Tag: M.W=100-200

Reference of 123-32-0, A common heterocyclic compound, 123-32-0, name is 2,5-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.

Preparation of 3,6-dimethyl-2- (2-thenoyl) pyrazine, comprising the steps of:(1) 2,5-dimethyl pyrazine take 0.2mmol, 2- benzoyl-carboxylic acid thiophene 0.4mmol, 0.02 mmol silver phosphate, potassium persulfate 5mL reaction tube was placed 0.4mmol, 1.4mL was added dichloro methane, 0.6 mL of distilled water was added, and the reaction mixture was placed in a 5mL tube and placed in an oil bath at 40 heated, reaction 24h, cooled to room temperature to obtain a reaction solution;(2) The step (1) the resulting reaction mixture was directly concentrated to give a concentrate, the concentrate with ethyl acetate / petroleum ether = 1/2 (v / v) as the developing solvent, separation by thin layer chromatography to give 30mg target The product, in 69% yield.

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; Henan Agricultural University; Wu Zhiyong; Zhao Mingqin; Li Yuan; (10 pag.)CN108101856; (2018); A;,
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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 91476-80-1

The title compound was prepared from 5,6,7,8-tetrahydroimidazo[1,2-c]pyrazine (31.3 mg, 0.254 mmol, from Step B), (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(3,4-difluorophenyl)butanoic acid (80 mg, mmol), DIPEA (32.8 mg, 0.254 mmol), HOBT (41.2 mg, 0.305 mmol) and EDC (73 mg, 0.381 mmol) in 5 mL of dichloromethane, using a procedure analogous to that described in Example 1, Step C. Purification by HPLC (Gilson; YMC-Pack Pro C18 column, 100×20 mm I.D.; solvent gradient system from 10% acetonitrile, 90% water, and 0.1% trifluoroacetic acid to 90% acetonitrile, 10% water, and 0.1% trifluoroacetic acid) gave 75 mg of the title compound as a viscous oil. 1H NMR (500 MHz, CDCl3) delta 1.38 (s, 9H), 2.05 (bs, 1H), 2.62 (m, 2H), 2.89 (m, 2H) 3.81-4.04 (m, 5H), 4.64-4.88 (m, 2H). 5.38 (m, 1H) 6.88 (m, 2H), 7.05 (m, 3H). ESI-MS 421 (M+1)

According to the analysis of related databases, 91476-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Corp.; Edmondson, Scott D.; Fisher, Michael H.; Kim, Dooseop; Maccoss, Malcolm; Parmee, Emma R.; Weber, Ann E.; Xu, Jinyou; US2015/359793; (2015); A1;,
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Pyrazine | C4H4N2 – PubChem

Electric Literature of 36070-80-1,Some common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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 title compound is prepared by essentially following the procedure of Method C, using 5-chloro-pyrazine-2-carboxylic acid (Kiener, A.; Roduit, J.-P.; Tschech, A.; Tinschert, A.; Heinzmann, K. Synlett 1994, 814-16), (0.096 g, 1.20 mmol), oxalyl chloride (0.35 mL, 3.99 mmol) and N*2*-(2-dimethylamino-ethyl)-N*2*-methyl-benzothiazole-2,6-diamine (0.20 g, 0.80 mmol) to afford 0.21 g, (67%). MS (m/z): calcd for Ci7Hi9ClN6OS (M+H)+: 391.9; found: 391.2.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/66173; (2006); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 1174321-06-2, name is 5-(Difluoromethyl)pyrazine-2-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. name: 5-(Difluoromethyl)pyrazine-2-carboxylic acid

Example 193 N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-5-(difluoromethyl)pyrazine-2-carboxamide The title compound was synthesized by procedures and steps analogous to those described in Method Z, Example 186 above, but using 5-(difluoromethyl)pyrazine-2-carboxylic acid (Aurigene Discovery Technologies). MS m/z=466.1 [M+H]+. Calculated for C18H14F7N5O2: 465.32 1H NMR (300 MHz, CHLOROFORM-d) delta=9.65 (br. s., 1H), 9.52 (s, 1H), 8.93 (s, 1H), 8.14-8.02 (m, 1H), 7.15 (br. s., 1H), 6.99-6.60 (m, 1H), 4.13-3.98 (m, 1H), 2.81 (d, J=13.6 Hz, 1H), 1.94 (t, J=13.1 Hz, 1H), 1.67 (s, 3H)

The synthetic route of 5-(Difluoromethyl)pyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 870787-06-7, name is 3-(Trifluoromethyl)pyrazine-2-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. Product Details of 870787-06-7

N- [2- (3,5- dichloro-pyridin-2-yl) -2- (tert- Butokishiimino) ethyl] -3-(trifluoromethyl) pyrazine-2-carboxamide 3- (tri N in dichloromethane 3ml solution of fluoromethyl) pyrazine-2-carboxylic acid 74mg, added N- dimethylformamide 10mg and oxalyl chloride 57mg, I was stirred at room temperature for 1 hour.After completion of the reaction, distilling off the solvent under reduced pressure, the residue was dissolved in dichloromethane 10ml, stirring under ice cooling, 2-amino-1- (3,5-dichloro-2-yl) ethanone -O- ( was added tert- butyl) oxime and triethylamine 89mg 39mg, it was continued for a further 1 hour stirring at room temperature.After completion of the reaction, extracted with added water 10ml reaction mixture chloroform (10mlx1), and the organic layer brine then dehydrated and dried in this order over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.The residue was ethyl acetate – hexane (1: 9 to 3: 7 gradient) was purified by silica gel column chromatography eluting with a respective geometric isomers 22mg (isomer A) of the object and 111mg (isomers The B) it was obtained as a colorless resin-like substance

The synthetic route of 3-(Trifluoromethyl)pyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES LIMITED; Iwasa, Motoyoshi; Tomizawa, Mitsutaka; Tsuji, Keisuke; Nakamura, Toshiyuki; Mita, Takeshi; Kuwahara, Hidehito; asahi, Miho; Imanaka, Hotaka; (342 pag.)JP2016/11286; (2016); A;,
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 912773-21-8 as follows. Safety of 2-Bromo-5-chloropyrazine

A mixture of 2-bromo-5-chloro-pyrazine (4 g, 20.68 mmol), 2-benzyloxy-3-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (6.81 g, 20.68 mmol), CS2CO3 (13.47 g, 41.36 mmol) and Pd(dppf)Cl2 (2.27 g, 3.1 mmol) in 1,4- dioxane (30 mL) and water (3 mL) was stirred at 50 C under N2 for 16 hours. After cooling to room temperature, the mixture was filtered, and the filtrate was concentrated. Water (50 mL) was added and the aqueous layer was extracted with EtOAc (50 mL x 2). The combined organic layer was washed with brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 15% to 30%) to give the product (5.5 g, 17.42 mmol, 84% yield) as a solid. ‘H NMR (400MHz, DMSO-r) dH= 9.15 (s, 1H), 8.85 (s, 1H), 8.77 (s, 1H), 8.37 (d, 1H), 7.52 – 7.46 (m, 2H), 7.44 – 7.32 (m, 3H), 5.51 (s, 2H).

According to the analysis of related databases, 912773-21-8, the application of this compound in the production field has become more and more popular.

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

Some common heterocyclic compound, 768-05-8, name is Pyrazinoic acid hydrazide, molecular formula is C5H6N4O, 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. COA of Formula: C5H6N4O

General procedure: To the solution of pyrazine carboxylic acid hydrazide (0.55 g, 4 mmol) in methanol (30 mL) was added dropwise with continuous stirring, a solution of 2-benzoyl pyridine (0.73 g, 4 mmol) in the same solvent. The reaction mixture was then refluxed for 5 h. The solid product so obtained was filtered and recrystallised in hot methanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 768-05-8, its application will become more common.

Reference:
Article; Devi, Jai; Batra, Nisha; Malhotra, Rajesh; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 97; (2012); p. 397 – 405,9;,
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. 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. category: Pyrazines

[0538] To a mixture of (R)-5-(2-(4-aminopiperidin-1-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride(60 mg, 0.16 mmol) and 5-cyano-2-fluoropyridine (20 mg, 0.16 mmol) in N-methylpyrolidinone (550 ml) was addedDIEA (57 ml, 0.33 mmol) in a microwave tube at room temperature. The tube was sealed and heated at 100C for 4 h.The mixture was cooled and partitioned between EtOAc/hexanes (2:1) and water. The aqueous layer was extractedwith EtOAc (2x). The combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated. Theresulting residue was purified by prep TLC (silica gel, 10% MeOH/DCM) to provide (R)-6-(1-(2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperidin-4-ylamino)nicotinonitrile. 1H-NMR (CDCl3, 500 MHz), delta 8.39 (m, 1H),7.82 (s, 2H), 7.60 (m, 1H), 6.41 (m, 1H), 5.29 (s, 2H), 4.92 (m, 1H), 3.23 (m, 1H), 2.96 (m, 1H), 2.39-2.46 (m, 4H), 2.18(s, 3H), 2.02 (m, 4H); LC-MS (IE, m/z): 393 [M + 1]+:_[0542] 5-((1R)-2-(6-([1,2,4]Triazolo[4,3-a]pyrazin-8-ylamino)-3-azabicyclo[3.1.0]hexan-3-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one was prepared in a similar fashion to that described for the synthesis of EXAMPLE 111 startingfrom 5-((1R)-2-(6-Amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochlorideand 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine. _LC-MS (IE, m/z): 407 [M + 1]+.

The synthetic route of 68774-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; (136 pag.)EP2755656; (2016); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 4744-50-7,Some common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, molecular formula is C6H2N2O3, 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 stirred solution of 5.05 g (33.63 mmol) of commercially available 2,3- pyrazinedicarboxylic anhydride in 300 mL of CHCI3 was added 12.34 g (33.63 mmol) of (tert-butoxycarbonylmethylene)-triphenylphosphorane. The resulting solution was heated to 62 C for 2 days. The reaction mixture was concentrated in vacuo and the residue purified via flash column chromatography over silica gel (monitored by thin layer chromatography) and eluted with 1 : 1 (v/v) hexanes:ethyl acetate. Evaporation of the collected fractions yielded 2.99 g (36% yield) of (E)l(Z)-tert-buty 2-(7-oxofuro[3,4-b]pyrazin-5(7H)-ylidene)acetate (Compound 1) as a mixture of geometrical isomers (~1 : 1) that was not separated: 1H NMR (CDCI3, 300 MHz): 5ppm 9.03 (d, J= 2.4 Hz, 1H), 8.96 (d, J= 2.4 Hz, 1H), 8.92 (d, J= 2.4 Hz, 1H), 8.90 (d, J= 2.4 Hz, 1H), 6.32 (s, 2H), 1.58 (s, 18H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Pyrazinecarboxylic anhydride, its application will become more common.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; WASMUTH, Andrew; LANDRY, Donald, W.; DENG, Shi, Xian; RAMASAMY, Ravichandran; SCHMIDT, Ann Marie; MYLARI, Banavara, L.; WO2012/9553; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 57948-41-1, These common heterocyclic compound, 57948-41-1, name is 3-Bromoimidazo[1,2-a]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.

3-Bromoimidazo[1 ,2-a]pyrazine (1.66 g, 7.13 mmol, Intermediate 2), sodium carbonate (3.78 g, 35.6 mmol) and phenylboronic acid (1.043 g, 8.55 mmol) were dissolved in 1 ,2-dimethoxyethane (DME) (40 ml) and water (20 ml). Bis(triphenylphosphine)palladium (II) chloride (0.250 g, 0.356 mmol) was added and the biphasic solution heated at 80 0C for 16 h. The aqueous phase was extracted with ethyl acetate (3 x 100ml) and the combined extracts washed with saturated sodium bicarbonate solution (100 ml), water (100 ml), brine (100 ml) and dried by passing through a hydromatrix cartridge (Varian). The filtrate was concentrated in vacuo to afford a crude oil (2.44g). The crude product was purified by flash chromatography (Biotage SP4, 40+M, eluting with a 0-100% gradient of ethylacetate in hexane) – (the product elutes in 100% ethyl acetate), to afford 3- phenylimidazo[1 ,2-a]pyrazine (1.22 g, 6.25 mmol, 88 % yield). LC/MS [M+H]+ = 196, retention time = 1.63 minutes (5 minute method).

Statistics shows that 3-Bromoimidazo[1,2-a]pyrazine is playing an increasingly important role. we look forward to future research findings about 57948-41-1.

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