Month: August 2021

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. 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, A new synthetic method of this compound is introduced below., Formula: C5H2ClN3

General procedure: In a degassed solution of DME/H2O (2:1) (12mL/mmol of diazine), were successively introduced S-Phos (10mol%) and Pd(OAc)2 (5mol%). The solution was heated at 80C for 10min then sodium carbonate (4.0equiv), appropriate boronic acid (1.05 or 1.5equiv) and appropriate diazine (1.0equiv) were added. The solution was then refluxed (15min or overnight) under Ar. The resulting mixture was filtered on Celite and washed with ethyl acetate and water. The aqueous phase was then extracted three times with ethyl acetate. The combined organic phase was dried over MgSO4 and evaporated to dryness. The residue was purified by column chromatography (eluent: PE/EtOAc) to give the desired product.

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; Fresneau, Nathalie; Cailly, Thomas; Fabis, Frederic; Bouillon, Jean-Philippe; Tetrahedron; vol. 69; 26; (2013); p. 5393 – 5400;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 1196152-38-1, A common heterocyclic compound, 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, molecular formula is C5H2BrF3N2, 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.

1,1 -dimethyl ethyl (lS,4S,6S)-4-ethynyl-3-azabicyclo[4.1.0]heptane-3-carboxylate D17 (150 mg), 2-bromo-5-(trifluoromethyl)pyrazine (154 mg, 0.678 mmol), DIPEA (0.592 ml, 3.39 mmol), Pd[(C6H5)3P]4 (78 mg, 0.068 mmol) and copper(I) iodide (25.8 mg, 0.136 mmol) were collected together and dissolved in DMF (5 ml).The reaction was stirred at 23 C for 3 hours.A saturated solution of NaHC03 (20 ml) was added and the aqueous layer was back extracted with Et20 (3 x 10 ml). The collected organic layers were washed with brine (3 x 5 ml), dried over Na2S04, filtered, and concentrated under vacuum to give the crude product. The crude product was purified by silica gel chromatography (SNAP KP-Sil 25g cartridge; eluted with Cy/EtOAc 5 CV from 100% Cy to 90/10, 5 CV 90/10).Evaporation of the fractions gave the title compound D18 (140 mg).UPLC (IPQC): rt = 1.38 minutes, peak observed: 312 [M+l- C(CH3)3]

The synthetic route of 1196152-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89607; (2012); 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 58138-79-7 as follows. Recommanded Product: 58138-79-7

General procedure: OUY-2 [2], OUK-2 [3] and OUJ-2 were prepared by Stillecoupling of stannyl compound 1 [3] with 3,5-dibromopyridine,2,6-diiodopyrazine, and 2,4-dichloro-1,3,5-triazine, respectively,by using Pd(PPh3)4 as a catalyst in toluene at 110 C underan argon atmosphere (Scheme 1)

According to the analysis of related databases, 58138-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Imato, Keiichi; Enoki, Toshiaki; Uenaka, Koji; Ooyama, Yousuke; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1712 – 1721;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

98-97-5, name is Pyrazine-2-carboxylic acid, 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. Application In Synthesis of Pyrazine-2-carboxylic acid

Example 1; Methyl pyrazine-2-carboxylate (Formula 3). 20.0 g (805.8 mmole) of pyrazine-2-carboxylic acid was added to 160 mL of methanol, and 1.0 mL of a concentrated sulfuric acid was gradually dropwise added thereto with stirring. A reaction solution was refluxed at a temperature of 80 to 85C for 5 hours. The reaction solution was cooled to a temperature of 20 to 22 C and concentrated to a volume of 25mL. Then, 80 mL of methylenechloride and 40 mL of water were added to the resultant concentrate. The resultant solution was then neutralized by gradual addition of 40 mL of a saturated sodium hydrogen carbonate solution to get a pH of 8.5. An organic layer was separated and a water layer was extracted again with 40 mL of methylenechloride. The combined organic layer was dried over anhydrous magnesium sulfate, filtered, and washed with 20 mL of methylenechloride. A filtrate was concentrated to give 21.1 g of the titled compound as a pale brown solid (yield 94.8%). Melting point: 60-61 C

The synthetic route of 98-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CJ CORPORATION; WO2004/48369; (2004); 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. 179323-60-5, name is 1-(Pyrazin-2-yl)ethanamine, A new synthetic method of this compound is introduced below., name: 1-(Pyrazin-2-yl)ethanamine

To a mixture of 5-(isobutyl(methyl)carbamoyl)-4′-methylbiphenyl-3-carboxylic acid (21 mg, 0.064 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (25 mg, 0.13 mmol), 1-hydroxybenzotriazole hydrate (9.9 mg, 0.064 mmol), and CH2Cl2 (3 mL) were added l-(pyrazin-2- yl)ethanamine (12 mg, 0.097 mmol) and NN-diisopropylethylamine (17 muL, 0.097 mmol). The mixture was stirred at room temperature overnight, and then concentrated in vacuo. The residue was purified by preparative HPLC (100 x 21.2 mm Cl 8 column, 30-70% MeCnu/water[10 mM Et2NH]) to afford a white foam.LC-MS: 431.1 [M+l]+; 1H NMR (400 MHz, CD3OD): (rotamers) delta 8.70 (s, IH), 8.59 (m, IH), 8.49 (d, IH, J = 2.8 Hz), 8.20 (t, IH, J = 1.6 Hz), 7.84-7.75 (m, 2H), 7.62-7.57 (m, 2H), 7.30 (d, 2H, J = 8.0 Hz), 5.36 (q, IH, J = 7.2 Hz), 3.42 (d, IH, J = 7.6 Hz), 3.19 (d, IH, J = 7.6 Hz), 3.10 and 3.01 (s, 3H), 2.39 (s, 3H), 2.15 and 1.98 (m, IH), 1.66 (d, 3H, J = 7.2 Hz), 1.02 and 0.78 (d, 6H, J = 6.4 Hz).

The synthetic route of 179323-60-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
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. 768-05-8, name is Pyrazinoic acid hydrazide, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Pyrazinoic acid hydrazide

General procedure: 2.3. General procedure for the synthesis of N’-(2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)pyrazine-2-carbohydrazide(8-14)The quest for the synthesis of N’-(2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)pyrazine-2-carbohydrazide (8-14) wasaccomplished in two steps as outlined in Scheme 1. A mixture of2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-one (1-7) (1 mmol),commercially available pyrazine-2-carbohydrazide (PZH)(1.5 mmol) in methanol and chloroform mixture (1:1 v/v), andcatalytic amount of acetic acid (0.1 mL) was added and refluxed for2-3 h. On the completion of reaction, a solid mass was formed.After cooling to room temperature, the precipitate was filtered offand washed with cold mixture of ethanol and water. The crude product was recrystallized from ethanol [16].

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 768-05-8.

Reference:
Article; Mangalam; Sebastian Antony Selvan; Sankar; Journal of Molecular Structure; vol. 1129; (2017); p. 305 – 312;,
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

In a 250mL round-bottom flask, 2-acetylpyrazine (1.22g, 10.00mmol) was added to a solution of 4-chlorobenzaldehyde (0.700g, 5.00mmol) in EtOH (30mL) upon stirring. KOH pellets (0.560g, 10.0mmol) were then added, and followed by aqueous NH3 (28%, 25mL). The resulting brownish solution was stirred at room temperature overnight, during which time gray solid had formed. The solid was collected by filtration, washed with EtOH and dried in vacuo over P2O5. L2 was isolated as pure product (1.00g, 58.0%). UV-Vis lambdamax/nm (2.5×10-5moldm-3, CH2Cl2-MeOH) 250 (epsilon/103dm3mol-1cm-1 18.7), 285 (26.1), 320sh (8.1). FT-IR (solid, cm-1): 1603s, 1571w, 1521w, 1496s, 1472m, 1428m, 1372s, 1245w, 1117m, 1050m, 1017s, 852m, 822s, 738w, 690m. 1H NMR (400MHz, CDCl3)delta 9.92 (s, 2 H, HA3), 8.85(dd, J=6.4, 1.0Hz, 4 H, HA5/A6), 8.72 (s, 2 H, HB3), 8.03(d, J=8.7Hz, 2H, HC3), 7.67 (d, J=7.67Hz, 2 H, HC2) ppm; 13CNMR (101MHz, CDCl3)delta154.39, 149.58, 148.79, 145.59, 144.10, 143.11, 134.71, 129.44, 128.95, 118.97ppm. HR-MS: m/z 346.0863 [M+H]+ (calc. 346.0859), 368.0679 [M+Na]+ (calc. 368.0679).

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, Acetylpyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Li; Liu; Xiong, Hangxing; Chan, Corinna; Manke, David R.; Golen, James A.; Zhang, Guoqi; Polyhedron; vol. 132; (2017); p. 64 – 69;,
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. 33332-25-1, name is Methyl 5-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 5-chloropyrazine-2-carboxylate

Dissolve 5-chloro-pyrazine-2-carboxylic acid methyl ester (10.0 g, 57.9 mmol) in THF (65 mL) and MeOH (65 mL). Cool the solution to 0 0C before adding IN NaOH (63.7 mL) with stirring. Warm the mixture to room temperature and stir for 5 h. Concentrate the mixture in vacuo to 1/3 volume. Quench with IN HCl (75 mL) to form a white precipitate. Dilute with CH2Cl2 (200 mL) and filter. Wash the filter cake with water and CH2Cl2. Separate the phases, dry the organic phase over MgSO4, filter, and concentrate. Add the aqueous layer to the concentrated organic residue and concentrate. Purify by silica gel flash column chromatography, eluting with 40% ethyl acetate/n-hexane, followed by 10% MeOH, 3% acetic acid and 87% EPO CH2Ch- Collect the mixed fractions and concentrate. Take up the resulting solid with CH2CI2 (50 mL) and H2O (50 mL) and stir. Filter the solid and add it to the first filter cake. Add 5.0N NaOH to the filtrate to make the solution basic. Separate the two layers. Discard the organic layer, add 5.0N HCl to the aqueous layer until acidic. Extract with CH2Cl2 (3 x 100 mL). Dry the organic layer over Na2SO4, filter, and concentrate. Add the solid to the pure fractions from the column. Combine the pure filter cakes with the pure fractions from the column, yielding the desired product (8.46 g, 92%). mass spectrum (exact mass): 157.99.

According to the analysis of related databases, 33332-25-1, the application of this compound in the production field has become more and more popular.

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

These common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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. Recommanded Product: (3-Chloropyrazin-2-yl)methanamine hydrochloride

To a solution of(3S,6S)-l-((benzyloxy)carbonyl)-6-(hydroxymethyl)piperidine- 3-carboxylic acid (0.78 g, 2.66 mmol) in 20 mL of DMF was added HATU (1.21 g, 3.2 mmol). After stiring for 30 min under N2, (3-Chloro-pyrazin-2-yl) methanamine hydrochloride (0.48 g, 2.66 mol) and Et3N (0.8 g, 7.98 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours under N2. The mixture was partitioned between EA and water. The organic layer was washed with 1 N HC1 and water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford (2S,5R)-benzyl 5-(((3- chloropyrazin-2-yl)methyl)carbamoyl)-2-(hydroxymethyl)piperidine-l -carboxylate (0.7 g, 63.0% yield). 1HNMR (400 MHz, CD3OD): delta= 8.50 ~ 8.54 (m, 1 H), 8.35 (d, / = 2.4 Hz, 1 H), 7.31 ~ 7.41 (m, 5 H), 5.16 (s, 2 H), 4.63 (s, 2 H), 4.34 ~ 4.38 (m, 1 H), 4.21 ~ 4.25 (m, 1 H), 3.72 ~ 3.77 (m, 1 H), 3.63 ~ 3.67 (m, 1 H), 3.01 ~ 3.07 (m, 1 H), 2.46 ~ 2.54 (m, 1 H), 1.80 ~ 1.93 (m, 3 H), 1.61 ~ 1.71 (m, 1 H). MS (ESI): M/Z (M+l): 419.1

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 312736-49-5, name is 3,5-Dichloropyrazine-2-carboxylic acid, 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 312736-49-5, category: Pyrazines

To a 100 mL round-bottomed flask, 3,5-dichloropyrazine-2-carboxylic acid(3.65 g, 18.9 mmol) and NaHCO3 (4.70 g, 22.7 mmol) are dissolved in dimethylformamide (38mL). lodomethane (7.14 mL, 113 mmol) is added dropwise and the resulting mixture is stirred overnight at room temperature. The mixture is diluted in water (50 mL) and extracted with ethyl acetate (3 x 15 mL). The combined organic layers are washed with brine (4 x 10 mL), dried over anhydrous Na2504, filtered and concentrated under reduced pressure. Methyl 3,5-dichloropyrazine-2-carboxylate (3.77 g, 96%) is obtained as a yellowish solid after drying under high vacuum for 2-3 h. NMR ?H (500 MHz, CDC13) oe 8.57 (s, 1H), 4.03 (s, 3H).

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; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; GIORDANETTO, Fabrizio; GREISMAN, Jack, Benjamin; MARAGAKIS, Paul; TAYLOR, Alexander, M.; DIPIETRO, Lucian, V.; KELLEY, Elizabeth, H.; LESCARBEAU, Andre; MURCKO, Mark, Andrew; PIERCE, Levi Charles, Thomas; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; BHAT, Sathesh; THERRIEN, Eric; DAHLGREN, Markus, Kristofer; (156 pag.)WO2018/81091; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem