Pyridine-derivatives

Synthetic Route of 641569-94-0, 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. 641569-94-0, name is 4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid. A new synthetic method of this compound is introduced below.

4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid (100 g, 0.326 mole) and 5-(4-methyl- IH-imidazol-1-yl)-3-(trifluoromethyl)benzenamine (78.75 g, 0.326 mole) were stirred in N-methyl pyrrolidone (700 ml) at 55-60C. Thionyl chloride (83 ml, 0.978 mole) was added and the temperature of the reaction mass was raised to 75C and stirred for 6 hours. The reaction masswas cooled to 40-45C, and water (500 ml) was added. The reaction mass was cooled to 20-25C and acetone (3000 ml) was added. The reaction mass was further stirred for 12 hours. The solid was isolated by filtration and washed with acetone to obtain nilotinib base.Yield :- 200 g

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,641569-94-0, its application will become more common.

Reference:
Patent; CIPLA LIMITED; KING, Lawrence; RAO, Dharmaraj Ramachandra; MALHOTRA, Geena; PATHI, Srinivas Laxminarayan; CHINIMILLI, Venugopalarao; GANGRADE, Manish Gopaldas; (21 pag.)WO2016/151304; (2016); 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. 5832-44-0, name is 4-Methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-Methyl-3-nitropyridine

Example 6; Scheme F; A mixture of f-1 (0.0094 mol) and paraformaldehyde (0.0075 mol) in DMSO (4.5 ml) and triton B (0.35 ml) was stirred at 90C for 4 hours, and then purified by column chromatography over silica gel (eluent: CH2Cl2; 15mum). The pure fractions were collected and the solvent was evaporated, yielding: 0.15 g of intermediate f-2 (10%).

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, 5832-44-0, 4-Methyl-3-nitropyridine.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/136562; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65001-21-0, 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 65001-21-0, name is 5-Bromopyridine-3-sulfonyl chloride. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 5-bromopyridine-3-sulfonyl chloride (3.5 g, 14 mmol) (described in the synthesis of Example 170) and glycine ethylester (2.1 g, 20 mmol), diisopropyl ethyl amine (2.6 g, 20 mmol) in THF (70 mL) was stirred at room temperature for 16 h. The reaction mixture was partitioned between saturated aqueous sodium chloride and ethyl acetate. The organic solution was separated, dried and evaporated under reduced pressure. The residue was purified using flash column chromatography using ethyl acetate/hexanes as eluent to obtain ethyl 2-(5- bromopyridine-3-sulfonamido)acetate (600 mg, 14 %). LCMS Method I: retention time 1.31min; [M+l] = 323,325.

According to the analysis of related databases, 65001-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; JOHNSON, James A.; LLOYD, John; FINLAY, Heather; JIANG, Ji; NEELS, James; DHONDI, Naveen Kumar; GUNAGA, Prashantha; BANERJEE, Abhisek; ADISECHAN, Ashokkumar; WO2011/28741; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6937-03-7, Adding some certain compound to certain chemical reactions, such as: 6937-03-7, name is Methyl 2-aminoisonicotinate,molecular formula is C7H8N2O2, 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 6937-03-7.

General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product.

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. 6937-03-7, Methyl 2-aminoisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Yanchun; Wang, Yuexiu; Xue, Han; Cao, Shuxia; Zhao, Yufen; Tetrahedron; vol. 75; 11; (2019); p. 1481 – 1491;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74420-15-8, 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. 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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.

[0393] 3-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine: [0394] 3-bromo-lH-pyrrolo[2,3-b]pyridine (10.7 kg, 54.3 moles) was added to 94.3 kg of THF in a 200 L glass-lined reactor. The solid was dissolved completely by stirring. After the mixture was cooled to about 10-15 C, NaH (3.4 kg, 85 moles) was added in portions (about 200-250 g each portion) every 3 to 5 minutes while venting any gas released by the reaction. After the addition of NaH, the mixture was stirred for one hour while maintaining the temperature of about 10-20 C. 4-methylbenzenesulfonylchloride (12.4 kg, 65.0 moles) was added at a rate of 0.5 kg/10 minutes at about 10-20 C. After the addition was complete, the temperature was maintained at about 10-20 C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the peak area of 3-bromo-lH-pyrrolo[2,3-b]pyridine was less than 1% (after about 1.5 hours). Typical retention time for 3-bromo-l-tosyl-lH-pyrrolo[2,3- bjpyridine was 20.2 minutes. [0395] The reaction was quenched with water (10.7 kg) while maintaining the temperature below 20 C. Dichloromethane (41.3 kg) was added to the mixture. Then 3% HC1 acid (42.8 kg) was added into the mixture while maintaining the temperature below 25 C. After the addition, the phases were allowed to separate for 0.5 hour. The aqueous phase was extracted twice with dichloromethane. During each extraction, the mixture was stirred for 15 minutes and then held for 15 minutes. All the organic phases were combined. The combined organic phases were washed with 3% HC1 acid (33.4 kg) and water (40 kg). During each wash, the mixture was stirred for 15 minutes and then held for 30 minutes. [0396] The mixture was transferred into a 50 L vacuum filter and filtered through silica gel (3 kg). The cake was washed with dichloromethane (35 kg) twice. The filtrate and washings were combined. The organic phase was concentrated below 40 C under vacuum of a pressure less than -0.085 MPa until 10 L mixture remained. Petroleum ether (9 kg) was added into the residue. The mixture was stirred until it was homogeneous. The slurry was transferred into a 50 L vacuum filter and filtered. The cake was washed with petroleum ether (9 kg). A light brown solid resulted (17 kg, 99.7% purity as measured by HPLC analysis (method A), 94% yield of 3-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridine).

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 74420-15-8, 3-Bromo-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HOOCK, Thomas Carl; CHAVAN, Ajit Bhiwaji; CHEN, Yingxue; GARG, Varun; HUANG, Jiayin; MAHNKE, Lisa Ann; ROBERTSON, Sarah Marie; SEWELL, Kathryn Lea; TAYLOR, Lori Kell; WO2014/201332; (2014); A1;,
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.867267-24-1, name is 2,5-Dimethoxypyridine, molecular formula is C7H9NO2, molecular weight is 139.1519, as common compound, the synthetic route is as follows.Recommanded Product: 867267-24-1

General procedure: At -78 C., lithium diisopropylamide (2 M in tetrahydrothranlheptane/ethylbenzene) was added to a solution of the appropriate pyridine derivative in tetrahydrofuran (3 ml/mmol), the mixture was stirred for 2-4 h and triisopropyl borate was then added quickly. The reaction mixture was maintained at -78 C. for a further 2-3 hand then slowly thawed to RT overnight. Afier addition of water, the tetrahydrofuran was removed under reduced pressure and the aqueous phase was extracted twice with ethyl acetate. The aqueous phase was acidified with aqueous hydrochloric acid (2M), generally resulting in formation of a precipitate which was filtered off, washed with water and dried. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure.;11.53 g (82.9 mmol) of 2,5-dimethoxypyridine were reacted according to General Method l. The desired product precipitated out after acidification of the aqueous phase. Yield: 9.53 g (61% of theory)10599] LC/MS [Method 1]: R=0.47 mm; MS (ESIpos):mlz=184 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,867267-24-1, 2,5-Dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHRIG, Susanne; HILLISCH, Alexander; STRASSBURGER, Julia; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; BUCHMUeLLER, Anja; GERDES, Christoph; SCHAeFER, Martina; TELLER, Henrik; JIMENEZ NUNEZ, Eloisa; SCHIROK, Hartmut; KLAR, Juergen; (66 pag.)US2016/272637; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 916325-85-4 , The common heterocyclic compound, 916325-85-4, name is 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid, molecular formula is C7H4BrN3O2, 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.

Compound Ic (1.0 g, 4.13 mrnol) and 3-(t°7?-butyl-dimethyl-si]anyloxymethyl)- benzene-l,2-diamine Compound 6a (1.05 g, 4.17 mmol), HATU (1.58 g, 4.16 mmol) EPO and DIPEA (2.5 mL, 35.9 mmol) in DMF (50 mL) was stirred at room temperature overnight. The solvent was removed and the residue was dissolved in ethyl acetate (100 mL), then sequentially washed with hydrochloric acid (20 mL, IM), water (30 mL x 3) and brine (20 mL). The organic solution was evaporated to dryness, in vacuo and purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes) to yield 5-bromo-lH-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-3-(tert-butyl- dimethyl-silanyloxymethyl)-phenyl]-amide Compound 6b (1.21g, 61% yield) as a yellow powder. 1H NMR (300 MHz, CDCl3) delta 8.91 (d, IH, J = 2.1 Hz), 8.73 (s, IH), 8.67 (d, IH, 7 = 2.1 Hz), 7.47 (d, IH, 7 = 7.2 Hz), 7.01 (d, IH, 7 = 7.2 Hz), 6.83 (t, IH, J = 7.2 Hz), 4.78 (s, 2H), 0.95 (s, 9H), 0.11 (s, 6H); MS (ESI) m/z: 477 (M+H+).

The synthetic route of 916325-85-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/130673; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 10177-31-8, name is 4-Methoxynicotinic acid. A new synthetic method of this compound is introduced below., name: 4-Methoxynicotinic acid

[0350] A solution of 4-(4-(2,4-difluorophenoxy)piperidin-l -yl)-6-methoxypyridin-3-amine (40 mg, 0.1 19 mmol), 4-methoxynicoiinic acid (36.5 mg, 0.239 mmol), HATU (91 mg, 0.239 mmol) and DIPEA (0,052 mL, 0,298 mmol) m NMP (0.5 mL) was heated at 50C for 8 hours. More HATU (50 rng) was added and the reaction mixture was heated at 50C for 17 hours. The solution was diluted with DMF (0.3 mL) and MeOH (0.2 mL) and purified by preparative HPLC, eluting with ACN/water (basic mode) to give the title compound as a white solid (34 mg, 61 %). NuMKappa (500 MHzeta, DMSO-ifc) delta ppm 1.74 – 1.84 (m, 2 H), 2.04 (ddd, J=9.52, 6.35, 3, 17 Hz, 2 H), 2.90 (ddd,./ 12.08. 8.91, 2.93 Hz, 2 H), 3.19 – 3.27 (rn, 2 H), 3.83 (s, 3 H), 4.07 (s, 3 H), 4.51 (tt, J-8.05, 3.91Hz, 1H), 6.48 (s, 1H), 6.97 – 7.05 (m, 1H), 7.25 – 7.34 (m, 3 H), 8.56 (s, 1 1 1). 8.61 (d,.7=5.86 Hz, 1H), 8,90 (s, 1H), 9.65 (s, 1H); ESI-MS m/z [M+H]+ 471.

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, 10177-31-8, 4-Methoxynicotinic acid.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 40381-90-6, 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 40381-90-6, name is 2,6-Dichloropyridine-3-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2,6-dichioronicotinonitrile (050 g, 2.89 mmoi) in MeOH (10 mL)was added sodium methanolate (0.62 g, 2.89 mmol) at ambient temperature. The reactionmixture was stirred at 60 C for 12 h. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure, diluted with water (40 ml) and extracted with ethyl acetate (2 x 75 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by preparativeHPLC [Xbridge Phenyl (21.2 x 250 ID) 5 micron; Solvent A: 0.1% TFA, Solvent B:Acetonitrile, Gradient: 5-25% B over 25 mm, Flow: 20 mL/minj to 23A (0.48 g, 19%) as an off white solid. ?HNMR (400 MHz, CDCI3) ppm 4.08 (s, 3 H). 7.01 — 7.03 (d, J= 7.2 Hz, I H), 7.80 7.82 (s, J= 8.0 Hz, IH). LCMS MethodD): retention time 1.94 mm, [M+H] 169.2.

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 40381-90-6, 2,6-Dichloropyridine-3-carbonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19337-97-4, 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.19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid, molecular formula is C8H7NO2, molecular weight is 149.15, as common compound, the synthetic route is as follows.

General procedure: Compound 1c-9c (1.0mmol) was dissolved in anhydrous tetrahydrofuran (20mL). To the solution, triethylamine (1.2mmol) was slowly added and the solution was cooled to-20C, pivaloyl chloride (1.2mmol) was then added, and the reaction mixture was stirred for about 45min. Next, the compound 13 or 15 and n-butyllithium were added to the reaction solution and stirred for 1h, checked for product formation via TLC. Then saturated aqueous solution of ammonium chloride (10mL) was added to quench the n-butyllithium in the reaction and extracted with ethyl acetate, the organic phase was washed with saturated brine (30mL×3), Dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (PE/EA=3: 1) to afford 1-9.

Statistics shows that 19337-97-4 is playing an increasingly important role. we look forward to future research findings about trans-3-(3-Pyridyl)acrylic acid.

Reference:
Article; Zou, Yu; Yan, Chang; Zhang, Huibin; Xu, Jinyi; Zhang, Dayong; Huang, Zhangjian; Zhang, Yihua; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 313 – 319;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem