Category: pyridine-derivatives

Related Products of 870997-87-8, 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.870997-87-8, name is 2-Amino-N-methylnicotinamide, molecular formula is C7H9N3O, molecular weight is 151.17, as common compound, the synthetic route is as follows.

(2) Production of 3-methyl-2-[4-(3-piperidin-1-ylpropoxy)phenyl]pyrido[2,3-d]-pyrimidin-4(3H)-one: 2-Amino-N-methylnicotinamide (105 mg, 0.69 mmol), 4-(3-piperidin-1-ylpropoxy)benzamide (171 mg, 0.69 mmol) and p-toluenesulfonic acid monohydrate (66 mg, 0.35 mmol) were suspended in toluene (2 mL), and stirred under reflux for 24 hours. After cooled to room temperature, DDQ (157 mg, 0.69 mmol) and THF (2 mL) were added thereto and stirred at room temperature for 5 hours. The reaction solution was diluted with ethyl acetate, then washed with aqueous 1 N sodium hydroxide solution and saturated saline water, and the organic layer was dried with magnesium sulfate. The solvent was evaporated off, and the residue was purified through silica gel column chromatography (chloroform/methanol = 3/1) to obtain the intended compound (52.5 mg, 20 %) as a colorless solid (m.p. 109-112C). 1H-NMR (400 MHz, CD3 OD) delta: 1.44-1.55 (2H, m), 1.63 (4H, quint., J=5.6 Hz), 2.00-2.07 (2H, m), 2.36-2.54 (4H, m), 2.56 (2H, t, J=7.7 Hz), 3.54 (3H, s), 4.12 (2H, t, J=5.9 Hz), 7.08 (2H, d, J=8.8 Hz), 7.54 (1H, dd, J=4.4, 8.1 Hz), 7.65 (2H, d, J=8.8 Hz), 8.64 (1H, dd, J=1.5, 8.1 Hz), 8.90 (1H, dd, J=1.5, 4.4 Hz)

Statistics shows that 870997-87-8 is playing an increasingly important role. we look forward to future research findings about 2-Amino-N-methylnicotinamide.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1757594; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886365-46-4, 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 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

5-Chloro-3-methylpicolinic acid (42.1 mg, 240 muiotaetaomicron) was suspended in dichloromethane (3 mL), the suspension was cooled to 0-5C (ice bath) and oxalyl chloride (42.6 mg, 29.4 muL·, 336 mupiiotaomicron) as well as dimethylformamide (0.137 M in toluene, 43.8 mu, 6 mupiiotaomicron) were added. The mixture was stirred for 17 h at room temperature. Then, it was concentrated in vacuo (40C, 5 mbar) to afford 5-chloro-3-methylpicolinoyl chloride as brown oil (48 mg, quant.). After that, tert-butyl ((4aR,5R,9R)-5-(6-amino-3-fluoropyridin-2-yl)-3,3-difluoro-5,8,8-trimethyl-9-oxido- 2,3,4,4a,5,8-hexahydro-[l,4]thiazino[2, l-f][l,2]thiazin-7-yl)carbamate (Int-51AAp, 80 mg, 168 mumol) was dissolved in dichloromethane (5 mL), the solution cooled to 0-5C (ice bath) and N,N-diisopropylethylamine (41.3 mg, 55.8 muL·, 320 muiotaetaomicron) was added, followed by a solution of 5-chloro-3-methylpicolinoyl chloride (vide supra, 50.6 mg, 240 mupiiotaomicron) in dichloromethane (3 mL). The reaction mixture was stirred for 15 min at 0-5C, followed by 90 min at room temperature. Then, an aqueous solution of sodium carbonate (10%, 15 mL) was added, the mixture was stirred for 10 min at room temperature. After phase separation, the aqueous layer was extracted the dichloromethane (2 x 10 mL), the combined organics were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 12 g, eluting with ethyl acetate / n-heptane, gradient 10:90 to 40:60) to yield, after drying in vacuo (40C, 5 mbar), the title compound as an off-white solid (61 mg, 58%). HPLC (method LCMS_gradient) tR = 3.86 min. MS (ES+) m/z 629.2 [M+H] .

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 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17117-17-8, 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.17117-17-8, name is 3-Bromo-5-ethoxypyridine, molecular formula is C7H8BrNO, molecular weight is 202.05, as common compound, the synthetic route is as follows.

1-Benzyl-1,7-diazaspiro[4.4]nonane (500.0 mg, 2.4 mmol) was dissolved in dry toluene (15 mL) in a 50 mL round bottom flask equipped with a magnetic stirring bar. Nitrogen was bubbled through the solution in a slow stream. To the stirring solution was added 3-bromo-5-ethoxypyridine (513.8 mg, 2.55 mmol), potassium tert-butoxide (1039.0 mg, 9.26 mmol), rac-2,2′-bis(diphenylphosphino-1,1′-binaphthyl (86.4 mg, 0.14 mmol) and tris(dibenzylideneacetone)dipalladium(0) (63.6 mg, 0.06 mmol), while continuing to purge with nitrogen. Nitrogen flow was discontinued and the flask was sealed and heated at 90 C for 8 h. The reaction was cooled and the solvent was removed by rotary evaporation. The resulting residue was suspended in saturated aqueous sodium bicarbonate (10 mL) and extracted with chloroform (4 x 25 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to a thick dark mass. Purification by column chromatography, using methanol/chloroform (2:98, v/v) as the eluent, gave 0.54 g of the desired compound as a light brown viscous liquid (69 %).

The chemical industry reduces the impact on the environment during synthesis 17117-17-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TARGACEPT, INC.; WO2004/5293; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 56826-61-0, 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 56826-61-0 as follows.

(2-Methyl-pyridin-3-yl)-methanol (1.0 g, 8.13 mmol) was dissolved in dry CH2Cl2 (30 mL) and argon gas was purged for 10 min. Dess-Martin periodinane (4.5 g, 10.5 mmol) was added to the reaction mixture at 0 C, The reaction mixture was allowed to come to rt and further stirred for 2 h. The reaction mixture was quenched with saturated NaHCO3 solution. The organic product was extracted with EtOAc, The combined organic extracts were washed with saturated sodium thiosulfate solution, water and brine solution. Solvent was removed under reduced pressure to the crude 2-methylnicotinaldehyde (600 mg, crude), which was used as such for the next step. TLC: 100% EtOAc, Rf = 0.4. 1H NMR (300 MHz, CDCl3) delta 10.33 (s, 1H), 8.70-8.68 (dd, J = 4.8 Hz, 1.8 Hz, 1H), 8.12-8.09 (dd, J = 7.7 Hz, 1.8 Hz, 1H), 7.36-7.32 (dd, J = 7.7 Hz, 4.8 Hz, 1H), 2.89 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56826-61-0, its application will become more common.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; WO2013/19621; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89978-52-9, 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 89978-52-9, name is Ethyl 2-bromoisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Example 19; 2-(3-Cyano-4-phenylpyrrole-1-yl)isonicotinic acid ethyl ester; To a solution of 4-phenyl-1H-pyrrole-3-carbonitrile (0.1 g) in toluene (0.70mL) were added 2-bromo-isonicotinic acid ethyl ester (0.19 g), potassium phosphate (0.31 g), (1R,2R)-(-)-N,N’-dimethylcyclohexane-1,2-diamine (0.02 g) and copper iodide (0.007 g) at room temperature, and this mixture was stirred at 110C for 24 hours. The insoluble material was removed by filtration through Celite, and this filtrate was concentrated. This obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane = 10/90 – 66/34) to give the title compound (0.066 g).

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 89978-52-9, Ethyl 2-bromoisonicotinate.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2133331; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1032943-43-3, name is 4-Bromo-1H-pyrazolo[3,4-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4BrN3

1001371 To a solution of 4-bromo-1H-pyrazolo[3,4-c]pyridine (215 mg, 1.08 mmol) in THF (6.08 mL) at 5 C was added NaH (60:40 sodium hydride:mineral oil, 54.9 mg, 1.37 mmol). The mixture was stirred for 5 minutes at rt and then cooled again in ice bath to 5 C. Cyclopropanesulfonylchloride (141.0 uL, 1.36 mmol) was added dropwise and the mixture was allowed to stir for 15 mm. The reaction mixture was quenched with ammonium chloride (2 M aq. solution, 5 mL) and was partitioned between ethyl acetate and water. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by column chromatography to provide 4-bromo-2-(cyclopropylsulfonyl)-2H- pyrazolo[3,4-c]pyridine (36 mg, 11%) LCMS (AA): m/z = 358.4 (M+H) and 4-bromo-1- (cyclopropylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (237 mg, 72%). LCMS (AA): m/z = 358.4 (M+H).

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, 1032943-43-3, 4-Bromo-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CULLIS, Courtney A.; D’AMORE, Natalie; FLEMING, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Krista E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen G.; VOS, Tricia J.; XU, He; YE, Yingchun; WO2015/108881; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 722550-01-8, 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 722550-01-8, name is 4-(Pyrrolidin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-bromo-1-(5-bromo-2,4-dimethoxyphenyl)ethanone 7 (124 rng, 0.367 mmol) and 4-(pyrrolidin-1-yl)pyridin-2-amine 8 (60 mg, 0.367 mmol) in acetone (4 mL) was heated at 75 C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration and solid was washed with acetone. The solid was suspended in aqueous ammonia solution (10 ml.) and stirred for 2 h. The free base was collected by filtration and solid was washed with water, dried under reduced pressure to yield 2-(5-bromo-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 9a (51 mg, 35%) as an off-white solid. 1H NMR (300 MHz, CDCl3): delta 8.55 (s, 1H), 7.83 (d, J = 7.4 Hz, 1H), 7,80 (s, 1H), 6.55 (s, 1H), 6,43 (d, J = 2.2 Hz, 1H), 6.33 (dd, J = 2,2, 7,4 Hz, 1H), 3 ,99 (s, 3H), 3 ,94 (s, 3H), 3.40-3,30 (m, 4H), 2.10-2.00 (m, 4H); HPLC (Method 2) >99% (AUC), tR= 19.12 min: APCI MS m/z 404 [M + H]+.

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 722550-01-8, 4-(Pyrrolidin-1-yl)pyridin-2-amine.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55404-31-4, Adding some certain compound to certain chemical reactions, such as: 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine,molecular formula is C6H5BrClN, 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 55404-31-4.

Example 1Synthesis of 3-bromo-4-methylpyridin-2(1H)-oneTo a resealable pressure vessel charged with 3-bromo-2-chloro-4-picoline (1.200 g, 5.81 mmol) was added formic acid (13.1 ml, 348 mmol) and H2O (4.00 ml,.222 mmol). The tube was sealed and the solution heated to 1200C. After 72 hrs, the solution was cooled to RT and concentrated in vacuo. The residue was purified by reverse phase chromatography (neutral) to afford 3-bromo-4-methylpyridin- 2(1H)-one as a white solid. MH+ = 188.0.

According to the analysis of related databases, 55404-31-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2008/8493; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65515-39-1, 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. 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, 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.

(a) 4-(but-3-en-l-yl)-2-methoxy-6-methylnicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (1.5 g, 9.25 mmol) in THF (40 mL) was added LiHMDS (10.17 mL, 10.17 mmol) at -78 C, and the mixture was stirred at -78 C for 1 h. 3-Bromoprop-l-ene (0.880 mL, 10.17 mmol) was added and the mixture was stirred at -78 C for 1 h and warmed to 0 C over 1 h. The mixture was then stirred at 0 C for 3 h. The reaction was quenched with saturated aqueous H4C1 solution and extracted with EtOAc (3x). The combined organics were dried over Na2SC”4 and concentrated. The residue was purified using reverse phase HPLC using Trilution software, with a phenomenex Gemini 5u CI 8(2) 100 A, AXIA 30×100 mm 5 micron, 10- minute run (30 mL/min, 40% CH3CN/H20, 0.1% formic acid to 80% CH3CN/H20, 0.1% formic acid) with UV detection at 254 nm to afford 4-(but-3-en-l-yl)-2-methoxy-6- methylnicotinonitrile (1.01 g, 54%) as a pale yellow oil. LC-MS(ES) m/z = 203 [M+H]+.

According to the analysis of related databases, 65515-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 72141-44-7, 4-Chloro-2-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, COA of Formula: C6H6ClNO, blongs to pyridine-derivatives compound. COA of Formula: C6H6ClNO

To a solution of LDA (1.0 M solution in hexane) (29.3 mL, 29.3 mmol) in THF (45 mL) was added a solution of 4-chloro-2-methoxypyridine (3.5 g, 24.38 mmol) in THF (8 mL) dropwise at -78 C. The reaction mixture turned into light yellow solution and was stirred at-78 C for 1 h, then DMF (3.78 mL, 48.8 mmol) was added dropwise. The reaction mixture was stirred at -78 C for lh. The reaction mixture was quenched with saturated NH4C1 solution at -78 C and the resulting mixture was stirred for 10 min and warmed up to rt. The resulting mixture was mixed with saturated NaHC03 solution and ethyl acetate. The organic layer was separated and washed with saturated NaHC03 solution, dried over MgS04. The filtrate was concentrated in vacuo. The residue was dissolved in DCM, purified via silica gel flash column chromatography, eluting with 0-25% ethyl acetate in hexane to give Intermediate 24A (white solid, 2.6 g, 15.15 mmol, 60% yield). LC-MS Anal. Calc’d for CvHeClNC 171.01, found [M+H] 172.1. Tr = 0.71 min (Method A). NMR (499MHz, chloroform-d) delta 10.47 (s, 1H), 8.20 (d, J=5.5 Hz, 1H), 7.01 (d, J=5.5 Hz, 1H), 4.08 (s, 3H)

The synthetic route of 72141-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; ZHANG, Liping; HUANG, Audris; SHAN, Weifang; WILLIAMS, David K.; ZHU, Xiao; GUO, Weiwei; (213 pag.)WO2018/209049; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem