Tag: M.W=100-200

Related Products of 68774-77-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 68774-77-6 name is 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A mixture of chloro compound (50 mg) and amine derivative (2 equiv.) in PEG 400 (2 mL) wasstirred at 120 C for 5 min. After completion the reaction was then cooled to room temperature. DCM and water were added and the phases were separated. The aqueous phase was extracted withDCM and the organic phase was dried and filtered. The removal of solvent gave the product as solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Chloro[1,2,4]triazolo[4,3-a]pyrazine, and friends who are interested can also refer to it.

Reference:
Article; Campos, Joana F.; Loubidi, Mohammed; Scherrmann, Marie-Christine; Berteina-Raboin, Sabine; Molecules; vol. 23; 3; (2018);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1435953-98-2, name is 5-Methoxy-3-methylpyrazin-2-amine, 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 1435953-98-2, category: Pyrazines

l,l’-Thiocarbonyldiimidazole (226 mg, 1.21 mmol) and then hydrochloric acid in dioxane (0.55 mL, 2.2 mmol, 4 mol/L) were added to a solution of 5-methoxy-3-methyl-pyrazin-2-amine (153 mg, 1.10 mmol) in DCM (5.5 mL) under air. The reaction was stirred at r.t. for 4 hours, filtered and the solid washed with DCM (2 x 10 mL). The filtrate was concentrated in vacuo and purified by flash column chromatography on silica (gradient elution with 0% to 100% EtOAc in isohexanes) to give the title compound (127 mg, 40 % Yield). A few drops of isobutylamine were added to the LCMS sample of the product before analysis LCMS [M+H]+ 255, RT 1.46 minutes [M = l-isobutyl-3-(5-methoxy-3- methyl-pyrazin-2-yl)thiourea] (Method 4).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methoxy-3-methylpyrazin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 22047-25-2, name is Acetylpyrazine, 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 22047-25-2, Formula: C6H6N2O

General procedure: A 100 mL round-bottom flask charged with 2-acetylpyrazine (1.47 g, 2 mmol) was added MeOH (30 mL), KOH pellets (0.675 g,2 mmol) and water (2 mL). The resulting mixture was stirred for10 min and then added corresponding n,n?-dimethoxybenzaldehydes (1.0 g, 1 mmol) and ammonium solution (6 mL) was added slowly stirring at room temperature for 4 h, a white precipitate obtained was filtered, washed with MeOH and diethyl ether. The crude products on recrystallization in a mixture of CHCl3:MeOH (1:1) gave white crystals of desired compounds, 1-4. 2,2?-[4-(2,3-dimethyoxyphenyl)pyridine-2,6-diyl]dipyrazine(1): Yield: 65%; M.P.: 212 C; 1H NMR (400 MHz, CDCl3, delta ppm): 3.737 (s, 3H, OCH3), 3.945 (s, 3H, OCH3), 7.041e7.045 (d, 1H, ArHC4),7.114e7.119 (d, 1H, ArHC6), 7.134e7.165 (t, 1H, ArHC5), 8.635-8.650(t, 4H, pz, HAA’5,6), 8.683 (s, 2H, pz, HAA’3), 9.869-9.871 (s, 2H, py,HB3,5); 13C{1H} NMR (100 MHz, CDCl3, delta ppm): 153.84 (C2,6 of py),151.02 (C4 of py), 148.73 (C3,30 of pz), 144.58 (C6,60 of pz), 143.57(C5,50 of pz), 133.59 (C6 of ph), 122.11 (C1 of ph), 122.04 (C3,5 of py),110.77 (C5 of ph), 101.31 (C3 of ph), 61.06 (OCH3), 55.08 (OCH3); FTIR (KBr disc, nu cm-1): 2965 (w), 1739 (s), 1588 (m), 1465 (s), 1415(m), 1365 (s), 1270 (s), 1220 (m), 1109 (s), 1053 (s), 1003 (s), 852 (s),786 (s).

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:
Article; Golla, Ramesh; Kumar, P. Raghavendra; Suchethan; Foro, Sabine; Nagaraju; Journal of Molecular Structure; vol. 1201; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 89123-58-0, A common heterocyclic compound, 89123-58-0, name is 5-Bromopyrazine-2,3-diamine, molecular formula is C4H5BrN4, 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 50 mL round bottom flask fitted with a reflux condenser, under nitrogen were added 5-bromopyrazine-2,3-diamine (400 mg, 2.1 mmol) and triethyl orthoformate (3.1 g, 21.2 mmol). The mixture was heated to reflux and stirred for 24 h. The reaction was cooled to rt, concentrated to dryness and the residue purified by HPLC to give 320 mg (76% yield) of the title compound. MS (ESI): mass calcd. for C5H3BrN4, 197.95; m/z found, 199.1 [M+H]+.

The synthetic route of 89123-58-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2015/252008; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 13134-31-1,Some common heterocyclic compound, 13134-31-1, name is 2,3-Diaminopyrazine, molecular formula is C4H6N4, 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) 2-(2,4-Dimethoxy-5-chlorosulfonyl-phenyl)-imidazo-[4,5-b]-pyrazine was prepared analogous to Example 2 from 2,3-diaminopyrazine and 2,4-dimethoxy-5-chlorosulfonyl-benzoylchloride. M.p. 294-296 C.

The synthetic route of 13134-31-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Karl Thomae GmbH; US4656171; (1987); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

17231-51-5, name is 3-Amino-6-bromopyrazine-2-carbonitrile, 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: C5H3BrN4

Step 2 : (EJ-S-amino–bromo-TV-hydroxypyrazine-l-carboximidamide[00568] 3-amino-6-bromo-pyrazine-2-carbonitrile (4.5958 g, 23.09 mmol) was dissolved in MeOH (91.92 niL), cooled to 00C and treated with hydroxylamine hydrochloride (1.605 g, 23.09 mmol) and triethylamine (2.336 g, 3.218 mL, 23.09 mmol). The reaction was allowed to warm to ambient temperature, stirred for 48 hours and then evaporated to dryness. Methanol (a minimum amount) was added, the mixture sonicated, filtered and washed with MeOH to give the product as a brown solid 5.27 g, 98% Yield). IH NMR (400.0 MHz, DMSO) d 5.88 (s, 2H), 7.64 (br s, 2H), 8.14 (s, IH) and 10.38 (s, IH) ppm; MS (ES+) 233.75

The synthetic route of 17231-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-damien; DURRANT, Steven; KAY, David; O’DONNELL, Michael; KNEGTEL, Ronald; MACCORMICK, Somhairle; PINDER, Joanne; VIRANI, Anisa; YOUNG, Stephen; BINCH, Hayley; CLEVELAND, Thomas; FANNING, Lev, T.d.; HURLEY, Dennis; JOSHI, Pramod; SHETH, Urvi; SILINA, Alina; WO2010/54398; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 88625-24-5, name is 5-Chloropyrazine-2-carbaldehyde, 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 88625-24-5, Product Details of 88625-24-5

A solution of 5-chloropyrazine-2-carbaldehyde (5.20 g, 36.5 mmol) in 50 mL of methanol was cooled to O0C. Sodium borohydride (1.45 g, 38.3 mmol) was added and the reaction mixture was allowed to stir at ambient temperature for 3 hour. Saturated aqueous ammonium chloride (5 mL) was added, and the methanol was removed in vacuo. The resulting residue was dissolved in ethyl acetate (50 mL) and washed with aqueous sodium bicarbonate (2 x 50 mL) and brine (50 mL). The combined organic extracts were dried, filtered and concentrated in vacuo to provide the title compound that gave a proton NMR spectra consistent with theory.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloropyrazine-2-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/134668; (2009); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 121246-96-6, These common heterocyclic compound, 121246-96-6, name is 3-Chloropyrazine-2-carbaldehyde, 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.

2,2,6,6-Tetramethylpiperidine (19.7ml, 117mmol) was added to a solution of n-butyl lithium (69.3ml of a 1.6M solution in hexane, lllmmol) in anhydrous THF (200ml) at -760C under an atmosphere of nitrogen, keeping the reaction temperature below -7O0C. The reaction mixture was stirred at -7O0C for 15 minutes then allowed to warm to O0C and stirred for a further 30 minutes before being cooled to -760C. 2-Chloropyrazine (1Og, 87.3mmol) was added dropwise such that the reaction temperature was kept below -7O0C. The reaction mixture was then stirred at -700C for 30 minutes. Ethyl formate (7.5ml, 98mmol) was then added such that the reaction temperature was kept below -700C. The reaction mixture was then stirred at -7O0C for 1.5 hours. Glacial acetic acid (13ml,.218mmol) was added at -7O0C and the mixture then allowed to warm to ambient temperature and the volatiles were removed by evaporation. The residue dissolved in ethanol (100ml) and hydroxylamine (6.83g, 105mmol) and triethylamine (24.2ml, 175mmol) were added. The mixture was heated at 500C for 18 hours and the volatiles were then removed by evaporation. The residue was dissolved in diethylether and any remaining insoluble material was removed by filtration. The filtrate was washed with water, the solvent removed from the organic layer by evaporation and the residue purified by chromatography on silica gel eluting with DCM, then with diethylether / DCM (1:4) and finally with EtOAc to give 3-chloropyrazine-2- carboxaldehyde oxime (5.21g, 37.9%) as a solid; NMR Spectrum 8.37 (s, IH), 8.50 (d, IH), 8.70 (d, IH), 12.25 (s, IH).

The synthetic route of 121246-96-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/106307; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 313339-92-3, 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. 313339-92-3, name is 3,5-Dichloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

11360] tert-l3utyl (2R,3R)-2-methylpiperidin-3-ylcarbam- ate (310) (1.1 g, 5.1 mmol) was dissolved in THF (20 mE).the stirred solution was added DIEA (1.34 mE, 7.7 mmol), followed by 3,5-dichloropyrazine-2-cabonitrile (1.07 g,mmol). The reaction was stirred at room temperature forhout An additional amount of 3,5-dichioropyrazine-2-carbo- nitrile (200 mg, 1.2 mmol) was added, and the reaction was stirred for another hour. The solvent was removed under reduced pressure, and the residue was suspended in EtOAc. The organic mixture was washed with iN HC1 (aq), saturated NaHCO3(aq) and brine, dried, and concentrated in vacuo. The residue was then purified by silica flash column chromatography (EtOAc/hexanes) to give tert-butyl (2R,3R)-1 -(6- chioro-5-cyanopyrazin-2-yl)-2-methylpiperidin-3-ylcar- bamate (311), (1.54 g, 4.38 mmol, 86% yield).

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

Reference:
Patent; JIA, Zhaozhong J.; CHEN, Wei; THOMAS, William D.; US2015/158865; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4744-50-7, A common heterocyclic compound, 4744-50-7, name is 2,3-Pyrazinecarboxylic anhydride, molecular formula is C6H2N2O3, 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.

General procedure: A solution of 3,4,5-trimethoxyaniline (1.83 g, 10 mmol) and acid anhydride (10 mmol) in glacial acetic acid (15 mL) was heated under reflux for 12 h. After the evaporation of the reaction mixture to dryness under reduced pressure, the residue was neutralized by a solution of sodium bicarbonate (4%) until effervescence ceased. The precipitate obtained was washed with water, dried (P2O5) and recrystallized from an appropriate solvent.

The synthetic route of 4744-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abdel-Aziz, Alaa A.-M.; Eltahir, Kamal E.H.; Asiri, Yousif A.; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1648 – 1655;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem