Tag: M.W=200-300

Reference of 41270-66-0, A common heterocyclic compound, 41270-66-0, name is 5-Chloro-2,3-diphenylpyrazine, molecular formula is C16H11ClN2, 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.

30 g of 2-chloro-5,6-diphenylpyrazin and 131.22 g (0.3 mol) of 4-isopropylamino-1-butanol were added into a 500 mL flask, the mixture was heated to 190 C. and reacted at this temperature for 10 hours, cooled, samples were taken for testing, HPLC purity of the product was 63.5%. The reaction solution was poured into 1 L of ice water, the mixture was extracted with ether 200 mL¡Á3, the organic phases were combined and the solvent was concentrated to dryness, then the residue was purified by column chromatography, and 22.96 g of 4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]-1-butanol was obtained, HPLC purity was 97.2%, the molar yield was 56%. (0083) 1H-NMR data: 1H-NMR (400 MHz, CDCl3) delta 8.02 (s, 1H), 7.46 (d, 2H, J=7.6 Hz), 7.36 (d, 2H, J=7.2 Hz), 7.28-7.22 (m, 6H), 4.80-4.78 (m, 1H), 3.71 (t, 2H, J=6.4 Hz), 3.45 (t, 2H, J=7.6 Hz), 1.77-1.74 (m, 2H), 1.66-1.64 (m, 2H), 1.29 (d, 6H, J=6.8 Hz).

The synthetic route of 41270-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Seasons Biotechnology (Taizhou) Co., Ltd.; TANG, Fanghui; MA, Chi; JIA, Qiang; (11 pag.)US2018/29998; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 63744-22-9, A common heterocyclic compound, 63744-22-9, name is 6,8-Dibromoimidazo[1,2-a]pyrazine, molecular formula is C6H3Br2N3, 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.

Step 1. Preparation of [4-(6-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-phenyl]-morpholin-4-yl-methanone A solution of 6,8-dibromoimidazo[1,2-a]pyrazine (500 mg, 1.8 mmol), (4-aminophenyl)(morpholino)-methanone (408 mg, 1.98 mmol) and CSA (356 mg, 1.53 mmol) in iPrOH (30 mL) was stirred at 90 C. overnight. The solvent was evaporated. The residue was dissolved in DCM (30 mL). A NaHCO3 solution (10 mL) was added to adjust to pH=8. The organic layer was separated and dried over Na2SO4. The drying agent was removed by filtration and the resultant solution was concentrated in vacuo. The residue was purified through a silica-gel column (ethyl acetate:petroleum ether=1:1) to give the desired product as a yellow solid (500 mg, 69% yield). LC-MS: 404 [M+1]+, tR=1.409 min.

The synthetic route of 63744-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Brotherton-Pleiss, Christine E.; Lopez-Tapia, Francisco Javier; Lou, Yan; US2013/150360; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 41270-66-0, 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. 41270-66-0 name is 5-Chloro-2,3-diphenylpyrazine, 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.

Step 3: 2-Azido-5,6-diphenylpyrazine. To a stirred solution of 2-Chloro-5,6-diphenylpyrazine (45 mg, 0.17 mmol) in 500 muL DMF at room temperature under nitrogen was added sodium azide (11 mg, 0.17 mmol) and the reaction was warmed to 100 C. After stirring overnight, the reaction was cooled to room temperature, diluted with EtOAc (30 mL) and washed 4*30 mL with H2O and 1*30 mL with saturated NaCl. The organics were islolated, dried (MgSO4), filtered and concentrated to the 2-azidopyrazine, which exists as a yellow solid (45 mg, quantitative). 1H-NMR (400 MHz, CDCl3) delta9.73 (s, 1H), 7.58-7.42 (m, 6H), 7.36-7.23 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-2,3-diphenylpyrazine, and friends who are interested can also refer to it.

Reference:
Patent; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 17890-77-6, 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 17890-77-6 as follows.

To a solution of 3-amino-6-bromopyrazine-2-carboxamide (200 mg, 0.92 mmol) in triethoxymethane (10 mL) was added Ac20 (2 mL). The mixture was stirred at 130C for 1 h and 90C for 3 h. After being cooled to RT and extracted with EtOAc, the combined organic phaseswere basified to pH = 8 with a.q. NaHCO3, washed with brine, dried over Na2504, filtered andevaporated. The crude product was purified by prep-TLC (DCM : MeOH = 50: 1) to give theproduct of 6-bromopteridin-4(3H)-one (100 mg, yield: 48%). ?H-NMR (DMSO-d6, 400 MHz)8.59 (s, 1H), 7.89 (s, 1H). MS (M+H): 227 / 229.

According to the analysis of related databases, 17890-77-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 32111-21-0,Some common heterocyclic compound, 32111-21-0, name is 2-Iodopyrazine, molecular formula is C4H3IN2, 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 solution of N- (5-chloro-7-ethynyl-1, 3-benzodioxol-4-yl)-6-methoxy-7- (3- morpholin-4-ylpropoxy) quinazolin-4-amine (0.12g, 0. 24mmol), 3-iodopyrazine (O. lg, 0. 48mmol) and diisopropylamine (0. 066ml, 0. 48mmol) in ethyl acetate (3ml) was cooled to- 20 C under a nitrogen atmosphere. To this was added copper (I) iodide (0.014g, 0.072mmol) and bis (triphenylphospine) palladium (It) chloride (0.034g, 0. 048mmol). The reaction mixture was allowed to warm to ambient temperature and then stirred overnight. The mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography on silica eluting with a mixture of 0-10% methanol in dichloromethane to give the product as a light yellow solid (0.052g, 38%). NMR Spectrum: (DMSOd6) 1.99 (t, 2H), 2.40 (brs, 4H), 2.50 (t, 2H) partially obscured by DMSO peak, 3.59 (s, 4H), 3.97 (s, 3H), 4.23 (t, 2H), 6.27 (s, 2H), 7.19 (s, 1H), 7.35 (s, 1H), 7.89 (s, 1H), 8.42 (s, 1H), 8.74 (s, 1H), 8.78 (s, 1H), 8.96 (s, 1H), 9.66 (s, 1H). Mass Spectrum: M+H+ 575 and M+H-573.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodopyrazine, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/4732; (2004); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 32111-21-0, name is 2-Iodopyrazine, 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 32111-21-0, Quality Control of 2-Iodopyrazine

Example 55; N-(3-(5-(4-chlorophenyl’>-4-oxo-6-f4-fpyrazin-2-vDphenyl’)-4.5-dihvdro- 1 H-pyrazolof 3.4- d]p yrirnidin- 1 -yDphenyPmethanesulfonamide; [00189] A solution of N-(3-{5-(4-chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[ 1 ,3,2]dioxa-borolan-2-yl)phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyriinidin-l -yl} -phenyl)- methane sulfonamide (prepared as described in example 35, 0.50 g, 0.81 mmol) in N,N- dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 2-iodopyrazine (0.25 g, 1.21 mmol), cesium carbonate (0.527 g, 1.61 mmol), Pd(dppf)2Cl2 (0.06 g, 0.082 mmol) are added and the resulting solution is degassed with argon for 0.5 h. The reaction mixture is then heated at 100 0C for 3 h. The reaction mixture is cooled to it and diluted with water and extracted with ethyl acetate (3 *). The combined organic layer is washed with brine, dried over Na2SO-I, concentrated, and purified by column chromatography to afford N-{3-[5-(4- chloro-phenyl)-4-oxo-6-(4-pyrazin-2-yl-phenyl)-4,5-dihydro-pytauazolo[3 ,4-d]pyrimidin- 1 -yl]- phenyl} -methane sulfonamide. 1H NMR (DMSO-d6, 400 MHz) delta 10.15 (br, 1 H), 9.26 (d, IH), 8.71 (d, IH), 8.62 (d, IH), 8.52 (s, IH), 8.06 (m, 3H), 7.82 (m, IH), 7.60 (m, 2H), 7.52 (m, IH), 7.40 (m, 4H), 7.18 (m, IH), 3.02 (s, 3H); LC-MS calculated for C28H20ClN7O3S (M+H+) 570.1, found 570.0.

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; IRM LLC; WO2007/120454; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1053656-22-6, The chemical industry reduces the impact on the environment during synthesis 1053656-22-6, name is 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, I believe this compound will play a more active role in future production and life.

A solution of 7-tert-butyl 2-ethyl-5,6-dihydroimidazo[1,2-a]pyrazin-2,7(8H)-dicarboxylate (300 mg, 1.02 mmole) in THF (15 ml) was cooled to -78 C. and DIBAL-H (1 M in hexane, 2.0 ml, 2.0 mmole) was slowly added under a N2 atmosphere. The reaction mixture was stirred for 1 hour at this temperature and Na2SO4¡Á10 H2O was then added until the evolution of gas was no longer observed. Further Na2SO4¡Á10 H2O was added, filtered, and the residue was washed with DCM (25 ml). The filtrate was concentrated and the crude product obtained (450 mg) was used without further purification in the next stage

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, 7-tert-Butyl 2-ethyl 5,6-dihydroimidazo[1,2-a]pyrazine-2,7(8H)-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUENENTHAL GmbH; US2009/186899; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 24241-18-7, 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. 24241-18-7 name is 2-Amino-3,5-dibromopyrazine, 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.

(Trimethylsilyl)acetylene (1.845 g, 2.655 mL, 18.78 mmol) was added dropwise to a solution of 3,5-dibromopyrazin-2-amine 1 (5 g, 19.77 mmol) in DMF (25 mL)Triethylamine (10.00 g, 13.77 mL, 98.85 mmol), copper(I) iodide (451.7 mg, 2.372 mmol) and Pd(PPh3)4 (1.142 g, 0.9885 mmol) were then added and the resulting solution stirred at RT for 30 minutes. The reaction mixture was diluted with EtOAc and water and the layers separated. The aqueous layer was extracted further with EtOAc and the combined organic layers washed with water, dried (MgS04) and concentrated in vacuo. The residue was purified by column chromatography eluting with 15% EtO Ac/Petroleum ether to give the product as a yellow solid (3.99g, 75% Yield). XH NMR (400.0 MHz, DMSO) ? 0.30 (9H, s), 8.06 (IH, s); MS (ES+) 271.82

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-3,5-dibromopyrazine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; STORCK, Pierre-Henri; STUDLEY, John; PIERARD, Francoise Yvonne, Theodora Marie; DURRANT, Steven, John; LITTLER, Benjamin, Joseph; ANGELL, Paul; HUGHES, Robert, Michael; SIESEL, David, Andrew; URBINA, Armando; ZWICKER, Carl; LOCONTE, Nicholas; BARDER, Timothy; WO2013/49722; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 762240-92-6,Some common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, 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.

Into a 50 mL round-bottom flask was added 20 mL dichloromethane, followed by the addition of phenyl-butyric acid derivative (3.23 g, 0.01 mol) and triazolopyrazine hydrochloride (228 g, 0.01 mol). The temperature of the reaction mixture was cooled down to 0 C. in an ice-salt bath. 1-Hydroxylbenzotriazole (1.62 g, 0.012 mol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.29 g, 0.012 mol) were further added. 3 g Triethylamine was then added dropwise and the mixture was stirred at room temperature for 24 h. The reaction solution was washed with 3¡Á20 mL distilled water. The obtained organic layers were collected and dried over anhydrous magnesium sulfate for 1 h. Then, the desiccant was filtered off and the resulting reactant was concentrated to 4.67 g. The yield was 94%.

The synthetic route of 762240-92-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG HISOAR PHARMACEUTICAL CO., LTD.; Pan, Xianhua; Li, Weijin; Zhang, Qunhui; Ruan, Libo; Yu, Wansheng; Deng, Fei; Ma, Tianhua; Huang, Mingwang; He, Minhuan; US2013/281695; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, 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 87486-34-8, SDS of cas: 87486-34-8

A solution of tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate (2d, 1.7 g, 5.7 mmol, 1 equiv.), 3,5-dibromo-1-methylpyrazin-2(1H)-one (2e, 1.8 g, 6.8 mmol, 1.2 equiv.)and N,N-diisopropylethylamine (1.48 mL, 8.5 mmol, 1.5 equiv.) in N,N-dimethylacetamide (5 mL) was stirred in a sealed vial at 105 C for 30 h. The reaction was cooled to room temperature and EtOAc (20 mL) was then added. The solid precipitate was filtered and dried on high vacuum overnight to provide tert-butyl 4-(4-((6-bromo-4-methyl-3-oxo-3 ,4- dihydropyrazin-2-yl)amino)benzoyl)piperazine- 1 -carboxylate 2f. The product was carriedonto the next step without further purification.

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; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DOBROVOLSKY, Dennis; HUANG, Hai-Tsang; (152 pag.)WO2018/98275; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem