Category: pyridine-derivatives

Reference of 127561-18-6, 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. 127561-18-6, name is 1-(6-(Trifluoromethyl)pyridin-2-yl)piperazine. A new synthetic method of this compound is introduced below.

A-9 (0.33g, 1.40mmol), C-1 (0.30g, 1.30mmol),Triethylamine Anhydrous(0.263 g, 2.60 mmol) was dissolved in 25 mL of anhydrous acetonitrile, and HATU (0.513 g, 1.40 mmol) was added, and the reaction was performed at room temperature for 30 min. After the reaction, it was diluted with water, extracted with ethyl acetate, washed with dilute hydrochloric acid, washed with sodium bicarbonate solution, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated and purified by silica gel column chromatography (PE: EA = 2: 1, v / v) to obtain 470.385 g of the compound with a yield of 66.6%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,127561-18-6, 1-(6-(Trifluoromethyl)pyridin-2-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Patent; Hangzhou Weitan Pharmaceutical Technology Co., Ltd.; Cheng Yunfeng; Hu Yongzhou; (45 pag.)CN110357833; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71902-33-5, 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. 71902-33-5, name is 3,5-Difluoropyridine. A new synthetic method of this compound is introduced below.

INTERMEDIATE 63 : 3, 5-Difluoro-4-tributylstannanyl-pyridine [00224]. n-Butyl lithium (1.0 eq, 76 mmol, 47.6 mL, 1.6 M in hexanes) was added via dropping funnel to a solution of diisopropylamine (1.05 eq, 80 mmol, 11.2 mL) in THF (300 mL) at-78 °C under nitrogen (N2). The solution was stirred for 30 min at-78 °C, then a solution of 3,5- difluoropyridine (1.05 eq, 80 mmol, 9.2 g) in THF (20 mL) was added dropwise via syringe. A beige precipitate was observed to form. The reaction stirred at-78 °C for 90 min then tributyltin chloride (1.0 eq, 76 mmol, 20.7 mL) was added dropwise via syringe and the resulting solution allowed to warm to RT over 2 h. Water (5 mL) was added, then roughly 250 mL of THF was removed on a rotary evaporator. The resulting material was diluted with diethyl –139– ether (350 mL) and washed successively with water (2X200 mL), saturated sodium chloride solution (1X150 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford the 3,5-Difluoro-4-tributylstannanyl-pyridine as a colourless oil (27.5 g, 88percent). This material was used crude without further purification. Retention Time (LC, method: ammonium acetate standard): 3.35 min. MS (M+H+) : 406.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71902-33-5, its application will become more common.

Reference:
Patent; MILLENIUM PHARMACEUTICALS, INC.; WO2004/92167; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1050501-88-6, 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 1050501-88-6, name is 2-Bromo-6-chloropyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: synthesis of 5-chloro-1H-pyrrolo[3,2-bjpyridine-2-carboxylic acid (intermediate 20b)2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g, 34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of 2-bromo-6- chloropyridin-3-amine 20a (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol) in dry DMF (300 ml). The reaction mixture was stirred at 100C overnight. The solvent was then evaporated, water was added and the water layer was washed with EtOAc.The water layer was acidified with conc. HC1. The precipitate was filtered off and dried, yielding 25.21 g of the wanted product 20b (82.6 %). m/z = 197.1 (M+H), Cl pattern.

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 1050501-88-6, 2-Bromo-6-chloropyridin-3-amine.

Reference:
Patent; JANSSEN R&D IRELAND; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; HU, Lili; DEMIN, Samuel Dominique; COOYMANS, Ludwig Paul; WO2014/60411; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 103041-38-9, name is Ethyl 3-(pyridin-2-ylamino)propanoate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C10H14N2O2

EXAMPLE 1 Preparation of Ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]-propanoate (II) 100 g of compound I was dissolved in 1 L of dichloromethane under nitrogen atmosphere and cooled to 0-5 C. Thionyl chloride was added to the reaction mixture for 1 h and the reaction mixture was boiled to reflux. Maintained the reaction mass under the same temperature for 5-6 h. After completion of the reaction, excess thionyl chloride was removed by co-distillation with dichloromethane and finally the solvent was completely removed under vacuum. The acid chloride was then dissolved in dichloromethane under an inert atmosphere and triethyl amine was added to the reaction mixture. To the reaction mixture was added slowly a solution of ethyl-3-(pyridine-2-ylamino) propanoate in dichloromethane. The reaction mixture was maintained at the same temperature for another 6-12 h. After completion of the reaction, the reaction mass was diluted water and extracted the product with dichloromethane. The combined organic layers were separated and dried over anhydrous sodium sulphate. The solvent was distilled off under vacuum and the product was purified by hexane. Yield: 80%, HPLC: >98%

With the rapid development of chemical substances, we look forward to future research findings about 103041-38-9.

Reference:
Patent; Biophore India Pharmeuticals PVT. Ltd.; Pullagurla, Manik Reddy; Rangisetty, Jagadeesh Babu; Nandakumar, Mecheril Valsan; (8 pag.)US2015/246900; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 110651-92-8, 7-Chloro-6-nitrothieno[3,2-b]pyridine, 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, 110651-92-8, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (381 mg, 1.78 mmol), [(1R,2R,4S)-4-amino-2-methoxycyclohexyl]acetonitrile (racemic) (310 mg, 1.8 mmol) and N,N-diisopropylethylamine (1.2 mL, 7.1 mmol) in isopropyl alcohol (4.2 mL) was heated at 90 C. for 2 h. The crude was concentrated and purified with flash chromatography to give the desired product (485 mg, 78%). LCMS calculated for C15H19N4O3S (M+H)+: m/z=347.1. Found: 347.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,110651-92-8, its application will become more common.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Zhu, Wenyu; Mei, Song; Glenn, Joseph; US2014/121198; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1374639-78-7, 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.1374639-78-7, name is tert-Butyl 4-(6-((7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate, molecular formula is C28H38N8O3, molecular weight is 534.65, as common compound, the synthetic route is as follows.

In a nitrogen environment at about 25±2 C., mix 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbamide and 4-(6-aminopyyrol-3-yl)piperazin-1-carboxyl tert-butylate into tetrahydrofuran THF) added with lithium bis(trimethyl)amine (LiHMDS) and stir for about 1 h to obtain the intermediate 4-[6-[[7-cyclopentyl-6-[(dimethylamino)carbonyl]-7H-pyrrolo[2,3-pyrimidine-2-yl]amino]-3-pyridine]-1-piperazinecarboxyl 1,1-dimethylethylate. Cool the mixture to about 8±2 C. and keep the mixture at this temperature while an aqueous hydrogen chloride solution is subsequently added slowly and mixed into the mixture. After that, using a separatory funnel and ethyl acetate as an extracting agent, perform an extraction process in duplicate to acquire the aqueous phase. When the extracted solution is cooled to about 5 C. or lower, slowly add an aqueous sodium hydroxide solution until the pH reaches 12.5. Heat the solution to 25 C. and stir for about 16 h. Next, filter the solution to obtain the solid matter (or filter cake), and rinse the filter cake with DD water until the pH of the rinsing liquid is equal to or lower than 9. Lastly, dry the filter cake at about 55±5 C. to yield yellowish brown solids, which are 7-cyclopentyl-N,N-dimethyl-2-{[5-(piperazin-1-yl)pyridin-2-yl]amino}-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, whose molar recovery rate can be 98% or higher, with 98% or higher purity.

The chemical industry reduces the impact on the environment during synthesis 1374639-78-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHUNGHWA CHEMICAL SYNTHESIS & BIOTECH CO. LTD.; Kamani, Satyanarayana; Lu, Tzu-Chiang; Chang, Hsin-Yun; Mai, Chin-Cheng; (30 pag.)US10336763; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6283-81-4 ,Some common heterocyclic compound, 6283-81-4, molecular formula is C10H11NO3, 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.

2-Ethyl-5-pyridin-3-yl-2H-pyrazol-3-ol: To 3-oxo-3-pyridin-3-yl-propionic acid ethyl ester (500 mg, 3.57 mmol) in AcOH was added ethylhydrazine oxalate (231.9 mg, 3.86 mmol) and the mixture refluxed for 16 h. After which, the AcOH was evaporated and crude mass neutralized with aq. Na2CO3 solution. Following extraction with EtOAc, the organic phase was washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by column chromatography using 2% MeOH-DCM as an eluent to give 2-ethyl-5-pyridin-3-yl-2H-pyrazol-3-ol (110 mg, 22.5%) as a 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,6283-81-4, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; Bhagirath, Niala; Brameld, Kenneth Albert; Kennedy-Smith, Joshua; US2013/90333; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 175205-81-9, name is 2-Bromo-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Bromo-4-(trifluoromethyl)pyridine

General procedure: To a solution of 4-amino-l-((tr<3i)-3-(benzyloxy)cyclobutyl)-lH-pyrazolo[3,4- d]pyrimidin-3-ol (3) (200 mg, 642 mumol,, 1 eq) in DMSO (10 mL) was added 2-bromo-4- (trifluoromethyl)pyridine (IB) (233 mg, 1.28 mmol, 2 eq) and IGCO3 (178 mg, 1.28 mmol, 2 eq) and the mixture was stirred at 125°C for about 3 h. The mixture was filtered and the filtrate was purified by prep-HPLC (TFA condition) to give l -((trans)-3- (benzyloxy)cyclobutyl)-3-((4-(trifluoromethyl)pyridin-2-yl)oxy)-l H-pyrazolo[3,4- d]pyrimidin-4-amlne (4) (150 mg, 263 mumol, 40.9percent yield) as a white solid. With the rapid development of chemical substances, we look forward to future research findings about 175205-81-9. Reference:
Patent; VYERA PHARMACEUTICALS, LLC; WASHINGTON UNIVERSITY; HOPPER, Allen, T.; SIBLEY, L., David; JANETKA, James, W.; HELANDER, Jon; (149 pag.)WO2019/36001; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H7Br2NO

Preparation of 2-Methyl-5-nitro-phenyl)-(5-pyridin-4-yl-oxazol-2-yl)-amineTo a solution of 4-bromoacetylpyridine hydrobromide (5 g, 17.8 mmol) in 😯 mL of water was added sodium azide (1.16 g, 17.8 mmol) and the contents stirred at room temperature for 30 min. The reaction mixture was cooled to O0C, treated slowly with saturated aqueous NaHCO3 until pH=6-7, extracted with dichloromethane (3×3 OmL) and the combined organic phases were dried over MgSO4, concentrated at room temperature under reduced pressure to a final volume of 25 mL, and diluted with dioxane (30 mL). The resulting solution was concentrated to remove the remaining EPO (lower boiling) dichloromethane. To the final volume (25 mL) was added at O0C, 2- methyl-5-nitrophenyl isocyanate (1.58 g, 8.9 mmol) (commercially available) and portion wise triphenylphosphine (2.62 g, 8.9 mmol). The reaction mixture was then stirred for 1 h at room temperature and heated for an additional 2 h at 100C. After evaporation of the solvent under reduced pressure the residue was crystallized in dichloromethane/ethanol (10mL/5mL), to give the title compound as yellow crystals (0.9 g, 34%). m p > 220 C

With the rapid development of chemical substances, we look forward to future research findings about 5349-17-7.

Reference:
Patent; AB SCIENCE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE(CNRS); INSTITUT CURIE; WO2006/106437; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 677728-92-6 ,Some common heterocyclic compound, 677728-92-6, molecular formula is C6H4FNO, 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.

[001077] A mixture of 6-fluoronicotinaldehyde (4.7 g, 37.6 mmol) and titanium isopropoxide (1.37 g, 75.2 mmol) in dry THF (90 mL) was stirred at r.t. for 30 mins under nitrogen. Then a solution of 2-methyl-2-propanesulfinamide (4.56 g, 37.6 mmol) in dry THF (10 mL) was added. The reaction mixture was stirred at r.t. for 16 h, diluted with EtOAc (200 mL) and MeOH (50 mL), and then brine (100 mL) was added slowly. The mixture was stirred at r.t. for 30 mins and filtered. The solid was washed with EtOAc (200 mL x 2). The filtrate was extracted with EtOAc (200 mL x 3). The combined organics were washed with brine (50 mL x 2), dried over Na2S04, and concentrated. The residue was purified by SGC (PE/EtOAc = 5/1) to give the title compound. LC-MS: m/z = 303 (M+H)+, RT = 1.61 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; QUARTET MEDICINE, INC.; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); TEBBE, Mark, Joseph; ATTON, Holly, Victoria; AVERY, Craig; BROMIDGE, Steven, Mark; KERRY, Mark; KOTEY, Adrian, Kotei; MONCK, Nathaniel, J.; MENICONI, Mirco; RIDGILL, Mark, Peter; TYE, Heather; SAIAH, Eddine; JOHNSSON, Kai, Peter; GORSKA, Katarzyna, Irena; PENG, Hairuo; MCCALL, John, Michael; (356 pag.)WO2017/59191; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem