Day: February 8, 2021

Reference of 17282-40-5, 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. 17282-40-5, name is 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide, molecular formula is C9H12BrNO2, The 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.

27G. Methyl (4-(6-(l-((tert-butoxycarbonyl)amino)but-3-en-l-yl)-2-oxo-l,2- dihydropyridin-4-yl)-3-nitrophenyl)carbamate: To a solution of 27F (3.0 g, 7.15 mmol) and l-(2-ethoxy-2-oxoethyl)pyridinium bromide (1.189 g, 7.15 mmol) in EtOH (130 mL), was added ammonium acetate (11.03 g, 143 mmol) portion wise. After 15 min, the mixture was stirred at 75 C. The reaction mixture was then concentrated and dissolved in EtOAc. The organic layer was then washed with 1.0 N HC1, H20, saturated sodium bicarbonate solution and finally by brine. The organic phase was dried over sodium sulfate, filtered and concentrated to yield a residue which was purified by normal phase chromatography to isolate the desired product (2.2 g, 67%) as a brown solid. MS (ESI) m/z: 459.3 (M+H)+.

According to the analysis of related databases, 17282-40-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAM, Patrick Y.S.; CLARK, Charles G.; CORTE, James R.; EWING, William R.; GILLIGAN, Paul J.; JEON, Yoon; YANG, Wu; SMITH, Leon, M., II.; WANG, Yufeng; WO2013/22814; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 131803-48-0 ,Some common heterocyclic compound, 131803-48-0, molecular formula is C8H8BrNO2, 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.

To a solution of tert-butyl 4-(N-phenylsulfamoyl)piperazine-1-carboxylate (0.600 g, 1.757 mmol) in N,N-dimethylformide (10 mL) was slowly added sodium hydride (60.00 %, 0.091 g, 2.285 mmol) at the room temperature, and the mixture was stirred for 5 min at the same temperature. The reaction mixture was treated with methyl 6-(bromomethyl)nicotinate (0.485 g, 2.109 mmol), and stirred at the same temperature for additional 16 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (SiO2, 40 g cartridge; ethyl acetate / hexane = 10 % to 50 %) to give the crude product, which was dissolved in hexane (100 mL), and stirred. The resulting precipitates were collected by filtration, washed by hexane, and dried to give tert-butyl 4-(N-((5-(methoxycarbonyl)pyridin-2-yl)methyl)-N-phenylsulfamoyl)piperazine-1-carboxylate as white solid (0.585 g, 67.9 %).

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. 131803-48-0, Methyl 6-(bromomethyl)nicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; MIN, Jaeki; BAE, Miseon; KIM, Dohoon; JIN, Seokmin; KYUNG, Jangbeen; (191 pag.)WO2017/18805; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 272-23-1, Adding some certain compound to certain chemical reactions, such as: 272-23-1, name is Thieno[2,3-b]pyridine,molecular formula is C7H5NS, 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 272-23-1.

Thieno[2,3-b]pyridine-2-carbaldehyde: In an atmosphere of argon a mixture of 1.3 mL (2.08 mmol) of 0.8 M n-butyllithium in hexane and 0.3 mL (3.3 mmol) of N,N,N?,N?-tetramethylethylenediamine was stirred magnetically at room temperature for 30 minutes, diluted with 5 mL of hexane, cooled in a bath of dry ice-ethanol, and treated (with vigorous stirring) dropwise (from a syringe with a small needle) with 0.23 g (1.7 mmol) of thieno[2,3-b] pyridine. The mixture was stirred in the bath for 7 h longer and then for 12 h while it warmed to room temperature. It was cooled in ice, treated with 0.15 g (2.1 mmol) of dimethylformamide, stirred for one hour, and then treated successively with 1 mL of ethanol, 3 mL of saturated aqueous ammonium chloride solution, and 4 mL of water. The layers were separated. The organic layer (plus chloroform extracts of the aqueous layer) was dried (magnesium sulfate) and evaporated. The residue was triturated with hexane to give 0.18 g (66%) of brown solid; m.p. 131.5-132.5 C. Recrystallizations from ethanol (once with charcoal) gave white needles. 1H NMR (300 MHz, CDCl3) ppm 7.41 (dd, J = 4.5 Hz, 8.1 Hz, 1 H), 7.99 (s, 1 H), 8.24 (dd, J = 1.8 Hz, 8.1 Hz, 1 H), 8.73 (dd, J = 1.8 Hz, 4.5 Hz, 1 H), 10.12 (s, 1 H). 13C NMR (75 MHz, CDCl3) ppm 120.7, 131.8, 132.3, 134.0, 143.2, 150.5, 163.8, 185.0. IR (CHCl3, cm-1) 1682 (C=O). MS (EI, 70 eV): m/z [%] = 162[M]+ (100), 134[M-CO]+ (26). HRMS (FAB+) calculated for C8H6NOS [M+1] 164.0170, found 164.0167.

According to the analysis of related databases, 272-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Garcia-Carrillo, Mario Alfredo; Guzman, Angel; Diaz, Eduardo; Tetrahedron Letters; vol. 58; 20; (2017); p. 1952 – 1956;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1152617-24-7, 3-Chloro-4-iodopyridin-2-amine, 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, Product Details of 1152617-24-7, blongs to pyridine-derivatives compound. Product Details of 1152617-24-7

Step b: To a solution of 3-amino-5-chloropyrazine-2-thiol (100 mg, 0.619 mmol), 3-chloro-4-iodopyridin-2- amine (315 mg, 1.238 mmol), XantPhos (35.8 mg, 0.062 mmol), and Pd2(dba)3 (28.3 mg, 0.03 mmol) in dioxane (3 mE) was added (at RT and under N2) DIPEA (324 IL, 1.856 mmol). The resulting solution was stirred in a microwave reactor for 2.5 h at 100 C. After cooling to RT, the reaction was diluted with EtOAc and it was filtered through a pad of Celite with EtOAc (10 mE). The combined filtrates were concentrated and the resulting residue was purified by silica chromatography (0 to 5% gradient of MeOH/DCM) to give 3-((2-amino-3-chloropyridin-4-yl)thio)-6-chloropyrazin-2-amine (180 mg, 0.627 mmol). ?H NMR (400 MHz, METHANOE-d4) oe ppm 7.88 (s, 1H), 7.68 (d, J=5.56 Hz, 1H), 6.06 (d, J=5.56 Hz, 1H), 1.35-1.43 (m, 2H). MS mlz288.2 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1152617-24-7, 3-Chloro-4-iodopyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; Chen, Zhuoliang; Dore, Michael; Fortanet, Jorge Garcia; Karki, Rajesh; Kato, Mitsunori; LaMarche, Matthew J.; Perez, Lawrence Blas; Williams, Sarah; Sendzik, Martin; (63 pag.)US2017/1975; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109-09-1, 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. 109-09-1, name is 2-Chloropyridine, molecular formula is C5H4ClN, The 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.

Example 21 was repeated in the absence of zinc chloride. A yield in moles of 4-(2′-pyridyl)benzaldehyde of 26% was obtained relative to the 2-chloropyridine added, palladium turnover of 520.

According to the analysis of related databases, 109-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Euticals Prime European Therapeutical SpA; US6765097; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 769-28-8 , The common heterocyclic compound, 769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, molecular formula is C8H8N2O, 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.

The titledproduct was obtained from carbonitrile B7c according to the general procedure describedpreviously for the reduction reaction of carbonitrile as a light yellow solid (6.3 g). The crude product was dissolved with menthol in ice bath below 0 C, the 4 N hydrogenchloride ethanol solution (20 mL) was added dropwise. The stirring was continued for 60min, and the solid filtered off and washed with ethanol. After drying, hydrochloride saltwas obtained as a white solid (5.0 g, 97%). 1H NMR (600 MHz, DMSO-d6) delta (ppm): 11.84(br, 1H), 8.04 (s, 3H), 5.97 (s, 1H), 3.77 (s, 2H), 2.21 (s, 3H), 2.16 (s, 3H). Compounds B1~B5were obtained from different carbonitrile (B6a-c, B7a-b) to provide the correspondingproducts according to the general procedure described previously for the reductionreaction of carbonitrile.

The synthetic route of 769-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Guoliang; Du, Fangyu; Sun, Wenjiao; Wang, Lihui; Wu, Chunfu; Yang, Cheng; Zhou, Qifan; Molecules; vol. 25; 9; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15128-82-2, 2-Nitropyridin-3-ol, 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, 15128-82-2, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Nitropyridin-3-ol

300 g of TM2, 205 g of SM2 and 540 g of triphenylphosphine were dissolved in 2 L of THF and 361 g of DEAD was added dropwise at 0 C. After completion of the dropwise addition, the mixture was stirred at room temperature for two hours, and the reaction was complete by TLC (PE / EA = 3: 1).The ethyl acetate layer was dried and concentrated to 2 C to 0 C to precipitate a large amount of solid which was collected by filtration and the filtrate was concentrated to a final concentration of ethyl acetate. 1L. After cooling, the solid was separated. The solids were collected by filtration twice, washed with PE / EA = 5: 1 and filtered to remove solids (about 500 g), and the filtrate was evaporated to remove the solvent.Column chromatography gave 400 g of TM3 (pale yellow solid, eluent PE / EA = 7: 1) in 80% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15128-82-2, its application will become more common.

Reference:
Patent; JINAN TRIO PHARMATECH CO LTD; SUN, XUEYING; LI, JIE; LI, WANHU; GAO, YANFANG; YANFANG, KUN; (17 pag.)CN103664896; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1480-87-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1480-87-1, name is 2-Fluoro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: At room temperature, fluoro-nitro-pyridine (fluoro-nitro-benzene) (1 eq.), amino alcohol (ether, ester) (1 eq.), such as (S)-2-amino-3-(p-tolyl)propan-l-ol, and potassium carbonate (excess) are mixed in dimethylformamide. The reaction was stirred at room temperature for overnight. After filtration and removing solvent, the residue was purified by flash chromatography using 20-30% hexanes in ethyl acetate as eluent. Giving diamine compounds, such as (S)-2-((3-nitropyridin-2-yl)amino)-3-(p-tolyl)propan-l-ol, as yellow solid or oil.Reaction of 2-fluoro-3-nitro pyridine with (S)-2-amino-3-(p-tolyl)propan-l-ol yielded the product as yellow solid (50%). ‘ H NMR (400 MHz, CDCl3) d 8.44 – 8.30 (m, 3H), 7.17 (d, J = 8.0 Hz, 2H), 7.11 (d, J = 7.9 Hz, 2H), 6.66 (dd, J = 8.3, 4.5 Hz, 1H), 4.67 – 4.55 (m, 1H), 3.85 (d, J = 10.9 Hz, 1H), 3.73 (dd, J = 10.6, 6.0 Hz, 1H), 3.11 (s, 1H), 2.97 (dddd, J = 13.8, 13.8, 13.8, 7.0 Hz, 2H), 2.31 (s, 3H). 13C NMR (101 MHz, CDCl3) d 155.27, 152.67, 136.33, 135.69, 134.26, 129.36, 129.13, 128.34, 112.11, 65.38, 54.96, 37.22, 21.04.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1480-87-1, 2-Fluoro-3-nitropyridine.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DE BRABANDER, Jef; ROSENBAUM, Daniel; LIANG, Qiren; WANG, Wentian; (343 pag.)WO2019/191327; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine, molecular formula is C6H7BrN2O, The 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. Recommanded Product: 2-Bromo-6-methoxypyridin-4-amine

In a 50 mL single collar flask 500 mg (2.4 mmol, 1 eq) of 2 bromo-6-methoxy-pyridin-4- ylamine were introduced, to which was added 20 mL of toluene and 586 mg (4.92 mmol, 2 eq) of thionyl chloride, and the mixture heated at reflux for 3 hours. The reaction medium was dry concentrated under vacuum, and the residue was returned to solution in 20 mL of acetonitrile. 325 mg (2.46 mmol, 1 eq) of 2-hydroxy-2-methyl-pentanoic acid was then added at ambient temperature. After 16 hours at ambient temperature, the reaction mixture was heated to 80C for 4 hours, then to 60C for 3 days, and the reaction mixture was then dry concentrated. The residue was dissolved in 50 mL ethyl acetate. The solution was washed twice with 50 mL of an aqueous solution saturated with ammonium chloride, and then twice with 50 mL of water. The organic phase was then dried over magnesium sulphate and then dry concentrated under vacuum. A brown oil was obtained which was purified by chromatography on silica with a 1/1 (v/v)heptane/ethyl acetate mixture as the eluent. A brown solid was then obtained and purified by chromatography on grafted C18 silica with a water / acetonitrile mixture as the eluent (gradient 5 at 100% acetonitrile). 2-Hydroxy-2-methyl-pentanoic acid (2-bromo-6- methoxy-pyridin-4-yl)-amide was obtained in the form of a white solid. Melting point = 122C. NMR (1H, DMSO): 0.9 (t; 3H; J=4 Hz); 1.1 -1.3 (m; 1 H); 1.4 (s; 3H); 1.4-1 .5 (m; 1 H); 1.6 (m; 1 H); 1 .7 (m; 1 H); 3.9 (s; 3H); 5.8 (s; 1 H); 7.4 (d; 1 H; J=1 .4 Hz); 7.8 (d; 1 H; J=1 .4 Hz); 10.2 (s; 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 1196152-34-7.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; POINSARD, Cedric; WO2013/64681; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1462-86-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1462-86-8, name is 3-Aminopicolinic acid, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

3-Aminopicolinic acid (145 mg, 1.05 mmol) was carefully added in 3 aliquots to a slurry of UAIH4 (143 mg, 3.78 mmol) in dry tetrahydrofuran (6 ml). The resulting mixture was stirred at 15C overnight. After cooling in an ice bath, the reaction mixture was quenched with careful addition of water (1 ml) dropwise, followed by 15% aqueous NaOH (1 ml), and then water (3 ml). The resulting solid was filtered and washed several times with tetrahydrofuran. The filtrate was concentrated. The residue was purified by flash chromatography on silica gel using 5% CH3OH (NH3) /ethyl acetate as eluent to yield the title compound as a yellow oil. 1 0 mg.MS (electrospray): m/z [M+H]+ = 125

Statistics shows that 1462-86-8 is playing an increasingly important role. we look forward to future research findings about 3-Aminopicolinic acid.

Reference:
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem