Pyridine-derivatives

Related Products of 3731-51-9, 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. 3731-51-9, name is Pyridin-2-ylmethanamine. A new synthetic method of this compound is introduced below.

General procedure: A mixture of 1.2 mmol o-phenylenediamine, 2-aminophenol or 2-aminothiophenol and 1 mmol primary amine, 10 mol % FeCl3, 1 mol % 3-methyl-4-oxa-5-azahomoadamantane, 5 ml H2O were mixed in a 10-ml three-necked flask, then O2 was bubbled into the flask at flow rate of 20 ml/min. The reaction mixture was stirred at 100 C for several hours, and reaction progress was monitored by TLC. The final reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was directly purified by column chromatography on silica gel using hexane/ethyl acetate (7:3) as eluent to afford the pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3731-51-9, Pyridin-2-ylmethanamine, and friends who are interested can also refer to it.

Reference:
Article; Yu, Jiatao; Lu, Ming; Research on Chemical Intermediates; vol. 41; 12; (2015); p. 10017 – 10025;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16179-97-8, 2-(Pyridin-2-yl)acetic acid hydrochloride, 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: 2-(Pyridin-2-yl)acetic acid hydrochloride, blongs to pyridine-derivatives compound. Recommanded Product: 2-(Pyridin-2-yl)acetic acid hydrochloride

Step 4. N-(6-(6-chloro-5-(-isopropylamino)pyridin-3-yl)benzo[d1thiazol-2-yl)-2-(pyridin-2-yl)acetamide; 6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2 -amine (121.8 mg, 0.382 mmol) and HATU (215.9 mg, 0.568 mmol) were suspended in DCM (2.9 ml) and diisopropylethylamine (0.21 ml, 1.2 mmol) and 2-pyridylacetic acid hydrochloride (94.3 mg, 0.543 mmol) were added. The reaction was stirred under nitrogen at room temperature overnight, concentrated and purified on a silica gel column (20: 1 DCM / MeOH). Fractions with product were collected, concentrated, and purified on HPLC (10% to 100% MeCN / water with 0.1 % TFA over 30 minutes). Fractions with product were collected, concentrated, and dried under high vacuum in a water bath (~ 50 C), then at room temperature overnight to afford N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)-2-(pyridin-2-yl)acetamide (57.5 mg, 34% yield). MS (ESI pos. ion) m/z: 438. Calculated exact mass for C22H20ClN5OS 437.

The synthetic route of 16179-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/17822; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 34941-91-8, 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 34941-91-8 as follows.

Step A: 2-Chloro-4-i uoropyridine~3~carboxylic acid (64-2)A solution of LDA (97 ml, 1.8 M heptane/THF/ethylbenzene, 175 mmol) and THF (304 ml) were combined and cooled to -78C. 2-Chloro-4-fluoropyridine (20.0 g, 152 mmol) was dissolved in 50 ml THF and then added dropwise over 20 minutes and then the solution was stirred for 1 hour. The reaction was poured onto dry ice and -the dry ice was allowed to evaporate. Water and 1 N NaOH were added to the residue. The mixture was extracted with Et20 and the organic layer discarded. The aqueous was acidified with 1 N HC1 and then extracted with EtOAc. The organic portion was washed with brine, dried (MgS04) and concentrated to give 64^2 (19 g, 71.2%) as an orange solid. MS (ESI): m/z = 176.0 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,34941-91-8, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BUNGARD, Christopher, James; PERKINS, James, J.; MANIKOWSKI, Jesse, J.; DE LEON, Pablo; MEISSNER, Robert, S.; WO2011/53574; (2011); 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. 112575-13-0, name is 6-Bromo-N,N-dimethylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Bromo-N,N-dimethylpyridin-2-amine

b (3R,4S)-4-[4-(6-Dimethylaminopyridin-2-yl)phenoxy]-1-pyridin-3-ylpentan-3-ol Prepared according to the method described in Example 15g) from toluene (4 ml), 2M aqueous sodium carbonate (0.5 ml), (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-yl-butoxy]benzeneboronic acid (0.200 g, Example 15f)), ethanol (1 ml), 6-bromo-2-N,N-dimethylaminopyridine (0.201 g, Example 18a)) and tetrakis(triphenylphosphine)palladium(0) (0.020 g) with heating at 120 C. for 4 hours. The product was purified by normal-phase HPLC eluding with a gradient of 0-25% ethanol in dichloromethane to give the title compound as an oil (0.091 g). MS (APCI) 378 (M+H)+ 1 H NMR (DMSO) 8.43(1H, s); 8.38(1H, d); 7.95(2H, d); 7.63(1H, d); 7.52(1H, t); 7.32-7.27(1H, m); 7.04(1H, d); 6.95(2H, d); 6.52(1H, d); 4.98(1H, d); 4.37-4.29(1H, m); 3.60-3.51(1H, m); 3.08 (6H, s); 2.84-2.76(1H, m); 2.69-2.61(1H, m); 1.91-1.81(1H, m); 1.69-1.58(1H, m); 1.24(3H, d).

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, 112575-13-0, 6-Bromo-N,N-dimethylpyridin-2-amine.

Reference:
Patent; AstraZeneca UK Limited; US6143751; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 771579-27-2 ,Some common heterocyclic compound, 771579-27-2, molecular formula is C8H12N2O, 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.

g) 6-bromo-N-((l,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-l-isopropyl-3-methyl-lH- indazole-4-carboxamideTo a stirred solution of 6-bromo-l-isopropyl-3-methyl-lH-indazole-4-carboxylic acid, 1 (6.5 g, 21.88 mmol) in DCM (250 mL) was added EDC HCl (5.01 g, 26.23 mmol), HOBt (3.545 g, 26.20 mmol) followed by diisopropyl ethyl amine (14.1 1 g, 109.37 mmol) and stirred at room temperature for 15 min. To the resulting mixture, 3-(amino methyl)-4,6-dimethylpyridin-2(lH)-one (3.32 g, 21.84 mmol) followed by DMAP (catalytic amount) was added and the reaction mixture was stirred at room temperature for 5 h. The reaction mixture was diluted with DCM (300 mL) and washed with IN HC1 solution (250 mL), saturated NaHC03 solution (250 mL) and brine solution. The organic layer was dried over anhydrous Na2S04 , filtered, and concentrated under reduced pressure. The residue was triturated with diethyl ether (100 mL), filtered, and dried to afford 6-bromo-N-((l,2-dihydro-4,6- dimethyl-2-oxopyridin-3-yl)methyl)-l-isopropyl-3-methyl-lH-indazole-4-carboxamide as an off white solid (5.5 g, 58 %). :H NMR (DMSO-d6, 400 MHz): delta 1.412 (d, J = 6.4 Hz, 6H), 2.1 12 (s, 3H), 2.215 (s, 3H), 2.383 (s, 3H), 4.319 (d, J = 5.2 Hz, 2H), 4.907 – 4.972 (m, 1H), 5.864 (s, 1H), 7.129 (d, J = 1.2 Hz, 1H), 8.01 1 (d, J = 1.2 Hz, 1H), 8.473 (t, J = 5 Hz, 1H), 11.479 (brs, 1H). LCMS (ES+): 431.02 [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. 771579-27-2, 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; DUQUENNE, Celine; JOHNSON, Neil; KNIGHT, Steven, D.; LaFRANCE, Louis; MILLER, William, H.; NEWLANDER, Kenneth; ROMERIL, Stuart; ROUSE, Meagan, B.; TIAN, Xinrong; VERMA, Sharad, Kumar; WO2011/140325; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1142194-24-8, 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.1142194-24-8, name is 4-Bromo-2-isopropoxypyridine, molecular formula is C8H10BrNO, molecular weight is 216.08, as common compound, the synthetic route is as follows.

General procedure: To 1.76 mmol of the appropriate amine in 10 mL dioxane are added 1.76 mmol pyridyl halide, 7.02 mmol NaOtBu, 0.70 mmol 2-(di-tert-butylphosphino)biphenyl and 0.18 mmol Pd2(dba)3. The mixture is degassed thoroughly and stirred at 45 C over night. The reaction mixture is filtered, the solvent removed in vacuo and the residue is purified by HPLC.

The chemical industry reduces the impact on the environment during synthesis 1142194-24-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/114578; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 886364-86-9, Adding some certain compound to certain chemical reactions, such as: 886364-86-9, name is 5-Bromo-4-methylpicolinonitrile,molecular formula is C7H5BrN2, 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 886364-86-9.

A mixture of 4-chloro-N-(2-hydroxy-phenyl)-N-methyl-3-(4,4,5,5- tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzamide (100 mg, 0.26 mmol), 5-bromo-4- methyl-pyridine-2-carbonitrile (61 mg, 0.31 mmol), Pd(PPh3)4 (15 mg, 0.013 mmol), K2CO3 (90 mg, 0.65 mmol) in dioxane (1.2 mL), was heated at 95 0C for 12 hrs. The mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4) and concentrated in vacuo. Silica gel column chromatography (eluent: ethyl acetate/hexane(1/4 up to 4/1 )) yielded 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2- hydroxy-phenyl)-N-methyl-benzamide 8-1 (68 mg).

According to the analysis of related databases, 886364-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124610; (2008); 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. 94166-64-0, name is 2-Chloro-6-nitropyridine, the common compound, a new synthetic route is introduced below. Formula: C5H3ClN2O2

Preparation of N-(3-(4-(6-Nitropyridin-2-yl)piperazin-l- yl)propyl)cyclohexanecarboxamideN-(3-(Piperazin-l-yl)propyl)cyclohexanecarboxamide (128 mg, 0.50 mmol), and 2- chloro-6-nitropyridine (79 mg, 0.50 mmol) were dissolved in dry acetonitrile (8 ml) in a 10 mL microwave tube and diisopropylethylamine (87 muL·, 0.50 mmol) added. The mixture was stirred and then heated in the microwave oven at 120C for 60 min. TLC (5% MeOH-EtOAc) showed the presence of 2 close running products of Rf 0.16 and 0.10. The reaction mixture was evaporated under reduced pressure to give a brown residue that was purified by chromatography on silica gel eluting with a 0-10% methanol in ethyl acetate gradient. The product was further purified by semi-preparative HPLC using a gradient of 50-95% methanol in water over 20 min (at) 18 ml/min (Gemini C18, 11 OA, 150 x 21.2 mm, 5 muiotaeta; Rt 10.8 min) to give the product (37 mg, 19%).LCMS: calcd for C19H29N5O3, 375.2; found 376.1 [M+H] . and 13C NMR were consistent with the structure.Purity was 96% by HPLC (UV 254nm).

The synthetic route of 94166-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GE HEALTHCARE LIMITED; MEDI-PHYSICS, INC.; NEWINGTON, Ian, Martin; WYNN, Duncan George; NAIRNE, Robert James Domett; GUILBERT, Benedicte; MANDAL, Subrata; JINTO, Jose; VARADARAJAN, Sunderaraman; RANGASWAMY, Chitralekha; BETTS, Helen; DAVIS, Rebecca; WO2011/150183; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 100-54-9 , The common heterocyclic compound, 100-54-9, name is Nicotinonitrile, molecular formula is C6H4N2, 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: A solution of the appropriate cyanophenyl 1a-1j (0.1mol), hydroxylamine hydrochloride (0.2 mol), and TEA (0.2 mol) in methanol was stirred at room temperature for 1 h, then heated under reflux until the disappearance of the starting materials (TLC analysis). After cooling, the solvent was evaporated to dryness under reduced pressure to give the crude, which was dissolved in ethyl acetate (400 mL) and washed with brine (3×100 mL) and dried with Na2SO4. Ethyl acetate was evaporated under reduced pressure to yield the compounds 2a-2j.

The synthetic route of 100-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cai, Jin; Wei, Hongtao; Hong, Kwon Ho; Wu, Xiaoqing; Cao, Meng; Zong, Xi; Li, Lushen; Sun, Chunlong; Chen, Junqing; Ji, Min; European Journal of Medicinal Chemistry; vol. 96; (2015); p. 1 – 13;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 68325-15-5, 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 68325-15-5, name is 3-Chloro-4-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To an ice-cooled solution of 2-methyl-2-(morpholin-4-yl)propan-1 -ol (4.00 g, 25.1 mmol) in THF (12.5 ml) under an argon atmosphere was added NaH 60% dispersion on mineral oil (1 .1 g, 27.4 mmol) slowly portionwise. The reaction mixture was stirred with ice-cooling for 1 h and a solution of 3-chloropyridine-4-carbonitrile (4.10 g, 29.6 mmol) in THF (64.5 ml) was added. The reaction was allowed to warm slowly to RT and stirred at this temperature for 16h. The reaction was then heated under reflux conditions for 2h. The reaction mixture was quenched with a sat. NH4CI solution and extracted with EtOAc. The organics were combined and washed with sat. NaCI, filtered through a hydrophobic filter and concentrated. The residue was crystallized with MTBE and collected by filtration to give the title compound (2 g, 35% yield) which was used without further purification.1H-NMR (400MHz, DMSO-d6): delta [ppm]= 8.75 (s, 1 H), 8.38 (d, 1 H), 7.78 (d, 1 H), 4.19 (s, 2H), 3.44 – 3.52 (m, 4H), 2.57 – 2.62 (m, 4H), 1.10 – 1 .23 (m, 6H).

According to the analysis of related databases, 68325-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; DANA FARBER CANCER INSTITUTE; SIEGEL, Stephan; SIEGEL, Franziska; SCHULZE, Volker; BERGER, Markus; GRAHAM, Keith; KLAR, Ulrich; KNUT, Eis; SUeLZLE, Detlev; BOeMER, Ulf; KORR, Daniel; PETERSEN, Kirstin; MOeNNING, Ursula; EBERSPAeCHER, Uwe; MOOSMAYER, Dieter; MEYERSON, Matthew; GREULICH, Heidi; KAPLAN, Bethany; HARB, Hassan, Youssef; DINH, Phi, Manh; (324 pag.)WO2019/81486; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem