Tag: M.W=100-200

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, category: Pyrazines

To a stirred solution of 2,5-dichloro-pyrazine (0.5 g, 3.37 mmol) in toluene (10 ml_) was added 6-(tert-butyl- dimethyl-silanyloxy)-naphthalen-2-yl-boronic acid (1.02 g, 3.37 mmol), EtOH (10 ml_), water (2 ml_) and NaHCO3 (0.42 g, 5.0 mmol). Argon was bubbled through the reaction mixture for 30 min. Then Pd(PPh3)4 (0.19 g, 0.16 mmol) was added and the mixture was heated at 45¡ãC for 2 hours. The EtOH was evaporated under vacuum and the mixture was diluted with ethyl acetate (35 ml_). The reaction mixture was then filtered through celite. The organic layer was washed with water (1 x 10 ml_), and brine (1 x 10 ml_), then dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silica gel (ethyl acetate: hexane, 1 :19) to afford the title compound as a white solid (450 mg). 1H NMR (400 MHz, DMSO-d6): delta= 0.28 (6H, s), 1.00 (9H, s), 7.20 (1 H, d), 7.38 (1 H, s), 7.99 (2H, m), 8.17 (1 H, m), 8.70 (1 H, s), 8.75 (1 H, s), 9.40 (1 H, s). LCMS (System 1 ) (run time = 5 min): Rt = 3.45 min, 371 [M+H]+

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Reference:
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; PRYDE, David Cameron; TRAN, Thien Duc; WO2011/4276; (2011); A1;,
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Application of 889447-19-2, 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. 889447-19-2, name is 2-Chloro-5H-pyrrolo[2,3-b]pyrazine belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-chloro-5H-pyrrolo[2,3-b]pyrazine (423 mg, 3.09 mmol) in2-methyltetrahydrofuran (10 mL) was added NIS (787 mg,3.39 mmol), and the reaction mixturewas stirred at rt overnight. Saturated aqueous sodium thiosulfate (50 mL) was added to quenchthe reaction, and the resulting mixture was partitioned. The aqueous layer was extracted withEtOAc (50 mL x 2). The combined organic layers were washed with saturated brine (80 mL),dried over anhydrous Na2S04, filtered, and the filtrate was concentrated in vacuo. The residuewas purified by silica gel chromatograph (PE/EtOAc (v/v) = 2011-4/1) to give the title compoundas a white solid (814 mg, 100 %).MS (ESI,neg.ion) m/z: 262.1 [M-Hr.

The synthetic route of 2-Chloro-5H-pyrrolo[2,3-b]pyrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
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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 4744-50-7 as follows. Application In Synthesis of 2,3-Pyrazinecarboxylic anhydride

General procedure: Sodium dodecyl sulfate (SDS, 6 mmol) was added to a stirred heterogeneous suspension of amine (5 mmol) in water (20 mL) until a homogeneous solution was formed, (in case of turbidity, the mixture was warmed to obtain a clear solution). Anhydride 17(5 mmol) dissolved in acetonitrile (5 mL) was added to this solution in one lot. After stirring for 1 h at room temperature, the acetonitrile was evaporated and the product precipitated from the aqueous layer. To the aqueous solution containing precipitate, solid sodium hydrogen carbonate was added pinch-wise until the effervescence ceased and the pH was 6.0. The remaining precipitated product was filtered, washed with water (20 mL), dried in a vacuum desiccator. In cases where the product did not precipitate, the reaction mixturewas extracted with ethyl acetate (2 25 mL). The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed in a rotary evaporator under reduced pressure to yield the pure product.

According to the analysis of related databases, 4744-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Saudi, Milind; Zmurko, Joanna; Kaptein, Suzanne; Rozenski, Jef; Neyts, Johan; Van Aerschot, Arthur; European Journal of Medicinal Chemistry; vol. 87; (2014); p. 529 – 539;,
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Related Products of 33332-28-4,Some common heterocyclic compound, 33332-28-4, name is 2-Amino-6-chloropyrazine, molecular formula is C4H4ClN3, 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 6-chloro-2-pyrazinamine (4 kg, 31 mol, 1.00 equiv), Et3N (4.7 kg,46.5 mol, 1.50 equiv), Pd(OAc)2 (139 g, 0.62mo1, 0.02 equiv), dppf (343 g, 0.62 mol, 0.02equiv) in methanol (60 L) was placed in a 100 L pressure tank reactor(10 atm).The resulting solution was allowed to react for 5 h while maintaining the temperature at 85C. The reaction progress was monitored by TLC (DCM: MeOH = 20: 1) until the starting material was consumed completely, and cooled to room temperature. The resulting mixture was concentrated under vacuum. The residue was washed with water 50 L. Thefilter was collected and dried. The product (3.8 kg, purity = 95 %, 80 % yield)obtained as a pale brown solid.1H-NIVIR (300 MHz, DMSO-d6) : 8.27(1H, s), 8.06(1H, s), 6.87(2H, b), 3.84(3H, s). LC-MS: m / z = 154(M+H) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-chloropyrazine, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CUI, Haifeng; HENNESSY, Alan; JIN, Qi; MILES, Timothy James; MOSS, Stephen Frederick; PEARSON, Neil David; (173 pag.)WO2017/29602; (2017); A2;,
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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. 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. HPLC 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;,
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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. 43029-19-2, name is 3-Aminopyrazin-2(1H)-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Aminopyrazin-2(1H)-one

3-Aminopyrazin-2(1H)-one (1.5 g, 13.5 mmol) was dissolved inacetic anhydride (6 mL) and the mixture was heated at 100 for 2 h.After the reaction completed (TLC control), the solvent was evaporatedand the residue was slurried in ethyl acetate to afford the crude brownyellow product. The crude product was subjected to refluxed ethanol(60 mL) in the presence of charcoal (30 mg) to give 22 as a yellowprecipitate (0.85 g, yield 50%).

According to the analysis of related databases, 43029-19-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guo, Shuang; Xu, Mingshuo; Guo, Qi; Zhu, Fuqiang; Jiang, Xiangrui; Xie, Yuanchao; Shen, Jingshan; Bioorganic and Medicinal Chemistry; vol. 27; 5; (2019); p. 748 – 759;,
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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. 91476-80-1, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H9N3

5,6,7,8-Tetrahydroimidazo[1 ,2-a]pyrazine(l17) (4.53 g, 36.8 mmol) and triethylamine (6.16 mL, 44.2 mmol) were dissolved in dichloromethane (DCM) (200 mL) and treated with di-tert-butyl dicarbonate (10.25 mL, 44.2 mmol). The solution was stirred at RT for 48 h and concentrated in vacuo to afford a crude oil. The crude product was purified by flash chromatography (Isolera, 340 g, 0-100% 2M ammonia in methanokdichloromethane (1 :9)/dichloromethane) to afford 3 fractions. Fraction 2 was identified by LC/MS as containing desired product. The residue was dissolved in ethyl acetate (300 ml), washed with saturated sodium bicarbonate solution (50 ml_), water (2 x 50 ml_), brine (50 ml_), dried over anhydrous sodium sulfate and concentrated to afford product in 6.77g. LC/MS = 224 (M+H)+, retention time = 0.71 minutes (2 minute method (high pH)).

According to the analysis of related databases, 91476-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALL, Ian David; WALTER, Daryl Simon; WO2010/125101; (2010); A1;,
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Pyrazine | C4H4N2 – PubChem

Related Products of 63286-28-2, 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 63286-28-2 as follows.

Step 3. N’-(3-chloropyrazin-2-yl)-l-(5-ethylpyrimidin-2-yl)piperidine-4- carbohydrazide[0323] To a solution of l-(5-ethylpyrimidin-2-yl)piperidine-4-carboxylic acid (3.0 g, 13 mmol) in DMF (50 niL), was added 0-(7-Azabenzotriazol-l-yl)- N,N,N’,N’-tetramethyluronium hexafluorophosphate (5.2 g, 14 mmol), diisopropylethylamine (2.5 mL, 14 mmol), and 2-chloro-3-hydrazinylpyrazine (2.0 g, 14 mmol). After 1 h at rt, the solution is diluted with DCM (200 mL), and washed with brine (100 mL) and water (100 mL), concentrated to residue, and taken up in ethyl acetate (50 mL). The resulting precipitate is isolated by filtration to give Nu’-(3-chloropyrazin-2-yl)-l-(5-ethylpyrimidin-2-yl)piperidine-4- carbohydrazide as off-white solid (3.3 g, 71%). 1H NMR (400 MHz, DMSOd6) delta 9.89 (s, IH), 8.93 (s, IH), 8.22 (s, 2H), 8.06 (d, IH), 7.73 (d, IH), 4.60 (d, 2H), 2.92 (t, 2H), 2.56 (m, IH), 2.40 (q, 2H), 1.78 (m, 2H), 1.49 (m, 2H), 1.10 (t, 3H). LCMS: 362.2 (M+H)+.

According to the analysis of related databases, 63286-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KALYPSYS, INC.; KAHRAMAN, Mehmet; SMITH, Nicholas, D.; BONNEFOUS, Celine; NOBLE, Stewart, A.; PAYNE, Joseph, E.; WO2010/88518; (2010); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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: 5-Methylpyrazine-2-carboxylic acid

General procedure: Under Argon, a stirred solution of carboxylic acid (0.37 mmol,1.0 eq.) and Et3N (0.48 mmol, 1.3 eq.) in dry THF (7 mL) was cooledto 10 C. Ethyl chloroformate (0.55 mmol, 1.5 eq.) was drop wiseadded and the resulting mixture was stirred for 2 h. Afterwards, asolution of sodium azide (0.63 mmol, 1.7 eq.) in water (2 mL) wasadded in one portion. After 1 h at 10 C, the reactionwas found tobe complete (TLC) and was quenched into iced water (5 mL). Themixture was extracted with EtOAc (3 10 mL) and the combinedorganic layers were successively dried over MgSO4, filtered andevaporated. The crude acyl azide was placed in dry toluene (20 mL)and heated at reflux for 1 h to give the corresponding crude isocyanate.The latter was placed in dry dioxane (7 mL) prior to addingthe appropriate amine 8, 9 or 10 (0.37 mmol, 1.0 eq.). The solutionwas heated at 100 C for 24 h. The reaction mixture was cooled andthe volatiles were removed to dryness in vacuum at 40 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5521-55-1, its application will become more common.

Reference:
Article; Boulahjar, Rajaa; Ouach, Aziz; Bourg, Stephane; Bonnet, Pascal; Lozach, Olivier; Meijer, Laurent; Guguen-Guillouzo, Christiane; Le Guevel, Remy; Lazar, Said; Akssira, Mohamed; Troin, Yves; Guillaumet, Gerald; Routier, Sylvain; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 274 – 287;,
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Pyrazine | C4H4N2 – PubChem

Synthetic Route of 50866-30-3, 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. 50866-30-3, name is 5-Methylpyrazine-2-carbaldehyde belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(1R,2S)-1-Hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methylpyrazin-2-yl)propane-2-sulfonamide and (1S,2R)-1-hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methylpyrazin-2-yl)propane-2-sulfonamide, Example 27.2 (1063) To a solution of N,N-bis(4-methoxybenzyl)ethanesulfonamide (Example 12.0, 73.13 g, 0.209 mol, 1.2 equivalent.) in anhydrous THF (600 mL) at -78 C. was slowly added n-butyl lithium (83.71 mL, 0.209 mol, 2.5 M solution in hexanes, 1.2 equivalent.) via additional funnel, and the resulting mixture was stirred for 10 min. Next, a solution of 5-methylpyrazine-2-carbaldehyde (Example 27.1, 21.3 g, 0.174 mol, 1.0 equivalent.) in anhydrous THF (150 mL) was added, and the mixture was stirred at the same temperature for 45 min and then allowed to warm to RT for 2 h. The reaction mixture was then quenched by addition of aqueous ammonium chloride (200 mL) and extracted with EtOAc (2¡Á2 L). The combined organic layers were washed with brine (2¡Á500 mL). No product was observed in the ammonium chloride or brine layers. After drying over anhydrous Na2SO4, the filtrate was concentrated in vacuo, to afford the product as an oil. The product thus obtained was purified by flash column chromatography (silica gel, 230-400 mesh) to afford the two isomers. The faster moving isomer (32 g) was obtained as a white solid from the column with a gradient of 10% to 30% EtOAc in petroleum ether. 1H NMR (400 MHz, DMSO-d6) delta 8.61 (d, J=1.5 Hz, 1H), 8.51 (d, J=1.5 Hz, 1H), 7.22-7.11 (m, 4H), 6.90-6.80 (m, 4H), 6.10 (d, J=5.9 Hz, 1H), 5.29 (dd, J=5.9, 2.2 Hz, 1H), 4.36-4.16 (m, 4H), 3.73 (app s, 6H), 3.70-3.66 (m, 1H) 2.50 (merged with solvent peak, 3H) and 1.10 (d, J=7.0 Hz, 3H). LCMS (ESI positive ion) m/z: 472.4 (M+H)+. (1S,2S)-1-Hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methyl-pyrazin-2-yl)propane-2-sulfonamide and (1R,2R)-1-hydroxy-N,N-bis(4-methoxybenzyl)-1-(5-methyl-pyrazin-2-yl)propane-2-sulfonamide, Example 28.3 (1064) Further elution of the mixture in Example 27.2 with a gradient of 30% to 35% 21 EtOAc in 201 petroleum ether yielded Example 27.3 (16 g, pale yellow gummy liquid). 1H NMR (400 MHz, CDCl3) delta 8.62 (d, J=1.6 Hz, 1H), 8.44 (d, J=1.5 Hz, 1H), 7.25-7.12 (m, 4H), 6.93-6.82 (m, 4H), 5.17 (d, J=7.1 Hz, 1H), 4.47 (d, J=15.2 Hz, 3H), 4.14 (d, J=15.4 Hz, 2H), 3.82 (s, 3H), 3.82 (s, 3H), 3.66-3.61 (m, 1H), 2.60 (d, J=2.0 Hz, 3H), and 1.08 (dd, J=7.2, 2.1 Hz, 3H). LCMS (ESI positive ion) m/z: 472.4 (M+H)+.

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

Reference:
Patent; AMGEN INC.; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEDLEY, Simon J.; HOUZE, Jonathan; JUDD, Ted C.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YEH, Wen-Chen; (415 pag.)US2017/320860; (2017); A1;,
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