Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 36070-80-1, name is 5-Chloropyrazine-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 36070-80-1, Application In Synthesis of 5-Chloropyrazine-2-carboxylic acid

To a cooled solution of 26 (3 g, 18.92 mmol, 1.0 eq), in N,N-dimethylformamide (30 mE) was added 1-[l3is (dimethylamino)methylene] -1 H-i ,2,3-triazolo[4,5-b]pyri- dinium 3-oxid hexafluorophosphate (8.65 g, 22.70 mmol, 1 .2 eq) and stirred at room temperature for 20 mm. Reaction mixture again cooled diisopropylethylamine (7.32 mE, 56.76 mmol, 3.0 eq) was added followed by addition of dimethylamine (0.851 g, 18.92 mmol, 1.0 eq). The reaction mixture was stirred at room temperature for 2 h. After completion of reaction, reaction mixture was transferred into water and product was extracted with ethyl acetate. Organic layer was combined, washed with brine solution, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was thrther purified by column chromatography and the compound was eluted in 0.9% methanol in dichioromethane to obtain 26.1(2.5 g, 71.18%). MS(ES): mlz 186.61 [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; Nimbus Lakshmi, Inc.; Masse, Craig E.; Greenwood, Jeremy Robert; Mondal, Sayan; Cowen, Scott D.; McLean, Thomas H.; (624 pag.)US2019/31664; (2019); A1;,
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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, COA of Formula: C6H6N2O

[0146] To a stirred solution of compound I (2 g; 16.4 mmol; 1 eq) in methanol (20 mL) were added ammonium acetate (12.6 g; 164 mmol; 10 eq) and sodium cyanoborohydride (1 g; 16.4 mmol; 1 eq) and the resulting mixture was stirred at 23 C for 17 h. The mixture was quenched with water (50 mL) and the organic components were extracted with ethyl acetate (2 x 200 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and the solvents were removed in vacuo to afford crude compound, which was purified by silica gel (230-400 mesh) column chromatography, eluting with 10% MeOH/CH2C12, to afford the title compound (0.8 g, 40%). 1H NMR (CDC13) oe 8.60 (s, 1H), 8.49 (m, 1H), 8.43 (d, 1H, J= 2Hz), 4.20 (m, 1H), 1.45 (d, 3H, J= 7Hz).

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; ASANA BIOSCIENCES, LLC; THOMPSON, Scott; VENKATESAN, Aranapakam; PRIESTLEY, Tony; KUNDU, Mrinal; SAHA, Ashis; WO2015/95128; (2015); A1;,
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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. 75907-74-3, name is (3,5,6-Trimethylpyrazin-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H12N2O

The obtained 7.5 g of TMP-OH (49.3 mmol) was dissolved in 50 ml of absolute ethanol to add active manganese dioxide.(6.4g, 73.6mmol) was oxidized and reacted in an oil bath at 84 C for 2 h. After the TLC reaction was completed,The reaction solution was carefully filtered with a five-layer filter paper while hot, and the manganese dioxide powder was removed.After filtration, a clear filtrate was obtained, which was evaporated to dryness under reduced pressure on a rotary evaporator. Wet loading column chromatography:The mobile phase EA:PE (1:5) was separated and purified, and the fraction was monitored by TLC. Collecting the compound 1a-4 fraction,Combine the same fraction and distill it to obtain a crystalline white solid.5.5g (36.7mmol),[M+H]+=151 is 1a-4 (TMP-CHO), yield 75%.

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 75907-74-3.

Reference:
Patent; Guangzhou Xique Pharmaceutical Co., Ltd.; Wang Yuqiang; Yao Hui; Wu Chuanbin; Tao Liang; Sun Yewei; (27 pag.)CN103804309; (2019); B;,
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Synthetic Route of 56423-63-3, 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. 56423-63-3, name is 2-Bromopyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Reaction Scheme 6EXAMPLE 30: l-(4-methoxybeDzylV3-methyl-5-(pyrazin-2-ylVlH-pyrazolor3.4- blpyridine To a stirred solution of compound 8 (230 mg, 0.627 mmol) and 2-bromopyrazine 43 (100 mg, 0.63 mmol) in DME (3 mL), ethanol (1 mL) and water (0.2 mL) was added sodium carbonate (135 mg, 1.26 mmol) and was degassed for 10 min followed by the charging Pd(PPh3)4 (7.5 mg, 0.03 equivalent). The resulting reaction mixture was purged with N2 and degassing was submitted for heating at 80C overnight under pressure in a sealed tube. After completion of the reaction the reaction was diluted with ethyl acetate and water. The organic layer was separated and aqueous phase was extracted with ethyl acetate. The combined organic layer was washed with brine and dried over sodium sulphate and evaporated. The crude product was flash chromatographed with 100-200 mesh silica gel eluting the pure compound at 20% ethyl acetate in hexane as off white colored solid of compound 44 in 30 mg. The product 44 was confirmed by 1H NMR (400 MHz, CDC13) delta: 9.18 (s, 1H), 9.17 (s, 1H), 9.10 (d, J=1.58 Hz, 2H), 8.67 (s, 1H), 8.64 (s, 1H), 7.35 (d, 2H), 6.84 (d, 1H), 5.62 (d, 2H), 3.76 (s, 3H), 2.62 (s, 3H).

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

Reference:
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); A1;,
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Electric Literature of 77112-53-9,Some common heterocyclic compound, 77112-53-9, name is Imidazo[1,2-a]pyrazine-2-carboxylic acid, molecular formula is C7H5N3O2, 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.

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).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Imidazo[1,2-a]pyrazine-2-carboxylic acid, its application will become more common.

Reference:
Article; Jyothi, Boggavarapu; Madhavi, Nannapaneni; Asian Journal of Chemistry; vol. 32; 1; (2020); p. 84 – 90;,
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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. 98-97-5, name is Pyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C5H4N2O2

General procedure: A catalytic amount of concentrated H2SO4 wasadded to a solution of carboxylic acids 16(a-j) (1.0 mmol)in 50 mL of methanol, and the mixture was refluxed for 6 h. It was allowed to cool. The saturated solution ofNaHCO3 was added to the reaction mixture, and it wasextracted with EtOAc (2 X 50 mL). The combined organiclayer was dried Na2SO4 and concentrated to obtain puremethyl esters 17(a-j).

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; Murty; Penthala, Raju; Polepalli, Sowjanya; Jain; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 627 – 643;,
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These common heterocyclic compound, 14667-55-1, name is 2,3,5-Trimethylpyrazine, 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: 2,3,5-Trimethylpyrazine

General procedure: An equimolecular mixture of 2,3-dimethylpyrazine (0.46 mmol, 50 mg) and 3,5-dichlorosalicylic acid (0.46 mmol, 95.8 mg) was dissolved in 15 mL ethanol at room temperature and stirred for about 30 min, followed by filtrating and slow evaporation. Colorless block-like crystals were obtained within 2 weeks with the total yield of 23.3%. IR (KBr pellet, cm-1): 3456, 3084, 2856, 2423, 1669, 1580, 1441, 1358, 1313, 1225, 1169, 1008, 875, 803, 742, 697, 608, 553. The colorlessblock-like crystal of cocrystal 2 and colorless needle crystals of cocrystal 3 were obtained in the similar way as cocrystal 1, but utilized 2,5-DMP and TMP instead of 2,3-DMP, with the total yield of 30.2% and 25.2%, respectively. IR (KBr pellet, cm-1) for cocrystal 2: 3445, 3079, 2868, 2402, 1669, 1586, 1447, 1363, 1308, 1225, 1175, 1053, 880, 803, 753, 692, 608, 558. IR (KBr pellet, cm-1) for cocrystal 3: 3445, 3073, 2935, 2402, 1669, 1586, 1441, 1391, 1352, 1285, 1241, 1175, 1024, 886, 708, 603, 558.

The synthetic route of 2,3,5-Trimethylpyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Ya-an; Yan, Cui-Min; Chen, Chen; Zhao, Xiao-Qing; Li, Tian; Sun, Bai-Wang; Research on Chemical Intermediates; vol. 45; 11; (2019); p. 5745 – 5760;,
Pyrazine – Wikipedia,
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Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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: 939412-86-9

(e) (trans)-benzyl 7-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-4-oxohexahydro-1H-pyrido[1,2-a]pyrazine-2(6H)-carboxylate A mixture of (trans)-2-((benzyloxy)carbonyl)-4-oxooctahydro-1H-pyrido[1,2-a]pyrazine-7-carboxylic acid (1.3 g, 3.9 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (840 mg, 4.7 mmol), HATU (2.2 g, 5.8 mmol) and TEA (1.6 g, 15.6 is mmol) in DMF (20 mL) was stirred at 25 C. for overnight. Then the reaction mixture was poured into water and extracted with EA (50 ml*3). The combined organic phase was washed with brine (100 mL), dried over Na2SO4, concentrated under vacuum to give the crude residue, which was purified by silica gel column chromatography (PE/THF=1/3) to give (trans)-benzyl 7-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-4-oxohexahydro-1H-pyrido[1,2-a]pyrazine-2(6H)-carboxylate (600 mg, yield 35.3%). 1H NMR (400 MHz, CD3OD) delta=8.52 (d, J=2.5 Hz, 1H), 8.33 (d, J=2.3 Hz, 1H), 7.40-7.29 (m, 5H), 5.15 (br. s., 2H), 4.77-4.67 (m, 1H), 4.12 (br. s., 1H), 3.96-3.85 (m, 1H), 3.48 (br. s., 2H), 2.71 (t, J=12.5 Hz, 1H), 2.52-2.36 (m, 1H), 2.11-1.97 (m, 2H), 1.90-1.71 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939412-86-9, its application will become more common.

Reference:
Patent; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
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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., name: Methyl 5-chloropyrazine-2-carboxylate

Preparation 10 To a solution of methyl 5-chloropyrazine-2-carboxylate (500 mg) in MeOH (5 mL) was added 28% NH3 aqueous solution (5 mL), and the mixture was stirred at ambient temperature. The precipitated solid was collected by filtration and washed with diisopropyl ether to afford 5-chloropyrazine-2-carboxamide (303 mg) as a solid.

The synthetic route of 33332-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; EP2123651; (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 50866-30-3 as follows. Recommanded Product: 50866-30-3

To a solution of 6-[(3S,4S)-4-ethylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (4.4 g) in dimethylformamide (62 mL) was added acetic acid (2.4 mL), 5-methylpyrazine-2-carbaldehyde (2 g) and sodium triacetoxyborohydride (5.27 g). The reaction mixture stirred for 2 h at ambient temperature and was carefully quenched with saturated sodium bicarbonate solution, extracted 3* with methylene chloride, dried with magnesium sulfate, filtered and concentrated. Purification via Biotage MPLC chromatography eluding with 1-4% methanolmethylene chloride/0.5% saturated ammonium hydroxide provided the title compound (3.9 g). 400 MHz 1H NMR (CDCl3) delta 8.52-8.48 (m, 1H), 8.38 (s, 1H), 8.02 (s, 1H), 4.81-4.75 (m, 1H), 4.11-4.01 (m, 3H), 3.79-3.75 (m, 1H), 3.60-3.53 (m, 2H), 3.40-3.32 (m, 1H), 3.10-3.08 (m, 1H), 2.94 (m, 1H), 2.63-2.57 (m, 1H), 2.53 (d, J=7.5 Hz, 1H), 2.37-2.18 (m, 4H), 1.90-1.83 (m, 2H), 1.67-1.60 (m, 1H), 1.54-1.47 (m, 1H), 0.95-0.92 (m, 3H). MS: (M+H m/z 424.2).

According to the analysis of related databases, 50866-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2009/30003; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem