Tag: M.W:100-200

Related Products of 867267-24-1 ,Some common heterocyclic compound, 867267-24-1, molecular formula is C7H9NO2, 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.

66.9 g (661.1 mmol) of A/A-diisopropylamine were dissolved in 380 g of THF and cooled to a temperature of -60C. 395.2 mL (632.4 mmol) of w-butyllithium (1.6 M in hexane) were added within 45 min while keeping the temperature below -50C. The mixture was stirred at -60C for another 15 min. Then 80 g (574.9 mmol) of 2,5-dimethoxypyridine were added within 45 min while keeping the temperature between -50 and -60C. After completion of the addition the adding funnel was washed with another 10 mL of THF. The reaction mixture was stirred at -60C for 2 h, before 118.9 g (632.4 mmol) triisopropyl borate was added within 30 min. Again the adding funnel was washed with 10 mL of THF. The reaction mixture was warmed to 20C and stirred for 30 min. Then a mixture of acetic acid (106 g) and water (602 g) was added within 15 min and the mixture was stirred for another 30 min. Then the organic solvents (650 g) were evaporated in vacuo (300 mbar) at a temperature of maximum 70C and the resulting suspension cooled to 20C and filtered. The product cake was washed with cold water (three times 100 mL) and dried at 40C for about 16 hours under reduced pressure in a drying oven. Yield: 78.6 g (75% of theory). MS (ESI+): m/z = 184.1 [M+H]+ ; ‘H-NMR (400MHz, DMSO-cL): d [ppm] = 8.15 (hr s, 2H), 7.80 (s, 1H), 6.76 (s, 1H), 3.78 (d, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,867267-24-1, its application will become more common.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; EGGER, Julian; GOeTZ, Daniel; SOWA, Michal; (43 pag.)WO2019/175043; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 166526-03-0, Adding some certain compound to certain chemical reactions, such as: 166526-03-0, name is 4,6-Dichloronicotinonitrile,molecular formula is C6H2Cl2N2, 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 166526-03-0.

A mixture of 4,6-dichloronicotinonitrile (100 mg, 0.58 mmol), 2-fluoro-5-methoxy-N-(4- (4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide (259 mg, 0.636 mmol), Pd(dppf)C12DCM (24 mg, 0.024 mmol) and Cs2CO3 (381 mg, 1.16 mmol) in dioxane (3 mL) and H20 (0.5 mL) was heated under N2 at 100 C for 6 h. The mixture was cooled to room temperature, diluted with EtOAc (30 mL), filtered through celite, concentrated and purified by silica gel chromatography eluting with ethyl acetate in hexane (0-30 percent) to afford the title compound (244 mg, yield: 100%).

According to the analysis of related databases, 166526-03-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEW ERA PHARMA, INC.; XIAN, Jun; (82 pag.)WO2018/106459; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1034921-05-5, Methyl 4-chloro-3-fluoropicolinate, 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, Safety of Methyl 4-chloro-3-fluoropicolinate, blongs to pyridine-derivatives compound. Safety of Methyl 4-chloro-3-fluoropicolinate

A. Synthesis of 3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinic acid To a suspension of N-(4-methylpyridin-2-yl)-5-thiocyanatothiazol-2-amine (3.4 g, 13.69 mmol, described in the synthesis of thiocyanates, Example C) in methanol (150 mL, previously bubbled with argon) was added dithiothreitol (3.70 g, 23.96 mmol). The reaction was stirred at 23 C. for 10 minutes, then methyl 4-chloro-3-fluoropicolinate (2.27 g, 11.98 mmol) was added followed by an aqueous solution of NaOH (1N, 12 mL, 11.98 mmol). The resulting reaction mixture was stirred for 1 hour, then concentrated to about one-fourth of the volume. The mixture was then diluted with water (200 mL) and neutralized with ammonium chloride. The resulting solid was collected by filtration and vacuum dried to give the crude title material (5.7 g) as a solid. This solid was purified on silica gel Biotage chromatography (ethyl acetate) to give the title material (3.01 g, 70%) as a solid. 1H NMR of the compound showed contamination with dithiothreitol. The compound was used as such in the next reaction. The solid was dissolved in THF (100 mL) and the solution was treated with aqueous sodium hydroxide (1N, 12 mL, 11.95 mmol). The reaction was stirred at 23 C. for 2 hours, then diluted with water and neutralized with 1N aq. HCl. The mixture was concentrated to remove THF and the resulting off-white solid was collected by filtration and vacuum dried to give the title material (1.86 g, 64%) as a solid. 1H NMR (400 MHz, DMSO-d6) delta ppm: 2.31 (3H, s), 6.67-6.73 (1H, m), 6.84 (1H, d, J=4.55 Hz), 6.92 (1H, s), 7.74-7.78 (1H, m), 8.04 (1H, d, J=4.29 Hz), 8.17 (1H, t, J=4.55 Hz).

The synthetic route of 1034921-05-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; US2010/48581; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13362-28-2, 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 13362-28-2 as follows.

The starting material was prepared as follows: (2S,4S)-1-(4-Nitrobenzyloxycarbonyl)-4-acetylthiocarboxypyrrolidine (1.5 g, 4 mmol) was treated at ambient temperature, for 5 hours, with thionyl chloride (12 ml) and a catalytic amount of DMF (15 mg). The solvent was evaporated, the residue taken up in CH2 Cl2, evaporated, dried under reduced pressure for 1 hour and solubilized in CH2 Cl2 (10 ml). This solution was added to a cold (0 C.) solution of 2-amino-4-carboxypyridine (560 mg, 4 mmol) diisopropylethylamine (2.12 ml, 12 mmol) and trimethylsilylchloride (1 ml, 12 mmol) in dry CH2 Cl2. After 12 hours at ambient temperature, the solvent was evaporated, the residue purified by subjecting to chromatography on HP20SS resin, (eluant: CH3 CN/H2 O) to give (2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-(4-carboxy-2-pyridylcarbamoyl)pyrrolidin-4-ylthioacetate (650 mg, 32.5%). NMR: delta1.9 (m, 1H); 2.32 (s, 3H); 2.83 (m, 1H); 3.36 (m, 1H); 4.0 (m, 2H); 4.64 (s, 1H); 4.9-5.35 (m, 2H); 7.4-7.7 (m, 3H); 7.92 (s, 1H); 8.2 (s, 1H); 8.47 (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,13362-28-2, its application will become more common.

Reference:
Patent; Zeneca Limited; US5444057; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 100-26-5, name is 2,5-Pyridinedicarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2,5-Pyridinedicarboxylic acid

A mixture of TbCl3·6H2O (0.0373 g, 0.10 mmol), CuCl2·2H2O (0.0171 g, 0.10 mmol), H2pydc (0.0419 g, 0.25 mmol), NaOH (0.0020 g, 0.50 mmol), and H2O (6 mL) was sealed in a 10-mL Teflon-lined stainless steel container and heated at 170 C for 3 day. Upon being cooled to room temperature at a rate of 5 C/h, dark-blue block crystals were obtained in 43% yield (based on Cu). Anal. for C42H50N6O40Cu3Tb2 (%): C, 28.22; H, 2.82; N, 4.70. Found: C, 28.33; H, 2.74; N, 4.77. IR (solid KBr pellet, cm-1): 3399(m), 1638(s), 1610(s), 1554(s), 1456(m), 1394(s), 1352(s), 1276(m), 1171(w), 1150(w), 1039(w), 892(w), 823(m), 767(m), 691(m), 670(m), 510(m), 454(w).

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, 100-26-5, 2,5-Pyridinedicarboxylic acid.

Reference:
Article; Xia, Zheng-Qiang; Wei, Qing; Chen, San-Ping; Feng, Xin-Ming; Xie, Gang; Qiao, Cheng-Fang; Gao, Sheng-Li; Zhang, Guo-Chun; Journal of Solid State Chemistry; vol. 197; (2013); p. 489 – 498,10;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 98198-48-2, 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. 98198-48-2, name is 2-Amino-5-bromo-4-methylpyridine, molecular formula is C6H7BrN2, 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.

To a stirred solution of 5-bromo-4-methylpyridin-2-amine (1.0 g, 5.35 mmol) in DMF (25.0 mL) at 0 C was added portion wise NCS (1.428 g, 10.69 mmol). The mixture was stirred at room temperature for 5 h. The reaction was quenched with cold water. The reaction mixture was diluted with ethyl acetate and the layers were separated. The aqueous layer was extracted with ethyl acetate (2 x 50 mL), the combined organic layers was washed with water (50 mL), brine (10 mL), dried over sodium sulphate and concentrated to get crude material. The crude material was purified by ISCO using silica column 40 g silica column. The compound was eluted in 25% ethyl acetate in hexanes, the fractions was collected and concentrated to afford 5-bromo-3-chloro-4-methylpyridin- 2-amine (0.700 g, 3.16 mmol, 59% yield) as a light brown solid. MS (M+1) m/z: 222.9 (MH+). LC retention time 1.14 min [L].

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 98198-48-2, 2-Amino-5-bromo-4-methylpyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; MUSSARI, Christopher P.; SHERWOOD, Trevor C.; GILMORE, John L.; HAQUE, Tasir Shamsul; WHITELEY, Brian K.; TORTOLANI, David R.; POSY, Shoshana L.; MACOR, John E.; LOMBARDO, Louis J.; SISTLA, Ramesh Kumar; REDDY, Anupama Kandhi Ramachandra; HEGDE, Subramanya; PASUNOORI, Laxman; KUMAR, Sreekantha Ratna; (388 pag.)WO2019/99336; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1173081-96-3, 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride, 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, SDS of cas: 1173081-96-3, blongs to pyridine-derivatives compound. SDS of cas: 1173081-96-3

General procedure: To a solution of indole derivatives (1 mmol), EDCI (0.29 g, 1.5 mmol), HOBt (0.20 g, 1.5 mmol) indry dichloromethane (10 mL) Et3N (0.76 g, 5 mmol) was added and the mixture was stirred at roomtemperature for 30 min. Then, the corresponding pyridone derivatives (1 mmol) was added, and theresulting mixture was reacted at room temperature for indicated time while monitoring by TLC. Whenthe reaction was complete the reaction mixture was poured into water, extracted with dichloromethane(15 x 3 mL), and washed with water (3 x 15 mL) and brine (15 mL). The organic solution was driedwith anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The solid residuewas purified by column chromatography on silica gel.

The synthetic route of 1173081-96-3 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

Application of 636-73-7, 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 636-73-7, name is Pyridine-3-sulfonic acid. This compound has unique chemical properties. The synthetic route is as follows.

Preparation 27; A mixture of 3-pyridinesulfonic acid (10.0 g), phosphorous pentachloride (13.1 g) and phosphoryl chloride (10.0 ml) was stirred at 1300C for 3.5 hours. The solution was evaporated and diluted with acetone. The solution was evaporated and poured into water (200 ml) and EPO isopropyl ether (400 ml). The organic layer was separated, washed with brine twice, saturated sodium bicarbonate aqueous solution and brine and dried over magnesium sulfate. The solution was evaporated, covered with hexane (20 ml) and added hydrogen chloride in ethyl acetate (4N, 20 ml) dropwise with stirring. The resulting solid was collected by filtration and dried to give 3- pyridinesulfonyl chloride hydrochloride (9.49 g) .NMR (200 MHz, DMSO-d6, delta) : 8.12 (IH, dd, J=5, 8Hz), 8.72 (IH, dd, J=I.8, 3Hz), 8.95 (IH, d, J=5.5Hz),8.99 (IH, d, J=IHz), 14.25 (IH, br s)

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 636-73-7, Pyridine-3-sulfonic acid.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2006/33446; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14254-57-0, 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. 14254-57-0, name is Isonicotinoyl chloride. A new synthetic method of this compound is introduced below.

To a solution of tert-butyl 4-(aminomethyl)-4-(4-cyclopropylpiperazin-1- yl)piperidine-1 -carboxylate (0.769 mmol, 1.0 equiv.) and triethylamine (2.5 equiv.) in dichloromethane (7 ml) was added isonicotinyl chloride (0.769 mmol, 1.0 equiv.) and the reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with dichloromethane, successively washed with water and brine, dried over sodium sulphate and the solvent evaporated under reduced pressure to obtain the crude product which was purified by silica gel column chromatography. Yield: 70%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14254-57-0, Isonicotinoyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; WO2009/109364; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.1211530-54-9, name is 5-(Bromomethyl)nicotinonitrile, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.SDS of cas: 1211530-54-9

Racemic 8-bromo-2,2-difluoro-2H-1 ,4-benzoxazin-3(4H)-one (50 mg, 0.189 mmol, intermediate 4), 5-(bromomethyl)-3-pyridinecarbonitrile (37.3 mg, 0.189 mmol, intermediate 24), potassium carbonate (52.3 mg, 0.379 mmol) and potassium iodide (0.314 mg, 1.894 mumol) were dissolved in DMF (3000 mul) in a 10 ml. round-bottomed flask open to the atmosphere and stirred at room temperature overnight. The reaction mixture was evaporated to dryness, redissolved in EtOAc (30ml) and treated with saturated aqueous sodium bicarbonate (30ml). The aqueous layer was extracted with EtOAc (2x30ml) and the organic layers were combined, washed with brine (30ml), dried over magnesium sulfate, filtered and evaporated to dryness to give the crude product (119mg) as a light brown oil. The crude product was purified on a 25+S Biotage silica cartridge, eluting with a 0 to 70% mixture of EtOAc in hexane. This gave an off-white solid (54 mg). 47 mg of this racemic mixture was resolved using a Chiralpak AS column eluting with heptane: ethanol (90:10) v/v pump-mixed. Using these conditions the faster- running enantiomer (20 mg, Compound 57 or 58) and the slower-running enantiomer (15 mg, Compound 57 or 58) were obtained in >99% enantiomeric excess. 1H NMR (CD3OD) delta: 1.45 (3H, d), 5.23 (1 H, q), 5.41 (2H, s), 7.18 (1 H, dd), 7.25 (1 H, t), 7.42 (1 H, dd), 8.14 (1 H, s), 8.78 (1 H, d), 8.84 (1 H, d). m/z [M+H]+: 345.9. Retention time 0.81 min (LC/MS method 3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211530-54-9, 5-(Bromomethyl)nicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem