Month: April 2021

Electric Literature of 14667-55-1, A common heterocyclic compound, 14667-55-1, name is 2,3,5-Trimethylpyrazine, molecular formula is C7H10N2, 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.

A reaction mixture of AgNO3 (33.4 mg, 0.2 mmol), 2,3,5-trimethylpyrazine(tpyz) (24.2 mg, 0.2 mmol) and 2-nitroterephthalic acid (H2ntph) (42.2 mg, 0.2 mmol) and H2O (10 mL) was stirred for 30 min in air, then transferred and sealed in a 25 mL Teflon-linedstainless steel autoclave, which was heated to 100 C for 72 h. Aftercooling to room temperature, the resulting colorless prism crystals were washed with distilled water and dried in air. Yield based on silver is 68.72%. Elemental analysis: Anal. calc. (found) for AgC15H13N3O6:C, 39.95(41.00); H, 2.99 (2.96); N, 9.52 (9.57) %. IR (KBr, cm-1) data: 3275 (m), 3093 (w), 2922 (w), 2867 (w), 1707 (s), 1600 (vs), 1527 (vs),1396 (s), 1350 (s), 1292 (s), 1154 (m), 766 (m), 703 (m).

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:
Article; Yang, Yuan-Yuan; Zhou, Lin-Xia; Zheng, Yue-Qing; Zhu, Hong-Lin; Li, Wen-Ying; Journal of Solid State Chemistry; vol. 253; (2017); p. 211 – 218;,
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. 6270-63-9, name is Pyrazin-2(1H)-one belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. Safety of Pyrazin-2(1H)-one

To Pyrazin-2(1H)-one (0.333 g, 3.47 mmol) was added 5 N sodium hydroxide solution (2.1 ml) followed by chloroacetic acid (0.524 g, 5.54 mmol). The reaction mixture was heated at 100C for 2 h. After cooling to ambient temperature, 2 N hydrochloric acid (3.5 ml) was added and the reaction mixture was directly purified by reverse phase etaPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/ 0.1% trifluoroacetic acid in water gradient). The pure fractions were lyophilized overnight to yield the title compound as a yellow solid. LC/MS 155.2 (M+l)+.

The synthetic route of 6270-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/123870; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 939412-86-9, A common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

N,N-Diisopropylethylamine (19.35 mL, 111.09 mmol) was added dropwise in ten minutes to a mixture of (2S)-2-[benzyloxycarbonyl(methyl)amino]propanoic acid (6.59 g, 27.77 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (5.00 g, 27.77 mmol) and HATU (15.84 g, 41.66 mmol) in dichloromethane (250 mL) and the resulting mixture was stirred for three hours at 20 C. The mixture was washed once with aqueous saturated. sodium bicarbonate solution (200 mL) and once with aqueous saturated ammonium chloride solution (200 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash column chromatography on silicagel (0-100% ethyl acetate in heptane) to give benzyl N-[(1S)-2-[(3-chloropyrazin-2-yl)methylamino]-1-methyl-2- oxo-ethyl]-N-methyl-carbamate (9.2 g, 91.3%) as a colorless oil. Data: LC-MS (Method A) Rt: 5.32 min; m/z 363.2 (M+H)+.

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACERTA PHARMA B.V.; BARF, Tjeerd; DE ZWART, Edwin; VERKAIK, Saskia; HOOGENBOOM, Niels; DEMONT, Dennis; KAPTEIN, Allard; COVEY, Todd; (180 pag.)WO2019/239374; (2019); 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. 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H2BrF3N2

Example 44k (300 mg, 0.8 mmol), 2-Chloro-5-(trifluoromethyl)pyrimidine (199 mg, 1.09 mmol) and N,N-diisopropylethylamine (287 mul, 1.67 mmol) are dissolved in 4 ml of anhydrous DMSO and heated in a microwave reactor during 30 minutes at 150C. The crude is partitioned between EtOAc and water, the organic layer is dried over anhydrous Na2S04 then concentrated under reduced pressure to obtain 360 mg of the title product. HPLC-MS (Method 10): Rt = 3. MS (ES+): m/z = 505 [M+H]+ . The enantiomers are obtained by HPLC using a chiral stationary phase. Method for separation: HPLC apparatus type: Waters 600 Pump; column: Daicel Chiralpack AD-H, 5.0 muiotaeta, 250 mm x 20 mm; method: eluent hexane/ IPA 70:30; flow rate: 15 mL/min, Temperature: 25 C; UV Detection: 254 nm Example of separation by chiral HPLC: Submitted to separation: 665 mg of Example 1 prepared as described above; Obtained: 157 mg of enantiomer 1 (Exp. 2) and 40 mg of enantiomer 2 (Exp. 3). Example 109 is synthesized as described for example 1 starting from example 44g (80 mg, 0.24 mmol) instead of example 44k, 2-Bromo-5-(trifluoromethyl)pyrazine (70 mg, 0.31 mmol) instead of 2-Chloro-5-(trifluoromethyl)pyrimidine, N,N-diisopropylethylamine (80 mu, 0.48 mmol) and 1 ml of anhydrous DMSO; the reaction mixture is heated during 30 minutes at 100C in a microwave reactor. After the work-up the crude is purified by Silica gel flash chromatography using EtOAc/hexane/MeOH 80:20: 1 as eluent to obtain the title compound (80 mg, 70% yield). HPLC-MS (Method 5): Rt = 2.95 min. MS (APCI+): m/z = 487 [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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); 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. 24241-18-7, name is 2-Amino-3,5-dibromopyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H3Br2N3

Step 1: 5-Bromo-3-trimethylsilanylethynyl-pyrazin-2-ylamine To a 150 mL round-bottomed flask was added 3,5-dibromopyrazin-2-amine (3 g, 11.86mmol) and triethylamine (16.53 ml, 119 mmol) in THF (60 ml) to give a yellow suspension.To the stirring solution was added bis(triphenylphosphine)palladium(ll) chloride (833mg, 1.l86mmol) and copper(l) iodide (452mg, 2.373mmo1). Whilst maintaining the temperature below 10C, ethynyltrimethylsilane (1.844m1, 13.OSmmol) was added slowly and the reaction stirred at below 10C for 30mins before warming to room temperature and stirring for afurther 30mins.The reaction was concentrated under reduced pressure. After dilution with ethyl acetate the organics were washed with brine, the organic layer separated, dried over Mg504, filtered and the solvent removed under reduced pressure. The residue was loaded onto silica and purified by flash column chromatography, elution with iso hexane:ethyl acetate (0-30%) onan 80g silica column. The required fractions were combined and the solvent removed under reduced pressure to yield the product as a light brown solid (2.5g).

The synthetic route of 24241-18-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BELLENIE, Benjamin Richard; BLOOMFIELD, Graham Charles; BRUCE, Ian; CULSHAW, Andrew James; HALL, Edward Charles; HOLLINGWORTH, Gregory; NEEF, James; SPENDIFF, Matthew; WATSON, Simon James; (395 pag.)WO2015/162459; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 6164-79-0, These common heterocyclic compound, 6164-79-0, name is Methyl 2-pyrazinecarboxylate, 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.

Methyl pyrazine-2-carboxylate (0.5g; 3.6mmol) was dissolved in THF (5mL), and 98% hydrazine (0.53mL; 11mmol) was added. The mixture was refluxed for 3h and cooled to rt. The resulting solid was filtered off, washed with THF and dried over P2O5 to give 0.28g (56%) of a white solid. Rf=0.53 (CHCl3/MeOH 10:1). mp 166-169C (lit. 167-169C) [64]. 1H NMR (300MHz, DMSO): delta 10.11 (s, 1H, NH), 9.12 (s, 1H, Ar), 8.82 (d, J=2.4Hz, 1H, Ar), 8.68 (d, J=2.4Hz, 1H, Ar), 4.65 (s, 2H, NH2). 13C NMR (75MHz, DMSO): delta 161.7, 147.4, 145.1, 143.7, 143.4.

The synthetic route of 6164-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hru?kova, Kate?ina; Pot??kova, Eli?ka; Hergeselova, Tereza; Liptakova, Lucie; Ha?kova, Pavlina; Mingas, Panagiotis; Kova?ikova, Petra; ?im?nek, Toma?; Vavrova, Kate?ina; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 97 – 110;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 6863-73-6, 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 6863-73-6 as follows.

alpha-Bromo diethyl acetal (51.6 mL, 332.7 mmol, 2.5 eq) was added to a solution of 7.7 mL HBr (conc.) and 80 mL of H2O. The reaction was heated at reflux for 1 h. The reaction was cooled and extracted 2¡Á with Et2O (200 mL). The Et2O extracts were combined, washed with brine, and dried over Na2SO4 before being concentrated. The material was not left on the rotavap for an extended time or put under high vacuum. The oily residue was mixed with DME (200 mL) and the 2-amino-3-chloropyrazine (2, 17.240 g, 133.1 mmol) was added. HBr conc. (1-1.5 mL) was added and the reaction was heated at reflux. The reaction is heterogeneous reaction mixture, becomes homogenous after 10-15 minutes. After approximately 30 minutes a precipitate begins to form. After 1 hour at reflux the black reaction was cooled to room temperature, filtered, and washed with Et2O (4¡Á, 75 mL) to give compound 101 1H NMR (DMSO-d6, 400 MHz) 8.70 (d, J=2.0 Hz, 1H), 8.32 (s, 1H), 7.93 (s, 1H), 7.79 (d, J=3.0 Hz, 1H). LC/MS shows a mixture of two products (one product by LC and two by MS). By MS there is a mass for XCl (major) MH+=154 (m/z) and one for XBr (minor) MH+ 198 (m/z). This mixture gave the product in approximately 90% yield as the HBr salt.

According to the analysis of related databases, 6863-73-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US2007/105864; (2007); 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. 17231-51-5, name is 3-Amino-6-bromopyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 17231-51-5

REFERENTIAL EXAMPLE II-9 In 10 mL of tetrahydrofuran was dissolved 0.50 g of 3-amino-6-bromo-2-pyrazinecarbonitrile. After adding 0.15 g of 60% sodium hydride, the mixture was stirred at room temperature for 15 minutes. Then, 0.7 mL of di-t-butyl dicarbonate and 0.10 g of 60% sodium hydride were successively added, and the mixture thus formed was stirred at room temperature for one hour. The reaction mixture was added to a liquid mixture consisting of 30 mL of ethyl acetate and 60 mL of water, pH was adjusted to 5 with 2 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=5:1] to obtain 0.30 g of t-butyl 5-bromo-3-cyano-2-pyrazinylcarbamate as a white-colored solid product. IR(KBr) cm-1: 2239, 1708 1H-NMR (CDCl3+DMSO-d6) delta: 1.57(9H,s), 7.41(1H,brs), 8.62(1 H,s)

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

Reference:
Patent; Toyama Chemical Co., Ltd.; US2003/130213; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 91476-80-1, These common heterocyclic compound, 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[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.

C-1 a (50 mg; 0.16 mmol) is dissolved in dioxane. 5,6,7,8-tetrahydro-imidazo[1 ,2- a]pyrazine E-1a (19 mg; 0.16 mmol), sodium ie f-butoxide (40 mg; 0.42 mmol) and chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1 ,1 ‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-i-butyl ether adduct (9 mg; 0.01 mmol) are added and the reaction mixture is stirred at 75 C for 2 h. The solvents are evaporated under reduced pressure and the crude material is purified using reversed phase chromatography (method: prep. HPLC1 ) to afford I-029. Yield: 48 % (27 mg; 0.08 mmol) HPLC-MS: (M+H)+ = 362; tRet = 0.96 min; method LCMSBAS1

The synthetic route of 91476-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; ARNHOF, Heribert; CAROTTA, Sebastian; HOFMANN, Marco; KERENYI, Marc; SCHARN, Dirk; (118 pag.)WO2019/68613; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 56423-63-3, The chemical industry reduces the impact on the environment during synthesis 56423-63-3, name is 2-Bromopyrazine, I believe this compound will play a more active role in future production and life.

Methyl 4-(2-pyrazinyl) benzoate (0432) In a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen were combined a solution of [4-(methoxycarbonyl)phenyl]boronic acid (1 g, 5.56 mmol, 1.20 equiv) in 1,4-dioxane (30 mL), 2-bromopyrazine (800 mg, 5.03 mmol, 1.00 equiv), a solution of Na2CO3 (1.5 g, 14.15 mmol, 3.00 equiv) in water (30 mL), and Pd(Ph3P)2Cl2 (330 mg, 0.47 mmol, 0.10 equiv). The resulting solution was stirred for 16 h at 90 C. in an oil bath. The solids were filtered out. The resulting solution was extracted with 3¡Á30 mL of EtOAc, and the organic layers combined and concentrated under vacuum. This resulted in 0.8 g (74%) of the product as a white solid.

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

Reference:
Patent; Imago Biosciences, Inc.; Rienhoff, JR., Hugh Y.; McCall, John M.; Clare, Michael; Celatka, Cassandra; Tapper, Amy E.; (226 pag.)US2016/237043; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem