Month: April 2022

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

Reference of 1149-24-2, 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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate. A new synthetic method of this compound is introduced below.

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1149-24-2, its application will become more common.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-45-5 ,Some common heterocyclic compound, 884494-45-5, molecular formula is C6H5FIN, 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 mixture of racemic 1-(1H-indazol-6-yl)spiro[2.2lpentane-1-carbonitrile (300 mg, 1.43 mmol) (Q.3), 2-fluoro-4-iodo-6-methylpyridine (510 mg, 2.15 mmol), trans-N ,N?-dimethyl- 1,2-cyclohexanediamine (61.2 mg, 0.430 mmol), copper(I) iodide (82 mg, 0.43 mmol), and cesium carbonate (934 mg, 2.87 mmol) in a 20 mL microwave vial, was added DMSO (2 mL). The vial was sealed, degassed and backfilled with nitrogen (3x) and stirred at 50C overnight. The mixture was diluted with water (5 mL), and extracted with DCM (3 x 5 mL). The organic extracts were combined, dried over MgSO4 and concentrated to dryness. The residue waspurified by silica gel column chromatography (gradient elution: 0-50% EtOAc)/hexanes).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-45-5, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CANDITO, David Annunziato; GRAHAM, Thomas, H.; ACTON, John; CHAU, Ryan Wing-Kun; CHEN, Joanna, L.; ELLIS, J. Michael; FULLER, Peter, H.; GULATI, Anmol; GUNAYDIN, Hakan; KATTAR, Solomon; KEYLOR, Mitchell Henry; LAPOINTE, Blair, T.; LIU, Ping; LIU, Weiguo; METHOT, Joey, L.; NEELAMKAVIL, Santhosh, F.; SIMOV, Vladimir; TONG, Ling; WOOD, Harold, B.; (154 pag.)WO2019/74809; (2019); 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

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

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. 1357947-08-0, name is 5-Bromo-3-iodo-1H-pyrazolo[3,4-c]pyridine, the common compound, a new synthetic route is introduced below. Safety of 5-Bromo-3-iodo-1H-pyrazolo[3,4-c]pyridine

To a microwave tube was added 5-bromo-3-iodo-lH-pyrazolo[3,4-c]pyridine (100 mg, 0.31 mmol), pyridin-3-ylboronic acid (343 mg, 2.79 mmol), Pd(dppf)Cl2 (24 mg, 0.03 mmol), sodium carbonate (131 mg, 1.24 mmol), 1 ,2-dimethoxyethane (2 mL), ethanol (0.5 mL) and water (0.5 mL). The tube was flushed with nitrogen for 2 minutes and heated in a Biotage microwave at 160 C for 1 hour. The solvent was distilled off and the crude product was purified via reverse phase HPLC eluting with 15%> CH3CN in aqueous 10 mmol NH4HC03 to afford 176 as a pale yellow solid (30 mg, 28%). 1H NMR (500 MHz, DMSO) 1H NMR (500 MHz, DMSO) delta 14.1 (s, 1H), 9.44 (s, 1H), 9.37 (s, 3H), 9.26 (s, 1H), 8.71 (s, 1H), 8.67 – 8.66 (m, 1H), 8.60 – 8.59 (m, 2H), 8.56 -8.54 (m, 1H), 7.60 – 7.58 (m, 1H), 7.52 – 7.51 (m, 1H). ESI MS m/z = 274 (M+l)

The synthetic route of 1357947-08-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; LEE, Wendy; TSUI, Vickie Hsiao-Wei; WANG, Xiaojing; WEN, Zhaoyang; WO2013/24002; (2013); 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. 38222-83-2, name is 2,6-Di-Tert-butyl-4-methylpyridine. A new synthetic method of this compound is introduced below., Computed Properties of C14H23N

4-Bromomethyl-2,6-di-t-butylpyridine (Compound A) To a mixture of 2,6-di-t-butyl-4-methylpyridine (Aldrich, 2.0 g, 9.73 mmol) in 25 ml of dry CCl4 was added benzoyl peroxide (24 mg, 0.097 mmol) and NBS (1.9 g, 10.7 mmol). The reaction mixture was refluxed for 16 hours. After it cooled to room temperature, the solvent was removed in vacuo and the residue was purified by column chromatography (silica gel, hexane) to give an oil (1.957 g) which contained 82% of the desired product and 18% of the starting material. 1 H NMR delta 7.09 (s, 2H), 4.39 (s, 2H), 1.35 (s, 18H).

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, 38222-83-2, 2,6-Di-Tert-butyl-4-methylpyridine.

Reference:
Patent; Allergan; US5663357; (1997); A;,
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

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

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