Category: pyridine-derivatives

Reference of 1018505-59-3, 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.1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, molecular weight is 206.2874, as common compound, the synthetic route is as follows.

Preparation of 6-chloro-N-(5-(4-ethylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine A mixture of impure 5-(4-ethylpiperazin-1-yl)pyridin-2-amine (1.00 g, 4.85 mmol assumed), 8-bromo-6-chloroimidazo[1,2-a]pyridine hydrochloride salt (1.30 g, 4.85 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (634 mg, 1.02 mmol) and cesium carbonate (4.90 g, 15.0 mmol) in toluene (50 mL) was sparged with nitrogen while stirring for 10 min. Palladium(II) acetate (120 mg, 0.491 mmol) was then added and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted in a mixture of 1:1 methanol/methylene chloride (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, 1:19 methanol/methylene chloride to 1:6 methanol/methylene chloride) to afford 6-chloro-N-(5-(4-ethylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine as a yellow-green solid: 1H NMR (400 MHz, DMSO-d6.) d 9.12 (s, 1H), 8.30 (d, J=2.0 Hz, 1H), 8.26 (d, J=2.0 Hz, 1H), 7.99 (d, J=2.8 Hz, 1H), 7.89 (d, J=0.8 Hz, 1H), 7.55 (d, J=0.8 Hz, 1H), 7.43 (dd, J=8.8, 2.8 Hz, 1H), 7.35 (d, J=8.8 Hz, 1H), 3.11-3.10 (m, 4H), 2.50-2.49 (m, 4H, merged with DMSO peak), 2.38-2.37 (m, 2H), 1.04 (t, J=7.2 Hz, 3H).

Statistics shows that 1018505-59-3 is playing an increasingly important role. we look forward to future research findings about 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine.

Reference:
Patent; Gilead Connecticut, Inc.; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Mitchell, Scott A.; Schmitt, Aaron C.; Xu, Jianjun; Zhao, Zhongdong; US2014/148430; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 41288-96-4, Adding some certain compound to certain chemical reactions, such as: 41288-96-4, name is 2-Chloro-5-hydroxypyridine,molecular formula is C5H4ClNO, 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 41288-96-4.

General procedure: Using an apparatus previously described for method B [21] , potassium hydroxide (2.52 g, 45 mmol, 15 equiv) and water (2.52 g) were added to the reaction vessel and the mixture was allowed to stir until the potassium hydroxide was almost completely dissolved. Then, 2-bromo-3-pyridinol (0.354 g, 3 mmol) was added and the mixture stirred for 30 min, after which acetonitrile (10 mL) was added via syringe and the mixture stirred at room temperature. Fluoroform was then bubbled slowly into the mixture for 2 h, after which the resulting mixture was stirred for one additional hour. After being quenched with water and extracted with ethyl acetate, the ethyl acetate layer was washed with a saturated solution on sodium hydroxide, separated and concentrated. Additional impurities were removed via column chromatography on silica gel using an 80:20 mixture of hexanes/methylene chloride to give a 53% yield of the liquid product, 2-bromo-3-difluoromethoxypyridine (3d):

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. 41288-96-4, 2-Chloro-5-hydroxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Thomoson, Charles S.; Wang, Linhua; Dolbier, William R.; Journal of Fluorine Chemistry; vol. 168; (2014); p. 34 – 39;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 138588-22-4, 3-(Pyridin-2-yl)-1,2,4-thiadiazol-5-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, Product Details of 138588-22-4, blongs to pyridine-derivatives compound. Product Details of 138588-22-4

3-(Pyridin-2-yl)- 1 ,2,4-thiadiazol-5-amine (50 rag, 0.28 mmoi) was dissolved in 1.5 ml, pyridine. 4-Chlorobenzenesulfonyl chloride (65 mg, 0.31 mmol) was then added. The mixture was stirred for 16 hours at room temperature. The reaction was partitioned between dichloroniethane and water. The aqueous layer was extracted with dichloromethane. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to obtain Compound 14 as a tan solid. LCMS (M/Z): 352 (M + H). NMR (400 MHz, acetone) delta ppm 7.53 – 7.63 (m, 3 H) 7.91 (d, J 8.64 Hz, 2 H) 8.03 (td, J=7.75, 1.54 Hz, 1 H) 8.24 (d, J 8.00 Hz, 1 IT) 8.66 (d, J 4.49 Hz, 1 H).

The synthetic route of 138588-22-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCYNEXIS INC.; LIU, Hao; SLIGAR, Jessica, Marie; SPEAKE, Jason, Daniel; MOORE, Joseph, A., III; BECK, Brent, Christopher; WO2015/73797; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1220910-89-3, 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. 1220910-89-3, name is Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate. A new synthetic method of this compound is introduced below.

Under the protection of nitrogen, to a 100 L reactor, 2.60 kg (6.43 mol) of terdazolamide phosphate intermediate II and 50 L of anhydrous tetrahydrofuran were added and stirred to dissolve. 7.07 liters of 1 mol / L lithium hexamethyldisilazide in tetrahydrofuran solution was added dropwise.Stir at 10 15 for 2 hours, add 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone (DMPU) 0.83Kg, and lower the temperature to 0 5 . Add R-glycidyl butyrate 0.97Kg. Stir overnight at 10 C to 15 C to obtain a light yellow slurry.A solution of 33 g of sodium methoxide dissolved in 330 mL of methanol was added and stirred for 1 hour. Add ammonium chloride solution with a mass concentration of 10% (the mass concentration means the mass of ammonium chloride as a percentage of the total mass of ammonium chloride water) 17L.The two-phase mixture was concentrated. Water (13 L, 5 volumes) was added to the concentrated slurry, cooled to room temperature, and filtered. The filter cake was slurried with methanol and water (volume ratio 4: 1) (70 L), then filtered, and filtered The cake was rinsed with 12L of methanol and 12L of water, and the wet product was dried in a vacuum (pressure -0.01MPa -0.1MPa) drying oven at 45 C- 55 C for 8 hours 12 hours to obtain the white solid as terdazolamide phosphate intermediate V 2.01Kg, yield 84.4%. HPLC purity: 99.21%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1220910-89-3, its application will become more common.

Reference:
Patent; Shanghai Bozhi Yan Xin Pharmaceutical Co., Ltd.; Chen Jian; Liu Zhenfeng; Ying Shuhuan; (16 pag.)CN110804038; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 100367-55-3, 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.100367-55-3, name is 5-Nitropicolinonitrile, molecular formula is C6H3N3O2, molecular weight is 149.11, as common compound, the synthetic route is as follows.

To a solution of 5-nitropyridine-2-carbonitrile (7.0 g, 46.9 mmol) in methanol (150 mL) was added 10% palladium on carbon (2.0 g) and carbamic acid (7.0 g, 115 mmol). After being heated under reflux for 16 hours, the resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water (150 mL) and the resulting mixture was extracted with ethyl acetate (150 mL x 3). The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 5.1 g of 5-aminopyridine-2-carbonitrile (yield was 9 1.3%).

The chemical industry reduces the impact on the environment during synthesis 100367-55-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; WANG, Lisha; YUN, Hongying; ZHANG, Weixing; ZHENG, Xiufang; WO2015/22301; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 53710-18-2, name is 3,5-Diiodopyridine, molecular formula is C5H3I2N, 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. Recommanded Product: 3,5-Diiodopyridine

In a 75-mL sealed tube, 3,5-diiodo-pyridine (intermediate A-5, 6.6 g, 20 mmol), 5-chloro- 3,3-dimethyl-2,3-dihydro-isoindol-1-one (intermediate A-3, 1.95 g, 10 mmol), CuT (571 mg, 3 mmol), K3P04 (4.24 g, 20 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.7 mL, 6 mmol) were dissolved in 20 mL of dioxane. The resulting reaction mixture was heated at120C for 3 hours before it was poured into water (50 mL) and extracted with EtOAc (2 x125 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by silica gel flash chromatography (0-30% EtOAc-hexane gradient) to yield the title compound (1.8 g, 45%) as a light yellow solid. MS: 399.2 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 53710-18-2.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191338; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 850663-54-6, 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. 850663-54-6, name is 4-Chloro-5-nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

Into a 250 mL 3 -necked round-bottom flask purged and maintained with nitrogen was added a solution of 4-chloro-5-nitropyridin-2-ol (1 1.5 g, 65.9 mmol) in CH3CN (1 10 mL), followed by addition of POBr3 (23.1 g). The resulting solution was stirred at 80 C for 2 hours. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was suspended in 500 mL of ice water. The resulting solids were collected by filtration and dried under vacuum to afford 2,4- dibromo-5-nitropyridine (7.66 g, 41.1%) as a light yellow solid, which was carried forward without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,850663-54-6, its application will become more common.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 920966-03-6 ,Some common heterocyclic compound, 920966-03-6, molecular formula is C8H5ClN2O2, 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.

The compound 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid 11a (1.00 g, 5.10 mmol) and DMF (10 mL) were added to the reaction flask, was added CDI (0.91g, 5.61mmol), stirred at room temperature for 1 hour and ice-water bath, followed by addition of NH3.H2O (1.12mL) at 0 C, stirred at room temperature for 1 hour. TLC monitored the reaction was complete, the system was poured into water, extracted three times with ethyl acetate, washed with water, and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and concentrated, dichloromethane / petroleum ether = 5ml / 1ml beating, suction filtration, dried under reduced pressure using a rotary evaporator to give the title compound 11b (0.6g, 3.08mmol), in a yield of 60.3%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,920966-03-6, its application will become more common.

Reference:
Patent; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Qiang; Qu Minkai; Zhang Linli; Song Jinqian; Liu Lei; Chen Haiji; Liu Qiang; Wang Yijin; Ge Jian; (67 pag.)CN109535164; (2019); A;,
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. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. Product Details of 75806-86-9

Example 2: 2-Bromo-5-chloro-pyridin-3-ylamine; [00382] 2-Bromo-5-chloro-3-nitro-pyridine (11.87 g, 50 mmol) was dissolved in 100 mL ether. Tin(ll) chloride dihydrate (56.4g, 0.5 mol) was dissolved in 100 mL of concentrated hydrochloric acid and added drop wise over 15 minutes to the stirring ethereal solution of the nitro compound. The exothermic reaction brought the ether to boiling and it was allowed to evaporate off. After the addition was complete the reaction mixture was placed on a 50 C oil bath and stirred for 30 minutes to boil of the remaining ether. The flask was then cooled on in an ice bath. The precipitate formed was collected and by filtration and dissolved in 100 mL of water. The pH was adjusted to 9-10 by the addition of concentrated ammonium hydroxide solution and the product was extracted with ethyl acetate (2 x 100 mL). The organic layer was washed with diluted ammonium hydroxide, water and brine and dried over Na2SU4 and the solvent was evaporated to afford 7.4 g of tan crystalline solid. MS m/z : 208.9 (M+H).

The synthetic route of 75806-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 955372-86-8 ,Some common heterocyclic compound, 955372-86-8, molecular formula is C6H3BrFNO2, 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.

I ntermediate 7: 3-Bromo-5-( 2-ftuoro-phenylamino)-isonicotinic acid; Lithium bis(trimethylsilyl)amide (54.6 ml_, 1.0 M in THF, 54.6 mmol) was added to a solution of 2-fluoro aniline (3.5 mL, 36.4 mmol) in THF (100 ml_) at -78 0C. The resulting solution was for 1 h at -780C. S-Bromo-delta-fluoro-isonicotinic acid (1) (4.0 g, 18.2 mmol) was added as a solid, and the reaction solution was stirred for 48 h at room temperature. The reaction solution was concentrated via rotary evaporation; diluted with satd. NaHCO3, and washed with EtOAc. The aqueous solution was acidified with concentrated HCI. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to afford the desired product (4.2 g, 74%) as a yellow solid.

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. 955372-86-8, 3-Bromo-5-fluoroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem