Category: pyridine-derivatives

Application of 65001-21-0 ,Some common heterocyclic compound, 65001-21-0, molecular formula is C5H3BrClNO2S, 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.

Example 36A tert-Butyl 4-{[(5-bromopyridin-3-yl) sulphonyl]amino}piperidine-1-carboxylate 5-Bromopyridine-3-sulphonyl chloride (1 g, 3.9 mmol) was dissolved in dichloromethane (20 ml), the mixture was cooled to 0 C. and tert-butyl 4-aminopiperidine-1-carboxylate (1.18 g, 5.8 mmol) and N,N-diisopropylethylamine (1.7 ml, 9.7 mmol) were added. The reaction mixture was stirred at RT overnight and concentrated, and the residue was purified chromatographically by HPLC (Method 9). This gave 1.0 g (62% of theory) of the title compound. 1H NMR (300 MHz, DMSO-d6): delta=ppm 1.09-1.24 (m, 2H), 1.33 (s, 9H), 1.47-1.59 (m, 2H), 2.66-2.83 (m, 2H), 3.19-3.25 (m, 1H), 3.63-3.75 (m, 2H), 8.09 (br. s, 1H), 8.36 (t, 1H), 8.91 (d, 1H), 8.95 (d, 1H). LC-MS (Method 4): Rt=1.19 min; MS (ESIneg): m/z=420.3 [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. 65001-21-0, 5-Bromopyridine-3-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHN, Ulrike; ELLERMANN, Manuel; STRASSBURGER, Julia; WENDT, Astrid; ROeHRIG, Susanne; WEBSTER, Robert Alan; SCHMIDT, Martina Victoria; TERSTEEGEN, Adrian; BEYER, Kristin; SCHAeFER, Martina; BUCHMUeLLER, Anja; GERDES, Christoph; SPERZEL, Michael; SANDMANN, Steffen; HEITMEIER, Stefan; HILLISCH, Alexander; ACKERSTAFF, Jens; TERJUNG, Carsten; (163 pag.)US2016/244437; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 18227-67-3, 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 18227-67-3 as follows.

Amixture of 4-amino-3-methyl-5-nitropyridine (1. 198 g), iron powder (1.748 g), ethanol (52 mL) and hydrochloric acid (13 mL) was heated to reflux for 3 hours. After cooling to room temperature the ethanol was distilled off and the resulting suspension was diluted with water to 50 mL and the pH was adjusted to 13 by addition of 2N NaOH. Extraction with ethyl acetate (3 x 70 mL), drying of the combined organic phases of anhydrous sodium sulphate and evaporation of the solvent afforded 0.579 g (60%) of 3, 4-diamino-5-metl1ylpyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18227-67-3, its application will become more common.

Reference:
Patent; K.U. LEUVEN RESEARCH & DEVELOPMENT; GILEAD SCIENCES, INC.; PUERSTINGER, Gerhard; WO2005/63744; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 180995-12-4, Adding some certain compound to certain chemical reactions, such as: 180995-12-4, name is 2,4-Dichloronicotinonitrile,molecular formula is C6H2Cl2N2, 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 180995-12-4.

(114a) 2-chloro-4-(ethylthio)nicotinonitrile; N,N -dimethylacetamide (1 mL) solution of sodium thioethoxide (93 mg, 1.1 mmol) was added to N,N -dimethylacetamide (1 mL) solution of 2,4-dichloronicotinonitrile (173 mg, 1.00 mmol) which was produced in Example 111 (111a) at 0C and the mixture was stirred at room temperature for one hour. Water (3 mL) was added to the reaction liquid, and generated powder was separated by filtration and further purified by silica gel column chromatography (hexane/ethyl acetate =3:1) and the title compound was obtained (44 mg, yield 22%). Pale yellow powder Mp 97-98C; IR (KBr) numax 2226, 1556, 1518, 1431, 1379, 1199, 819 cm-1; 1H NMR(CDCl3, 500 MHz) delta 1.46 (3H, t, J = 7.3 Hz), 3.12 (2H, q, J = 7.3 Hz), 7.11 (1H, d, J = 5.9 Hz), 8.33 (1H, d, J = 5.9 Hz); HRMS m/z calcd for C8H7N235ClS 198.0018, found 198.0011; MS (EI) m/z: 198 [M+], 183, 170, 165, 147, 134, 126, 108, 98, 76, 69, 64, 46.

According to the analysis of related databases, 180995-12-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sankyo Company, Limited; EP1764367; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58483-95-7, 5-Amino-2-chloropyridine-4-carboxylic 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, HPLC of Formula: C6H5ClN2O2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5ClN2O2

The mixture of 5-amino-2-chloroisonicotinic acid (5.00g, 29.07mmol) and formamidine acetate (6.00g, 58.14mmol) was stirred at 160°C for 0.5h, cooled, water (100mL) was added. The mixture was refluxed under vigorous stirring for 20min, cooled again. The precipitate formed was collected, washed with water and dried to give 4.74g intermediate 15 as off-white power. Yield 90.4percent. mp>320°C. MS m/z (ESI) 182.4 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58483-95-7, 5-Amino-2-chloropyridine-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Hao; Wang, Jin; Zhao, Hong-Yi; Yang, Xue-Yan; Lei, Hao; Xin, Minhang; Cao, Yong-Xiao; Zhang, San-Qi; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3619 – 3633;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 38185-56-7, 5-Bromo-3-chloro-2-fluoropyridine, 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: 38185-56-7, blongs to pyridine-derivatives compound. Recommanded Product: 38185-56-7

STEP-1 : 5 -BROMO-3 -CHLORO-2-ISOBUTOXYP YRIDINE[00214] To a solution of 5-bromo-3-chloro-2-fluoropyridine (5.0 g, 23.7 mmol, LLB Chem) and 2-methylpropan-l-ol (5.28 g, 71.3 mmol, Spectrochem) in DMSO (100 mL) was added CS2CO3(23.0 g, 71.3 mmol, GLR) and the reaction was heated at 90 C for 3 h. The reaction mixture was allowed to cool to room temperature, water (500 mL) was added and the aqueous layer was extracted with diethyl ether (2 x 500 mL). The combined organic extract was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by column chromatography (silica gel 100-200 mesh and 0-5% ethyl acetate in hexanes) to obtain compound-3 (5.0 g, 86%) as colorless oil. TLC solvent system: 10% ethyl acetate in hexanes, product’s Rf: 0.8. MS (ESI, positive ion): No ionization.1H NMR (400 MHz, CDC13) delta 8.06 (d, J= 2.2 Hz, 1H), 7.74 (d, J= 2.2 Hz, 1H), 4.11 (d, J= 6.7 Hz, 2H), 2.12 (dp, J= 13.4, 6.7 Hz, 1H), 1.03 (d, J= 6.7 Hz, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38185-56-7, 5-Bromo-3-chloro-2-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; CHAKKA, Nagasree; DIMAURO, Erin F.; GAO, Hua; GUNAYDIN, Hakan; HUANG, Hongbing; OLIVIERI, Philip; SCHENKEL, Laurie; WEISS, Matthew; WO2015/51043; (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. 7598-35-8, name is 2-Bromopyridin-4-amine, the common compound, a new synthetic route is introduced below. COA of Formula: C5H5BrN2

A 50 mL single necked round bottom flask equipped with reflux condenser, under nitrogen atmosphere, was charged with 2-bromopyridin-4-amine (17) (5.0 g, 28.9 mmol, 1.0 equiv), NaOAc.3H2O (5.90 g, 43.3 mmol, 1.5 equiv), ICl (5.16 g, 31.8 mmol, 1.1 equiv) and glacial acetic acid (19.3 mL) and stirred, at 70 oC, for 16 hours. The reaction mixture was cooled and transferred to a separating funnel and was carefully quenched with portionwise addition of solid powdered NaHCO3 (31.1 g), water (50 mL) and EtOAc (50 mL). The layers were then separated and the aqueous layer was extracted with EtOAc (3 x 50 mL). The combined organic layers were dried over MgSO4 and the volatiles were evaporated. The residue was purified by portionwise flash column chromatography over silica using n-hexane/ EtOAc (99:1 to 50:50) mixtures as eluent to give 2-bromo-5-iodopyridin-4-amine 18 as a light brown solid (3.70 g, 43%). A sample of which had 1H NMR spectral data and low resolution GC/MS (EI) mass spectral data identical to those in the literature

The synthetic route of 7598-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Balfour, Michael N.; Zukerman-Schpector, Julio; Rodriguez, Maria Jose Davila; Reis, Joel Savi; Esteves, Carlos Henrique A.; Stefani, Helio A.; Synthetic Communications; vol. 49; 3; (2019); p. 351 – 358;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1003-68-5, 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 1003-68-5, name is 5-Methylpyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 21 1-(2’Imidazolyl)-5-methyl-2-(1H)-pyridone Following essentially the general procedure outlined in Example 1, the reaction of 5-methyl-2-(1H)-pyridone with 2-chloroimidazole affords 1-(2′-imidazolyl)-5-methyl-2-(1H)-pyridone in 82% yield.

According to the analysis of related databases, 1003-68-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Affiliated Medical Research, Inc.; US3974281; (1976); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6271-78-9, 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 6271-78-9, name is 6-Chloropyridine-3-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 23 4-Oxo-2-propyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide From 4.6 g (0.0029 mol) of 6-chloro-3-pyridinecarboxamide (Aldrich Chemical Company) and 8.6 g (0.040 mol) of 2-amino-5-propyl-3-thiophenecarboxylic acid, ethyl ester, following the procedure of Example 22 there is obtained 2.6 g of 4-oxo-2-propyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide; mp 260-264 C. after recrystallization from pyridine.

According to the analysis of related databases, 6271-78-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Warner-Lambert Company; US4230707; (1980); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 633328-33-3, 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. 633328-33-3, name is 3-Bromo-1H-pyrazolo[4,3-b]pyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 3-bromo-1 H-pyrazolo[4,3-b]pyridine (200 mg, 1.01 mmol) in DMF (5 mL), 3,4-dihydro- 2H-pyran (127 mg, 1.51 mmol) and a catalytic amount of pTSA were added at rt. The resulting solution was stirred at 85 C for 24h. The reaction was cooled to rt, diluted with water and extracted with EtOAc. The organic layer was washed with water and brine solution, dried over anhydrous Na2SC>4, and filtered. The resulting solution was concentrated under reduced pressure to get crude a residue that was purified by flash columnchromatography to afford the title compound (150 mg, 52.8 %).LC-MS (method 1): Rt = 2.24 min; m/z = 282.30 (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,633328-33-3, its application will become more common.

Reference:
Patent; ORYZON GENOMICS, S.A.; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; SALAS SOLANA, Jorge; (103 pag.)WO2019/110663; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84249-14-9, 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. 84249-14-9, name is 2-Amino-4-bromopyridine, molecular formula is C5H5BrN2, 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.

A solution of 4-bromopyridin-2-amine (5.00 g, 28.9 mmol) in dry THF (100 mL) was treated with LiHMDS (1 M, 57.8 mL) at -5 OC and the solution was stirred at -5 OC for 10 minutes. Then (Boc)2O (6.31 g, 28.9 mmol) was added and the mixture was allowed to warm to rt and stirred for 1 h. On completion, the reaction mixture was quenched with saturated ammonium chloride solution (20 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine (20 mL), dried with Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to give the title compound (6.50 g, 82% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta=8.92 (s, 1H), 8.27 (d, J=0.8 Hz, 1H), 8.13 (d, J=5.2 Hz, 1H), 7.12 (dd, J=1.6, 5.2 Hz, 1H), 1.55 (s, 9H).

According to the analysis of related databases, 84249-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem