Category: pyridine-derivatives

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 98-98-6, name is Picolinic acid. This compound has unique chemical properties. The synthetic route is as follows. 98-98-6

[00091] 4-Chloropicolinic acid methyl ester (CYD-1-1). A mixture of picolinic acid (10.0 g, 81.0 mmol, 1 equiv.) and sodium bromide (16.7 g, 162.0 mmol, 2 equiv.) in thionyl chloride (41 mL) was refluxed for 5 h at 80C. After that, the solvent was removed under the vacuum at 85C to afford the brown residue. 80 mL of anhydrous methanol was slowly added into the residue and the mixture was stirred at room temperature for half an hour. The solvent was evaporated, and the residue was taken up in the saturated sodium bicarbonate and extracted with ethyl acetate (three times). The organic layers were combined, washed with saturated brine, dried over anhydrous Na2S04 and evaporated. The residue was purified by silica gel column; eluting with 33% EtOAc in hexane afforded 4-chloropicolinic acid methyl ester (CYD-1-1) (8.0 g, 64%) as a brown solid; silica gel TLC Rf = 0.15 (1 :3 EtOAc/hexane); mp 55-56C; 1H NMR (600 MHz, CDC13) delta 8.67 (d, 1H, J = 4.8 Hz), 8.16 (d, 1H, J = 1.8 Hz), 7.51 (m, 1H), 4.04 (s, 3H).

Statistics shows that 98-98-6 is playing an increasingly important role. we look forward to future research findings about Picolinic acid.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHOU, Jia; DING, Chunyong; CUNNINGHAM, Kathryn, A.; WO2013/86266; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5223-06-3, Adding some certain compound to certain chemical reactions, such as: 5223-06-3, name is 2-(5-Ethylpyridin-2-yl)ethanol,molecular formula is C9H13NO, 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 5223-06-3.

General procedure: To a solution of A1B1 (1.0mmol) and triphenylphosphine (1.5mmol) in anhydrous tetrahydrofuran (3mL), added C1 or C2 (2.0mmol) and dropwise added diethyl azodicarboxylate (DEAD, 1.5mmol) in anhydrous and anoxybiotic conditions. The reaction mixture was stirred at-2C for 30min, and then stirred at room temperature for 24h. After completion of reaction was monitored through TLC, the reaction mixture was filtered and washed with ether and saturated salt water to get products because there would be a solid precipitate.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5223-06-3.

Reference:
Article; Wang, Fang; Sun, Jun-Rong; Huang, Mei-Yan; Wang, Hui-Ying; Sun, Ping-Hua; Lin, Jing; Chen, Wei-Min; European Journal of Medicinal Chemistry; vol. 72; (2014); p. 35 – 45;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

624-28-2, 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. 624-28-2, name is 2,5-Dibromopyridine, the common compound, a new synthetic route is introduced below.

A solution of 2,5-dibromopyridine (1.5 g, 6.3 mmol), L-Proline (0.08 g, 1.3 mmol), pyrrolidine (0.9 g, 0.0125 mol), AcOK (3.2 g, 33 mmol) and Cu I (0.3 g, 1.3 mmol) in DMF (40 mL) was stirred under N2 and at 850C for 12 h. The solution was filtered to remove the catalyst. The residue was diluted with H2O and was extracted with EA. The organic layer was washed with brine, dried over Na2SO4 and filtered. The filtrate was evaporated to give the target product (0.9 g, 63%). MS (m/z) (Mf+H): 243, 245.

Statistics shows that 624-28-2 is playing an increasingly important role. we look forward to future research findings about 2,5-Dibromopyridine.

Reference:
Patent; PROGENICS PHARMACEUTICALS, INC.; WO2009/155527; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1990-90-5 , The common heterocyclic compound, 1990-90-5, name is 3-Methylpyridin-4-amine, molecular formula is C6H8N2, 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 2-(5-Chloro-2-fluoro-phenyl)-4-iodo-6,6-dimethyl-6,7-dihydro-5H- cyclopentapyrimidine (100 mg, 0.25 mmol), 3-Methyl-pyridin-4-ylamine (30 mg,0.27 mmol), Pd(OAc)2 (3 mg, 12.42 mumol) and itoc-BINAP (12 mg, 18.63 mumol) in dry dioxane (3 mL) was added Cs2CO3 (121 mg, 0.37 mmol). The mixture was heated for 48 h at 85C, cooled and evaporated. HPLC purification gave, after lyophilization, the desired product of formula (60) as the TFA salt, which was a white solid (6.4 mg)

The synthetic route of 1990-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2006/35061; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

620-08-6, Adding a certain compound to certain chemical reactions, such as: 620-08-6, 4-Methoxypyridine, 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, 620-08-6, blongs to pyridine-derivatives compound.

General procedure: According to the raw material ratio of Table 1, a copper additive, elemental iodine, alkali, aryl ethyl ketone (IV), pyridine derivative (III), electron-deficient olefin (II) and organic solvent 1 ml were added to a 10 ml sealed tube, and the mixture was stirred and mixed uniformly. In Table 1, A is cuprous chloride; B is cuprous iodide; C is sodium carbonate; D is potassium carbonate; E is N-methylpyrrolidone; and F is N,N-dimethylformamide. After completion of the reaction according to the reaction conditions of Table 2, the reaction solution was transferred to a separatory funnel containing 10% sodium thiosulfate solution, and the aqueous phase was extracted three times with ethyl acetate. The mixture was dried, filtered, and the filtrate was added to a silica gel mixture, and the solvent was evaporated to dryness, and purified by silica gel column chromatography (eluent ethyl acetate and petroleum ether mixture) to obtain the corresponding C-3 arylformylpyridazine compound (I)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,620-08-6, its application will become more common.

Reference:
Patent; Guizhou Chinese Academy Of Sciences Natural Result Chemical Emphasis Experiment Shi (Guizhou Medical University Natural Result Chemical Emphasis Experiment Shi); Yang Yuzhu; Fang Youlai; Liu Xiaolan; He Lisheng; (14 pag.)CN110156776; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1122-62-9 , The common heterocyclic compound, 1122-62-9, name is 1-(Pyridin-2-yl)ethanone, molecular formula is C7H7NO, 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-Bromoacetyl)pyridin-1-ium bromide (A): To a stuffed solution of 1-(pyridin-2- yl)ethan-1-one (2.0 g, 16.6 mmol) in Cd4 (60 ml), bromine (2.7 g, 16.60 mmol) was added dropwise. After complete addition the final reaction mixture was refluxed for 1 h. The precipitate was collected by filtration and washed 2-3 times with diethylether and dried to obtain compound A as a beige solid (2.94 g, 93%).

The synthetic route of 1122-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VYOME BIOSCIENCES PVT. LTD.; SENGUPTA, Shiladitya; GHOSH, Shamik; GHOSH, Sumana; SINHA, Mau; SADHASIVAM, Suresh; BHATTACHARYYA, Anamika; MAVUDURU, Siva Ganesh; TANDON, Nupur; KUMAR, Deepak; (149 pag.)WO2017/17631; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, 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, 571188-59-5, blongs to pyridine-derivatives compound. 571188-59-5

To 2-chloro-4-cyclopentylamino-pyrimidine-5-carboxylic acid ethyl ester (-2 mmol) in butanol (1.7 mL) was added 4- (6-AMINO-PYRIDIN-3-YL)-PIPERAZINE-L- carboxylic acid tert-butyl ester (0.7g). This mixture was heated to 100 C. After 2 hrs, xylenes (2 mL) was added and the temperature was raised to 140 C. Heating was continued overnight. The mixture then was allowed to cool and diluted with ethyl acetate. The organic solution was washed twice with 1 M NAOH (aq), saturated ammonium chloride solution, then brine. After drying over magnesium sulfate, the solvents were evaporated and the residue was purified by chromatography on silica gel eluting with 35-45% ethyl acetate in hexanes to give 4- [6- (5-BROMO-4-CYCLOPENTYLAMINO-PYRIMIDIN-2-YLAMINO)-PYRIDIN-3-YL]- PIPERAZINE-1-CARBOXYLIC acid tert-butyl ester. MS (APCI) M++1 Calc’d, 519.18 ; Found, 520.0.

With the rapid development of chemical substances, we look forward to future research findings about 571188-59-5.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/65378; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

152460-10-1, 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. 152460-10-1, name is N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine, the common compound, a new synthetic route is introduced below.

General procedure: The imatinib analogs 3,4-R1,R2-N-(4-methyl-3(4-(pyridine-3-yl)pyrimidin-2-ylamino)phenyl)benzamide (R1 = R2 = H (1); R1 = H, R2 = SCH3 (2); R1 = NO2, R2 = H (3); R1 = NH2, R2 = H (4); R1 = R2 = NO (5)) and N-(4-methyl-3-(4-(pyridin-3-yl) pyrimidin-2-ylamino)phenyl)picolinamide (6) was synthesized following a modified procedure described in the literature16 as shown in Scheme 1. Briefly, an excess amount of benzoyl chloride compound 1b, 2b, 3b, 4b, 5b or 6b was added to a suspension of 6-methyl-N-(4-(pyridin-3-yl)pyrimidin-2-yl) benzene-1,3-diamine (0.5 g, 2 mmol) in dichloromethane (10 mL) containing TEA (0.58 mL, 4 mmol), and the mixture was reacted at 0 C for 4 h, and TLC of reaction mass indicated the absence of starting compound. The solution was then filtered and washed with dichloromethane, the excess dichloromethane was removed in vacuo, and the residue was purified by recrystallization from ethanol.

Statistics shows that 152460-10-1 is playing an increasingly important role. we look forward to future research findings about N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine.

Reference:
Article; Lue, Shuang; Luo, Qun; Hao, Xiang; Li, Xianchan; Ji, Liyun; Zheng, Wei; Wang, Fuyi; Bioorganic and Medicinal Chemistry Letters; vol. 21; 23; (2011); p. 6964 – 6968;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

145100-50-1, 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. 145100-50-1, name is 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methanesulfonamide, molecular formula is C7H4F6N2O4S2, 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 sodium bis(trimethylsilyl)amide (1.12 g, 6.13 mmol) in 16.2 mL of THF was cooled to -78C and a solution of ethyl 4-(2,2-dimethyl-4-oxo-thiochroman-6- ylethynyl)-benzoate (1.86 g, 5.10 mmol) in 15.0 mL was added slowly. After 30 minutes a solution of 2-[N,N-bis(trifluoromethanesulfonyl)amino]-5-pyridine (2.40 g, 6.13 mmol) in 10 mL of THF was added. After 5 minutes the solution was warmed to room temperature and stirred overnight. The reaction was quenched by the addition of saturated aqueous NH4CI and extracted with EtOAc. The combined organic layers were washed with 5% aqueous NaOH and H2O before being dried (MgSO4) and concentrated under reduced pressure. Ethyl 4-((2,2-dimethyl-4-trifluoromethanesulfonyloxy-(2H)- thiochromen-6-y-l)ethynyl)-benzoate, 1.53 g (61%), was isolated by column chromatography (2% EtOAc/hexanes) as a yellow solid. 1H NMR (300 MHz, CDCl3) delta: 8.03 (2H, d, J=8.4 Hz), 7.61 (IH5 d, J=I.8 Hz), 7.59 (2H, d, J=8.4 Hz), 7.41 (IH, dd, J=1.8, 8.1 Hz), 7.29 (IH, d, J=8.1 Hz), 5.91 (IH, s), 4.39 (2H, q, J=7.1 Hz), 1.53 (6H, s), 1.41 (3H, t, J=7. I Hz).

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. 145100-50-1, 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methanesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; WO2007/136653; (2007); A2;,
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.628-13-7, name is Pyridinehydrochloride, molecular formula is C5H6ClN, molecular weight is 115.56, as common compound, the synthetic route is as follows.628-13-7

2-Amino-4-chloro-5-cyanopyridine (200 mg, 1.30 mmol, Production example 215-3) was dissolved in ethoxyethanol (13.0 ml); 5-aminoindole-1-carboxylic acid phenylamide (408 mg, 1.62 mmol, Production example 201-2) and pyridine hydrochloride (315 mg, 2.73 mmol) were added thereto; and the reaction mixture was heated and stirred at 130 C for 4 hours. After cooling to room temperature, the reaction mixture was partitioned between a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate; the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane: ethyl acetate = 2: 3, ethyl acetate, ethyl acetate: methanol = 95: 5 in this order). The pale yellow oil obtained was solidified with diethyl ether; the crystals were suspended with diethyl ether, filtered off, washed with diethyl ether, and dried to yield the title compound (171 mg, 0.464 mmol, 35.7%) as colorless crystals.1H-NMR Spectrum (DMSO-d6) delta (ppm) : 5.77 (1H, s), 6.40 (2H, brs), 6.74 (1H, d, J=3.6 Hz), 7.13 (1H, t, J=7.6 Hz), 7.17 (1H, dd, J=2.4, 8.8 Hz), 7.38 (2H, t, J=7.6 Hz), 7.46 (1H, d, J=2.4 Hz), 7.64 (2H, d, J=7.6 Hz), 8.04 (1H, s), 8.05 (1H, d, J=3.6 Hz), 8.20 (1H, d, J=8.8 Hz), 8.35 (1H, s), 10.04 (1H, s).

Statistics shows that 628-13-7 is playing an increasingly important role. we look forward to future research findings about Pyridinehydrochloride.

Reference:
Patent; Eisai Co., Ltd.; EP1522540; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem