Month: January 2021

Application of 77112-53-9, 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. 77112-53-9, name is Imidazo[1,2-a]pyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Imidazo[1,2-a]pyrazine-2-carboxylic acid (5) (1.0 equiv.) Mukaiyama?s reagent and 2-chloro-1-methylpyridinium iodide (1.2 equiv.) were suspended in DMF (5.0 mL) under nitrogen atmosphere. Into the reaction mixture, aliphatic/aromatic amines (6a-l) (1.0 equiv.) and 1-methylimidazole (2.0 equiv.) were added. A homogeneous solution was formed after a gentle stirring. The reaction mixture was sealed in a microwave glass reactor and then irradiated by microwave oven at a constant temperature of 80 C with continuous stirring (1 min ramp, 15 min reaction time). After the reaction was completed, the solvent was removed through a rotary evaporator and the resulting residue was extracted by a biphasic system of 45 mL diethyl ether and 45 mL water. After the layer separation, the ether layer was dried by anhydrous sodium sulphate, followed by an evaporation of ether to get compounds 7a-l (Scheme-I).

The chemical industry reduces the impact on the environment during synthesis Imidazo[1,2-a]pyrazine-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Jyothi, Boggavarapu; Madhavi, Nannapaneni; Asian Journal of Chemistry; vol. 32; 1; (2020); p. 84 – 90;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 4858-85-9,Some common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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 mixture of 2,3-dichloropyrazine (2.80 g, 18.8 mmol), racemic 2- methylpiperazine (1.88 g, 18.8 mmol) and K2CO3 (3.90 g, 28.2 mmol) in acetonitrile (25 mL) was heated at 65 C for 15 h with stirring. The reaction mixture was filtered and concentrated. The crude product was purified by flash chromatography on silica gel using CHCl3/MeOH (15: 1) as eluent to give 3.2 g (79%) of the title compound. MS m/z 213 (M+H) +.

The synthetic route of 4858-85-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOVITRUM AB; WO2004/9586; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 109-08-0, 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. 109-08-0, name is 2-Methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

In the glove box,Mn(CO)5Br (0.005mmol), [(E)-2-(2-(1-(2-pyridine)ethylidene))Pyridine] (0.006 mmol), added to 1.0 mL of toluene,After stirring for two hours, 2-methylpyrazine 1a (2 mmol) was added.Benzyl alcohol 2d (1mmol), after reacting at 135 ¡ã C for 48 hours, the reaction was stopped, and the solvent was evaporated to dryness.Column chromatography ethyl acetate / petroleum ether (1:10),Trans-disubstituted olefin derivative 3d. The product was a white solid with a yield of 68percent.

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

Reference:
Patent; Qingdao University of Science and Technology; Zhang Chunyan; (19 pag.)CN108250153; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 2423-65-6,Some common heterocyclic compound, 2423-65-6, name is Pyrazine 1-oxide, molecular formula is C4H4N2O, 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 20 ml_ microwave vial was charged with pyrazine N-oxide [Fagnou et al, JACS 2005, 127: 18020-1] (0.346 g, 3.60 mmol), potassium carbonate (0.497 g, 3.60 mmol), palladium acetate (0.020g, 0.089 mmol), tri-n-butylphosphonium tetrafluoroborate (0.052 g, 0.179 mmol) and pivalic acid (0.055 g, 0.541 mmol). A solution of 2-(3-amino-3-oxopropyl)- 3′-hydroxybiphenyl-4-yl trifluoromethanesulfonate (0.700 g, 1.798 mmol) in toluene (4 ml_) was added, the vial purged under nitrogen for 10 min, sealed and heated at reflux for 4 h. On cooling, chloroform (10 ml_) was added, the resultant precipitate filtered and washed successively with dichloromethane and ethyl acetate / methanol. The organics were combined, concentrated and purified by flash chromatography (acetone / dichloromethane / methanol) to give the title compound as a colourless solid (0.460 g, 76%). H NMR (400 MHz, DMSO-d6) delta ppm 9.56 (s, 1 H), 8.81 (s, 1 H), 8.52 – 8.49 (m, 1 H), 8.45 (d, J = 4.1 Hz, 1 H), 7.78 – 7.73 (m, 2 H), 7.30 – 7.26 (m, 1 H), 7.25 (d, J = 8.0 Hz, 1 H), 7.22 (br. s., 1 H), 6.80 (ddd, J = 0.8, 2.3, 8.2 Hz, 1 H), 6.78 – 6.75 (m, 1 H), 6.75 – 6.70 (m, 2 H), 2.82 (dd, J = 6.9, 9.1 Hz, 2 H), 2.31 – 2.24 (m, 2 H). LCMS [M+H]+ = 336.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Pyrazine 1-oxide, its application will become more common.

Reference:
Patent; VECTUS BIOSYSTEMS LIMITED; DUGGAN, Karen Annette; (120 pag.)WO2018/18091; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 109-08-0, 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. 109-08-0, name is 2-Methylpyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Reaction of AgNO3 (33.8 mg, 0.2 mmol), methylpyrazine (mpyz)(19 mg, 0.2 mmol) and isophthalic acid (H2ipa) (33.3 mg, 0.2 mmol) took place in methanol-DMF (DMF = N,N-dimethylformamide) solvents (6 ml, v/v = 1:1) under ultrasonic treatment (160 W, 40 KHz,30 min) at 50 ¡ãC. Addition of ammonia (25percent, 0.5 mL) was found to be an efficient way to eliminate the white precipitate. The resultant solution was allowed slowly and quietly to evaporate at room temperature. The pale pink and prismatic crystals of compound 1 are obtained after several days in the darkness. The crystals were isolated by filtration and washed by deionized water and enthanol and dried in the air. Yield: ca. 80percent based on Ag. Elemental analysis: Anal. Calc. for Ag2C13H10N2O4: C, 32.94; H,2.13; N, 5.91. Found: C, 32.04; H, 2.24; N 6.09percent. Selected IR peaks(cm1): 3355 (s), 3068 (m), 2370 (w), 1606 (s), 1556 (s), 1477(m), 1429 (s), 1379 (s), 1263 (w), 1157 (w), 1062 (m), 1027 (m),943 (w), 906 (w), 821(w), 723 (s), 711 (s), 655 (m), 507 (w), 445(w), 406 (m).

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

Reference:
Article; Wang, Dan-Feng; Wang, Zhan-Hui; Zhang, Ting; Dai, Si-Min; Huang, Rong-Bin; Zheng, Lan-Sun; Inorganica Chimica Acta; vol. 415; (2014); p. 61 – 68;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 113305-94-5, These common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, 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.

Reflux a solution of 2.24 g (18.65 mmol) of 5-aminopyrazine-2-carbonitrile and 9.45 mL (74.40 mmol) of boron trifluoride etherate in 50 mL of methanol for 2 h. Concentrate the reaction mixture under reduced pressure and take up the residue obtained in 200 mL of EtOAc and 10 mL of a saturated aqueous solution of NaHCO3. Dry the organic phase over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluding with a cyclohexane/EtOAc 1:1 mixture. After concentration under reduced pressure, we obtain 1.4 g of methyl 5-aminopyrazine-2-carboxylate in the form of oil. Yield=49%

Statistics shows that 5-Aminopyrazine-2-carbonitrile is playing an increasingly important role. we look forward to future research findings about 113305-94-5.

Reference:
Patent; Sanofi Aventis; US2009/318473; (2009); 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 25911-65-3 as follows. Computed Properties of C5H4N4

d) 2-[(4-Acetyl-3-hydroxy-2-propylphenoxy)methyl]-4-aminopteridine Obtained using the procedure described in section c of Example 2, starting with 3.6 g (0.030 mole) of 3-amino-2-pyrazinecarbonitrile and the above solution of 2-(4-acetyl-3-hydroxy-2-propylphenoxy)acetamidine in absolute ethanol. Refluxing time: 6 hours. Yld: 3.2 g (30%), m.p. 178-180 C. (ethanol/N,N-dimethylformamide). An analytic sample was obtained by a further recrystallization from a mixture of ethanol and N,N-dimethylformamide. M.p. 179-181 C. IR: nu (C=0)=1640 cm-1. NMR (DMSO-d6): delta=0.9 (3H, t); 1.1-1.9 (2H, m); 2.5 (3H, s); 2.5-2.9 (2H, m); 5.2 (2H, s); 6.6 (1H, d); 7.7 (1H, d); 8.3 (2H, peak exchangeable with CF3 COOD); 8.8 (1H, d); 9.0 (1H, d); 13.9 (1H, peak exchangeable with CF3 COOD).

According to the analysis of related databases, 25911-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lipha, Lyonnaise Industrielle Pharmaceutique; US5167949; (1992); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 221136-66-9, name is Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, 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 221136-66-9, HPLC of Formula: C9H11BrN2O3

Example 8 r3-(2,2-Difluoro-2-phenyl-ethylamino)-6-methyl-2-oxo-2H-pyrazin-1-vn- acetic acid ethyl ester(3-Bromo-6-methyl-2-oxo-2H-pyrazin-1 -yl)-acetic acid ethyl ester was reacted with 2,2-difluoro-2-phenyl-ethylamine in the presence of a base, at elevated temperature, to yield the title compound as shown in the Scheme above. Table 5 below lists the reagent amounts, base and temperature combinations applied to this reaction, as well as yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(3-bromo-6-methyl-2-oxopyrazin-1(2H)-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/146553; (2007); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

5521-55-1, name is 5-Methylpyrazine-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. SDS of cas: 5521-55-1

EXAMPLE 185-Methyl-pyrazine-2-carboxylic acid {3-[(1-methyl-1H-pyrazole-3-carbonyl)-amino]-adamantan-1-yl}-amide; Example 18 was synthesized via the process of Scheme 2 using commercially available carboxylic acids, supra, as follows:To a solution of adamantane-1,3-diamine (20 mg, 0.1 mmol; Zerenex Molecular Ltd., Greater Manchester, UK) in DCM (2 mL) was added DIEA (26 mg, 0.15 mmol), 1-methyl-1H-pyrazole-3-carboxylic acid (14 mg, 0.11 mmol), 5-methyl-pyrazine-2-carboxylic acid (15 mg, 0.11 mmol) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (110 mg, 0.20 mmol). After stirring for 3 hours at rt, the reaction mixture was partitioned into dichloromethane and saturated sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on a RP-HPLC/MS purification system (Gradient: acetonitrile in water, 25-95%, in 3.4 minutes with a cycle time of 5 min. A shallow gradient between 25-50% of acetonitrile was used between 0.75-3.3 min to separate close-eluting impurities. Flow rate: 100 mL/min. Mobile phase additive: 25 mM of ammonium formate. Column: Inertsil C8, 30¡Á50 mm, 5 mum particle size (GL Sciences, Tokyo, Japan)) to afford 15 mg (37%) of the title compound, 5-methyl-pyrazine-2-carboxylic acid {3-[(1-methyl-1H-pyrazole-3-carbonyl)-amino]-adamantan-1-yl}-amide, as a colorless oil. 1H NMR (400 MHz, CDCl3) delta9.22 (s, 1H), 8.34-8.33 (m, 1H), 7.67 (s, br, 1H), 7.33 (d, J=2.3 Hz, 1H), 6.76-6.72 (m, 2H), 3.89 (s, 3H), 2.64 (s, 3H), 2.54 (s, br, 2H), 2.37-2.09 (m, 10H), 1.73-1.68 (m, 2H). ESI-MS m/z: 395.0 (M+H)+.

The synthetic route of 5521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; US2010/22546; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2423-65-6, name is Pyrazine 1-oxide, 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 2423-65-6, Application In Synthesis of Pyrazine 1-oxide

10219] Procedure:10220] Pd(OAc)2 (39.0 mg, 0.17 mmoles), [P(t-13u)3H] HF4 (151 mg, 0.52 mmoles), Pyrazine-i-oxide (1.0 g, 10.4 mmoles), and K2C03 (959 mg, 6.9 mmoles) were added to a dried flask. The flask was fitted with a reflux condenser capped with a septum, evacuated, and purged with nitrogen (.-5 times). A degassed solution of 2-bromopyridine (548 mg, 3.5 mmoles) in dry dioxane (17 mE) was added via syringe, and the reaction was stirred at 1100 C. for 18 hours. The reaction mixture was cooled and filtered through Celite, and the filtrate was concentrated under reduced pressure. The crude product was then purified by chromatography on silica (30% acetone in hexanes) to afford the title compound (312 mg, 52%) as a pale yellow solid. ?H NMR (400 MHz, CDC13) oe 9.35 (s, 1H), 8.75-8.72 (m, 2H), 8.38 (d, J=4.0 Hz, 1H), 8.15 (dd, J=0.4, 4.0 Hz, 1H), 7.81 (ddd, J=i.6, 2.0, 8.0 Hz, 1H), 7.25 (ddd, J=0.8, 4.8, 8.0 Hz, 1H); ?3C NMR (100 MHz, CDC13) oe 149.9, 149.7, 147.3,145.8, 142.2, 136.5, 134.5, 125.4, 124.8; HRMS (ESI) mlz174.0662 [calc?d for C9H8N30 (M+H) 174.0662].

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, Pyrazine 1-oxide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; RAINES, Ronald T.; Vasta, James; (50 pag.)US2016/280701; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem