Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 15197-75-8, 3-(2-Pyridyl)propionic Acid, 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, Computed Properties of C8H9NO2, blongs to pyridine-derivatives compound. Computed Properties of C8H9NO2

General procedure: In air, a round bottom flask was charged with [Pd(mu-Cl)(Cl)(NHC)]2 (0.2 mmol, 225 mg), 2-pyridylacetic acid hydrochloride(0.4 mmol, 70 mg), KOtBu (1.0 mmol, 112 mg) and THF(2.0 mL). After stirring for 6 h at room temperature, the mixturewas condensed under vacuum. The solid residue was filtered byflash chromatography on short silica gel with CH2Cl2 and recrystallizedfrom n-hexane/CH2Cl2 to provide the desired products.

The synthetic route of 15197-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Wei; Yang, Jin; Journal of Organometallic Chemistry; vol. 872; (2018); p. 24 – 30;,
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

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

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

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

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

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

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.102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), molecular formula is C11H8N2O2S, molecular weight is 232.2584, as common compound, the synthetic route is as follows.HPLC of Formula: C11H8N2O2S

Steps b, c : N-((cis)-3-isothiocyanatocyclobutyl)-3-(4-methoxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide. A similar procedure to that described for the synthesis of N-(cis-(3-isothiocyanatocyclobutyl))-5-methoxy-[2,3′-bipyridine]-6′-carboxamide step c) and step d) was followed by using tert-butyl((cis)-3-(3-(4-methoxyphenyl)bicyclo[1.1.1]pentane1carboxamido) cyclobutyl) carbamate (58.0 mg, 0.15 mmol) to produce N-((cis)-3-isothiocyanatocyclobutyl)-3-(4-methoxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide (26.0 mg, 52%). 1H NMR (400 MHz, CDCl3): delta 7.14 (d, J=8.0 Hz, 2H); 6.67 (brs, 1H); 5.75-5.63 (brs, 1H); 4.25-4.13 (m, 1H); 3.90-3.81 (m, 1H); 3.80 (s, 3H); 2.95-2.70 (m, 2H); 2.25 (s, 6H); 2.24-2.15 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,102368-13-8, 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), and friends who are interested can also refer to it.

Reference:
Patent; Northeastern University; Malamas, Michael S.; Makriyannis, Alexandros; Farah, Shrouq I.; Zvonok, Alexander M.; Alapafuja, Shakiru Olajire; (47 pag.)US2019/345132; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 152460-09-8, name is N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine. A new synthetic method of this compound is introduced below., Quality Control of N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

170 L of Cone. Hydrochloric acid is charged into the reactor. 70 Kg of stannous chloride dihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Added compound of the formula (VI) slowly during 3-4 hours at 0-5 C. reaction mass is brought to 25-35C. Maintained 1 V2 hour at 25-35C. Charged 500 Its of DM water to the reaction mass and charged slowly 400 L of 50% sodium hydroxide solution at 25-3 5C. Reaction mass is extracted with 2 x 250 L chloroform. The chloroform layer is water wash thoroughly and carbon treatment is given . Distilled off chloroform completely under vacuum and charged 20 L ethyl acetate. Cooled to 0-10C. Maintained 1 hour at 0-10C. Centrifuged and washed with 10 L ethyl acetate to provide N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield: 10 Kg (61.5%)MR: 141-144C.PuritybyHPLC:99.8%.Step -3:The preparation of N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine (VII)20 L of Cone. Hydrochloric acid is charged into the reactor. 7 Kg of stannous chloridedihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Addedcompound of the formula (VI) slowly during 2-3 hours at 0-5C. reaction mass is broughtto 25-35C. Maintained 3 hours at 25-35C. Charged 500 Its of DM water to thereaction mass and charged slowly 40 L of 50% sodium hydroxide solution at 25-35C.Reaction mass is extracted with 2 x 35 L chloroform. The chloroform layer is waterwash thoroughly and carbon treatment is given . Distilled off chloroform completelyunder vacuum and charged 2 L ethyl acetate. Cooled to 0-10C. Maintained 1 hour at 0-10C. Centrifuged and washed with 1 L ethyl acetate to provide N-(5-amino-2-methylphenyi)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield: 0.98Kg(60%)MR: 140-143C.Purity by HPLC: 99.8%.Step -3: The preparation of N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine of theformula [VH] 17 L of Cone. Hydrochloric acid is charged into the reactor. 7 Kg of stannous chloride dihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Added compound of the formula (VI) slowly during 2-3 hours at 0-5C. reaction mass is brought to 25-35C. Maintained 3 hours at 25-35C. Charged 500 Its of DM water to the reaction mass and charged slowly 40 L of 50% sodium hydroxide solution at 25-35C. Reaction mass is extracted with 2 x 50 L chloroform. The chloroform layer is waterwash thoroughly and carbon treatment is given . Distilled off chloroform completelyunder vacuum and charged 2 L ethyl acetate. Cooled to 0-10C. Maintainedl hour at 0-10C. Centrifuged and washed with 1 L ethyl acetate to provide N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield : 0.97 Kg (60%)MR: 140-143C.Purity by HPLC: 99.7%. Step -3 ;The preparation of N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine of theformula [VII]19 L of Cone. Hydrochloric acid is charged into the reactor. 7 Kg of stannous chloridedihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Addedcompound of the formula (VI) slowly during 2-3 hours at 0-5C. reaction mass is broughtto 25-35C. Maintained 2 1A hour at 25-35C. Charged 500 Its of DM water to thereaction mass and charged slowly 40 L of 50% sodium hydroxide solution at 25-35C.Reaction mass is extracted with 2 x 50 L chloroform. The chloroform layer is waterwash thoroughly and carbon treatment is given . Distilled off chloroform completelyunder vacuum and charged 2 L ethyl acetate. Cooled to 0-10C. Maintained 1 hour at 0-10C. Centrifuged and washed with 1 L ethyl acetate to provide N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield: 1.05 Kg (64.5%)MR: 142-144C.Purity by HPLC: 99.85%.

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, 152460-09-8, N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine.

Reference:
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala; BHUJANGA RAO, Adibhatla, Kali, Sathya; VENKAIAH CHOWDARY, Nannapaneni; WO2004/108699; (2004); 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. 56026-36-9, name is Methyl 6-(hydroxymethyl)nicotinate, molecular formula is C8H9NO3, 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. Application In Synthesis of Methyl 6-(hydroxymethyl)nicotinate

A mixture of methyl 6-(hydroxymethyl)nicotinate (7 g , 37 mmol) and Mn02 (32,3 g , 372 mmol) in DCM ( 200 mL ) was stirred at 20 C for 4 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (PE/EtOAc = 5/1) to afford methyl 6-formylnicotinate (6 g , 97%).MS-ESI (m/z): 166.2 (M+l) + (LC-MS method C; Ret. time: 0.36 min).

With the rapid development of chemical substances, we look forward to future research findings about 56026-36-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem