Category: pyridine-derivatives

Reference of 72716-80-4 ,Some common heterocyclic compound, 72716-80-4, molecular formula is C8H8N2O, 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.

To a suspension of 3-cyano-5,6-dimethyl-2-pyridone (1-013-02) (12.0 g) in water (293 mL) was added conc. hydrochloric acid (293 mL), and the reaction mixture was reflux with stirring in oil-bath at 135 DEG C. After 3 days, the reaction mixture was cooled, and evaporated under reduced pressure. To the residue (24.75 g) were added chloroform (300 mL) and methanol (15 mL), and the reaction mixture was heated in a water bath at 65 DEG C, and the dissolble material was filtered off. Furthermore, the dissolble material was treated by chloroform (200 mL) and methanol (10 mL) in a similar manner to described above. The combined filtrates were evaporated under reduced pressure. To the obtained residue (13.26 g) were added methanol (150 mL) and potassium carbonate (10 g). After stirred at room temperature for 30 min, the dissolble material was filtered off. The filtrate was evaporated under reduced pressure. To the obtained residue (14.7 g) was added chloroform (200 mL), and the dissolble material was filtered off again. The filtrate was evaporated under reduced pressure to give 5,6-dimethyl-2-pyridone (1-013-03) (9.41 g, 94.3%, m.p.: 202-207 DEG C)<1>H NMR (300 MHz, CDCl3): delta 2.05 (s, 3H), 2.31 (s, 3H), 6.38 (d, J = 9.0 Hz, 1H), 7.26 (d, J = 9.0 Hz, 1H), 13.17 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72716-80-4, its application will become more common.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1357111; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53636-70-7, 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 53636-70-7, name is 6-Methyl-2,3-pyridinedicarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLES Example 1 N-(2-Amino-6-methylpyridin-3-ylmethel .-N- {2-[2-[(2-amino-6-methyl-pyndin-3- ylmethyl fbrmylammo]-l- (2-hydroxyethyl)-propenyldisulfanyl]-4-hydroxy-l- methylbut-1-enyl} formamide (III-13) [0115] a) 2-Methylfuro[3,4-b]pyridine-5,7-dione. To a solution of 6-methyl-2,3- pyridinedicarboxylic acid (41*5g, 229mmol) and acetic anhydride (70mL) in 250mL of 1,2-dimethoxyethane was added pyridine (37mL). The reaction mixture was stirred at room temperature for 90 min. The solution was diluted with ether (50mL) and hexane (150mL) was added until the solution became cloudy. The solution was stirred in an ice-water bath until a white precipitate formed. The precipitated solid was collected by filtration and dried under vacuum overnight to give 20.7g (55%) of the title compound as a white crystalline solid. 1H NMR (CDCl3) 8 2. 85 (s, 3H), 7. 68 (d, 1H), 8.25 (d, 1H).

According to the analysis of related databases, 53636-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2005/95344; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75073-11-9, 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.75073-11-9, name is 5-Iodo-6-methylpyridin-2-amine, molecular formula is C6H7IN2, molecular weight is 234.04, as common compound, the synthetic route is as follows.

(B) 6-iodo-5-methylimidazo[1,2-a]pyridine (0308) To a solution of 5-iodo-6-methylpyridin-2-amine (7.5 g, 32 mmol) in ethanol (400 mL) was added 2-chloroacetaldehyde aqueous solution (18 mL, 40%), and the mixture was stirred at 80 C for 16 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with water, neutralized with 30% aqueous sodium hydroxide solution, and extracted with dichloromethane (150 mL×3). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (6.0 g). MS: [M+H]+ 259.1

Statistics shows that 75073-11-9 is playing an increasingly important role. we look forward to future research findings about 5-Iodo-6-methylpyridin-2-amine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1149-24-2, Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, 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 C13H17NO4, blongs to pyridine-derivatives compound. Computed Properties of C13H17NO4

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1149-24-2, Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 60753-14-2, 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.60753-14-2, name is 4-(Pyridin-3-yl)butan-1-ol, molecular formula is C9H13NO, molecular weight is 151.21, as common compound, the synthetic route is as follows.

EXAMPLE 122 Preparation of alpha-oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid methyl ester (4:1) molar hydrate A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.14 g), 3-pyridinebutanol (1.04 g), triphenylphosphine (2.07 g), and tetrahydrofuran (25 mL) was stirred at 0 C. while adding dropwise a solution of diethyl azodicarboxylate (1.37 g) in tetrahydrofuran (10 mL). The mixture was stirred for 2 hours at 0 C. and evaporated to dryness. The material was purified by HPLC (hexane-acetone; 2:1) to provide 1.4 g of alpha-oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid methyl ester (4:1) molar hydrate as a colorless oil. Analysis Calculated for C18 H19 NO4.4:1H2 O: C, 68.02; H, 6.18; N, 4.41. Found: C, 68.24; H, 6.19; N, 4.68.

The chemical industry reduces the impact on the environment during synthesis 60753-14-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoffman-La Roche Inc.; US5344843; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 914942-88-4 ,Some common heterocyclic compound, 914942-88-4, molecular formula is C13H18IN5O2, 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.

Copper iodide (5.0mg, 0.025mmol) and dichlorobis(triphenylphosphine) palladium (4.0mg, 0.050mmol) were each added in one portion to a mixture of Al.12 (lOOmg, 0.25mmol), phenylacetylene (28mg, 0.28mmol) and triethylamine (0.11ml, 0.75mmol) in dichloromethane (0.5ml) at room temperature under a nitrogen atmosphere. The resulting mixture was heated to 40 0C for 24hrs before cooling to room temperature and evaporating in vacuo. The residue was purified by column chromatography using ethyl acetate as eluent to give 62mg of A1.13. LC/MS Phenomenex S5 4.6x30mm (2min gradient) Found: M+H = 378.27 at 1.51 min

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. 914942-88-4, tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 66909-38-4, 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 66909-38-4 as follows.

An aqueous solution of sodium, nitrite (0.5M, 50.5 mL) was added to a cold (0- 5C) solution of 6-chloro-4-methylpyridin-3-amine (3 g, 21.04 mmol) in.50% aqueous H2SO4 (75 mL) over 1 h, maintaining a temperature of 0-5C. The reaction mixture was allowed to stir for 20 minutes, then added to acetic acid (60 ml. ) at 1 ()0″C over 30 minutes. Stirring was continued for 2 h, then the reaction mixture was cooled and neutralised with saturated aqueous NaHC03 solution, followed by solid NaHCOa, to pH 7. The residue was extracted with EtOAc (4 x 200 ml.) and dried (Na2S04), then filtered and concentrated. Purification by Biotage (eluent 0-100% EtOAc:heptanes; RF 0.33 in 1 :1 EtOAciheptane) afforded the title compound (1.47 g, 48.8%). deltaEta (500 MHz, DMSO- d6) 10.05 (s, 1H), 7.83 (s, GammaEta), 7.23 (s, 1H), 2.14 (s, 3H). Method B HPLC-MS: MH+ mlz 143.9/145.9, RT 1.48 minutes (100%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,66909-38-4, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHOVATIA, Prafulkumar Tulshibhai; FOULKES, Gregory; JOHNSON, James Andrew; JONES, Severine Danielle; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LOKE, Pui Leng; LOWE, Martin Alexander; MANDAL, Ajay; NORMAN, Timothy John; PALMER, Christopher Francis; PEREZ-FUERTES, Yolanda; PORTER, John Robert; SMYTH, Donald; TRANI, Giancarlo; UDDIN, Muhammed; ZHU, Zhaoning; (207 pag.)WO2016/198400; (2016); 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. 936342-91-5, name is 5-Bromo-2-(chloromethyl)pyridine hydrochloride, the common compound, a new synthetic route is introduced below. Recommanded Product: 5-Bromo-2-(chloromethyl)pyridine hydrochloride

To an N,N-dimethylformamide (40.0 mL) solution of 4-fluorophenol (3.00 g, 26.8 mmol) was added sodium hydride (1.00 g, 25.0 mmol, 60percent in oil) on an ice bath (0° C.) under nitrogen atmosphere, which was stirred for 20 minutes at room temperature. To the reaction solution was then added a mixture of 5-bromo-2-chloromethyl-pyridine hydrochloride (4.6 g, 22.3 mmol) described in Manufacturing Example 54-1-2 and triethylamine (30.6 mL, 20.4 mmol), which was stirred for 10 minutes at room temperature. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. This organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated from the filtrate under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate_heptane=1:4) to obtain the title compound (4.0 g, 63.6percent). 1H-NMR Spectrum (CDCl3) delta (ppm): 5.10 (2H, s), 6.88-6.91 (2H, m), 6.95-6.99 (2H, m), 7.40-7.42 (1H, m), 7.81-7.84 (1H, m), 8.64-8.65 (1H, m).

The synthetic route of 936342-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 112006-57-2, 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 112006-57-2, name is 2-(Benzylthio)-N,N-dimethylnicotinamide. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 N,N-Dimethyl-2-aminosulfonyl-3-pyridinecarboxamide A mixture of 4.4 ml of concentrated hydrochloric acid, 66 ml of methylene chloride, 34 ml of water and 4.0 g (14.7 mmol) of the N,N-dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide was cooled to 0 C. Maintaining a temperature of -5 to 3 C., 60 ml (40.5 mmol) of 5% sodium hypochlorite was added dropwise over 15 minutes. The resulting yellow emulsion was stirred at 0 C. an additional 20 minutes. The reaction mixture was then poured into water and extracted with methylene chloride. The combined organic extracts were kept at 0 C. and washed with a saturated sodium bisulfite solution and dried over sodium sulfate. After 30 minutes, the yellow solution was filtered into a reaction flask and cooled to -78 C. and 5 ml (431 mmol) of dry ammonia added. The reaction mixture was allowed to warm to room temperature and the solvent removed under reduced pressure. The resulting solid was slurried with 5 ml of water and the insoluble white solid collected by filtration to provide 2.0 g of the subject compound, m.p. 198-209 C.(d). NMR (DMSO): delta 2.70 (s, 3H, NCH3); 2.93 (s, 3H, NCH3); 7.60-7.75 (m, 1H); 7.90 (m, 1H); and 8.75 (m, 1H).

According to the analysis of related databases, 112006-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4789393; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89809-63-2, Adding some certain compound to certain chemical reactions, such as: 89809-63-2, name is 5-Methoxypicolinonitrile,molecular formula is C7H6N2O, 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 89809-63-2.

To a suspension of 5-(methyloxy)-2-pyridinecarbonitrile (3 g, 22.4 mmol) in dry EtOH (35 mL) was added NaOMe (0.12 g, 2.24 mmol). The resulting mixture was stirred at room temperature for 17 hr. Ammonium chloride (1 .56 g, 29.1 mmol) was added then the resulting mixture refluxed for 1 hr. The mixture was allowed to cool to room temperature then concentrated under reduced pressure to give the crude product as a brown solid. The crude product was triturated with diethyl ether and the resulting suspension filtered under vacuum then dried at 40C under vacuum to give the title compound as an orange solid (4.3g). LCMS (Method B): Rt = 0.49min, MH+ 152.0

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. 89809-63-2, 5-Methoxypicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Stephen John; BARKER, Michael David; CAMPBELL, Matthew; HUMPHREYS, Philip; LIDDLE, John; SHEPPARD, Robert John; WILSON, David; WO2012/52390; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem