Pyridine-derivatives

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1072438-56-2, name is Methyl 6-(aminomethyl)nicotinate hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Methyl 6-(aminomethyl)nicotinate hydrochloride

[0112j To a solution of methyl 6-(aminomethyl)nicotinate hydrochloride (0.4 g, 1.67 mmol) in dichloromethane (20 mL) was added triethylamine (1.2 mL, 8.37 mmol)) followed by 4- fluoro-3-chlorobenzenesulfonyl chloride (0.24 ml, 1.67 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. The crude was purified by silica gel column chromatography, using 40% ethyl acetate in hexane to afford the title compound methyl 6-((3 -chloro-4-fluorophenylsulfonamido)methyl)nicotinate (0.22 g, 37%yield) as a brownish solid. Calculated M+H: 359.02; Found M+H: 359.1.

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, 1072438-56-2, Methyl 6-(aminomethyl)nicotinate hydrochloride.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); 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.98197-88-7, name is 2-(Hydroxymethyl)-4-nitropyridine, molecular formula is C6H6N2O3, molecular weight is 154.12, as common compound, the synthetic route is as follows.SDS of cas: 98197-88-7

A 200-mL round-bottomed flask was charged with isopropanol (50 mL) and NaH (2.12 g, 53 57 mmol) and stirred at 0 C under inert atmosphere for 1 h. After, (4-nitropyridin-2- yl)methanol (1.0 g, 6.5 mmol) was added to the stirring reaction mixture. The resulting reaction mixture was refluxed for 20 h. After this period, the reaction mixture was cooled with an ice bath, quenched with saturated aqueous NHUCI and concentrated in vacuo. The resulting reside was extracted with EtOAc (3 >< 75 mL). The combined organic layers were dried over anhydrous NaaSC filtered, and concentrated in vacuo. The crude material purified by flash chromatography (60 to 100% EtOAc in hexanes) on silica gel (55 mL) to afford (4~isopropoxypyridin-2-yl)methano (242 mg, 22% yield) as a brown oil. At the same time, in my other blogs, there are other synthetic methods of this type of compound,98197-88-7, 2-(Hydroxymethyl)-4-nitropyridine, and friends who are interested can also refer to it. Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; KOIDE, Kazunori; BEIN, Kiflai; BRESSIN, Robert, Kruger; BURROWS, James, Proviano; GAMBINO, Adriana; LEIKAUF, George, D.; PHAM, Dianne; (80 pag.)WO2020/27905; (2020); A2;,
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Pyridine | C5H5N – PubChem

Synthetic Route of 13269-19-7, 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 13269-19-7 as follows.

In a round bottom-flask fitted with a calcium chloride drying tube, acetic anhydride (756 muL, 8 mmol) and formic acid (302 muL, 8 mmol) are stirred at 55 C for 2 h. The mixture is cooled to room temperature before addition of 2-nitropyridin-3-amine (556 mg, 4 mmol) in diethyl ether (10 mL), and stirred overnight at room temperature. The crude mixture is filtered through a short pad of silica gel to afford N-(2-nitropyridin-3-yl)formamide as an orange solid (623 mg, 93%). 1H NMR (CDCl3, 200 MHz) delta (ppm) 10.10 (brs, 1H), 9.30 (d, J = 8.5 Hz, 1H), 8.64 (s, 1H), 8.38 (dd, J1 = 4.3 Hz, J2 = 1.4 Hz, 1H), 7.71 (dd, J1 = 8.5 Hz, J2 = 4.3 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13269-19-7, its application will become more common.

Reference:
Article; Bejot, Romain; Carroll, Laurence; Bhakoo, Kishore; Declerck, Jerome; Gouverneur, Veronique; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 324 – 329;,
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Pyridine | C5H5N – PubChem

Application of 123853-39-4, 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.123853-39-4, name is 4-(2,3-Dichlorophenyl)-5-(methoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid, molecular formula is C16H15Cl2NO4, molecular weight is 356.2, as common compound, the synthetic route is as follows.

Example-5: Preparation of Clevidipine:100 gm of 1 ,4-dihydro-2,6-dimethyl-4-(2′,3′-dichorophenyl)-5-methoxycarbonyl-3- pyridinecarboxylic acid and 35.4 gm of Sodium bicarbonate is stirred in DMF under nitrogen atmosphere. 49.9 gm of Chloromethyl butyrate was added and reaction mixture was heated at about 80C for 4 hrs. The solvent was distilled out and residue was treated with methylene chloride. The obtained reaction mass was washed with water and the methylene chloride layer was dried over sodium sulphate. Methylene chloride was distilled out under vacuum. Diisopropyl ether (800 ml) was added to the residual mass and stirred at 25-30C for one hour. The reaction mass was filtered, the wet cake was washed with diisopropyl ether to give crude clevidipine (Wt. = 97.5 gms HPLC Purity > 99%).

The chemical industry reduces the impact on the environment during synthesis 123853-39-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CADILA PHARMACEUTICALS LIMITED; KHAMAR, Bakulesh Mafatlal; SHARMA, Arun Omprakash; PARIKH, Sanjay Natvarlal; BHATT, Achyut Pravinbhai; PANSURIYA, Akshay Madhubhai; JADEJA, Krunal Aniruddhbhai; BAPAT, Uday Rajaram; MODI, Indravadan Ambalal; WO2012/69989; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 121643-44-5, 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. 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, 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.

Preparation Example 36 2-Methoxy-3-(trifluoromethyl)pyridine (8 g), 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (17 g), and trifluoroacetic acid (32 mL) were mixed, followed by stirring at room temperature for 22 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added diisopropyl ether. The precipitated solid was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine (9.4 g) as an oil.

According to the analysis of related databases, 121643-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; TAKAHASHI, Taisuke; KOIKE, Takanori; NEGORO, Kenji; TANAKA, Hiroaki; MAEDA, Jun; YOKOYAMA, Kazuhiro; TAKAMATSU, Hajime; (146 pag.)EP3153511; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 133928-73-1, Adding some certain compound to certain chemical reactions, such as: 133928-73-1, name is 2-Chloro-3-methyl-4-pyridinecarboxylic Acid,molecular formula is C7H6ClNO2, 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 133928-73-1.

[01652] Step 4: Synthesis of methyl 2-chl hylpyridine-4-carboxylate[01653] To a stirred solution of 2-chloro-3-methylpyridine-4-carboxylic acid (780 mg, 4.5 mmol) in anhydrous DMF (5.0 ml), was added potassium carbonate (1 .25 g, 9.1 mmol), followed by methyl iodide (0.42 ml, 6.8 mmol) dropwise. A further 4 ml of DMF was added and the reaction mixture was stirred at room temperature under nitrogen for 18.5 hours. The solvent was removed in-vacuo and the residue was then partitioned between CI b b (20 ml) and water (20 ml). The layers were separated and the aqueous layer was extracted with CH2C12 (3 x 15 ml). The combined organic layers were washed with water (2 x 30 ml), brine (40 ml), dried (MgS0 ), filtered and concentrated in-vacuo. The residue was purified by column chromatography (l Og SNAP cartridge, Isolera, 0-6% ethyl acetate:heptanes) to give the title compound (591 mg, 59%) as a colourless oil. LC-MS 84%, m/z = 185.9, 1 87.9; NMR (500 MHz, Chloroform-d) delta ppm 8.33 (d, J=5.04 Hz, 1 H) 7.54 (d, J=5.04 Hz, 1 H) 3.95 (s, 3 H) 2.60 (s, 3 H).

According to the analysis of related databases, 133928-73-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 717843-51-1, Adding some certain compound to certain chemical reactions, such as: 717843-51-1, name is 3-Bromo-2-methoxy-4-methylpyridine,molecular formula is C7H8BrNO, 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 717843-51-1.

To a pressure tube was added 3-bromo-2-methoxy-4-methylpyridine (396 mg, 1.96 mmol), bis(pinacolato)diboron (597 mg, 2.35 mmol), Pd(dppf)2Cl2 (143 mg, 0.20 mmol), potassium acetate (384 mg, 3.92 mmol) and 1,4-dioxane (15 mL). The mixture was stirred at 95 C. for 4 hours. The residue was purified by silica gel flash chromatography (petroleum ether/ethyl acetate, 4:1) to give 2-methoxy-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (250 mg, 51% yield) as a colourless oil. LCMS (ESI): [M+H]+=249.3.

According to the analysis of related databases, 717843-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1235036-15-3, tert-Butyl 3-bromo-6-chloropicolinate, 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, Formula: C10H11BrClNO2, blongs to pyridine-derivatives compound. Formula: C10H11BrClNO2

Example 14A methyl 2-(5-bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-8-carboxylate Methyl 4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-8-carboxylate (500 mg), EXAMPLE 1D (572 mg), and triethylamine (0.545 mL) in anhydrous dimethylsulfoxide (6.5 mL) was heated to 100 C. overnight, and the mixture was then cooled to room temperature. The reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (15 mL) and ethyl acetate (15 mL). The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2*15 mL). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel with 0-40% ethyl acetate/hexanes to provide the title product.

The synthetic route of 1235036-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; WANG, LE; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96120; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 90395-45-2, 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 90395-45-2, name is 1-(4-(Pyridin-3-yl)phenyl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

1-(4-Pyridin-3-ylphenyl)-ethanone (50 g, 253.51 mmole),4-bromo-benzaldehyde (44.67g, 241.44mmole),Add 893 ml of ethanol and stir in the reaction flask.Finally, sodium tert-butoxide (34.77 g, 362.16 mmole) was added and stirred at room temperature.After the reaction has been completed, add 200 ml of deionized water and stir to filter.After filtering the solid with deionized water and methanol, the solid was filtered with 100 ml of deionized water and 200 ml of methanol for 30 minutes.The solid was dried twice to obtain 48 g of pale yellow solid 3-(4-bromophenyl)-1-(4-pyridin-3-ylphenyl)-propanone (3-(4-Bromo-phenyl)-1 -(4-pyridin-3-yl-phenyl)-propanone),The yield was 54.58%.

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 90395-45-2, 1-(4-(Pyridin-3-yl)phenyl)ethanone.

Reference:
Patent; Yulei Optoelectric Technology Co., Ltd.; Huang Helong; Guo Huangming; Zhao Dengzhi; Lin Qizhen; Zhang Minzhong; (29 pag.)CN109988159; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, 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, COA of Formula: C5H2BrClIN, blongs to pyridine-derivatives compound. COA of Formula: C5H2BrClIN

1-(5-Bromo-2-chloropyridin-3-yl)-2-(2-chloro-3-fluoro-6-methoxyphenyl)propan-1 -olA solution of 5-bromo-2-chloro-3-iodopyridine (0.750 g, 2.36 mmol) in anhydrous THF (5.5 mL) was cooled to -50 C and dropwise charged with 2.0 M of isopropylmagnesium chloride in THF (1.41 mL, 2.83 mmol) over an 8 min period and the mixture was stirred at -50 C for an additional 30 min. After 30 min., the mixture was charged with 2-(2-chloro-3-fluoro- 6-methoxyphenyl)propanal (0.766 g, 3.53 mmol) and stirred at -40 C for 1 h then allowed to warm to 0 C and charged with brine (10 mL) and allowed to stir for 15 min. The reaction mixture was partitioned between EtOAc and H20 and separated. The aqueous was re- extracted with EtOAc (3x) and the combined organic fractions were dried over Na2S04, filtered and concentrated in vacuo resulting in 930 mg of a crude oil/solid mixture. The mixture was recrystallized from 20% EtOAc in hexanes resulting in 245 mg of a white solid (diastereomer A). The mother liquor was purified by chromatography on silica gel [Jones Flashmaster, 20 g cartridge, eluting with 12% EtOAc in hexanes] resulting in 31 1 mg of a white foam (mainly diastereomer B). These two diastereomers were combined for the subsequent oxidation step. Diastereomer A: 1H NMR (400 MHz, CDCI3): delta = 1.34 (d, J = 6.23 Hz, 3H), 3.62 (br. s., 1 H), 3.89 (br. s., 3H), 5.43 (br. s., 1 H), 6.70-6.80 (m, 1 H), 6.94-7.03 (m, 1 H), 8.1 1 (d, J = 1.5 Hz, 1 H), 8.30 (d, J = 1.5 Hz, 1 H). MS (ES+): m/z 407.73, 409.77, 41 1 .74 [MH+]. HPLC: tR = 3.12 min (nonpolar_5min, ZQ3). Diastereomer B: 1H NMR (400 MHz, CDCI3): delta = 1 .41 (d, J = 7.3 Hz, 3H), 3.93-3.97 (m, 3H), 3.97-4.05 (m, 1 H), 5.44 (br. s., 1 H), 5.55 (dd, J = 4.6, 6.6 Hz, 1 H), 6.83 (dd, J = 4.3, 9.1 Hz, 1 H), 7.03 (dd, J = 8.1 , 9.1 Hz, 1 H), 7.76 (d, J = 0.5 Hz, 1 H), 8.33 (d, J = 2.5 Hz, 1 H). MS (ES+): m/z 407.73, 409.76, 41 1.74 (100/68/17) [MH+]. HPLC: fR = 3.35 min (nonpolar_5min, ZQ3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,928653-73-0, 5-Bromo-2-chloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; LI, An-Hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WO2011/143646; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem