Day: September 18, 2021

Application of 54221-96-4 ,Some common heterocyclic compound, 54221-96-4, molecular formula is C7H7NO2, 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.

6-Methoxy-2-pyridinecarboxaldehyde (1.0 mL, 8.31 mmol) and 2-naphthylamine (1.19 g,8.33 mmol) were dissolved in 25 mL of anhydrous methanol and the resulting mixture washeated at reflux temperature for 6 h. The solvent was removed under reduced pressure togive brown solids. Yield: 1.58 g (72percent). Anal. Calcd (percent) for C17H14N2O (M = 262.31 g mol?1): C,77.84; H, 5.38; N, 10.68. Found: C, 77.88; H, 5.43; N, 10.71. FT-IR (KBr, cm?1): 3439(w), 3051(w),2976(w), 2840(w), 1632(m), 1586(s), 1569(m), 1508(w), 1467(s), 1438(m), 1413(w), 1350(w),1334(m), 1321(m), 1267(s), 1229(w), 1208(w), 1167(w), 1151(m), 1120(w), 1078(w), 1032(m),985(w), 961(w), 911(w), 887(w), 860(s), 824(m), 808(s), 750(s), 734(w), 666(w), 626(w), 603(w),523(w), 504(w), 478(w), 430(w). 1H NMR (400 MHz, CDCl3): delta 8.63 (s, 1H, CH = N), 7.52?7.87(m, 7H, Naphthalene-H), 6.84?7.02 (m, 3H, Py-H3,4,5), 4.03 (s, 3H, ?OCH3) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54221-96-4, its application will become more common.

Reference:
Article; Dong, Yu-Wei; Wang, Ping; Fan, Rui-Qing; Chen, Wei; Wang, A-Ni; Yang, Yu-Lin; Journal of Coordination Chemistry; vol. 70; 11; (2017); p. 1953 – 1972;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 677728-92-6, 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 677728-92-6, name is 2-Fluoropyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 24: (trans-4-{ri-(5-formylpyridin-2-yl)piperidin-4-yl1oxy|cvclohexyl)acetic acidA mixture of [trans-4-(piperidin-4-yloxy)cyclohexyl] acetic acid (0.8 g, 3.32 mmol), 3- fluoro-5-formylpyridine (0.415 g, 3.32 mmol) and sodium bicarbonate (1.67 g, 19.89 mmol) in NMP (6 ml) was heated at 110C in an oil bath over night under N2. The reaction mixture was cooled to room temperature then concentrated under vacuum. The residual was applied onto a silica gel column and eluted with acetone/dichloromethane 0-100%. This resulted in 0.28 g (24.4%) of: (trans-4-{[l-(5-formylpyridin-2-yl)piperidin-4-yl]oxy}cyclohexyl)acetic acid as a white solid. LC-MS (ES, m/z): Ci9H26N204: 346; Found: 347 [M+H]+.

According to the analysis of related databases, 677728-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; DE VITA, Robert, J.; HONG, QingMei; LAI, Zhong; DYKSTRA, Kevin, D.; YU, Yang; LIU, Jian; SPERBECK, Donald; JIAN, Tianying; GUIADEEN, Deodial; XU-QIANG YANG, Ginger; WU, Zhicai; HE, Shuwen; TING, Pauline, C.; ASLANIAN, Robert; KUETHE, Jeffrey, T.; BALKOVEC, James, M.; KUANG, Rongze; ZHOU, Gang; WU, Heping; WO2012/164071; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1174229-72-1, Ethyl 2-(6-aminopyridin-3-yl)acetate, 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, 1174229-72-1, blongs to pyridine-derivatives compound. Recommanded Product: 1174229-72-1

A 20-mL vial was charged with 4-chloro-2-(3-chlorophenyl)-6- cyclopropylpyrimidine (0.380 g, 1.43 mmol), ethyl 2-(6-aminopyridin-3-yl)acetate (0.410 g, 2.27 mmol), palladium acetate (0.016 g, 0.071 mmol), rac-BINAP (0.069 g, 0.11 mmol) and cesium carbonate (1.17 g, 3.58 mmol) in dioxane (10 mL) under argon. The reaction mixture was heated to 110 C under microwave irradiation for 1.25 h. The reaction mixture was cooled, and diluted with ethyl acetate and filtered through celite. The filtrate was washed with saturated sodium chloride (2 x 10 mL), dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on silica using hexanes/ethyl acetate (10:0 to 0: 10) as eluent to afford the title compound (0.504 g, 86%) as an off-white solid. MW = 408.88. M.p. 133-135 C. ]H NMR (DMSO- , 500 MHz) delta 10.13 (s, 1H), 8.31-8.29 (m, 1H), 8.27 (dt, / = 7.0, 1.5 Hz, 1H), 8.22 (d, / = 2.0 Hz, 1H), 7.75-7.68 (m, 2H), 7.62 (br s, 1H), 7.59-7.52 (m, 2H), 4.10 (q, / = 7.5 Hz, 2H), 3.68 (s, 2H), 2.07 (septet, / = 4.5 Hz, 1H), 1.21 (t, / = 7.0 Hz, 3H), 1.14-1.10 (m, 2H), 1.06-1.00 (m, 2H); APCI MS m/z 409 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1174229-72-1, its application will become more common.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC.; GURNEY, Mark, E.; HAGEN, Timothy, J.; MO, Xuesheng; VELLEKOOP, A.; ROMERO, Donna, L.; CAMPBELL, Robert, F.; WALKER, Joel, R.; ZHU, Lei; WO2014/66659; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6188-23-4, 6-Bromoimidazo[1,2-a]pyridine, 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, Recommanded Product: 6188-23-4, blongs to pyridine-derivatives compound. Recommanded Product: 6188-23-4

A mixture of the compound of example 1 (1.0 g, 5.08 mmol) and t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (1.97 g, 5.08 mmol) were treated with [1 ,1 ‘-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.124 g, 0.152 mmol) and sodium carbonate (2.15 g, 20.30 mmol) in dry dimethylformamide (100 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.05 g (54.68 %); 1H NMR (DMSO-d6, 300 MHz): delta 1.39 (s, 9H, 3CH3), 3.44 (s, 4H, 2CH2), 3.55 (s, 4H, 2CH2), 6.95 (d, 1H, J=8.7 Hz, Ar), 7.50-7.62 (m, 3H, Ar), 7.87 (d, 1H, J=2.4 Hz, Ar), 7.90 (s, 1H, Ar), 8.46 (d, 1H, J=2.4 Hz, Ar), 8.83 (s, 1H, Ar); MS (ES+): m/e 380 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6188-23-4, 6-Bromoimidazo[1,2-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GHOSH, Usha; MORE, Tulsidas; KULKARNI, Mahesh; BAJAJ, Komal; BURUDKAR, Sandeep; RIZVI, Zejah; WO2014/80241; (2014); 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 13472-81-6, name is 3,5-Dibromo-2-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H3Br2NO

3,5-Dibromo-2-hydroxypyridine (9.36 g, 37 mmol; purchased from Tokyo Chemical Industry Co., Ltd.), 1,4-butane sultone (6.58 g, 48.3 mmol), and NaOH (1.97 g, 49.3 mmol) were added to 160 mL of ethanol, and the mixture was stirred for 24 h at 60 C. The white precipitate was separated by filtration, and recrystallization from THF containing a small amount of water gave Monomer-1 (7.17 g, 47%). 1H NMR (300 MHz, D2O) delta: 7.93 (d, J = 2.4 Hz, 1H), 7.77 (d, J = 2.4 Hz, 1H), 3.90 (t, J = 6.9 Hz, 2H), 2.78 (t, J = 7.5 Hz, 2H), 1.71 (m, 2H), 1.60 (m, 2H). IR (KBr) 1656, 1593, 1188, 1052 cm-1. Anal. Calcd for C9H10Br2NNaO4S: C, 26.30%; H, 2.45%; Br, 38.88%; N, 3.41%; S, 7.80%. Found: C, 25.80%; H, 2.52%; Br, 39.04%; N, 3.34%; S, 7.71%.

With the rapid development of chemical substances, we look forward to future research findings about 13472-81-6.

Reference:
Article; Yamamoto, Takakazu; Takei, Tohru; Kumagai, Naoto; Harada, Yosuke; Ohki, Takumi; Kudoh, Yasuo; Kojima, Takahiro; Koizumi, Take-Aki; Shiramizu, Kohei; Abe, Masahiro; Oota, Masashi; Polymer; vol. 53; 26; (2012); p. 5995 – 5999;,
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. 944401-56-3, name is 5-Bromo-4-(trifluoromethyl)pyridin-2-amine. A new synthetic method of this compound is introduced below., name: 5-Bromo-4-(trifluoromethyl)pyridin-2-amine

To a dry flask was added 5-bromo-4-(trifluoromethyl)pyridin-2-amine (2200.91 mmol), potassium acetate (446 mg, 4.55 mmol), bis(pinacolato)diboron (279 mg,1.10 mmol, 1.1 eq.) and dioxane (5 mL). N2 was bubbled through the solution for 1.5 minutes, at which time 1 ,1- bis(diphenylphosphino)ferrocene-palladium(II) (32 mg, 45iimol) was added. The reaction was stirred at 100 C for 16 hours under N2. After cooling to room temperature, the dioxane was removed in vacuo. EA was added and the resulting slurry was sonicated and filtered. Additional ethyl acetate was used to wash the solid. The combined organic was concentrated and the crude material was purified by silica gel chromatography using Petroleum ether : Ethyl acetate (10:1) affording to compound 30 (60 mg, 23%) as a light yellow solid. ?H NMR (400 MHz, CDC13): 8.47 (s, 1H), 6.76 (s, 1H), 5.15 (bs, 2H), 1.34 (s, 12H).

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, 944401-56-3, 5-Bromo-4-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; SUZHOU KINTOR PHARMACEUTICALS, INC.; GUO, Chuangxin; TONG, Youzhi; (160 pag.)WO2017/219800; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1346575-64-1, 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.1346575-64-1, name is 3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-one, molecular formula is C10H16N2O, molecular weight is 180.25, as common compound, the synthetic route is as follows.

Example 11l-(l-Methylethyl)- V-[(6-methyl-2-oxo-4-propyl-l,2-dihydro-3-pyridinyl)methyl]-6-(4- pyridinyl)-l -pyrazolo[3,4-6]pyridine-4-carboxamidel-(l-Methylethyl)-6-(4-pyridinyl)-l H-pyrazolo [3, 4-b]pyridine-4-carboxylic acid (150 mg, 0.531 mmol), 3-(aminomethyl)-6-methyl-4-propyl-2(lH)-pyridinone (1 15 mg, 0.531 mmol), EDC (122 mg, 0.638 mmol), HOAt (72.3 mg, 0.531 mmol), and N- methylmorpholine (0.233 mL, 2.12 mmol) were suspended in DMF (5 mL) and stirred at room temperature overnight, water was added to the reaction mixture, and the contents were filtered. The filter cake was washed with addional water (2x). The crude solid was purified by reverse phase HPLC (mobile phase: 10-30% ACN in H20, 0.1% TFA). The isolated solid was then neutralized with saturated NaHC03, and washed with EtOAc (5 x 15 mL). The combined organic layers were dried over Na2S04, filtered, and concentrated in vacuo to afford the title compound as an off-white solid, 0.060 g (24%). LCMS E-S (M+H) = 445.3. 1H NMR (400 MHz, DMSO-d6) ? ppm 0.84 – 0.92 (m, 3 H), 1.47 – 1.54 (m, 2 H), 1.57 (d, J=6.82 Hz, 6 H), 2.14 (s, 3 H), 2.48 – 2.52 (m, 2 H), 4.42 – 4.49 (m, 2 H), 5.33 – 5.43 (m, 1 H), 5.90 – 5.96 (m, 1 H), 8.28 – 8.37 (m, 3 H), 8.44 – 8.48 (m, 1 H), 8.82 – 8.87 (m, 2 H), 8.99 – 9.04 (m, 1 H), 11.58 (s, 1 H).

Statistics shows that 1346575-64-1 is playing an increasingly important role. we look forward to future research findings about 3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-one.

Reference:
Patent; GLAX0SMITHKLINE LLC; BURGESS, Joelle, Lorraine; JOHNSON, Neil, W.; KNIGHT, Steven, David; LAFRANCE, Louis, Vincent, III; MILLER, William, H.; NEWLANDER, Kenneth, Allen; ROMERIL, Stuart, Paul; ROUSE, Meagan, B.; SUAREZ, Dominic; TIAN, Xinrong; VERMA, Sharad, Kumar; WO2013/39988; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 142266-62-4, 2,5,6-Trichloronicotinamide, 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, Application In Synthesis of 2,5,6-Trichloronicotinamide, blongs to pyridine-derivatives compound. Application In Synthesis of 2,5,6-Trichloronicotinamide

Step 2: 2,5,6-Trichloro-N-((2-ethyl-4-methylpyridin-3-yl)carbamoyl)nicotinamide To a solution of 2,5,6-trichloronicotinamide (Intermediate P, 2.5 g, 11.1 mmol) in THF (20 mL) was added oxalyl chloride (2 M solution in DCM, 5.4 mL, 10.8 mmol) slowly via syringe. The resulting mixture was heated at 65 C. for 1.5 h, then heating was stopped and the reaction was allowed to cool to room temperature. A solution of 2-ethyl-4-methylpyridin-3-amine (Intermediate W, 1.5 g, 10.7 mmol) in THF (15 mL) was added via cannula. The resulting mixture was stirred at room temperature for 1 h, and then was partially concentrated to remove most of the THF. The residue was partitioned between saturated aqueous sodium bicarbonate (30 mL) and EtOAc (50 mL). The organic layer was washed with brine (1*), dried over anhydrous sodium sulfate and concentrated. The residue was suspended in 10:1 heptane/EtOAc (60 mL) and filtered to provide 2,5,6-trichloro-N-((2-ethyl-4-methylpyridin-3-yl)carbamoyl)nicotinamide. The product was carried on directly into the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,142266-62-4, 2,5,6-Trichloronicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; KOPECKY, David John; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; BOOKER, Shon; NISHIMURA, Nobuko; SHIN, Youngsook; TAMAYO, Nuria A.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; (266 pag.)US2018/334454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 68325-15-5, Adding some certain compound to certain chemical reactions, such as: 68325-15-5, name is 3-Chloro-4-cyanopyridine,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 68325-15-5.

Step B: Preparation of 3-(2-(trimethylsilyl)ethoxy)isonicotinonitrile: A flask was charged with 2-(trimethylsilyl)ethanol (1.02 g, 8.66 mmol) and added THF (20 mL). Sodium hydride (0.219 g, 8.66 mmol) was added and the reaction was stirred at ambient temperature for 1 hour. 3-Chloroisonicotinonitrile (1.00 g, 7.22 mmol) was added, and the reaction mixture was stirred at ambient temperature for 1 hour and then at 50 0C overnight. A saturated solution of ammonium chloride was added. The reaction mixture was extracted with ethyl acetate, dried and concentrated to give the desired product (1.30 g, 81.7% yield) as light brown semi solid material.

According to the analysis of related databases, 68325-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2008/91770; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 33674-96-3, 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 33674-96-3, name is (6-Bromopyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of ( 6-bromopyridin-2-yl) methanol (5.22 g) , PPh3 (8.74 g) and benzotrifluoride (210 mL) was added tetrabromomethane (11.1 g) at 0C. The mixture was stirred at 0C for 2 hr, and the insoluble substance was removed by filtration, and washed with ethyl acetate/diethyl ether. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (7.33 g) . XH NMR (300 MHz, CDCI3) delta 4.50 (2H, s) , 7.39-7.45 (2H, m) , 7.52-7.60 (1H, m) .

According to the analysis of related databases, 33674-96-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAJITA, Yuichi; MIKAMI, Satoshi; MIYANOHANA, Yuhei; KOIKE, Tatsuki; DAINI, Masaki; OYABU, Norio; OGINO, Masaki; TAKEUCHI, Kohei; ITO, Yoshiteru; TOKUNAGA, Norihito; SUGIMOTO, Takahiro; MIYAZAKI,Tohru; ODA, Tsuneo; HOASHI, Yasutaka; HATTORI,Yasushi; IMAMURA, Keisuke; (413 pag.)WO2019/27058; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem