Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 1461602-59-4, 3-(Methylamino)isonicotinic 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Example 20. Synthesis of Compound 127 Methyl 3-(methylamino)pyridine-4-carboxylate To a stirred solution of 3-(methylamino)pyridine-4-carboxylic acid (11 g, 72.296 mmol, 1 equiv.) in MeOH (500 mL, 12349.455 mmol, 170.82 equiv.) was added SOCl2 (43.01 g, 361.478 mmol, 5 equiv.) dropwise at 0 C. The resulting mixture was stirred for 30 hours at 70 C. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The resulting mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (50 mL). The mixture basified to pH 8 with saturated NaHCO3 (aq.). The resulting mixture was extracted with EtOAc (2*20 mL). The combined organic layers were washed with brine (1*30 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure to afford methyl 3-(methylamino)pyridine-4-carboxylate (9 g, crude) as a yellow solid.

The synthetic route of 1461602-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goldfinch Bio, Inc.; Ledeboer, Mark W.; Daniels, Matthew H.; Yu, Maolin; Harmange, Jean-Christophe P.; US2020/102301; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, Adding some certain compound to certain chemical reactions, such as: 33252-28-7, name is 6-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 33252-28-7.

General procedure: To a 0.5 M solution of 2-chloro-5-cyanopyridine (10 mmol) in isopropyl alcohol hydrazine hydrate (50 mmol) was added in portions over 1 hour. The reaction mixture was heated at reflux for 24 hours, cooled down to ambient temperature and the resulting precipitate of 5-cyano-2-hydrazinopyridine was separated by filtration, washed with isopropyl alcohol and air-dried. Without further purification, it was dissolved in the respective aliphatic carboxylic acid (0.5M) and heated at reflux for 48 hours. Upon cooling to room temperature, the volatiles were removed in vacuo and the residue was triturated with 1M aqueous sodium bicarbonate. The precipitate thus formed was filtered off, washed with water and air dried. The resulting 1,2,4-triazolo[4,3-a]pyridine 9 was dissolved in 7M methanolic ammonia (0.25 M with respect to 9) and was hydrogenated over Raney Nickel catalyst (0.5 equiv.) at 100 atm and 60 C over 48 hours. Once it reached room temperature, the mixture was filtered through a short plug of silica gel and concentrated in vacuo. Chromatography on silica gel using 05% MeOH in CH2Cl2 afforded analytically pure compounds 8a-e.

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mishchuk, Alexander; Shtil, Natalia; Poberezhnyk, Mykola; Nazarenko, Konstiantyn; Savchenko, Timur; Tolmachev, Andrey; Krasavin, Mikhail; Tetrahedron Letters; vol. 57; 9; (2016); p. 1056 – 1059;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 83766-88-5, 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 83766-88-5 as follows.

A 5-mL reactionvial was equipped with a stir bar, a rubber septum, and an argon inlet needle.The vial was charged with t-butoxypyridine(3) (1.2 mmol) and dry PhCH3(1 mL), and was allowed to stir at 0 C. MeOTf (1.2 mmol) was added dropwise tothe reaction mixture over 5 min. Upon complete addition, the reaction wasallowed to stir for 1h. The alcohol (1 mmol) dissolved in dry PhCH3or dry DCM (1 mL) depending upon the solubility of the alcohol, was added over30 seconds to the reaction mixture. The ice bath was removed and the reactionmixture was allowed to stir at room temperature (~ 23 C) for 1.5h. When thereaction was complete by TLC, the mixture was diluted in Et2O or DCMdepending upon the solubility of the product. Et2O was preferredbecause the hydroxypyridine/pyridone byproduct (5) was less soluble in this solvent than DCM. The diluted reactionmixture was washed with water (10 mL), then brine (10 mL). The organic fractionwas dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to isolate the crude productmixture. The crude mixture was purified by flash chromatography to yield thepure t-butyl ether.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83766-88-5, its application will become more common.

Reference:
Article; Salvati, Anna E.; Hubley, Christian T.; Albiniak, Philip A.; Tetrahedron Letters; vol. 55; 51; (2014); p. 7133 – 7135;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211523-71-5 , The common heterocyclic compound, 1211523-71-5, name is 2-(2-Bromopyridin-3-yl)acetonitrile, molecular formula is C7H5BrN2, 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.

General procedure: General procedure for indole synthesis by Cu-catalyzed amidation reaction. A dried re-sealable vialwith a Teflon stir bar was charged with amide (3.0 equiv, 1.5 mmol), CuI (5 mol%, 0.025 mmol), K3PO4(2.0 equiv, 1.0 mmol). The vial was sealed with a rubber septum and evacuated and refilled with argonthree times through a syringe needle. Under an argon atmosphere, toluene (0.5 mL),trans-1,2-diaminocyclohexane (20 mol%, 0.1 mmol) and aryl halide (0.50 mmol) were each added viasyringe. The rubber septum was then removed and quickly replaced with a Teflon screw cap and thereaction mixture was stirred at 110 C for 24 h. The resulting suspension was allowed to reach roomtemperature and filtered through a pad of silica gel eluting with AcOEt (10 mL). The filtrate wasconcentrated and the residue was purified by flash chromatography to afford a pure product.

The synthetic route of 1211523-71-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abe, Masahiro; Denneval, Charline; Nozawa-Kumada, Kanako; Kondo, Yoshinori; Heterocycles; vol. 92; 5; (2016); p. 900 – 909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 75358-90-6, 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. 75358-90-6, name is Ethyl 2-cyanonicotinate. A new synthetic method of this compound is introduced below.

Et3N (10 ml) was added to a solution of ethyl 2-cyanonicotinate (1.9 g, 10.78 mmol) in 20 ml of pyridine. Hydrogen sulfide was passed through the reaction mixture at 5 C. for 20 minutes, then the mixture was stirred for 1 hour at room temperature. For work up the solution was purged with nitrogen for 30 minutes, evaporated to dryness, and the remaining solid dissolved in 200 ml of dichloromethane. The organic layer was washed successively with water and brine, dried, evaporated and treated with ethylacetate to give 2.15 g of a red oil which was reacted without further purification.ESI-MS [M+H]+: 211.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75358-90-6, Ethyl 2-cyanonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Kling, Andreas; Mack, Helmul; Junios, Kaija; Mceller, Achim; Hombarger, Wllirled; Hulchins, Charles W.; US2010/216844; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-46-4, 5-Chloro-3-methylpyridine-2-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: C7H6ClNO2, blongs to pyridine-derivatives compound. HPLC of Formula: C7H6ClNO2

To a solution of Intermediates 14A and 14B (0.218 g, 0.415 mmol) in dicholomethane (4 mL) were added 5-chloro-3-methylpicolinic acid (0.075 g, 0.435 mmol), triethylamine (0.115 mL, 0.829 mmol) and (O-(7-azabenzotriazol-1-yl)-N,N,N?,N?-tetramethyluronium hexafluorophosphate) (0.173 g, 0.456 mmol). The mixture was stirred at room temperature for 90 minutes and then concentrated. The crude product was purified by silica-gel column chromatography, eluting with 5% to 40% ethyl acetate in heptanes, to provide two diastereomeric intermediates. The major diastereomer was redissolved in DCM (1.0 mL), and trifluoroacetic acid (0.39 mL, 5.3 mmol) was added. The reaction was stirred at ambient temperature for 30 minutes, concentrated, and partitioned between saturated aqueous sodium bicarbonate and DCM. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to provide the title compound (48 mg, 24% yield). 1H NMR (400 MHz, DMSO-d6) delta 10.67 (s, 1H), 8.60 (d, J=1.86 Hz, 1H), 8.03 (d, J=1.66 Hz, 1H), 7.90 (d, J=8.41 Hz, 1H), 7.64 (br. s., 1H), 7.06-7.25 (m, 1H), 6.01 (br. s., 2H), 2.56 (s, 3H), 2.25-2.42 (m, 1H), 1.83 (br. s., 3H), 1.71 (t, J=7.19 Hz, 2H), 1.56 (d, J=10.37 Hz, 1H), 1.50 (s, 3H), 1.41 (br. s., 3H). LC/MS (ESI+) m/z=479.0 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 3222-50-2, name is 4-Methylnicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 3222-50-2

4-Methylnicotinic acid (2.50 g, 14.4 mmol), EDCI (4.14 mg, 21.6 mmol) and HOBt (2.92 mg, 21.6 mmol) were combined in DMF (1 ml) and CH2Cl2 (75 ml) to give a pale yellow solution. To this solution was added ammonium chloride (2.31 g, 43.2 mmol) followed by DIPEA (12.5 ml, 72.0 mmol) and the resulting mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo and diluted with saturated aqueous NaHCO3 (50 ml) and CH2Cl2 (50 ml). The solution was then basicified to pH -14 with ION NaOH. The phases were separated and the aqueous layer was extracted with CH2Cl2 (5 x 50 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified by flash column chromatography on silica gel (94:5:1, CH2Cl2/MeOH/NH4OH) to generate 4-methyl-nicotinamide as an off-white solid (0.95 g, 48%). 1H-NMR (CDCl3) delta 2.53 (s, 3H), 7.20 (d, IH, J= 4 Hz), 8.53 (d, IH, J= 4 Hz), 8.69 (s, IH).

With the rapid development of chemical substances, we look forward to future research findings about 3222-50-2.

Reference:
Patent; ANORMED INC.; WO2006/138350; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 917364-11-5 , The common heterocyclic compound, 917364-11-5, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H10N2O2, 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.

Step (c) N-((l s,4s)-4-(5-fluor o-2-(3-iodophenoxy)nicotinamido)cyclohexyl)-5,6,7,8- tetrahydroimidazo [ 1 ,2-a] pyridine-2-carboxamideTo a solution of 5,6,7, 8-tetrahydroimidazo[l,2-a]pyridine-2-carboxylic acid (0.183 g, 1.10 mmol) in dry DMF (10 niL) was added DIPEA (0.575 mL, 3.29 mmol) followed by HATU (0.418 g, 1.10 mmol). The mixture was allowed to stir for 10 min at RT. To this mixture was added the N-((ls,4s)-4-aminocyclohexyl)-5-fluoro-2-(3-iodophenoxy Nicotinamide (0.5 g, 1.10 mmol) and the mixture stirred overnight, poured onto water and the crude product collected by filtration, dried in vacuo to give the sub-title compound. Yield: 0.354 g 1H NMR (300 MHz, CDCl3) delta 8.36 (dd, J= 8.0, 3.0 Hz, IH), 8.06 (d, J= 3.1 Hz, IH), 7.86 (d, J= 7.3 Hz, IH), 7.64 (dt, J= 7.2, 1.3 Hz, IH), 7.55 (t, J= 1.8 Hz, IH), 7.40 (s, IH), 7.23 – 7.12 (m, 2H), 6.94 (d, J= 7.3 Hz, IH), 4.20 (s, IH), 4.08 (d, J= 3.5 Hz, IH), 3.98 (t, J= 8.6 Hz, 3H), 2.85 (q, J= 6.2 Hz, 2H), 2.05 – 1.73 (m, HH). [M+H]+ =604 (MultiMode+)

The synthetic route of 917364-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); 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.169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine, molecular formula is C7H6N2OS, molecular weight is 166.2, as common compound, the synthetic route is as follows.category: pyridine-derivatives

EXAMPLE 27 4-OXAZOLO[4,5-b]PYRIDIN-2-YL-1,4-DIAZA-BICYCLO[3.2.2]NONANE The title compound was prepared from 2-(methylthio)oxazolo[4,5-b]pyridine (J. Org. Chem. 1995, 60, 5721) by the procedure described in Example 9 in 98% yield: 1H NMR (CDCl3, 400 MHz) delta 8.14 (dd, 1H, J=5.0, 1.2 Hz), 7.34 (dd, 1H, J=7.5, 1.2 Hz), 6.81 (dd, 1H, J=7.8, 5.0 Hz), 4.50 (s, 1H), 3.90 (t, 2H, J=5.8 Hz), 3.13-3.05 (m, 4H), 2.98-2.91 (m, 2H), 2.13-2.05 (m, 2H), 1.79-1.71 (m, 2H); 13C NMR (CDCl3, 100 MHz) delta 163.1, 158.7, 144.7, 141.4, 115.4, 114.8, 57.1, 50.6, 46.4, 46.3, 44.4, 30.3, 26.9; MS (Cl) m/z 245.2 (M+1); HPLC retention time=1.38 min. The hydrochloride salt was prepared by diluting in ethyl acetate and adding a 2.5 N HCl solution in ethyl acetate: mp>300 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,169205-95-2, 2-(Methylthio)oxazolo[4,5-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; O’Neill, Brian Thomas; Coe, Jotham Wadsworth; O’Donnell, Christopher John; US2002/86871; (2002); 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. 94170-15-7, name is 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde, molecular formula is C7H7NO2, 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. COA of Formula: C7H7NO2

1- (1,1-dioxotetrahydro-2H-thian-4-yl) -6-((trans) -4-methylpyrrolidin-3-yl) -1,5-dihydro -4H-pyrazolo [3,4-d] pyrimidin-4-one trifluoroacetate (97mg, 0.21mmol, 1.0eq),1-methyl-2-oxo-1,2-dihydropyridine-4-carboxaldehyde (34.2 mg, 0.25 mmol, 1.2 eq)And acetic acid (25mg, 0.42mmol, 2.0eq) were dissolved in methanol (5mL), heated to 45 C for 2h,Cool down to 0 ,Add sodium cyanoborohydride (39.2 mg, 0.63 mmol, 3.0 eq) and stir at this temperature for 2 h.TLC monitoring showed no complete reaction,Additional 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxaldehyde (114.3mg, 0.83mmol, 4.0eq) was added and stirred at this temperature for 2h,Add cyanoborohydride (39.2mg, 0.63mmol, 3.0eq), and react at 45 C for 2h.TLC monitoring showed complete reaction,Concentrated under reduced pressure, added saturated aqueous sodium carbonate (10 mL) and saturated brine (10 mL), and extracted with dichloromethane (50 mL x 4). The organic phases were combined, dried, filtered, and concentrated.The crude product was purified by preparative thin layer chromatography (MeOH: DCM = 1: 20)The product was obtained as an off-white solid (59 mg, yield: 45.6%).

With the rapid development of chemical substances, we look forward to future research findings about 94170-15-7.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Peng Peng; Li Lin; (59 pag.)CN110357888; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem