS)-N-((3-chloropyrazin-2-yl)methyl)-2,2-dimethyl-3- oxooctahydroindolizine-6-carboxamide. 1H NMR (400 MHz, CDC13) delta ppm 1.08 – 1.28 (m, 6 H), 1.40 – 1.55 (m, 1 H), 1.70 – 1.91 (m, 2 H), 1.95 – 2.21 (m, 3 H), 2.36 (t, J = 12.4 Hz, 1 H), 2.87 (t, J= 12.4 Hz, 1 H), 3.40 (d, J = 7.6 Hz, 1 H), 4.32 (dd, Ji = 13.2, J2 = 3.2 Hz, 1 H), 4.70 (m, 2 H), 7.05 (s, 1 H), 8.32 (s, 1 H), 8.44 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939412-86-9, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph, A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; XU, Jiayi; YU, Wensheng; YU, Younong; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (211 pag.)WO2016/109221; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 108-50-9, A common heterocyclic compound, 108-50-9, name is 2,6-Dimethylpyrazine, molecular formula is C6H8N2, 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.

The synthetic route chosen to synthesize certain compounds are illustrated below and in Figures 1A-D.

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; EMORY UNIVERSITY; GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.; SHIM, Hyunsuk; MOORING, Suazette Reid; BAI, Renren; (89 pag.)WO2017/11517; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6966-01-4, The chemical industry reduces the impact on the environment during synthesis 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, I believe this compound will play a more active role in future production and life.

Preparation 9. Synthesis of 3-amino-6-bromopyrazine-2-carbohydrazide[00222] Step 1 : To a suspension of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (2.5 g, 10.8 mmol) in ethanol (50 mL) was added hydrazine hydrate (3.2 g, 3 mL, 64.6 mmol) and the reaction mixture heated at 70 C for 1.5 hours forming a thick yellow solid. The reaction mixture was filtered and the solid washed with water (20 mL) and ethanol (40 mL). The solid was dried in vacuo to yield 3-amino-6-bromo-pyrazine-2-carbohydrazide (2.7 g, 94% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 4.53 (d, J = 3.5 Hz, 2H), 7.62 (s, 2H), 8.31 (s, 1H) and 9.78 (s, 1H) ppm; LC/MS m/z 233.1 [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, Methyl 3-amino-6-bromopyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; MACCORMICK, Somhairle; STORCK, Pierre-Henri; PINDER, Joanne; O’DONNELL, Michael, Edward; KNEGTEL, Ronald Marcellus, Alphonsus; YOUNG, Stephen, Clinton Young; KAY, David; REAPER, Philip, Michael; DURRANT, Steven, John; TWIN, Heather, Clare; DAVIS, Christopher, John; WO2012/138938; (2012); A1;,
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. 274-79-3, name is Imidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

lmidazo[1 ,2-a]pyrazine (0.715 g, 6 mmol, Intermediate 1 ), 2-bromopyridine (0.644 ml_, 6.60 mmol), triphenylphosphine (0.315 g, 1.200 mmol), and palladium(ll) acetate (0.135 g, 0.600 mmol) were heated in Lambda/,Lambda/-dimethylacetamide (DMA) (8 ml.) at 150 0C for 5 hr in a microwave reactor. The bulk of the DMA was removed in vacuo and the residue partitioned between 10% isopropanol/DCM (100 ml) and saturated sodium bicarbonate solution (50 ml). Solids were removed by filtration through celite and the filtrated separated. The aqueous phase was extracted with 10% isopropanol/DCM (3 x 50 ml. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to afford a crude oil, (2.6 g). The crude oil was partially purified by flash chromatography (Biotage SP4, 40+M, eluting with a 0-100% gradient of [(2M ammonia methanol/Ethyl acetate]/ethyl acetate) to afford material (1.59 g) which was repurified by flash chromatography (Biotage SP4, 40+M, eluting with a 0-100% gradient of [(2M ammonia methanol/Ethyl acetate]/ethyl acetate) to afford 3-(2-pyridinyl)imidazo[1 ,2-a]pyrazine (0.319 g, 1.626 mmol, 27.1 % yield).1H NMR (CDCI3, 400 MHZ) d 9.82 (dd, 1 H, J = 3.6, 1.2 Hz), 9.19 (d, 1 H, J = 1.6Hz), 8.72 (1 H, m), 8.03 (d, 1 H, J = 4.8 Hz), 7.84-7.91 m (2H), 7.29-7.21 m (2H).

According to the analysis of related databases, 274-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (2010); 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 59303-10-5 as follows. Application In Synthesis of 2-Chloro-5-methylpyrazine

A mixture of N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide (600 mg), 2-chloro-5-methyl-pyrazine (100 mg), and cesium carbonate (300 mg) in N,N-dimethylformamide (10 mL) is stirred for 3 days at 80 C. After cooling to room temperature ethyl acetate and water are added. The organic phase is separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (ethyl acetate/methanol 7:3) to give the title compound. LC (method 1): tR=1.08 min; Mass spectrum (ESI+): m/z=404 [M+H]+.

According to the analysis of related databases, 59303-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NOSSE, Bernd; BLUM, Andreas; BREITFELDER, Steffen; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; WELLENZOHN, Bernd; ASHWEEK, Neil J.; HARRIOTT, Nicole; US2013/65906; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem