Day: April 15, 2022

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

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

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

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

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

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a solution of 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (24.0 g, 93.02 mmol, 1.0 eq) in methanol (200 mL), was added 30% NaOMe (33.08 mL, 186.04 mmol, 2.0 eq). Then, the reaction mixture was heated at 70C for 6 h. TLC analysis indicated formation of a non-polar spot. The reaction mixture was diluted with water and extracted with EtOAc (3 X 200mL). The separated organic layer was dried over sodium sulfate and concentrated under reduced pressure at 30C. The crude compound was purified by column chromatography (silica gel, 100-200 mesh) using 5% EtOAc in pet ether as an eluent to give 5-bromo-2-methoxy-4-(trifluoromethyl)pyridine (15g, 63.47%) as an off white solid. TLC: 5% EtOAc in pet ether; Rf: 0.8.

The synthetic route of 823221-93-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 59942-87-9, 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.59942-87-9, name is Pyrazolo[1,5-a]pyridin-2(1H)-one, molecular formula is C7H6N2O, molecular weight is 134.1353, as common compound, the synthetic route is as follows.

To a solution of pyrazolo[1,5-a]pyridin-2-ol (120 mg, 0.89 mmol) in 4 mL of anhydrous DMF, were added K2CO3 (270 mg, 1.95 mmol), 4-(2-chloroethyl)morpholine hydrochloride (183 mg, 0.98 mmol) and Nal (134 mg, 0.89 mmol) and the mixture heated to 80 ºC for 18 h under nitrogen. The solvent was evaporated under reduced pressure and the residue poured into a mixture of EtOAc and water, to afford after drying and evaporation of organic layers, 112 mg of an oil that was purified by silica gel flash chromatography with EtOAc/MeOH (9:1) as eluent to afford 57 mg of 4-(2-(pyrazolo[1,5-a]pyridin-2-yloxy)ethyl)morpholine. 40 mg (0.43 mmol) of anhydrous oxalic acid in 0.5 mL of acetone were added to a solution of 98 mg of 4-(2-(pyrazolo[1,5-a]pyridin-2-yloxy)ethyl)morpholine base oil in 0.5 mL of acetone.

Statistics shows that 59942-87-9 is playing an increasingly important role. we look forward to future research findings about Pyrazolo[1,5-a]pyridin-2(1H)-one.

Reference:
Patent; Laboratorios del. Dr. Esteve, S.A.; Diaz-Fernandez,Jose-Luis; Cuberes-Altisent,Mª Rosa; EP2631236; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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: 156094-63-2, blongs to pyridine-derivatives compound. SDS of cas: 156094-63-2

To 3-iodo-4-nitro-lH-indazole (5.01 g, 17.3 mmol) in DMF (40 mL) was added K2CO3 (4.79 g, 34.7 mmol) and 2-(bromomethyl)-6-methoxypyridine (4.20 g, 20.8 mmol). The reaction mixture was stirred for 4 hours. The reaction mixture was concentrated to remove DMF, diluted with EtOAc and washed with H20 and brine. The organic phase was dried (Na2S04) and concentrated. Silica gel chromatography (EtOAc/Hexane 1 :5) gave the desired product (5.68 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BRADLEY, Michael; DELISLE, Robert Kirk; HENNINGS, D. David; KENNEDY, April L.; MARMSATER, Fredrik P.; MEDINA, Matthew; MUNSON, Mark C.; RAST, Bryson; RIZZI, James P.; RODRIGUEZ, Martha E.; TOPALOV, George T.; ZHAO, Qian; WO2011/79076; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 123853-39-4, 4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic 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, 123853-39-4, blongs to pyridine-derivatives compound. Product Details of 123853-39-4

The 75mg about 0.21mmol prepared above S14,80mg, about 0.21mmol compound S12,55mg about 0.4mmol K2CO3 in single-neck flask, 5mL DMF, in a nitrogen atmosphere Heated to 50 C, the reaction 2h, cooled to 30 C overnight reaction, until the reaction is complete, add 20mL Water was added and extracted with chloroform, the organic phases were pooled washed with water and saturated brine, dried over anhydrous sodium sulfate Dry, filtered, and solvent was removed by rotary evaporation, the residue was purified by column chromatography to give the present invention provides Compound 9,46mg, a yield of 35%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,123853-39-4, its application will become more common.

Reference:
Patent; JiangsuSimcere Pharmaceutical Company, Ltd; JiangsuSimcere Pharmaceutical Research Co. Ltd.; Chen, Rong; Liu, Fei; Cong, Xin; Feng, Lin; Li, Haidao; Dong, Qingli; (62 pag.)CN102464608; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 801303-22-0, 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. 801303-22-0, name is 2-Amino-5-fluoronicotinonitrile. A new synthetic method of this compound is introduced below.

To a solution of furan (16.6 mmol) in 50 mL THF at -78 C was slowly added 17 mmol n-BuLi (6.8 mL of a 2.5 M solution in hexanes). The solution was transferred to an ice water bath, and allowed to stir for 1.5 hours. The furanyllitium solution was returned to the -78 C bath prior to the addition of 2-amino-5-fluoronicotinonitrile (570 mg, 4.16 mmol) dissolved in 15 mL THF. The combined mixture was then returned to the 0 C ice water bath. After 30 minutes at 0 C the reaction was quenched with NH4CI (aq) and the organic layer washed several times with water, dried (MgS04), and concentrated under vacuum to yield 800 mg product, MS (M+H) = 206, H NMR (300 MHz, DMSO-D6) # ppm 6.69 (dd, J=3.39, 1.88 Hz, 1 H) 6.94 (d, J=3.39 Hz, 1 H) 7.30 (s, 2 H) 7.67 (dd, J=9.80, 3.01 Hz, 1 H) 7.96 (d, J=1.51 Hz, 1 H) 8.12 (d, J=3.01 Hz, 1 H) 10.85 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,801303-22-0, 2-Amino-5-fluoronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2005/111001; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem