Pyridine-derivatives

Application of 1180132-17-5, 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 1180132-17-5, name is 5-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5a (0.10 g, 0.33 mmol) and 9a (0.07 g, 0.33 mmol) in 1,4-dioxane (2 mL), were added Cs2CO3 (0.21 g, 0.65 mmol), Pd2(dba)3 (0.03 g, 0.03 mmol) and XantPhos (0.03 g, 0.06 mmol). The mixture was heated to 120 C for 60 min with microwave, then cooled to room temperature, diluted with water (10 mL), and extracted with DCM (40 mL × 3). The combined organic layers were washed with water (40 mL) and brine (40 mL), dried over anhydrous Na2SO4, concentrated under vacuum, and purified by silica gel column chromatography (DCM / MeOH = 20:1) to give compound 10a (0.02 g, 12.40%) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz), delta: 9.97 (s, 1H), 8.68 (d, 1H), 8.17 (d, 2H), 8.06 (s, 1H), 7.70 (m, 2H), 4.22 (m, 2H), 3.43 (s, 2H), 3.01 (m, 2H), 2.69 (m, 2H), 2.33 (m, 10H), 0.96 (m, 3H). MS (ESI): mass calcd. for C26H28F2N8 490, m/z found 491 [M+H] +.

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 1180132-17-5, 5-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine.

Reference:
Article; Wang, Yan; Liu, Wen-Jian; Yin, Lei; Li, Heng; Chen, Zhen-Hua; Zhu, Dian-Xi; Song, Xiu-Qing; Cheng, Zhen-Zhen; Song, Peng; Wang, Zhan; Li, Zhi-Gang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 5; (2018); p. 974 – 978;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 113118-81-3, 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. 113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, 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.

General procedure: Steps 1 To a solution of 5-bromopyridin-3-amine (XIX) (535 mg, 3.09 mmol) in MeOH (62 mL) was added acetone (296 muL, 4.02 mL). The pH was adjusted to 4 using HOAc and stirred for 30 min. NaCNBH3 (272 mg, 4.33 mmol) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and evaporated under vacuum. The crude product was purified on a silica gel column (100% hexane?90:10 hexane:EtOAc) to produce 5-bromo-N-isopropylpyridin-3-amine (XXXVII) as an oil which slowly solidified into an off-white solid (309 mg, 1.44 mmol, 47% yield). 1H NMR (DMSO-d6, 500 MHz) delta ppm 1.12 (d, J=6.3 Hz, 6H), 3.55-3.59 (m, 1H), 6.03 (d, J=7.9 Hz, 1H), 7.05-7.06 (m, 1H), 7.75 (d, J=2 Hz, 1H), 7.90 (d, J=2 Hz, 1H); ESIMS found C8H11BrN2 m/z 215.1 (M+H).

According to the analysis of related databases, 113118-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (262 pag.)US2016/68547; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5345-47-1 ,Some common heterocyclic compound, 5345-47-1, molecular formula is C6H6N2O2, 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.

2-Amino-nicotinic acid (2 g, 14.48 mmol) was dispersed in glacial acetic acid. To this suspension was added a solution of bromine (1.2 mL) in glacial acetic acid (5 mL). The mixture was stirred at room temperature for 20 h. The mixture was filtered and washed with glacial acetic acid (10 mL) and water in several portions. The precipitate was collected and dried to give 2-amino-5-bromonicotinic acid (3.0 g, 95 % yield) as yellow solid. XH-NMR (DMSO- d6, 400 MHz) delta 8.31 (d, J= 2.4 Hz, 1H), 8.18 (d, J= 2.8 Hz, 1H), 5.06-5.27 (m, 2H). MS (M+H)+: 218 / 220.

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. 5345-47-1, 2-Aminonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); 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. 17368-12-6, name is 2-Chloro-4-hydroxypyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-4-hydroxypyridine

To a solution of 2-chloropyridin-4-ol (1 g, 7.75 mmol) in DMA (10 ml) was added bromocyclopropane (2.8 g, 23.2 mmol), Nal (1.16 g, 7.75 mmol) and CS2CO3 (5 g, 15.5 mmol). The mixture was stirred at MW 170 C for 20 minutes, and then MW 180 C for 30 minutes. The reaction mixture was extracted with EA. The organic layer was dried and concentrated. The residue was purified by flash column chromatography to give 300 mg of 2-chloro-4-cyclopropoxypyridine. 1H NMR (400MHz, CDC13 ) delta = 8.19 (d, J=5.8 Hz, IH), 7.02 (d, J=2.0 Hz, IH), 6.87 (dd, J=2.0, 5.8 Hz, IH), 3.80 (tt, J=3.0, 6.0 Hz, IH), 0.91 – 0.75 (m, 4H)

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, 17368-12-6, 2-Chloro-4-hydroxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/113932; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52833-94-0, 2-Amino-5-bromonicotinic 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, 52833-94-0, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5BrN2O2

A mixture of 2-amino-5-bromonicotinic acid (2.0 g, 9.20 mmol), HOBT (1.40 g, 11.2 mmol), EDCI (3.52 g, 18.4 mmol), Et3N (4.68 g, 46.0 mmol) and NH4C1 (2.48 g, 46.0 mmol) in DMF (100 mL) was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, suspended in water and extracted with CH2C12. The organic layer was washed with brine, dried over Na2S04 and concentrated to give the product of 2-amino-5- bromonicotinamide (1.80 g, yield: 80%), which was used for the next step without further purification. NMR (DMSO-i, 400 MHz) delta 8.14 (dd, J= 4.4 Hz, 2.4 Hz, 2H), 8.04 (s, 1H), 7.46 (s, 1H), 7.37 (s, 2H). MS (M+H)+: 216 / 218.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52833-94-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey, C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/209727; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58584-92-2, 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 58584-92-2 as follows.

2-Amino-6-chloronicotinamide (Inter. 3) To a 0.3 M solution of 2-amino-6-chloronicotinic acid (Inter. 2) (1 equiv) in anhydrous THF, under an inert atmosphere, was added thionyl chloride (3.3 equiv) in a dropwise fashion. The reaction mixture was stirred at room temperature for 2 hours. After this time the reaction was concentrated in vacuo to give a crude yellow solid residue. The crude solid was dissolved in THF (equal to initial reaction volume) and concentrated in vacuo again to give a yellow solid residue. The residue was dissolved once more in THF and concentrated as before to give a solid residue which was then dissolved in THF (to give a solution of 0.3M) and ammonia gas bubbled through the solution for 1 hour. The resultant precipitate was removed by filtration and the filtrate concentrated in vacuo to give a yellow precipitate which was triturated with water at 50 C. then dried to give the title compound (92% yield, 93% purity), suitably clean to be used without any further purification. m/z (LC-MS, ESP): 172 [M+H]+R/T=3.19 mins

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58584-92-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2009/99174; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13091-23-1, 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 13091-23-1 as follows.

Ammonia (74.0 mL, 3418.64 mmol) was condensed into THF (170 mL) cooled to -78 0C under nitrogen. Potassium tert-butoxide (23.98 g, 213.67 mmol) was added as a solid and the reaction mixture warmed to -35 0C. tert-Butyl hydroperoxide (5.5 M soln. in decane) (16.32 mL, 89.74 mmol) was added dropwise to 4-chloro-3-nitropyridine (13.55 g, 85.47 mmol) in THF (200 mL) cooled to 0 0C over a period of 5 minutes under nitrogen. The resulting solution was added slowly to the other flask and the mixture stirred at -35 0C for 1.5 hours. The reaction mixture was quenched with saturated NH4CI (50 mL) and allowed to warm to room temperature overnight. The reaction mixture was concentrated in vacuo and the brown precipitate filtered and washed with cold water to yield crude product. The solid was dried overnight under vacuum to yield 4-chloro-5-nitropyridin-2-ol (14.66 g, 83.99 mmol, 98 %) as a yellow solid. 1R NMR (400 MHz, DMSO) delta 6.36 (IH, s), 8.73 (IH, s). m/z 173 (M-H)”.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13091-23-1, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/24821; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 123531-52-2, Adding some certain compound to certain chemical reactions, such as: 123531-52-2, name is Ethyl imidazo[1,2-a]pyridine-3-carboxylate,molecular formula is C10H10N2O2, 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 123531-52-2.

Ethyl imidazo[1,2-a]pyridine-3-carboxylate(0.90 g, 4.7 mmol) and hydrazine (1.0 mL, 13 mmol, 40%) are combined in EtOH (10 mL). The mixture is stirred under microwave conditions at 100 C. for 2 hrs. The solvent is removed to give the title compound (0.82 g, 93%) which can be used without further purification. LC/MS (m/z): 177 (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. 123531-52-2, Ethyl imidazo[1,2-a]pyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; Hu, Zhi Long; Liu, Lian Zhu; Ma, Tianwei; Zhang, Haizhen; Zhou, Jingye; (25 pag.)US2018/194755; (2018); 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.55240-51-2, name is 2-Phenylisonicotinic acid, molecular formula is C12H9NO2, molecular weight is 199.21, as common compound, the synthetic route is as follows.name: 2-Phenylisonicotinic acid

To a flask containing 1 10 mg (0.553 mmol) of Hppy-C02H, 275 mg (0.529 mmol) of Ru(bpy)2Cl2, 183 mg (1.08 mmol) of AgN03, and 28 mg (0.70 mmol) of NaOH was added 30 mL of a degassed aqueous methanol solution (H20:MeOH 1 :5 v/v). The reaction mixture was heated at reflux for 18 hrs, cooled, and then filtered through celite to afford a dark red/orange filtrate. The solvent was removed in vacuo and then passed through a silica column (acetone:MeOH:KN03 (sal, aq) 2: 1 : 1). The sample was passed through a silica column (MeOH:CHCl3 3: 1) a second time and 56 mg of a red-purple product was obtained after recrystallization from CH2CI2 and hexanes (yield = 14 %). NMR (CD3OD): 6.42 (dd, 1H, J = 7 Hz, l = 1 Hz), 6.79 (td, 1H, J = 7 Hz, l = 1 Hz), 6.89 (td, 1H, = 7 Hz, 4./ = 1 Hz), 7.19-7.28 (m, 3H), 7.31 , (dd, 1H, J = 6 Hz, 4 J = 2 Hz), 7.46 (ddd, 1H, 3 J = 7 Hz, 5 Hz, 4 J = 1 Hz), 7.58 (d, 1H, 3 J = 6 Hz, 4 J = 1 Hz), 7.72- 7.91 (m, 7H), 8.02 (ddd, 1H, 3 J = 8 Hz, 8 Hz, J = 1 Hz), 8.10 (ddd, 1H, J = 5 Hz, 4J = 2 Hz, = 1 Hz), 8.41 (d, 1H, J = 8 Hz), 8.45 (d, 1H, 4 J = 1 Hz), 8.45 (d, 1H, J = 8 Hz), 8.51 (d, 1H, J = 8 Hz), 8.61 (d, 1H, J = 8 Hz). ESI-MS: m/z, 612.0 (calcd for {M+} 612.1) 13C NMR (CD3OD with 1 drop of NaOD): 194, 172, 169, 159, 159, 158, 157, 156, 151 , 151 , 151 , 150, 147, 146, 138, 136, 136, 135, 135, 130, 128, 128, 127, 127, 125, 125, 125, 124, 124, 123, 122, 1 19. Anal. Calcd. for C32H24N605Ru + CH3OH: C, 56.17; H, 4.00; N, 1 1.91. Found: C, 57.45; H, 4.40; N, 10.38.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55240-51-2, 2-Phenylisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; BERLINGUETTE, Curtis P.; KOIVISTO, Bryan; ROBSON, Kiyoshi; WO2011/32269; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1227628-78-5, 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 1227628-78-5 as follows.

To a solution of (R)-5-(2-hydroxy-l-phenylethyl)-amino)-pyridin-3-yl)-boronic acid (100 mg, 0.5 mmol) in DME/H20 (5 : 1, 6 mL) was added Pd(PPh3)4 (1 16 mg, 0.1 mmol), K2C03 (138 mg, 1.0 mmol) and 5-bromo-lH-pyrazolo[4,3-b]pyridine (125 mg, 0.5 mmol). The resulting mixture was degassed and then stirred for 10 hours at 95 C under an Ar atmosphere. After cooling, the mixture was diluted with water (30 mL) and then extracted with EtOAc (2 x 50 mL). The combined organic layers were washed with water and brine, and then dried. The solvent was concentrated and the residue was purified by Prep-HPLC to give (R)-2-phenyl-2-[5-(lH- pyrazolo[4,3-b]pyridin-5-yl)-pyridin-3-ylamino]-ethanol (5 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227628-78-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; YANG, Song; ZHOU, Chengang; WO2014/90692; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem