Tag: M.W=100-200

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

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

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

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

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

Adding a certain compound to certain chemical reactions, such as: 5521-55-1, name is 5-Methylpyrazine-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 5521-55-1, SDS of cas: 5521-55-1

To the solution of 5-methyl-2-pyrazine carboxylic acid (1) (0.01 mol) in absolute ethyl alcohol (10 mL), conc. H2SO4 (2 mL) was added. The mixture was refluxed for 4 hwith constant stirring. After completion of the reaction (monitored by the TLC), the mixture was poured into ice-cold water. Crude product was collected by filtration, washed with 10 % NaHCO3 solution, dried and recrystallized from ethyl alcohol to get pure 5-methyl-2-pyrazine carboxylic acid ethyl ester (2).

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

Reference:
Article; Maddireddi, Chandra Sekhara Reddi; Parimi, Uma Devi; Reddy, Sreenivasa Reddy Bhimi; Mandapati, Satyanarayana Reddy; Asian Journal of Chemistry; vol. 28; 11; (2016); p. 2453 – 2456;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19745-07-4, name is 2,5-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 19745-07-4, Computed Properties of C4H2Cl2N2

General procedure: m-DCzP, o-DCzP were synthesized by nucleophilic reaction without heavy metal catalysts. Carbazole (0.34 g,2 mmol), dichloropyrazine (0.148 g, 1 mmol), and K2CO3 (1.136 g, 8 mmol) were mixed in dimethyl sulfoxide (DMSO, 5ml), then the mixture was stirred at 150C for 4 h under a nitrogen atmosphere. After cooling to room temperature, the mixture was poured into water, stirred, and filtered. The residue was dried in vacuum drying over at 60C for 4 h, and thenpurified by column chromatography over silica gel with CH2Cl2/petroleum ether as the eluent to afford a yellow/white solid. To further purify the products, CH2Cl2/ethyl acetate was used as solvents for recrystallization resulting in pure single crystals of p-DCzP, m-DCzP and o-DCzP. They were obtained with high yields (75%) except for o-DCzP which was obtained with only 50% yield.

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; Zhang, Yanni; Zhao, Jianfeng; Zhu, Caixia; Bian, Lifang; Shi, Huifang; Zhang, Shiming; Ma, Huili; Huang, Wei; Chinese Chemical Letters; vol. 30; 11; (2019); p. 1974 – 1978;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 126069-70-3, name is 2-(Trifluoromethyl)-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. Quality Control of 2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

The title compound was prepared from 2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (277 mg, 1.45 mmol, from Example 1, Step B), (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid (Intermediate 1, 416 mg, 1.32 mmol), DIPEA (226 mg, 1.58 mol), HOBT (216 mg, 1.98 mol) and HATU (753 mg, 1.98 mol) in DMF (6 mL), using a procedure analogous to that described in Example 1 Step C, except for the purification method. The compound was purified by preparative TLC (silica gel, 20% hexane in ethyl acetate, then 10% methanol in dichloromethane) to give 360 mg of the title compound as a foamy solid. 1H NMR (500 MHz, CDCl3) delta 1.35 (s, 9H), 2.62 (m, 2H), 2.88 (m, 2H) 3.88-4.16 (m, 5H), 4.73 (s, 1H), 4.85 (m, 1H) 5.26-5.39 (m, 1H) 6.90 (bs, 1H), 7.06 (m, 2H), 7.24 (m, 1H). ESI-MS 489 (M+1)

The synthetic route of 2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Edmondson, Scott D.; Fisher, Michael H.; Kim, Dooseop; Maccoss, Malcolm; Parmee, Emma R.; Weber, Ann E.; Xu, Jinyou; US2015/359793; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

33332-29-5, name is 2-Amino-5-chloropyrazine, 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. Quality Control of 2-Amino-5-chloropyrazine

17 (1.1 g, 8.5 mmol) was dissolved in dichloromethane (25 mL) followed by the addition of NBS (1.52 g, 8.5 mmol) in batches over a period of 15 min at room temperature. When the reaction was completed, saturated aqueous Na2CO3 solution (10 mL) was added. After stirring for 10 min, the mixture was partitioned between dichloromethane (100 mL) and water (100 mL). The organic layer was dried over anhydrous Na2SO4, decolorized with activated charcoal (0.5 g), and concentrated to give a yellow solid (1.53 g, yield 87%). 2-Amino-3-bromo-5-chloropyrazine (18a) Yield: 87%, yellow solid, M.p.: 108-110 C. 1H NMR(400 MHz, CDCl3): delta 7.97 (s, 1H), 5.08 (s, 2H). 1H NMR(400 MHz, DMSO-d6): delta 8.10 (s, 1H), 6.99 (s, 2H). 13CNMR (125 MHz, CDCl3):delta 151.66, 140.26, 134.75, 123.27. EI-MS m/z: 207 (M+, Cl35, Br79,76), 209 (M+, Cl37,Br79 and Cl35,Br81,100), 211 (M+, Cl37, Br 81,26), 128 (M+,Cl35,-Br, 75), 130 (M+, Cl37,-Br, 25), 101 (M+, Cl35,-Br,-HCN, 30), 103 (M+, Cl37,-Br, -HCN, 10).

The synthetic route of 33332-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Qi; Xu, Mingshuo; Guo, Shuang; Zhu, Fuqiang; Xie, Yuanchao; Shen, Jingshan; Chemical Papers; vol. 73; 5; (2019); p. 1043 – 1051;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 1111638-10-8, 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 1111638-10-8 as follows.

To a stirring solution of product of step 2 (20 mg, 0.130 mmol) in acetic acid (1 ml) and water (2.0 ml) was added Hexamethylenetetramine (20.08 mg, 0.143 mmol) and the reaction mixture was heated for 5 h at l20C. After completion of reaction it was diluted with ethyl acetate (10 ml) and 10 ml of water. Organic layer was separated, dried over Na2S04 and evaporated to get desired product. ESI-MS (m/z): 180.00 (M-H).

According to the analysis of related databases, 1111638-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CADILA HEALTHCARE LIMITED; DESAI, Ranjit; PANDYA, Vrajesh; PUJARA, Mehul; ARGADE, Anil; JOSHI, Jignesh; SATYANAND, Anshul; (66 pag.)WO2019/239382; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem