Tag: M.W=100-200

Reference of 5521-58-4, A common heterocyclic compound, 5521-58-4, name is 5-Methylpyrazin-2-amine, molecular formula is C5H7N3, 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.

l-Chloro-N,N,2-trimethyl-l-propenylamine (0.042 mL, 0.31 mmol) was added to a solution of 3- { [5-(azetidin- 1 -ylcarbonyl)pyrazin-2-yl]oxy }-5- { [(Ii?)- 1 -methyl-2- (methyloxy)ethyl]oxy}benzoic acid (0.102 g, 0.0.31 mmol) in DCM (3 mL) under argon and stirred at RT for 40 minutes. 2-Amino-5-methylpyrazine (57 mg, 0.52 mmol) and pyridine (0.043 mL, 0.52 mmol) were added and the reaction stirred for a further 3 hours. The solvent was removed in vacuo and the residue taken up in ethyl acetate (30 mL), washed with water (2 x 10 mL), a saturated aqueous solution of sodium bicarbonate (10 mL), brine (10 mL), dried (MgSO4), filtered, and evaporated in vacuo. The crude material was chromatographed on silica, eluting with a gradient of 60-100% ethyl acetate in isohexane, to give the desired compound as a white foam (86 mg). SUP>1H NMR delta (CDCl3): 1.35 (d, 3H), 2.32 – 2.44 (m, 2H), 2.56 (s, 3H), 3.41 (s, 3H), 3.47 – 3.64 (m, 2H), 4.26 (t, 2H), 4.62 (q, IH), 4.69 (t, 2H), 6.98 (s, IH), 7.29 (s, IH), 7.41 (s, IH), 8.13 (s, IH), 8.35 (s, 2H), 8.86 (s, IH), 9.54 (s, IH); m/z 479 (M+H)⁺

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7041; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 939412-86-9, 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of SM (1.4 g, crude, 7.8 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (1.4 g, 7.8 mmol), HATU (2.7 mg, 7.8 mmol) and TEA (3.2 mg, 31.2 mmol) in DCM (30 mL) was stirred at 25C overnight. The mixture was quenched with H20 (60 mL) and it was extracted with DCM (25 mL X 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was purified by prep- TLC to give 1 (1.3 g, 50 %). LCMS: m/z = 309 [M+H]+.

The synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIAO, Xibin; SUZHOU BAIJIBUGONG PHARMACEUTICAL TECHNOLOGY CO. LTD.; LI, Jia; LU, Zhijian; ZHOU, Yubo; GAO, Anhui; (100 pag.)WO2018/175512; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 68774-77-6, name is 8-Chloro[1,2,4]triazolo[4,3-a]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 68774-77-6, HPLC of Formula: C5H3ClN4

A mixture of crude 4-methylbenzyl 4-(aminomethyl)-3,3-difluoropiperidine-1-carboxylate (600mg, 2.0 mmol), 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine (360 mg, 2.0 mmol) and DIPEA (0.76 mL, 4.0 mmol) in butyl alcohol (10 mL) was heated at 130 C overnight. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The concentrate was purified by column chromatography over silica gel (100% ethyl acetate) to afford the title compound as a light gray powder (150 mg, 18%). MS (ESI) calcd for C20H22F2N602: 416.2; found: 417.3 [M+H]. 1H NMR (400MHz, CD3OD) 6 9.16 (s, 1H), 7.77 (d, J = 4.8 Hz, 1H), 7.29 (d, J = 4.8 Hz, 1H), 7.24 (d, J = 8.0 Hz, 2H), 7.17 (d, J = 8.0 Hz, 2H), 5.09 (s, 2H), 4.33 (br s, 1H), 4.19-4.15 (m, 1H), 4.05-3.95 (m, 1H), 3.72-3.58 (m, 1H), 3.25-2.90 (m, 2H), 2.67-2.51 (m,1H), 2.33 (s, 3H), 1.99-1.93 (m, 1H), 1.62-1.52 (m, 1H).

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:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (246 pag.)WO2016/196513; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

3149-28-8, Adding some certain compound to certain chemical reactions, such as: 3149-28-8, name is 2-Methoxypyrazine, 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 3149-28-8.

To a solution of 2-methoxypyrazine (5.0g, 45.4mmol), in 40ml of anhydrous THF was added tributyltin hydride (15.0mL, 54.9mmol) and the resulting solution stirred under nitrogen at 0C. Cyclohexylcarbonyl chloride (8.0mL, 59.8mmol) was added over 10min and stirring continued until reaction completion in 20min as determined by TLC (neutral alumina, EtOAc/hexanes (1/19, v/v)). A 1M solution of HCl in methanol (20.0mL) was then added to the reaction mixture that was stirred under nitrogen at 0C until reaction completion in 30min as determined by TLC (SiO2, EtOAc/hexanes (2/3, v/v). The reaction mixture was quenched with 50mL of water, extracted with ethyl acetate (3×50mL), washed with saturated sodium bicarbonate (10mL), and then dried over anhydrous Na2SO4. Purification by silica gel flash column chromatography (100% hexanes: to remove tin by-products, followed by methanol / dichloromethane 2-5%) afforded 4-cyclohexanecarbonyl-1,2-dihydro-2-pyrazinone 3 (8.9g, 94%) as a pale yellow solid (mp 160-163C dec).

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 3149-28-8.

Reference:
Article; Williams, Alfred L.; St. Hilaire, Valentine R.; Tetrahedron; vol. 73; 48; (2017); p. 6712 – 6717;,
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. 100047-56-1, name is 5-Bromo-3-methylpyrazin-2-ol, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H5BrN2O

(ls,4s)-4-(l-Methylpiperidin-4-yloxy)cyclohexanol (1.2 g, 5.63 mmol) was dissolved inTHF (10 mL), 5-bromo-3-methylpyrazin-2-ol (1.170 g, 6.19 mmol) and triphenylphosphine (1.771 g, 6.75 mmol) were added, then cooled down in an ice -water bath. DIAD (1.329 ml, 6.75 mmol) was added dropwise under N2. The reaction mixture was slowly warmed to room temperature, stirred overnight, and concentrated. The residue was purified by preparative HPLC (15-80% CH3CN/H20 with 0.1 % TFA over 30 min) and column chromatography (5% methanol/ethyl acetate containing 1 % Et3N) to give the title compound (525 mg, 1.366 mmol, 24.3% yield). Exact mass calculated for Ci7H26BrN302: 383.1 , found: LCMS m/z = 384.2[M+H]+; lU NMR (400 MHz, CDC13) 5 ppm 1.45-1.62 (m, 4H), 1.65-1.75 (m, 2H), 1.91-2.05 (m, 4H), 2.05-2.15 (m, 2H), 2.39 (s, 3H), 2.36-2.42 (m, 2H), 2.42 (d, J = 0.7 Hz, 3H), 2.78-2.85 (m, 2H), 3.46-3.54 (m, 2H), 4.95-5.02 (m, 1H), 7.98 (d, J = 0.6 Hz, 1H).

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; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; BUZARD, Daniel J.; LEHMANN, Juerg; NARAYANAN, Sanju; YUE, Dawei; WO2011/127051; (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, Formula: C4H2Cl2N2

A solution of compound 8 (450.0 g, 3.02 mol) in cone. aq. NH3 (3.0 L) was stirred at 135°C overnight in a 10 L sealed pressure vessel. TLC and LC/MS showed complete conversion of the starting material. The reaction mixture was cooled to room temperature and filtered to afford a white solid. The solid was washed with water (200 mL x 3), and then dried to afford compound 9 (312 g, 80percent yield) as a solid. 1HNMR (400 MHz, DMSO- 6): delta 7.82 (s, 1 H), 7.12 (s, 1 H), 6.93 (s, 2H). MS Calcd.: 129 MS Found: 130 ([M+H]+).

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; IMARA, INC.; H. LUNDBECK A/S; SVENSTRUP, Niels; PARACHIKOVA, Anna I.; MCARTHUR, James; (133 pag.)WO2018/9424; (2018); A1;,
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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, A new synthetic method of this compound is introduced below., category: Pyrazines

Diisobutylaluminium hydride (1.0 M in toluene; 6.4 mL, 6.40 mmol) was added dropwise to a cooled solution of methyl 5-chloropyrazine-2-carboxylate (690 mg, 4.00 mmol) in THF (13.6 mL) at -55 C. The reaction was stirred under these conditions for 1 hour and then quenched by addition of saturated aqueous NH4C1 (25 mL) and EtOAc (25 mL). An emulsion formed and 2N aqueous HC1 was added to clear the emulsion (5 mL). The layers were separated, and the aqueous layer was extracted with EtOAc. The organic layerwas washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in heptane. Product fractions were evaporated to dryness to afford 5-chloropyrazine-2-carbaldehyde (385 mg, 68%) as a beige solid. ?H NMR (500 MHz, CDC13, 27 C) 8.75 (1H, d), 8.96 (1H, d), 10.15 (1H, 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; ASTRAZENECA AB; SCOTT, James, Stewart; MOSS, Thomas, Andrew; YANG, Bin; VARNES, Jeffrey, Gilbert; O’DONOVAN, Daniel, Hillebrand; NISSINK, Johannes, Wilhelmus, Maria; HUGHES, Samantha, Jayne; BARLAAM, Bernard, Christophe; WU, Dedong; BROO, Dan, Anders; (224 pag.)WO2018/19793; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 88625-24-5, 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. 88625-24-5 name is 5-Chloropyrazine-2-carbaldehyde, 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.

2) N,N-dimethylformamide (10 mL) was added to 5-chloropyrazine-2-carbaldehyde (500 mg), methyl 2,2-dimethyl-3-{[4-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)pyridin-2-yl]oxy}propanoate (1410 mg) and 2N aqueous sodium carbonate solution (5.26 mL), and after replacing the atmosphere with nitrogen, palladium chloride (dppf) methylene chloride complex (143 mg) was added to the mixture and the resulting mixture was stirred at 65C for 2 hours. To the reaction mixture were added ethyl acetate and water, and the liquids were separated. After filtration with Celite, the organic layer was separated, washed with water and then with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=100:0 to 70:30) to obtain methyl 3-{[5-(5-formylpyrazin-2-yl)-4-methylpyridin- 2-yl]oxy}-2,2-dimethylpropanoate (855 mg). MS (m/z): 330 [M+H]+

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; MITSUBISHI TANABE PHARMA CORPORATION; SAKURAI, Osamu; SARUTA, Kunio; HAYASHI, Norimitsu; GOI, Takashi; MOROKUMA, Kenji; TSUJISHIMA, Hidekazu; SAWAMOTO, Hiroaki; SHITAMA, Hiroaki; IMASHIRO, Ritsuo; WO2012/81736; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 89123-58-0, The chemical industry reduces the impact on the environment during synthesis 89123-58-0, name is 5-Bromopyrazine-2,3-diamine, I believe this compound will play a more active role in future production and life.

Oxalyl chloride (3ml) was added to a solution of 5-({5-chloro-2-[(2-methylpropyl)oxy]- phenyl}methyl)-2-furancarboxylic acid (3.09g, lOmmol) and one drop of DMF in dichloromethane (30ml) and left at room temperature for one hour. The resulting solution was evaporated to dryness, azeotroped with toluene and the residue dissolved in dichloromethane (15ml) and added dropwise to a stirred solution of 2,3-diamino-5- bromopyrazine (2.08g, 11mmol) and 4-dimethyaminopyridine (100mg, 0.82mmol) in pyridine (20ml) and stirred for one hour. The solution was evaporated and the residue dissolved in ether/water. The organic phase was dried with magnesium sulphate, evaporated and chromatographed on silica gel eluting with ethyl acetate/hexane (15:85) to give 3.35g of white solid which was dissolved in acetic acid (40ml) and stirred and refluxed for 5 days. The resulting solution was evaporated, dissolved in ethyl acetate and washed with 2M sodium hydroxide solution. The organic phase was dried with magnesium sulphate, evaporated and purified by flash chromatography on silica eluting with ethyl acetate/hexane (1 :3) to give a pale yellow solid. A sample was dissolved in methanol/dichloromethane and hydrogen chloride in ether (1ml) was added. The solvent was evaporated and the residue triturated with ether and filtered off to give the title compound as a solid. LC/MS: Rt=3.67, [MH]+ 463.11 , 464.16.

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-Bromopyrazine-2,3-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/114272; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products 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.

[0504] Compound 481A was prepared by an analogous method as that of 473B, except using compound 2-chloro-6-aminopyrazine in place of compound 2-bromo-6-aminopyridine.

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; Das, Jagabandhu; Padmanabha, Ramesh; Chen, Ping; Norris, Derek J.; Doweyko, Arthur M.P.; Barrish, Joel C.; Wityak, John; Lombardo, Louis J.; Lee, Francis Y.F.; US2004/54186; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem