Pyridine-derivatives

Electric Literature of 5398-44-7, 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.5398-44-7, name is 2,6-Dichloroisonicotinic acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.

a) A suspension of 2,6-dichloroisonicotinic acid (5.23 g, 27.24 mmol) in toluene (100 ml.) is heated to 800C and then slowly treated with N,N-dimethylformamide di-tert. butylacetal (19.94 g, 98.0 mmol). The mixture becomes slightly yellow and clear. Heating and stirring is continued for 3 h before the solution is cooled to rt, diluted with ether and washed with sat. aq. Na2CO3-solution. The org. extract is dried over MgSO4, filtered and the solvent is evaporated to give 2,6-isonicotinic acid tert.-butyl ester (6.97 g) which solidifies as beige fine needles. 1 H NMR (CDCI3): delta 1.60 (s, 6 H), 7.73 (s, 1 H).

Statistics shows that 5398-44-7 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloroisonicotinic acid.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/29371; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1083169-00-9, 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 1083169-00-9, name is 4-Bromo-2-methoxy-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of intermediate 6c (0.1M solution in THF, 66 mL,6.6 mmol) was added to a solution of 4-bromo-2-methoxy-6-methylpyridine (CAS: 1083169-00-9; 1.21 g, 6.00 mmol) and Pd(/-Bu3P)2 (140 mg, 0.27 mmol). The reaction mixture was stirred at room temperature for 16 h. The mixture was treated with NH4Cl (sat., aq.) and extracted with EtOAc. The organic layer was dried (Na2S04), filtered and the solvent was evaporated in vacuo. The crude mixture was purified by flash column chromatography (S1O2, (0434) EtOAc in heptane, gradient from 100:0 to 80:20) to afford intermediate 31 (1 g, 54%).

According to the analysis of related databases, 1083169-00-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana Isabel; TRESADERN, Gary John; CONDE-CEIDE, Susana; (212 pag.)WO2019/243528; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884495-22-1, 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.884495-22-1, name is 5-Bromo-2-fluoropyridin-3-amine, molecular formula is C5H4BrFN2, molecular weight is 191.0011, as common compound, the synthetic route is as follows.

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

The chemical industry reduces the impact on the environment during synthesis 884495-22-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.13143-47-0, name is 1-(4-Aminophenyl)-1H-pyridin-2-one, molecular formula is C11H10N2O, molecular weight is 186.21, as common compound, the synthetic route is as follows.Quality Control of 1-(4-Aminophenyl)-1H-pyridin-2-one

Step 2: To a solution of compound 12.2 (7.44 g, 40 mmol) in 100 mL DMF was added NBS(14.2 g, 80 mmol) in small portions. The mixture was stirred at RT overnight. It was diluted with 1000 mL ethyl acetate, washed with brine three times, dried, concentrated and subjected to flash column chromatography using 5 % methanol in DCM to isolate compound 12.3 (7.20 g, 68 %). MS found for C11H9BrN2O (M+H)+ 265.0, 267.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13143-47-0, 1-(4-Aminophenyl)-1H-pyridin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; SCARBOROUGH, Carroll; WO2008/86226; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59782-85-3, 2,5-Dichloronicotinic 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, Formula: C6H3Cl2NO2, blongs to pyridine-derivatives compound. Formula: C6H3Cl2NO2

Description 97: methyl 4-(1-(2,5-dichloronicotinamido)cyclopropyl)benzoate (D97)To a solution of 2,5-dichloronicotinic acid (1 .84g, 7.06 mmol) in dry dimethylformamide (15ml) 1 -Hydroxybenzotriazole hydrate (1 .08 g, 7.06 mmol) and 1 -ethyl-3-(3-dimethylaminopropyl) carbodiimide (2.03g, 10.58 mmol), a solution of methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (D7) (1 .67g, 7.06 mmol) and triethylamine (0.98ml, 7.06 mmol) in dry dimethylformamide (15ml) was added and the resulting mixture was stirred 1 h at room temperature. NH4CI saturated solution (50ml) was added the mixture was extracted with ethylacetate (3x50ml). Collected organics, after solvent evaporation, was purified by Biotage column SNAP-Si (50g) eluting with a mixture dichloromethane/ ethylacetate from 100/0 to 95:5. Collected organics after solvent evaporation afforded the title compound (D97) (1 .03 mg)MS: (ES/+) m/z: 365.1 [MH+] C17H14CI2N203 requires 364.41 H NMR (400MHz ,CHLOROFORM-d) delta = 8.46 (d, J = 2.4 Hz, 1 H), 8.14 (d, J = 2.4 Hz, 1 H), 8.05 – 7.99 (m, 2 H), 7.41 – 7.35 (m, 2 H), 7.17 (s, 1 H), 3.93 (s, 3 H), 1 .50 (s, 4 H).

The synthetic route of 59782-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 571189-16-7 ,Some common heterocyclic compound, 571189-16-7, molecular formula is C14H20N4O4, 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 the reaction flask was added compound 39 (5.65 g, 18.34 mmol)Soluble in methanol,0.5 g Pd / C was added,Catalytic hydrogenation at room temperature,TLC tracking, to be completely complete,Diatomaceous earth, the solvent was removed by distillation under reduced pressure,To obtain a crude solid,And then petroleum ether: ether (30: 1) beating to get pink powder,4.75 g of compound 7-10 was obtained by drying,Yield: 93.1%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,571189-16-7, its application will become more common.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhang Yinsheng; Gao Yong; Ren Jing; Wang Qinglin; Wang Zhao; (67 pag.)CN106905245; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 960298-00-4, 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. 960298-00-4, name is 2-(Benzyloxy)-4-bromopyridine, molecular formula is C12H10BrNO, 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.

Step 2: mc-tert-butyl O£4i?V4-r2-(benzyloxy)pyridin-4-yl1-3-alphacvclopropyP-(2- methoxyethoxyV 5-(3 -methoxypropyDbenzyl] amino ) carbonylM-hydroxypiperidine- 1 – carboxylate; To a solution of the title compound from step 1 (1.47 eq.) in THF (0.3 M) at -78 0C was added n-BuLi (2.5 M in hexanes, 1.6 eq.). The resulting solution was stirred at -78 0C for 30 min. MgBr2 (0.5 M in Et2O, 1.9 eq.) was added, and the resulting solution was stirred at -78 0C for 30 min. A solution of ketoamide 3.1 (0.1 M in THF, 1 eq.) was added, and the reaction mixture warmed to rt over 16 h, quenched with NaHCO3 (aq., sat.), extracted with 2 x EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by automated flash chromatography (SiO2; 10- 80% EtOAc in hexanes) to afford the title compound as a clear, colorless oil.

According to the analysis of related databases, 960298-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/70869; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1166828-13-2 ,Some common heterocyclic compound, 1166828-13-2, molecular formula is C7H6ClNO2, 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.

6-chloro-5-methyl-pyridine-2-carboxylic acid (0.85 g, 4.97 mmol) and sodium sulfite (CAN 7757-83-7, 1.5 g, 11.9 mmol) were added to water (3 mL) and ethanol (3 mL). The mixture was heated to 180C for 4 h in a sealed tube. After that the mixture was cooled to room temperature and a solid precipitated that was removed by filtration. The filtrate was concentrated and added to water (20 mL). The aqueous phase was washed with ethyl acetate (2 x 20 mL). Subsequently the aqueous phase was adjusted to pH = 2 with 2 N hydrochloric acid. Water was removed in vacuo to give the product as solid (1.2 g); MS (EI): m/e = 218.0 [M+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. 1166828-13-2, 6-Chloro-5-methylpyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14432-12-3, 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. 14432-12-3, name is 4-Amino-2-chloropyridine. A new synthetic method of this compound is introduced below.

A mixture of 2-chloro-pyridin-4-ylamine (0.642 g, 5 mmol), Zn (CN) 2 (0.323 g, 2.75 mmol) and Pd (PPh3) 4 (0.288 g, 0.025 mmol) in 5 mL of DMF was heated at 145 C for 20 hours. After the reaction mixture cooled to room temperature, it was partitioned between ethyl acetate and H2O. The aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried (MGS04), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 9: 1 HEXANES/ETHYL acetate to provide 0.29 g (20%) of the desired product. MS (DCI) m/e 120 (M+H) + ; IH NMR (300 MHz, DMSO-D6) 8 8.08 (d, J=5.76 Hz, 1H), 6.94 (d, J=2.34 Hz, 1H), 6.68 (dd, J=5. 76,2. 37 Hz, 1H), 6.59 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 21717-96-4, 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. 21717-96-4, name is 2-Amino-5-fluoropyridine, molecular formula is C5H5FN2, 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.

To a solution of 2-amino-5-fluoropyridine (10 g) in ethanol (200 mL), a solution of chloroacetaldehyde 50% in water (56 mL, 4.0 equiv.) was added. The reaction mixture was heated at reflux 2 Hrs, then was concentrated under reduced pressure to 100 mL. The residue was diluted in AcOEt (100 mL) and washed with a saturated aqueous solution of NaHCO3 (2* 150 mL). The combined aqueous were saturated with NaHCO3 and extracted back with AcOEt (2*100 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by flash-chromatography (MeOH 2.5% in CH2Cl2) afforded the product as a cream solid (8.7 g, 72%). M/Z (M+H)+ = 137.

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 21717-96-4, 2-Amino-5-fluoropyridine.

Reference:
Patent; Domain Therapeutics; EP2210891; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem