Category: pyridine-derivatives

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

Application of 69045-79-0 , The common heterocyclic compound, 69045-79-0, name is 2-Chloro-5-iodopyridine, molecular formula is C5H3ClIN, 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.

Synthesis of 2-hydrazinyl-5-iodopyridine (0815) The solution of 2-chloro-5-iodopyridine (2.0 g, 20.9 mmol), anhydrous hydrazine (3.3 mL, 105 mmol) in pyridine (40 mL) was heated at reflux overnight. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. To the residue was added 1 N sodium hydroxide solution and it was extracted with EtOAc. The organic layer was separated, dried (sodium sulfate) and concentrated under reduced pressure. To the residue was added hexanes, and the precipitate was collected and dried in vacuo to afford the title compound (1.35 g, 69% yield) as off-white crystals. MS (ES+, m/z): 236.2 (M++1).

The synthetic route of 69045-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tolero Pharmaceuticals, Inc.; Xu, Yong; Brenning, Benjamin Gary; Kultgen, Steven G.; Liu, Xiaohui; Saunders, Michael; Ho, Koc-Kan; (119 pag.)US9416132; (2016); B2;,
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

Synthetic Route of 1620-75-3 ,Some common heterocyclic compound, 1620-75-3, molecular formula is C7H6N2, 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 6-methylpyridine-2-carbonitrile (1 g, 8.46 mmol, 1 eq) in CCU (15 mL) was added NBS (1.51 g, 8.46 mmol, 1 eq) and AIBN (139.0 mg, 0.84 mmol, 0.1 eq). The mixture was stirred at 80 C for 16 hr. The reaction mixture was added H20 (30 mL) and extracted with EA (30 mL * 3). The combined organic layers were washed with brine (30 mL), dried with anhydrous Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography (40 g SepaFlash Silica Flash Column, EA/PE: 0-10%) to afford two main spots. To afford 6-(bromomethyl)pyridine-2-carbonitrile (979 mg, crude) as yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1620-75-3, its application will become more common.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (472 pag.)WO2020/97389; (2020); 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.113975-22-7, name is 2-Fluoro-3-iodopyridine, molecular formula is C5H3FIN, molecular weight is 222.99, as common compound, the synthetic route is as follows.COA of Formula: C5H3FIN

Hydrazine hydrate (12.50 mL, 256 mmol) was added dropwise to a solution of 2-fluoro-3-iodopyridine (preparation 26a, 5.72 g, 25.7 mmol) in ethanol (43 mL) and the resulting mixture was stirred at room temperature for 24 hours and then at 35 C for a further 24 hours. The solvent was then evaporated in vacuo and water was added. The white solid that formed was filtered, washed with water and dried to yield the title compound (2.78 g, 46%) as a white solid which was used without further purification. LRMS (m/z): 236 (M+1)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113975-22-7, 2-Fluoro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2113503; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 82671-06-5, 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 82671-06-5, name is 2,6-Dichloro-5-fluoropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

[0253] A mixture of 2,6-dichloro-5-fluoronicotinic acid (1.26 g, 6.0 mmol), 3-fluorophenethyl amine (1.25 ml_, 9.0 mmol), DIEA (3.14 ml_, 18 mmol) and MeCN (6 ml.) was refluxed for 48 hrs and concentrated. The residue was dissolved in EtOAc (120 ml_) and washed with saturated citric acid, water, brine, dried and concentrated. The organic layers were combined, dried (MgSO4) and concentrated. The residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give 6-chloro-5-fluoro-2-(3-fluorophenethylamino)nicotinic acid as a solid (920 mg, 49%). LRMS (M+H+) m/z 313.0.

According to the analysis of related databases, 82671-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYTOKINETICS, INCORPORATED; WO2008/16643; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74784-70-6 ,Some common heterocyclic compound, 74784-70-6, molecular formula is C6H5F3N2, 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.

EXAMPLE 614-(Aminomethyl)-l-(7H-pyrrolor2,3-dlpyrimidin-4-yl)-N-(5-(trifluoromethyl)pyridin-2- yl)piperidine-4-carboxamide; 6 IA. ferf-Butyl 4-cyano-4-(5-(trifluoromethyl)pyridin-2-ylcarbamoyl)piperidine- 1 – carboxylateHATU (1121 mg, 2.95 mmol) was added in one portion to l-(tert-butoxycarbonyl)-4- cyanopiperidine-4-carboxylic acid (Example 26A) (500mg, 1.97 mmol) and DIPEA (1.030 ml, 5.90 mmol) in DMA (5ml) at 2O0C under nitrogen. The resulting solution was stirred at 20 0C for 10 minutes then 2-amino-5-(trifluoromethyl)pyridine (383 mg, 2.36 mmol) added. The reaction mixture was stirred at 50 0C for 6 hours then at 20 0C for 18 hours. The reaction mixture was diluted with EtOAc (50 mL), and washed sequentially with water (2 x 50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 20 to 40% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford and triturated with diethyl ether to afford tert-butyl 4- cyano-4-(5-(trifluoromethyl)pyridin-2-ylcarbamoyl)piperidine-l -carboxylate (554 mg, 70.7 %) as a white solid.IH NMR (400.13 MHz, DMSO-d6) delta 1.42 (9H, s), 2.00 – 2.07 (2H, m), 2.25 (2H, d), 2.97 (2H, s), 4.04 (2H, d), 8.19 – 8.27 (2H, m), 8.80 (IH, t), 11.38 (IH, s) MS m/e M-H 397

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. 74784-70-6, 5-(Trifluoromethyl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75110; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem