Category: pyridine-derivatives

Related Products of 59290-82-3, 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 59290-82-3, name is 3-Nitroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-nitroisonicotinic acid (1.75 g, 10.1 mmol), l-amino-2-methylpropan-2-ol (968 ul, 10.1 mmol), 2-(lH-benzotriazole-l-yl)-l,l,3,3-tetramethyluronium tetrafluoroborate (4.86 g, 15.1 mmol) and triethylamine (4.9 ml, 35.3 mmol) in tetrahydrofurane (60 ml) was stirred over the week-end at rt. The reaction mixture was diluted with ethyl acetate, washed with water, with brine, dried with magnesium sulfate and concentrated. The crude product was purified by silica gel chromatography using a CH2Cl2/MeOH gradient as eluent, providing the title compound as off-white solid (255 mg, 11%).MS: M = 240.0 (M+H)+

According to the analysis of related databases, 59290-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; GRUBER, Felix; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; WO2011/154327; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, 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, Recommanded Product: 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, blongs to pyridine-derivatives compound. Recommanded Product: 5-Chloro-4-(trifluoromethyl)pyridin-2-amine

No. I.5-451: 5-Ethylcarbonyloxy-4-methyl-1-(5-chloro-4-trifluoromethylpyridin-2-yl)-1,5-dihydro-2H-pyrrol-2-one 5-Hydroxy-4-methyl-2,5-dihydrofuran-2-one (300 mg, 2.63 mmol, 1.0 equiv) and 2-amino-5-chloro-4-trifluoromethylpyridine (568 mg, 2.89 mmol, 1.1 equiv) were dissolved in abs. toluene (12 ml) and stirred under reflux conditions for 16 h. After cooling to room temperature, the reaction mixture was filtered off with suction and, after thorough drying, 5-(5-chloro-4-trifluoromethylpyridin-2-yl)amino-4-methyl-2,5-dihydrofuran-2-one was isolated without any further purification in the form of a colorless solid (530 mg, 68% of theory).). 1H-NMR (400 MHz, d6-DMSO delta, ppm) 8.43 (s, 1H), 8.36 (d, 1H), 7.06 (s, 1H), 6.78 (d, 1H), 6.15 (m, 1H), 2.07 (s, 3H). 5-(5-Chloro-4-trifluoromethylpyridin-2-yl)amino-4-methyl-2,5-dihydrofuran-2-one (250 mg, 0.85 mmol, 1.0 equiv) was dissolved in propionic anhydride (2.22 g, 20 equiv) and stirred at a temperature of 155 C. for 4 h. After cooling to room temperature, the reaction mixture was filtered off with suction, and final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-ethylcarbonyloxy-4-methyl-1-(5-chloro-4-trifluoromethylpyridin-2-yl)-1,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (35 mg, 12% of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 8.67 (s, 1H), 8.39 (s, 1H), 7.42 (s, 1H), 6.02 (m, 1H), 2.39-2.32 (m, 2H), 2.08 (s, 3H), 1.17 (t, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; Bayer Aktiengesellschaft; FRACKENPOHL, Jens; FRANKE, Jana; HELMKE, Hendrik; REINGRUBER, Anna Maria; DIETRICH, Hansjoerg; MACHETTIRA, Anu Bheemaiah; GATZWEILER, Elmar; ROSINGER, Christopher Hugh; SCHMUTZLER, Dirk; LUEMMEN, Peter; (181 pag.)US2020/79765; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55314-16-4 ,Some common heterocyclic compound, 55314-16-4, molecular formula is C10H12N2O, 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.

176 g (1.00 mol) of starting material III and 121.6 g (1.10 mol) of starting material IV hydrochloride salt wherein R is methyl was added to a solution of 44 g (1.1 mol) of sodium hydroxide in 1000 ml of methanol then stirred and dissolved. The reaction was heated at reflux for 8 hours. The reaction temperature was 65C. After completion of the reaction, the mixture was decolorized at 50C under reduced pressure (i.e., the solvent was removed, the same applies hereinafter). 400 ml of dichloromethane and 400 ml of pure water were further added to dissolve and stir and extract the liquid. The organic layer was washed once more with 400 ml of pure water. 50 g of anhydrous sodium sulfate for 1 hour. Filtered. Solvent was removed to obtain 173.7 g of a pale yellow oil 2-methoxy-4-(3-pyridyl)pyrimidine. The molar yield was 92.8%. HPLC purity 98.72%.

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. 55314-16-4, 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Peking University Founder Group Co., Ltd.; Southwest Synthetic Pharmaceutical Co., Ltd. of PKU International Healthcare Group Co., Ltd.; PKU Care Pharmaceutical R&D Center Co., Ltd.; PKU Healthcare Industry Group; Xu, Hong; Zhang, Zheng; Wang, Wei; (13 pag.)CN104230885; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 697300-73-5, 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.697300-73-5, name is 3-Bromo-5-iodopyridin-2-amine, molecular formula is C5H4BrIN2, molecular weight is 298.9071, as common compound, the synthetic route is as follows.

30 g of 3-bromo-5-iodopyridin-2-amine and 300 ml of ethanol were added1 g palladium / silica,First replace the air with nitrogen three times,And then replaced with hydrogen three times.Adjust the pressure of 0.05Mpa ~ 0.1Mpa,Temperature control at 20 ~ 30 , until the raw material reaction is complete.Filtration recovery catalyst,Concentrated part of the solvent,Add 300 ml of water,Then add 4.2 g of sodium hydroxide to neutralize,Cooled to 0 ~ 5 , filtered and dried.To give 16.8 g of 3-bromopyridin-2-amine,Yield 97%.

The chemical industry reduces the impact on the environment during synthesis 697300-73-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zhejiang Jiuzhou Pharmaceutical Co., Ltd.; Zheng, Hui; Luo, Lijun; Qiu, Zhichao; (5 pag.)CN106432068; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 2457-47-8, 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 2457-47-8 as follows.

PREPARATION 27 3,5-Dichloro-4-pyridinecarboxylic acid To a solution of 4.96 ml (0.036 mole) of diisopropylamine in 200 ml of tetrahydrofuran at -65 C. under a nitrogen blanket was added dropwise 14.9 ml of 2.5M n-butyllithium in hexane while maintaining the above temperature. Twenty minutes subsequent to that addition, a solution 5.0 g (0.034 mole) of 3,5-dichloropyridine in 30 ml tetrahydrofuran at -60 to -70 C. was added. The reaction mixture was stirred at -70 C. for 1/2 hr, poured onto a large excess of dry ice and allowed to evaporate overnight at room temperature. The residue was taken up in 100 ml of dilute aqueous sodium hydroxide, washed with 3*30 ml of methylenechloride and filtered. The filtrate was acidified to ~pH 2 with dilute hydrochloric acid to precipitate out the product. After cooling, the precipitate was collected and recrystallized from ethyl acetate/hexane giving 1.9 g (29%) of white analytically pure crystals, m.p. 231-35 C. (decomp.). Analysis: Calculated for C6 H3 NO2 Cl2: C, 37.53; H, 1.57; N, 7.30. Found: C, 37.33; H, 1.56; N, 7.21.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2457-47-8, its application will become more common.

Reference:
Patent; A. H. Robins Company, Inc.; US4705853; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 134363-45-4 , The common heterocyclic compound, 134363-45-4, name is 2-(Pyridin-3-yl)benzoic acid, molecular formula is C12H9NO2, 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.

Step 3: N-(Benzyloxy)-2-pyridin-3-ylbeiizamide; Ethyl 2-bromobenzoate (380 nag, 1.9 ?rmol), O-hydroxylbenzylamine (280 mg, 2.3 mmol), EDC (440 mg, 2.3 mmol), and HOBT (350 mg, 2.3 mmol) were combined in DMF (2 ml) and stirred over the 2 days at room temperature. The reaction was purified by RP-HPLC (C 18 column; H2CVCH3CN with 0.1% TFA) to afford the title compound. 1H NMR (400 MHz, de-DMSO, ppm): delta 11.6 (s, IH), 8.75 (s, IH), 8.72 (d, J= 4.8 Hz, IH), 8.07 (d, J= 8.0 Hz , IH), 7.73 (t, J= 6.6 Hz, IH), 7.63 (t, J= 7.3 Hz, IH)3 7.57-7.51 (m, 3H), 7.44-7.34 (m, 5H) and 4.76 (s, 2H). ES MS: m/z = 305 (M+l).

The synthetic route of 134363-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2008/10964; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58584-92-2, 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 58584-92-2, name is 2-Amino-6-chloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (4-aminomethyl-phenyl)-phenylamine described in Preparation Example 20 (345mg, 1.74mmol) and 2-amino-6-chloro-nicotinic acid (300mg, 1.74mmol) in N,N-dimethylformamide (10mL) were benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (924mg, 2.09mmol) and triethylamine (0.49mL, 3.48mmol), and the solution was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction solution, which was then partitioned, the organic layer was washed with water, and then, dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane : ethyl acetate), and the title compound (360mg, 59percent) was obtained as a pale yellow solid. 1H-NMR Spectrum (CDCl3) delta(ppm) : 4.51 (2H, d, J=5.2Hz), 5.74(1 H, s), 6.16(1H, brs), 6.57(1H, d, J=8.0Hz), 6.58(2H, s), 6.94-6.97(1 H, m), 7.04-7.09(4H, m), 7.21-7.30(4H, m), 7.52(1 H, d, J=8.0Hz).

According to the analysis of related databases, 58584-92-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1010120-55-4, 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 1010120-55-4, name is 5-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

1.1.3 General Procedure for Mono-Acylation to Afford Intermediate (4) To a solution of the 2-amino-triazolopyridine (3) (7.10 g, 33.3 mmol) in dry CH3CN (150 mL) at 5 C. is added Et3N (11.6 mL, 83.3 mmol) followed by cyclopropanecarbonyl chloride (83.3 mmol). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material (3) is consumed. If required, further Et3N (4.64 mL, 33.3 mmol) and cyclopropanecarbonyl chloride (33.3 mmol) is added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution (50 mL) and stirred at ambient temp. (for 1-16 h) to hydrolyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by trituration with Et2O (50 mL). The solids are collected by filtration, washed with H2O (2*50 mL), acetone (50 mL) and Et2O (50 mL), then dried in vacuo to give the required bromo intermediate (4).

According to the analysis of related databases, 1010120-55-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MENET, Christel Jeanne Marie; SMITS, Koen Kurt; US2010/331319; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14150-94-8 , The common heterocyclic compound, 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one, molecular formula is C6H5N3O5, 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.

General procedure: To a solution of dinitropyridone 1 (50.0 mg, 0.25 mmol) in ethanol (5 ml), were added enaminone 4a (38.8 mg, 0.25 mmol) and triethylamine (35mul, 0.25 mmol). The resultant mixture was heated at 100 C for 1 day. After evaporation, the residue was treated with column chromatography on alumina to afford 2-ethanoly-4-nitro-N-propylaniline (3a) (eluted with hexane/ethyl acetate = 8/2, 23.0 mg, 0.11 mmol, 43% (NMR Yield 63%)) as a yellow solid.

The synthetic route of 14150-94-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naito, Saki; Yokoyama, Soichi; Asahara, Haruyasu; Nishiwaki, Nagatoshi; Tetrahedron Letters; vol. 58; 50; (2017); p. 4699 – 4702;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22918-01-0, Adding some certain compound to certain chemical reactions, such as: 22918-01-0, name is 2-Bromo-4-chloropyridine,molecular formula is C5H3BrClN, 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 22918-01-0.

Example 103a 2-Bromo-4-chloronicotinaldehyde 103a To a solution of 2-bromo-4-chloropyridine (1.6 g, 8.0 mmol) in anhydrous tetrahydrofuran (40 mL) cooled at -70 C. was added the solution of lithium diisopropyl-amide (5.0 mL, 10.0 mmol, 2.0 M) over a period of 5 minutes and stirred at -70 C. for another 1h. Anhydrous DMF (1.3 g) was introduced over a period of 3 minutes and the mixture was stirred for another 30 minutes. It was then quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (20 mL*3). The combined organic layer was dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (20:1) to afford 103a as a yellow solid (900 mg, 48%). 1H NMR (500 MHz, DMSO-d6) delta 10.21 (s, 1H), 8.52 (d, J=5.5 Hz, 1H), 7.79 (d, J=5.0 Hz, 1H).

According to the analysis of related databases, 22918-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem