Pyridine-derivatives

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. 917023-06-4, name is Methyl 2-(5-bromopyridin-2-yl)acetate. This compound has unique chemical properties. The synthetic route is as follows. name: Methyl 2-(5-bromopyridin-2-yl)acetate

To a solution of methyl 2-(5-bromopyridin-2-yl)acetate (5.50 g, 23.91 mmol) and 1,4- dioxaspiro[4.5]decan-8-ylmethyl trifluoromethanesulfonate (6.85 g, 19.13 mmol) in THF (100 mL) was added LiHMDS (27.50 mL, 27.50 mmol, 1 M in THF) at -78C. The reaction mixture was stirred at 15C for 16 h under a nitrogen atmosphere. LC-MS showed the reaction was complete. The mixture was quenched with saturated NH4Cl solution (30 mL), diluted with water (60 mL), and extracted with EtOAc (50 mL x 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, 0-20% EtOAc/PE) to give the title compound.1H NMR (CDCl3, 400 MHz^^^^^^^^^^G^^J=2.0 Hz, 1H), 7.76 (dd, J=8.4, 2.2 Hz, 1H), 7.20 (d, J=8.6 Hz, 1H), 3.85-3.94 (m, 5H), 3.66 (s, 3H), 2.00-2.05 (m, 1H), 1.79-1.87 (m, 1H), 1.61-1.75 (m, 4H), 1.37-1.47 (m, 2H), 1.17-1.29 (m, 3H). MS (ESI) m/z 384.1/386.1 (M+H).

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, 917023-06-4, Methyl 2-(5-bromopyridin-2-yl)acetate.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; KUANG, Rongze; KUMAR, Puneet; DUFFY, Joseph, L.; ZHU, Cheng; ALI, Amjad; YANG, Meng; DEBENHAM, John, S.; (124 pag.)WO2018/39094; (2018); 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. 54189-82-1, name is 6-Chloro-N-methylnicotinamide. A new synthetic method of this compound is introduced below., SDS of cas: 54189-82-1

A mixture of 5-[(l-cyclobutylpiperidin-4-yl)oxy]-l,3-dihydrospiro[indene-2,4′- piperidine] (50 mg), 6-chloro-N-methylnicotmamide (37 mg) and K2CO3 (30 mg) in DMSO (5 mL) is heated at 12O0C overnight. The mixture is cooled to rt and water (20 mL) is added. The resulting mixture is extracted with DCM (20 mL x 2). The combined organic phase is washed with water, dried over Na2SO4, and the solvent is removed to give a residue which is purified through PTLC (5% TEA in EtOAc) to give the title compound. MS (M+ 1) 475.6.

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, 54189-82-1, 6-Chloro-N-methylnicotinamide.

Reference:
Patent; NEUROGEN CORPORATION; WO2009/39431; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 14254-57-0 ,Some common heterocyclic compound, 14254-57-0, molecular formula is C6H4ClNO, 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 a solution of fe/7-butyl 5-(2-(3-aminophenyl)-7-methoxy-6-(3- morpholinopropoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.064g, 0.102 mmol) in CH2Cl2 (4mL), DIEA (0.041g, 0.32mmol) and isonicotinoyl chloride (0.022g, 0.123 mmol) were added were added. The resulting mixture was stirred at RT for 2.5h. The volatiles were removed in vacua and the residue was taken up in CH2CIj (15 mL), washed with NaHCOi solution, water and brine, dried (Na2SO4) and filtered.[0379] The residue was taken up in CH2Cl2 (3 mL) and TFA (3 mL) was added. The mixture was stirred at RT for 2.5 h. The volatiles were removed in vacuo and the residue was washed with Et2O and hexane. The solid was dried under vacuum to give the desired product N-(3-(4-( 1 H-indazol-5-ylamino)-7-methoxy-6-(3-rnorpholinopropoxy)quinazolin -2-yl)phenyl)isonicotinamide (0.073g, 0.098mmol, 96%). MS 63 1 .3 (M+ 1 ). HPLC retention time 3.94 mins

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14254-57-0, its application will become more common.

Reference:
Patent; SURFACE LOGIX, INC.; SWEETNAM, Paul; BARTOLOZZI, Alessandra; CAMPBELL, Anthony; COLE, Bridget; FOUDOULAKIS, Hope; KIRK, Brian; SESHADRI, Hemalatha; RAM, Siya; WO2010/104851; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 103-74-2, 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 103-74-2, name is 2-(2-Hydroxyethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

The 250 ml flask is added in three 12.3g (0.1mol) 2-pyridine ethanol, 150 ml ethyl acetate, salt bath under the conditions of the above prepared dropping under stirring 13.1g (0.1mol) mountain ash acid radical chlorine with 50 ml ethyl acetate solution, completion of the dropping, stirring the mixture at room temperature for reaction 2h; filtering, the filter cake is washed with proper amount of ethyl acetate the washing, drying, to obtain light yellow solid 23.6g, yield 92.9%.

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 103-74-2, 2-(2-Hydroxyethyl)pyridine.

Reference:
Patent; Qingdao University of Science and Technology; Xu, liangzhong; ju, guangxiu; wang, minghui; chen, gexin; xu, shenshen; (7 pag.)CN105503704; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6345-27-3, 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. 6345-27-3, name is Isonicotinimidamide hydrochloride. A new synthetic method of this compound is introduced below.

2. 2-(4-Pyridinyl)-4-pyrimidinamine – A mixture containing 5.4 g. of sodium methoxide, 50 ml. of methanol and 31.6 g. of isonicotinamidine hydrochloride was stirred for thirty minutes and stripped to dryness to remove the solid. To the residue was added 250 ml. of tetrahydrofuran and the resulting slurry was stirred in an ice bath. To the stirred mixture was added dropwise over a period of thirty minutes 18 g. of alpha-chloroacrylonitrile. After the reaction mixture had been stirred for an additional two hours, it was allowed to stand at room temperature for one hour and then refluxed for four hours. To the reaction mixture was added 15 ml. of 35percent aqueous sodium hydroxide solution and the mixture chilled. The solid was collected, washed with water and dried to yield 21.1 g. of 2-(4-pyridinyl)-4-pyrimidinamine, m.p. 264°-267° C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6345-27-3, its application will become more common.

Reference:
Patent; Sterling Drug Inc.; US4109092; (1978); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 187242-88-2, 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. 187242-88-2, name is 2-Chloro-3-nitro-6-phenylpyridine. A new synthetic method of this compound is introduced below.

1? (48.0 g, 1.0 equiv.), 2? (59.0 g, 1.1 equiv.), and Na2CO3 (43.4 g, 2.0 equiv.) were charged to a 2 L, 3-neck flask. DMA (310 mL, 6.5 vol.) was added and the reaction was heated to 100 C. After 18.5 hours, HPLC analysis showed the reaction to be complete. The reaction was cooled to 9 C. and 2-MeTHF (960 mL, 20 vol.) was added. 10% aqueous solution of NaCl (720 mL, 15 vol.) was added resulting in some solid formation. The mixture was stirred for one hour and then transferred to a separatory funnel (rinsed the solids forward with 100 mL water). The layers were separated and the aqueous layer (Vaq1200 mL) was back extracted with 2-MeTHF (2×200 mL). The combined organics were then washed with 10% aqueous solution of NaCl (2×250 mL) and then analyzed by 1H NMR for DMA (0.3 wt %). After holding the solution overnight, an aliquot was taken out (6 mL) and was washed (3 mL) with water which resulted in a nice phase split (took >30 minutes). Water (650 mL, batch size) was added and stirred for 10 minutes and then transferred to a separatory funnel and allowed to sit. After 90 minutes, a partial phase split was realized (Vaq=250 mL). Brine (250 mL) was added resulting in a phase split. The organic layer (1300 mL, 27 vol., Kf=3.45%) was split off and charged to a 3-L RB flask. The flask was heated (atmospheric) to distill off some of the 2-MeTHF. Once 15 volumes of 2-MeTHF (720 mL) remained (30 minutes), the solution was reanalyzed for water content (Kf=0.24%). The reaction was then cooled to 50-55 C. and polished filtered through filter paper (very little solids present). The solution was then recharged to the 3-L flask (after cleaning flask) and the solution was distilled down to 9 volumes (430 mL). The solution was then heated to 70 C. and heptane was added in portions over one hour. The heat was then turned off and the solution was allowed to slowly cool to room temperature (after one hour the temperature was 48 C.). After stirring for 70 hours, the mother liquor was checked by HPLC analysis for 3 (2.7 mg/mL) and then filtered. The solids were washed with a 25% 2-MeTHF/heptane solution (75 mL, slurry) followed by 2×240 mL displacement wash with the same solution. The cake was washed one more time with heptane (240 mL) and then dried in a vacuum oven for 20 hours at room temperature. 3 (81.1 g, 86% yield, 99.2% AUC) was isolated as a dark red solid. 1H NMR (CDCl3) analysis showed no residual solvent present.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,187242-88-2, 2-Chloro-3-nitro-6-phenylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; ArQule, Inc.; Bates, Craig; Chen, Jian-Xie; Mao, Jianmin; Reed, David P.; US2015/266876; (2015); 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. 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate, the common compound, a new synthetic route is introduced below. COA of Formula: C7H5ClN2O4

11231] To a solution of 643-1 (1.5 g, 6.9 mmol) in DMF (20 mL) was added 2- benzyloxyl ethanol (6.3 g, 41 mmol) at 25 °C. The solution wras stirred for 6 h and then poured into 0 (20 mL). The mixture was extracted with EA (2 x 40 mL). The combined organic phase was washed with brine, dried over anhydrous Na^SC^ and concentrated under reduced pressure. The residue was purified by column chromatography using 5-10percent EA in PE as the eluent to give a mixture of 643-2 and 643-2 A ( 1 .50 g).

The synthetic route of 59237-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6271-78-9, 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 6271-78-9 as follows.

To a solution of 6-chloronicotinamide (20.0 g,128.20 mmol) in MeOH/ THF/ DMF (40/20/10.0 mL) was added 2M methyl amine solutionin THF (96.0 mL, 192.3 mmol) and heatedin a sealed bomb at 80 C for 12 h. After completion of the reaction thereaction mixture was concentrated under reduced pressure, the crude waspurified on Combiflash purifier with 6% Methanol in Dichloromethane as eluentto afford the title compound as off-white solid (6.0 g, 31%). 1H NMR(DMSO-d6, 400 MHz) delta 2.78 (d, J= 4.4 Hz, 3H), 6.39 (d, J = 8.0 Hz,1H), 6.93-6.94 (m, 2H), 7.60 (bs, 1H), 7.78 (dd, J = 2.0 Hz, J = 2.0 Hz,1H), 8.50 (d, J = 1.6 Hz, 1H); MS (ESI) m/z 152.1 (M+H)+; HPLC Purity 215nm, 99.15%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6271-78-9, its application will become more common.

Reference:
Article; Ruf, Sven; Hallur, Mahanandeesha Siddappa; Anchan, Nisha K.; Swamy, Indu N.; Murugesan, Karthikai Raj; Sarkar, Sayantani; Narasimhulu, Lokesh Kananti; Putta, V.P. Rama Kishore; Shaik, Shama; Chandrasekar, Devaraj Venkatapura; Mane, Vishal Subhash; Kadnur, Sanjay Venkatachalapathi; Suresh, Juluri; Bhamidipati, Ravi Kanth; Singh, Manvi; Burri, Raghunadha Reddy; Kristam, Rajendra; Schreuder, Herman; Czech, Joerg; Rudolph, Christine; Marker, Alexander; Langer, Thomas; Mullangi, Ramesh; Yura, Takeshi; Gosu, Ramachandraiah; Kannt, Aimo; Dhakshinamoorthy, Saravanakumar; Rajagopal, Sridharan; Bioorganic and Medicinal Chemistry Letters; vol. 28; 5; (2018); p. 922 – 925;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86447-11-2, 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. 86447-11-2, name is 1-Boc-1,2,5,6-tetrahydropyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below.

22.7 g of N-Boc-1,2,3,6-tetrahydropyridine-5-carboxylic acid (0.1 mol) and 120 mL of toluene were added to a 250 mL reaction flask, and 16.6 g (0.1 mol) of bromine was added dropwise at room temperature. After the completion of the addition, the reaction was stirred at room temperature for 30 minutes. After completion of the TLC reaction, 20 mL of sulfolane was added, the temperature was raised to 50-60 C, and 31.2 g (0.4 mol) of pyridine was added dropwise. After the dropwise addition, the bubble is no longer escaped, the temperature to 80-90 reaction 2-3 hours, vacuum distillation 18.1g of colorless liquid N-Boc-1, 2,3,6-tetrahydropyridine-5-bromide in 69% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,86447-11-2, 1-Boc-1,2,5,6-tetrahydropyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Cangzhou Puri Oriental Technology Co., Ltd; Leng, Yanguo; Yu, Weidong; Zhang, Jin; (6 pag.)CN105503924; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 110919-71-6, 2-Amino-5-fluoro-6-methylpyridine, 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, COA of Formula: C6H7FN2, blongs to pyridine-derivatives compound. COA of Formula: C6H7FN2

Step 1 Ethyl 6-chloro-4-(5-fluoro-6-methylpyridin-2-ylamino) pyridazine-3-carboxylate A pressure tube was charged with ethyl 4,6-dichloropyridazine-3-carboxylate (300 mg, 1.36 mmol), 5-fluoro-6-methylpyridin-2-amine (257 mg, 2.04 mmol), and acetonitrile (8 mL) and then heated at 140 C. for 3 d. After cooling to room temperature the reaction mixture was concentrated in vacuo and the residue purified by chromatography (silica, 50 mum, 80 g, Analogix, 0 to 10% acetone in dichloromethane, 25 min) to afford ethyl 6-chloro-4-(5-fluoro-6-methylpyridin-2-ylamino)pyridazine-3-carboxylate (69 mg, 16%) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 10.72 (br. s., 1H) 9.06 (s, 1H) 7.38 (s, 1H) 6.74-6.85 (m, 1H) 4.58 (q, J=7.07 Hz, 2H) 2.56 (d, J=3.03 Hz, 3H) 1.53 (t, J=7.07 Hz, 3H) 1.27 (s, 1H). LCMS (EI/CI) m/z: 311 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,110919-71-6, 2-Amino-5-fluoro-6-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Hoffman-La Roche Inc.; Hermann, Johannes Cornelius; Kennedy-Smith, Joshua; Lucas, Matthew C.; Padilla, Fernando; Soth, Michael; US2013/178478; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem