Month: April 2022

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. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid, the common compound, a new synthetic route is introduced below. COA of Formula: C6H3ClN2O4

To a suspension of 49.0 g (0.27 mol) 6-hydroxy-5-nitro-nicouenic acid in thionyl chloride (240 mi) are added 2 ml of DMF. This mixture is stirred at 60°C until the evolution of gaz has ended. Then it is stirred at 80°C for further 18 h. Residual thionyl chloride is removed under vacuo and the resulting residue is coevaporated three times with toluene. Subsequently this reaction mixture is dissolved in dichloromethane (100 mi) and cooled to 0°C before methanol (55.5 ml) is dropwise added. The precipitated solid is filtered off and dried under vacuo at 50°C to give 27.6 g (13.7 mmol/52 percent) of the title compound as a light yellow solid with a melting point of 78°C (dichloromethane/methanol).

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALTANA PHARMA AG; WO2005/77947; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 165547-79-5, 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 165547-79-5, name is 4-Chloro-3-nitro-2(1H)-pyridinone. This compound has unique chemical properties. The synthetic route is as follows.

Methyl iodide (2.06 ml_, 32.99 mmol) was added to a suspension of 4-chloro-2-hydroxy-3- nitropyridine (prepared as descibed in Bioorg. Med. Chem. Lett, 2003, 13, 125) (2.87 g, 16.49 mmol) and siver carbonate (4.55 g, 16.49 mmol) in toluene (100 ml.) and the mixture heated at 85 C for 3.5 h. On cooling to ambient temperature the mixture was filtered through dicalite and washed with toluene. The combined filtrate and washings were concentrated in vacuo and the crude product purified by chromatography on silica gel with EtOAc:heptane (1 :9, v/v) as eluent. The pure product was collected as a white solid (1.99 g, 64 %). Data for 4-chloro-2-hydroxy-3-nitropyridine: MS (ESI) m/z: 189/191 ([M+H]+).

According to the analysis of related databases, 165547-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; WO2007/39563; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75358-90-6, 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 75358-90-6, name is Ethyl 2-cyanonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

[0142] To a solution of ethyl 2-cyano-3-pyridinecarboxylate (2.5 g) and cone. HCl (5 mL) in 150 mL ethanol was added 10% Pd/C (wet, 250 mg) and the reaction mixture was hydrogenated using a hydrogen balloon and stirred for 12 h. The reaction was filtered through celite and ethanol was evaporated to give ethyl 2-(aminomethyl)-3- pyridinecarboxylate HCl as a white solid which was used in the next step without further purification.

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 75358-90-6, Ethyl 2-cyanonicotinate.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102142; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 213193-32-9, Adding some certain compound to certain chemical reactions, such as: 213193-32-9, name is 5-Acetyl-2-methoxypyridine,molecular formula is C8H9NO2, 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 213193-32-9.

2- methoxy-5-acetyl pyridine (1.51 g, 10 mmol) was treated with 6N HCl at 100C for 5 hours. The reaction mixture was neutralized with sodium hydroxide to pH 7 and then extracted several times with DCM. Organic layer was dried over sodium sulfate, evaporated and the residue was crystallized from ethyl acetate to give 5-acetyl-2(lH)- pyridone as a white solid, 1.06 g (78%). This compound (685.7 mg, 5 mmol) was reacted with iodobenzene (0.84 ml, 7.5 mmol) in the presence of CuI (95 mg, 0.5 mmol) and K2CO3 (691 mg, 5 mmol) in DMF (5 ml) at 1350C overnight. The reaction mixture was diluted with 10% ammonia (15 ml) and extracted with ethyl acetate. The organic extract was washed with saturated sodium chloride, dried over magnesium sulfate and evaporated. Column chromatography (10% ethyl acetate-DCM) afforded 407 mg (38%) of the target compound as a white solid. The 1H NMR spectra was consistent with the structure of Compound 16.

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. 213193-32-9, 5-Acetyl-2-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INTERMUNE, INC.; WO2006/122154; (2006); 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.22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine, molecular formula is C6H5ClN2O2, molecular weight is 172.57, as common compound, the synthetic route is as follows.name: 6-Chloro-2-methyl-3-nitropyridine

Preparation 6 2-Methoxy-5-Nitro-6-Methylpyridine Sodium metal (8.68 g, 378 mmol) was added to methanol (350 mL) pre-cooled to 0 C. After the sodium completely dissolved, 2-chloro-5-nitro-6-methylpyridine (40.78 g, 236 mmol) was slowly added as a solid. The reaction mixture was heated at reflux temperature overnight, then poured into ice-water. The product was filtered and dried in vacuo overnight to give 29.39 grams of the title compound. (73%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22280-60-0, 6-Chloro-2-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; US6358972; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 82523-07-7, Adding some certain compound to certain chemical reactions, such as: 82523-07-7, name is Methyl 3H-imidazo[4,5-c]pyridine-6-carboxylate,molecular formula is C8H7N3O2, 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 82523-07-7.

Cooling in the ice bath,5g (28.22mmol) of 3H-imidazo[4,5-c]pyridine-6-carboxylate40mL NaOH aqueous solution (2M) dissolved,After 4 h of reaction, the reaction mixture was adjusted to pH 7 with dilute hydrochloric acid (2M).Allow to stand and allow the solid to be analyzed. Filter, filter and wash with distilled water, dry,Yield 1.757 g (38%) of the title compound.It is a pale yellow solid.

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. 82523-07-7, Methyl 3H-imidazo[4,5-c]pyridine-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Capital University of Medical Sciences; Zhao Ming; Peng Shiqi; Wang Yuji; Wu Jianhui; Gui Lin; Wang Yongjian; (13 pag.)CN108976225; (2018); A;,
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. 33252-28-7, name is 6-Chloronicotinonitrile, the common compound, a new synthetic route is introduced below. Formula: C6H3ClN2

A 185 ml stirred autoclave was charged under argon with PdC12(dppp) (213 mg, 0.36 1 mmol), 6- chloro-nicotinonitrile (10 g, 72.2 mmol), dioxane (50 ml), deionized water (50 ml) and sodium, bicarbonate (15.2 g, 0.18 mol, 2.5 molar equivalents). The reaction vessel was closed, purged three times with carbon monoxide (15 bar) and finally charged with carbon monoxide to 60 bar. The mixture was stirred vigorously at 60C under constant pressure for 22 h; after this time no more carbon monoxide absorption was observed. The reaction mixture was transferred to a5 round-bottomed flask with aid of water and, after having removed the organic volatilecomponents on a rotary evaporator, the reaction mixture was worked-up as reported in Example1. Crystallization afforded 5-cyano-pyridine-2-carboxylic acid (9.55 g) as a white solid with 99.6a% purity by HPLC.Example 5a-h5-Cyano-pyridine-2-carboxylic acid A series of reaction conditions was tested using the same procedure described in Example 4. The results are included in the following table.Ex.PbarTCBase ImolarequivalentsSolvent Ivol/volratio2-Cl,5-CN-Py[a%]3-CN-Py-2-C0211[a % I3-CN-Py[a%]Isol.Yield(%)5a6060Na2CO31.25Water 1Dioxane 10.293.51.6895b6060NaOAc2.5Water 1Acetone 13.683.57.9n.d.5c4060Et3N2.5Water 1 t-BuOH 10.795.91.0895d1560Et3N2.5Water 1t-BuOH 4<0.195.41.992Se70100Et3N2.2Water 1THF40.453.825n.d.Sf3580Et3N2.5Water 1 CH3CN 4<0.193.54.9n.d.Sg3580Et3N2.5Water 1CH3CN 4MeOH 1<0.191.51.5n.d.5h4050Et3N2.5Water 1t-BuOH 110.586.60.5n.d.Example no. Sc: reaction time S h; example no. Sd and Sh: reaction time 16 h; example no. Sf:reaction time 12 h.Examples no. Se and Sf: S g of 2-Cl,S-CN-Py, S/C 330.Example no. Sg: crude mixture contains 3.7 a% of the methyl ester 3-CN-Py-2-CO2Me. a% S values are obtained by HPLC analysis. The synthetic route of 33252-28-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FETTES, Alec; MARTY, Hans-Peter; SCALONE, Michelangelo; WO2014/173917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59942-87-9, Pyrazolo[1,5-a]pyridin-2(1H)-one, 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, Safety of Pyrazolo[1,5-a]pyridin-2(1H)-one, blongs to pyridine-derivatives compound. Safety of Pyrazolo[1,5-a]pyridin-2(1H)-one

To a solution of 4a (3.10 g, 23.1 mmol) in THF (17 mL) and DMF (17mL) was added NaH (1.0 g, 25.4 mmol, 60% dispersion in oil) and Tf2NPh (9.90 g, 27.7 mmol) at 0 C. The mixture was stirred for 1 h, then it was added to ice-water and extracted with EtOAc. The organiclayer was washed with brine and dried (Na2SO4). The mixture was concentrated in vacuo. The crude material was purified by flash column chromatography (silica gel, hexane-EtOAc, 10:1) to give 3a as acolorless solid; yield: 6.10 g, 99%); mp 37-38 C.

The synthetic route of 59942-87-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Umei, Kentaro; Nishigaya, Yosuke; Kamiya, Megumi; Kohno, Yasushi; Seto, Shigeki; Synthesis; vol. 47; 20; (2015); p. 3221 – 3230;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 182275-70-3, Adding some certain compound to certain chemical reactions, such as: 182275-70-3, name is 2-Iodo-6-methoxypyridine,molecular formula is C6H6INO, 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 182275-70-3.

(-)-P7C3-S243: (S)-N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyaniline: (S)-9-(3- amino-2-fluoropropyl)-3,6-dibromo-9H-carbazole (72.2 mg, 0.18 mmol), 2-iodo-6-methoxypyridine 45.4 mg, 0.19 mmcl), copper iodide (2.9 mg, 0.015 mmcl) and cesium carbonate (119.4 mg, 0.36 mmcl) were added to an oven dried vial, which was nitrogen purged for 10 minutes. DMSO (0.36and 2,2,6,6-tetramethyl-3,5-heptanedione (4 il, 0.019 mmcl) were then added. The reaction was heated at 40 C for three hours. The cooled mixture was diluted with EtOAc and washed thrice witha solution of 9:1 saturated NH4CI: NH4OH and then thrice with water and then brine. The organic layer was dried over Na2SO4, filtered and concentrated. The well dried solid was dissolved in methylene chloride and passed through a short silica plug, which removed the small amount of unreacted amine. The filtrate was condensed to give white solid, which was purified by automated flash chromatography system in 50-80 % methylene chloride/hexanes. Isolated yield = 61%, ee =96%. Recrystallization to enhance ee was carried out by heating a solution of 15.8 mg of purified product in 1.0 ml of isopropanol. Overall Yield = 59 %, ee = 98.5 %1H NMR (CDCI3, 400 MHz) :5 8.16 (d, J = 1.9 Hz, 2H), 7.56 (d, J = 1.9 Hz, 2H), 7.35 – (t, J = 7.8 Hz, 1H),7.30 (d, J = 8.7 Hz, 1H), 6.04 (dd, J = 32.7, 8.0 Hz, 2H), 5.29 -5.02 (dm, 1H), 4.65 -4.46 (m, 3H), 3.87- 3.74 (m, 1H), 3.70 (s,3H), 3.66 – 3.49 (m, 1H). ESI m/z: 506.7 ([Mi-1], C22H19Br2FN2O requires504.98

According to the analysis of related databases, 182275-70-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; UNIVERSITY OF IOWA RESEARCH FOUNDATION; MCKNIGHT, Steven L.; READY, Joseph M.; PIEPER, Andrew A.; WO2015/70234; (2015); A3;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65515-39-1 , The common heterocyclic compound, 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, 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.

(a) 2-methoxy-6-methyl-4-(pent-4-en- -yl)nicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (2.5 g, 15.41 mmol) in THF (80 mL) was added LHMDS (1 M in THF, 16.18 mL, 16.18 mmol) at 0 C dropwise via dropping funnel over 10 min, and the reaction mixture turned an orange color. The mixture was stirred at 0 C for 50 min, then 4-bromobut-l-ene (1.878 mL, 18.50 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to 10 C for 2.5 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (40 mL) and the layers were separated and the aqueous layer was extracted with EtOAc (3x). The combined organics were concentrated and the residue adsorbed onto silica and purified by flash chromatography (CombiFlash, 0-5% EtOAc in hexane, 80 g column) to afford 2-methoxy-6-methyl-4-(pent-4-en-l-yl)nicotinonitrile (1.3 g, 6.01 mmol, 39.0% yield) as a colorless oil. LC-MS(ES) m/z = 217.0 [M+H]+.

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem