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. COA of Formula: C6H6N2O2

General procedure: To the dipeptide salt (7 or 11, 1 mmol) in Schemes 2 and 3 wasadded a solution of 7 N NH3 in CH3OH (10 mL) and reaction mixturewas stirred for 10 min at 0 C. The solvent was evaporatedunder reduced pressure to afford free peptides, which was dissolvedin DMF (4 mL) and cooled to 4 C. To this reaction mixturerequisite carboxylic acid (1 mmol), DIC (1.1 mmol) and HOBt(1.1 mmol) was added and stirring continued at 4 C for 36 h. Thesolvent was removed under reduced pressure and the resultingresidue purified by column chromatography over neutral alumina using CHCl3/CH3OH (4:1) as eluant to afford desired peptides.The peptides were checked for their homogeneity on aShimadzu SPD-M20A HPLC system using a Supelcosil LC-8(25 cm 4.6 mm ID) column. The peptides were analyzed by usingan isocratic solvent system of CH3CN-H2O-TFA (70:30:0.8%) usinga SUPELCOSIL C-18 column with a flow rate of 1 mL/min

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

Reference:
Article; Meena, Chhuttan L.; Thakur, Avinash; Nandekar, Prajwal P.; Sangamwar, Abhay T.; Sharma, Shyam S.; Jain, Rahul; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5641 – 5653;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 69214-33-1, name is 8-Chloroimidazo[1,2-a]pyrazine, 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 69214-33-1, Quality Control of 8-Chloroimidazo[1,2-a]pyrazine

N-(4-(Imidazo[1,2-a]pyrazin-8-ylamino)phenyl)-4-methylbenzenesulfonamide (35) All glassware was dried and purged with Arprior to use. Pd2(dba)3(2.97 mg, 1 mol%), DavePhos (3.83 mg, 3 mol%) and NaOtBu (43.8 mg, 0.456 mmol) were dissolved in anhydroustoluene (3 mL). 8-Chloroimidazo[1,2-a]pyrazine (49.8 mg, 0.324 mmol) and N-(4-aminophenyl)-4-methylbenzenesulfonamide23 (106 mg, 0.389 mmol) were addedand the reaction was stirred under reflux, under Ar for 16 h. The reaction was cooled to RT and solventremoved in vacuo, before the residuewas taken up in CH2Cl2 (50 mL) and washed with H2O(3 x 30 mL) and brine (30 mL), dried (MgSO4), filtered andconcentrated in vacuo. Flash chromatography (applied in pet. ether;eluted 2:1 pet. ether/EtOAc) afforded the title compound as a brown solid (69.7mg, 0.184 mmol, 56%). Mpt: Decomposed before melting; Rf = 0.30 (3:1 EtOAc/pet. ether); IR (numax/cm-1,thin film): 3338, 3045, 1537, 1505; 1H NMR (600 MHz, CDCl3):deltaH = 2.37 (s, 3H, 21-H),6.88 (s, 1H, 15-H), 7.06 (d, J = 8.8 Hz, 2H, 13-H), 7.21 (d, J = 8.3Hz, 2H, 19-H), 7.45 (d, J = 4.6 Hz, 1H, 6-H), 7.56-7.57 (m, 3H, 2,3,5-H),7.63 (d, J = 8.3 Hz, 2H, 18-H), 7.76 (d, J = 8.8 Hz, 2H, 12-H),8.19 (s, 1H, 10-H); 13CNMR (150 MHz, CDCl3): deltaC = 21.7 (C-21), 111.9 (C-5),115.2 (C-3), 120.3 (C-12), 123.9 (C-13), 127.4 (C-18),128.4 (C-6), 129.7 (C-19), 131.1 (C-14), 131.9 (C-2),133.2 (C-9), 136.2 (C-17), 137.4 (C-11), 143.9 (C-20),146.0 (C-8); LRMS m/z (ES+):380 [M+H]+, 402 [M+Na]+; HRMS m/z (ES+): Found380.1168 [M+H]+; C19H18N5O2Srequires 380.1181.

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; Sayer, James R.; Walldn, Karin; Pesnot, Thomas; Campbell, Frederick; Gane, Paul J.; Simone, Michela; Koss, Hans; Buelens, Floris; Boyle, Timothy P.; Selwood, David L.; Waksman, Gabriel; Tabor, Alethea B.; Bioorganic and Medicinal Chemistry; vol. 22; 22; (2014); p. 6459 – 6470;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 873-42-7, name is 2-Amino-3,5-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 873-42-7, Product Details of 873-42-7

General procedure: To the mixture of o-aminohalopyrazine (0.8 mmol) 1 in solvent was added NaOH (2.8 mmol, 3.5 eq), and stirred at T’ for 20 min. Isothiocyanate (0.92 mmol, 1.15 eq) 2 was added to the solution dropwise and heated at T”. The progress of the reaction was monitored by TLC. When all the starting material had been consumed, the mixture was allowed to room temperature. The product was isolated by the method described in Table 1.

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; Kwak, Se Hun; Lee, Gee-Hyung; Gong, Young-Dae; Bulletin of the Korean Chemical Society; vol. 33; 12; (2012); p. 4271 – 4274;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 33332-28-4, The chemical industry reduces the impact on the environment during synthesis 33332-28-4, name is 2-Amino-6-chloropyrazine, I believe this compound will play a more active role in future production and life.

Pre Step A 6-(Methyloxy)-2-pyrazinamine A mixture of 6-chloro-2-pyrazinamine (200 mg, 1.544 mmol) and sodium methoxide (250 mg, 4.63 mmol) in methanol (3.9 ml) was heated to 130 C. via a microwave reactor for 60 min. The crude product mixture was purified by RP-HPLC to give 6-(methyloxy)-2-pyrazinamine (154 mg, 1.231 mmol, 80% yield). MS (ES+) m/z 125.8 (MH+).

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-Amino-6-chloropyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Glaxosmithkline LLC; Aubart, Kelly M.; Benowitz, Andrew B.; Fang, Yuhong; Hoffman, James; Karpinski, Joseph M.; Knox, Andrew Nicholson; Liao, Xiangmin; Qin, Donghui; Shi, Dongchuan; Spletstoser, Jared T.; US2013/345120; (2013); A1;; ; Patent; GlaxoSmithKline Intellectual Property (No. 2) Limited; Aubart, Kelly M.; Benowitz, Andrew B.; Fang, Yuhong; Hoffman, James; Karpinski, Joseph M.; Knox, Andrew Nicholson; Liao, Xiangmin; Qin, Donghui; Shi, Dongchuan; Spletstoser, Jared T.; US8901119; (2014); B2;,
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, Safety of 5-Methylpyrazine-2-carboxylic acid

1) 5-Methylpyrazine-2-carboxylic acid N-methoxy-N-methylamide Triethylamine (28.9 mL) was added to a solution of 5-methylpyrazine-2-carboxylic acid (13.0 g), 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (19.8 g), 1-hydroxybenzotriazole (14.0 g), and N, O-dimethylhydroxyamine hydrochloride (10.1 g) in N, N-dimethylformamide (130 mL) at room temperature, and the resultant mixture was stirred for 63 hours. Water and ethyl acetate were added to the reaction solution, and the mixture was partitioned. The organic layer was dried over anhydrous sodium sulfate. After separation by filtration, a residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane-ethyl acetate), to obtain 5-methylpyrazine-2-carboxylic acid N-methoxy-N-methylamide (12.3 g, 72%) as an oily product. 1H-NMR(400MHz, CDCl3)delta: 2.63(3H, s), 3.41(3H, s), 3.74(3H, s), 8.46(1H, s), 8.82(1H, s). FAB-MSm/z: 182(M+H)+.

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:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1785418; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 23688-89-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 23688-89-3 name is 6-Chloropyrazine-2-carboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate 136-Ch[oro-N,N-dimethy[pyrazine-2-carboxamide A mixture of 6-ch[oropyrazine-2-carboxy[ic acid [CAS-RN: 23688-89-3] (510 mg,3.22 mmo[, 1.0 eq), dimethy[amine [CAS-RN: 124-40-3] (1.61 mL, 2M so[ution inTHF, 3.22 mmo[, 1.0 eq), HATU (1.47 g, 3.86 mmo[, 1 .2 eq) and DIPEA (1 .78 mL, 9.65 mmo[, 3.0 eq) was disso[ved in 15 mL DMF and stirred at rt overnight. The reaction mixture was partitioned between ethy[ acetate and water. The organic phase was washed with brine and separated by the use of a Whatman fi[ter. Thevo[ati[e components were removed in vacuo and the crude materia[ obtained was purified via preparative MPLC (Biotage Iso[era; 25 g SNAP cartridge: hexane/ethy[ acetate 8/2 -> hexane/ethy[ acetate 4/6) to give 330 mg (50% yie[d of theory) of the tit[e compound.UPLC-MS (Method 1): R = 0.67 mm; MS (EI0): m/z = 186 [M]¡Â.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Chloropyrazine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; PRECHTL, Stefan; SIEMEISTER, Gerhard; WENGNER, Antje Margret; ACKERSTAFF, Jens; NOWAK-REPPEL, Katrin; BADER, Benjamin; LIENAU, Philip; STOeCKIGT, Detlef; WO2014/118186; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 98-97-5, name is Pyrazine-2-carboxylic acid, molecular formula is C5H4N2O2, 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. Application In Synthesis of Pyrazine-2-carboxylic acid

The title compound (1, Scheme 1) was prepared following the previously described procedure [23] via the reaction of pyrazine-2-carboxylic acid (A) (5 mmol) with thionyl chloride (7.5 mmol) in dry toluene to yield the corresponding acyl chloride (B), which was subsequently reacted with 3-iodo-4-methylaniline (5 mmol) in dry acetone with pyridine (5 mmol). The reaction was stirred at room temperature for1 hour, then poured into cold water. The crude product was collected, adsorbed on silica and purified by flash chromatography(silica, gradient elution ethyl-acetate in hexane0 e30%). The yield of chromatographically pure product was 84% oftheoretical yield related to acid (A). Elementary composition(CHON) of 1 was in the range of ¡À0.4% of calculated values and themelting point was consistent with literature (141e142 C) measured, 142e143 C from literature [23]. The FT-IR spectrum(Fig. 1) was recorded using KBr pellets on a DR/JASCO FT-IR 6300 spectrometer. The FT-Raman spectrum (Fig. 2) was obtained on a Bruker RFS 100/s, Germany. For excitation of the spectrum, the emission of Nd:YAG laser was used with an excitation wavelengthof 1064 nm, a maximal power 150 mW; measurement of solid sample.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 98-97-5, its application will become more common.

Reference:
Article; Ranjith; Al-Abdullah, Ebtehal S.; Al-Omary, Fatmah A.M.; El-Emam, Ali A.; Anto; Sheena, Mary Y.; Armakovi?, Stevan; Armakovi?, Sanja J.; Zitko, Jan; Dolezal, Martin; Van Alsenoy; Journal of Molecular Structure; vol. 1136; (2017); p. 14 – 24;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 4858-85-9, A common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.

First, 5.06 g of 2,3-dichloropyrazine, 5.23 g of 4-fluorophenyl boronic acid, 22.16 g of cesium carbonate, and 200 mL of dioxane were put in a three-neck flask equipped with a reflux pipe, and 0.467 g of tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)3) and 2.5 mL of tricyclohexylphosphine (abbreviation: Cy3P) were added thereto while the mixture was stirred under a nitrogen atmosphere, and they were reacted at 85 C. for 11 hours. After the reaction, the reaction solution was cooled down to room temperature and filtrated. A solvent of the obtained filtrate was distilled off, and the obtained residue was refined with a column chromatography using dichloromethane as a development solvent, so that 2-chloro-3-(4-fluorophenyl)pyrazine was obtained (light yellow powder, yield: 55%).

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

Reference:
Patent; Semiconductor Energy Labratory Co., Ltd.; US2008/312437; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 19847-12-2, 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 19847-12-2 as follows.

General procedure: Sodium metal (23 mg) was dissolved in absolute methanol (20 ml) and was labeled as sodium methoxide solution in methanol. 2-Cyanopyridine (0.210 ml, 2 mmol) was dissolved in absolute methanol (10 ml) and to it was added sodium methoxide solution (0.5 ml) prepared above, the reaction contents were stirred at room temperature for 2 h. 4-(2-Aminoethyl) morpholine (0.26 ml, 2 mmol) was added to the reaction mixture. The reaction contents were heated under reflux for 8 h. Solvent was removed under reduced pressure and to the residue left behind was added diethyl ether, solid so obtained was filtered and washed with diethyl ether to give crude product. This crude product was purified by crystallization from ethyl acetate/methanol to give pure N-(2-morpholin-4-yl-ethyl)-pyridine-2-carboxamidine (3a).

According to the analysis of related databases, 19847-12-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Arya, Surbhi; Kumar, Nikhil; Roy, Partha; Sondhi; European Journal of Medicinal Chemistry; vol. 59; (2013); p. 7 – 14;,
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 14508-49-7 as follows. Computed Properties of C4H3ClN2

General procedure: Tetrakis(Triphenylphosphine)Palladium(0) (1-3% mol) is added to a mixture of 2- Chloropyrazine (1 eq), Aryl/Heteroaryl boronic acid (1 eq) and base (2 eq) suspended into the solvent. The reaction mixture is heated until the reaction is completed, the solvent isremoved under reduced pressure and the residue is partitioned between water and EtOAc (or iN aqueous NaOH and EtOAc); organic layer is separated, dried, concentrated under reduced pressure and the residue is purified by Silica gel flash chromatography using a suitable eluent.

According to the analysis of related databases, 14508-49-7, the application of this compound in the production field has become more and more popular.

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