Category: pyridine-derivatives

Synthetic Route of 213193-32-9, Adding some certain compound to certain chemical reactions, such as: 213193-32-9, name is 5-Acetyl-2-methoxypyridine,molecular formula is C8H9NO2, 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 213193-32-9.

To a solution of 111-2 (5 g, 33 mmol) in 20 mL of EtOH was added aq. HBr (48%, 60 mL), the reaction mixture was heated to reflux overnight. After being cooled to rt., the mixture was neutralized by addition of saturated aq. NaHCO3, extracted with EtOAc (100 mLx3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated to supply crude 111-3 (3 g, 65% yield) as white solid.

According to the analysis of related databases, 213193-32-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 915107-31-2, Adding some certain compound to certain chemical reactions, such as: 915107-31-2, name is Methyl 6-chloro-5-methoxynicotinate,molecular formula is C8H8ClNO3, 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 915107-31-2.

Step 3. Preparation of methyl 5-methoxy-6-(4-methyl-1 H-imidazol-1 – yl)nicotinate (C7). Methyl 6-chloro-5-methoxynicotinate (C6) (185 mg, 0.918 mmol) was combined with 4-methyl-1 H-imidazole (148 mg, 1 .80 mmol) and cesium fluoride (273 mg, 1 .80 mmol). After the mixture was purged with nitrogen, dimethyl sulfoxide (3.0 mL) was added and the mixture was heated at 1 10 C for 1 .25 hours. After cooling to room temperature, the reaction was combined with an identical reaction carried out on 0.15 mmol of substrate, and poured into aqueous sodium bicarbonate solution (25 mL). After extraction with ethyl acetate (3 x 25 mL), the organic layers were combined, washed with aqueous sodium bicarbonate solution (25 mL), washed with brine (25 mL), dried over magnesium sulfate and concentrated in vacuo. Chromatography on silica (Gradient: 0% to 40% [9:1 ethyl acetate: 2 M ammonia in methanol] in ethyl acetate), afforded the title product. Yield: 148 mg, 0.599 mmol, 56%. LCMS m/z 248.5 (M+1 ). 1 H NMR (400 MHz, CDCI3) delta 2.30 (d, J=0.9 Hz, 3H), 3.98 (s, 3H), 4.04 (s, 3H), 7.63 (m, 1 H), 7.93 (d, 1 .7 Hz, 1 H), 8.47 (d, J=1 .1 Hz, 1 H), 8.68 (d, J=1.8 Hz, 1 H).

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. 915107-31-2, Methyl 6-chloro-5-methoxynicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; AM ENDE, Christopher William; JOHNSON, Douglas Scott; O’DONNELL, Christopher John; PETTERSSON, Martin Youngjin; SUBRAMANYAM, Chakrapani; WO2011/48525; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 64951-08-2, 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 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 3 Synthesis of Imidazo[1,2-a]pyridine-2-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide DIPEA (220 mg, 0.3 mL, 1.7 mmol) was added to a stirred solution of imidazo[1,2-a]pyridine-2-carboxylic acid (55 mg, 0.34 mmol) in DMF (5 mL). HOBT (50 mg, 0.37 mmol) and EDCI (163 mg, 0.85 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride (138 mg, 0.37 mmol) (prepared according to a procedure similar to that described in Synthesis Procedure 1, using 5-fluoro-2-(trifluoromethyl)benzoic acid (Aldrich, St. Louis, Mo.) as a starting material) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the resulting precipitate was isolated by filtration. Purification by recrystallisation from 30% ethyl acetate in hexane afforded 70 mg (43%) of imidazo[1,2-a]pyridine-2-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 90.06%. 1H NMR (DMSO-d6): delta 8.62 (d, 1H), 8.42 (s, 1H), 8.34 (s, 1H), 7.98 (s, 1H), 7.68-7.44 (m, 3H), 7.4 (t, 1H), 7.02 (t, 1H), 4.3 (d, 2H), 3.8-3.44 (m, 6H), 3.28 (bd, 2H).

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 64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid.

Reference:
Patent; Bischoff, Alexander; Subramanya, Hosahalli; Sundaresan, Kumar; Sammeta, Srinivasa Raju; Vaka, Anil Kumar; US2010/160323; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 697739-13-2 ,Some common heterocyclic compound, 697739-13-2, molecular formula is C8H6N2O2, 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 212 (S)-(2,7-Dimethyl-3-(3,4,5-trifluorophenyl)-2,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl)(imidazo[1,5-a]pyridin-8-yl)methanone The title compound was prepared in a manner analogous to Example 288, using imidazo[1,5-a]pyridine-8-carboxylic acid instead of 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid. MS (ESI): mass calcd. for C22H18F3N5O, 425.1; m/z found, 426.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 8.51-8.38 (m, 2H), 7.55 (s, 2H), 7.24 (s, 1H), 6.84 (dd, J=6.5, 0.9 Hz, 1H), 6.74 (t, J=6.8 Hz, 1H), 5.64 (s, 1H), 4.40 (d, J=307.0 Hz, 1H), 3.80 (s, 4H), 2.64 (t, J=1.9 Hz, 1H), 2.45-2.24 (m, 1H), 1.50 (s, 3H).

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. 697739-13-2, Imidazo[1,5-a]pyridine-8-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Chen, Gang; Huang, Chaofeng; Laforteza, Brian Ngo; Ravula, Suchitra; Southgate, Emma Helen; Zhang, Wei; US2020/102303; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 64951-08-2, 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.64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, molecular weight is 162.15, as common compound, the synthetic route is as follows.

To a solution of imidazo[l,2-a]pyridine-2-carboxylic acid, (0.162 g, 1.0 mmol) in acetonitrile (10 mL) was added O-(7-azabenzotriazol-l-yl)-N,N,N’,N’- tetramethyluronium hexafiuoropfiosphate (HATU) (0. 38 g, 1.0 mmol) and the mixture was stirred at room temperature for 15 minutes. Triethylamine (0.46 mL, 3.0 mmol) and 4-(4-(2-(tert- butyl)-6-methylpyrimidin-4-yl)piperazin-l-yl)butan-l -amine (0.305 g, 1.0 mmol) were then added and the mixture was stirred at room temperature overnight. The mixture was then concentrated under reduced pressure, the residue obtained was dissolved in chloroform and washed with saturated aqueous sodium bicarbonate. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product thus obtained was purified by chromatography over a column of silica using CHCl3-MeOH (96:4) as the eluent to obtain 0.089 g (20%) of the desired product as colorless oil. TLC Rf 0.17 (CHCl3-MeOH, 95:5); 1H NMR (DMSO-d6) delta 1.25 (s, 9H), 1.44-1.60 (m, 4H), 2.23 (s, 3H), 2.23-2.46 (m, 6H), 3.24-3.44 (m, 2H), 3.58 (bs, 4H), 6.47 (s, 1H), 6.97 (td, 1H), 7.37 (td, 1H), 7.56 (dd, J= 9.4, 9.0 Hz, 1H), 8.34 (s, 1H), 8.37 (t, 1H), 8.56 (dt, 1H). ESI MS m/z 450 (MH)+. Anal. (C25H35N7O H20) Calcd: C, 64.21; H, 7.98; N, 20.97. Found: C, 64.53; H, 7.64; N, 20.94.

Statistics shows that 64951-08-2 is playing an increasingly important role. we look forward to future research findings about Imidazo[1,2-a]pyridine-2-carboxylic acid.

Reference:
Patent; SOUTHERN RESEARCH INSTITUTE; ANANTHAN, Subramaniam; WO2014/59265; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1227594-89-9, 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 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Step 8(f): 3-fluoro-1-[(4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-4-(trifluoromethyl)pyridin-2(1 H)-one (8-8) To a solution of 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (8-5; 50 mg; 0.34 mmol) in dioxane 1.7 mL) was added K2CO3 (51 mg; 0.373 mmol) and the mixture was stirred for 5minutes. 5-(chloromethyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (8-4; 68 mg; 0.373 mmol) was then added, and the mixture was stirred for 2 hours at room temperature. The mixture was diluted with water, and extracted with CH2Cl2. The organic extracts were dried (MgSO4) and concentrated in vacuo. Purification by ISCO CombiFlash provided the title compound. 1H NMR (400 MHz, CDCl3): delta 10.14 (s, 1 H); 8.11 (d, J=5.2 Hz, 1 H); 7.18 (t, J=4.7 Hz, 1 H); 5.40 (s, 2 H); 3.41 (s, 3 H).

According to the analysis of related databases, 1227594-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Burch, Jason; Cote, Bernard; Nguyen, Natalie; Li, Chun Sing; St-Onge, Miguel; Gauvreau, Danny; US2011/245296; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 670253-37-9 ,Some common heterocyclic compound, 670253-37-9, molecular formula is C5H4ClIN2, 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.

A suspension of 4-chloro-5-iodopyridin-2- amine (2.54 g, 10.0 mmol), sodium thiomethoxide (1.40 g, 20.0 mmol), copper(l) iodide (190 mg, 1.00 mmol), potassium carbonate (2.76 g, 20.0 mmol) and ethylene glycol (1.12 ml_, (1026) 20.0 mmol) in I PA (3 ml_) was stirred at 80 C under an N2 atmosphere for 19 h. The reaction mixture was allowed to cool to rt, filtered through Celite and the solids were washed using MeOH (3 x 20 ml_). The combined filtrates were concentrated under reduce pressure and water (30 ml_) was added to the residue. The resulting suspension was extracted with DCM (3 x 20 ml_) using a phase separator. The combined organic phases were concentrated under reduced pressure and the residue was purified by flash (1027) chromatography (20%; then 30%; then 40% EtOAc in cyclohexane (isocratic)) to give the title compound (779 mg, 44%) as an off-white crystalline solid. LCMS (Method A): RT = (1028) 0.41 min, m/z = 175, 177 [M+H]+. 1 H NMR (500 MHz, DMSO-cfe): d 8.01 (s, 1 H), 6.59 (s, 1 H), 6.34 (s, 2H), 2.32 (s, 3H).

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. 670253-37-9, 4-Chloro-5-iodopyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ROUNTREE, James Samuel Shane; WHITEHEAD, Steven Kristopher; TREDER, Adam Piotr; PROCTOR, Lauren Emma; SHEPHERD, Steven David; BURKAMP, Frank; COSTA, Joana Rita Castro; O’DOWD, Colin; HARRISON, Timonthy; (333 pag.)WO2019/150119; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 156094-63-2, Adding some certain compound to certain chemical reactions, such as: 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine,molecular formula is C7H8BrNO, 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 156094-63-2.

[00602] A 60 % dispersion of sodium hydride in mineral oil (0.019 g, 0.493 mmol) was added to a stirred solution of 2-(phenoxymethyl)-6,7-dihydropyrazolo[l,5-a]pyrazin- 4(5H)-one (0.1 g, 0.411 mmol) in DMF (4 mL) at 0 C. The mixture was stirred at room temperature for 15 min. Then 2-bromomethyl-6-methoxypyridine (0.99 g, 0.493 mmol) was added and the mixture was stirred at room temperature for 16 h. The mixture was cooled at 0 C, treated with water and extracted with AcOEt. The organic layer was separated, washed with brine, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash chromatography (silica; EtOAc in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to afford an impure product that was repurified by flash column chromatography (silica; DCM). The desired fractions were collected and the solvents evaporated in vacuo. The desired product was triturated with diethyl ether and filtered to yield 5-[(6-methoxypyridin-2-yl)methyl]-2-(phenoxymethyl)-6,7- dihydropyrazolo[l,5-a]pyrazin-4(5H)-one (0.105 g, 70.5% yield). C2oH2oN403 *H NMR (400 MHz, CDC13) delta ppm 3.87 (s, 3 H) 3.90 – 3.98 (m, 2 H) 4.37 – 4.44 (m, 2 H) 4.76 (s, 2 H) 5.09 (s, 2 H) 6.65 (d, J=8.1 Hz, 1 H) 6.90 (d, J=7.2 Hz, 1 H) 6.93 – 7.04 (m, 4 H) 7.26 – 7.33 (m, 2 H) 7.54 (dd, J=8.2, 7.3 Hz, 1 H).

According to the analysis of related databases, 156094-63-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, P., Jeffrey; LINDSLEY, Craig, W.; STAUFFER, Shaun, R.; BARTOLOME-NEBREDA, Jose Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; TONG, Han Min; ALCAZAR-VACA, Manuel Jesus; ANDRES-GIL, Jose Ignacio; WO2013/192350; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 99368-68-0, 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 99368-68-0 as follows.

A solution of 6-chloro-5-(trifluoromethyl)pyridin-3-amine (0.35 g, 1.78 mmol) in acetic anhydride (6 mL) was heated at 100 C. for 12h. The solution was evaporated until dryness. The residue was taken up in DCM. The organic layer was washed with a 10% aqueous solution of K2CO3, separated, dried over MgSO4, filtered and evaporated to give a crude product (0.44 g, 100%). This compound was used directly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99368-68-0, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; LU, Tianbao; CONNOLLY, Peter J.; CUMMINGS, Maxwell David; DIELS, Gaston Stanislas Marcella; THURING, Jan Willem; PHILIPPAR, Ulrike; EDWARDS, James Patrick; BERTHELOT, Didier Jean-Claude; WU, Tongfei; (65 pag.)US2019/381012; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92992-85-3, 2-Bromo-3,5-dimethylpyridine, 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, name: 2-Bromo-3,5-dimethylpyridine, blongs to pyridine-derivatives compound. name: 2-Bromo-3,5-dimethylpyridine

To a solution of 2-bromo-3,5-dimethylpyridine (2.0 g)in tetrahydrofuran (30 mL) was added under cooling at-78c 1.59 M n-butyllithium/hexane solution (7.04 mL) and the mixture was stirred for 1 hr. A solution of 1-(tert-butoxycarbonyl)-4-piperidone (2.23 g)in tetrahydrofuran (40 mL) was added, and the mixture was stirred at-78c for 30 min. The reaction mixture was heated to room temperature,saturated aqueous sodium carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine,dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane:ethyl acetate) and NH column chromatography (hexane:ethyl acetate)to give 4′-hydroxy-3,5-dimethyl-3′,4′,5′,6′-tetrahydro-2’H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (1.69 g).

The synthetic route of 92992-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem