Month: April 2022

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.6854-07-5, name is 5-Nitro-2-oxo-3-pyridinecarboxylic Acid, molecular formula is C6H4N2O5, molecular weight is 184.11, as common compound, the synthetic route is as follows.Recommanded Product: 6854-07-5

Step B 2-Methoxy-3-carbomethoxy-5-nitropyridine 2-Hydroxy-3-carboxy-5-nitropyridine was converted to 2-chloro-3-chlorocarbonyl-5-nitropyridine in situ and converted to the title compound by reaction with anhydrous methanol according to the procedure of A. Monge et al J. Het. Chem. (29), 1545 (1992). In a 500 mL was added starting material (10.2 g, 54 mmol) in 200 mL of chlorobenzene.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6854-07-5, 5-Nitro-2-oxo-3-pyridinecarboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US5750549; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 105166-53-8, [2,2′-Bipyridin]-3-amine, 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, Product Details of 105166-53-8, blongs to pyridine-derivatives compound. Product Details of 105166-53-8

General procedure: Trifluoroacetic acid (0.75 mL, 0.009 mol) was added to a cooled (0 C) solution (4.5 mL CH2Cl2) of3-amino-2,2?-bipyridine (0.513 g, 0.003 mol), followed by isoamyl nitrite (0.61 mL, 0.004 mol). After 1 h,the diazonium salt of 3-amino-2,2?-bipyridine was precipitated out by cooling the reaction mixtureto -78 C, followed by the addition of diethyl ether (30 mL). The precipitate was filtered. A sample(2 mmol; 0.27 g) of indol-2-one was dissolved in dilute potassium hydroxide solution (15 mL) andcooled in a saltice bath and then cold diazonium solution was added to this cooled solution portionwise by stirring. The solution was further stirred at 0-5 C for 1 h. The pH of the reaction mixturewas maintained at 4-6 by the addition of solid sodium acetate in portions. The mixture was stirredfor 24 h at room temperature. The resulting solid was filtered, washed with cold water, and air-dried.Crystallization from ethanol gave yellow crystalline.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105166-53-8, [2,2′-Bipyridin]-3-amine, and friends who are interested can also refer to it.

Reference:
Article; ?andrik, Robert; Tisovsky, Pavol; Csicsai, Klaudia; Donovalova, Jana; Gaplovsky, Martin; Sokolik, Robert; Filo, Juraj; Gaplovsky, Anton; Molecules; vol. 24; 14; (2019);,
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.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5F3N2O

General procedure: N,N-Dimethylformamide (2 mL), triethylamine (0.079 mL, 0.57 mmol) and 1- [bis(dimethylamino)methylene]-lH-l,2,3-triazolo[4,5-]pyridinium 3-oxid hexafluorophosphate (79 mg, 0.208 mmol, HATU) were added to a mixture of the product of Example 18A (59.4 mg, 0.189 mmol) and (5-(difluoromethoxy)pyridin-2-yl)methanamine (Enamine, 33 mg, 0.189 mmol) in sequential order. The reaction mixture was then stirred at ambient temperature for 30 minutes. The resulting solution was filtered through a glass microfiber frit and purified by preparative HPLC [YMC TriArt CI 8 Hybrid 5 mupiiota column, 50 x 100 mm, flow rate 90 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (56 mg, 0.119 mmol, 63% yield). JH NMR (501 MHz, DMSO-de) delta ppm 8.73 (s, 1H), 8.44 (t, J = 6.1 Hz, 1H), 8.40 (d, J = 2.8 Hz, 1H), 7.64 (dd, J = 8.6, 2.9 Hz, 1H), 7.50 (t, J = 8.9 Hz, 1H), 7.29 (dd, J = 8.6, 0.7 Hz, 1H), 7.27 (t, J = 73.5 Hz, 1H), 7.08 (dd, J = 11.4, 2.9 Hz, 1H), 6.86 (ddd, J = 8.9, 2.9, 1.2 Hz, 1H), 4.47 (s, 2H), 4.33 (d, J = 6.1 Hz, 2H), 2.22 (s, 6H); MS (ESI+) m/z 470 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89466-17-1, 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 89466-17-1, name is 6-Bromo-5-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 0.052 g ammonium chloride (1 mmol) in 4 mL water or methanol was added isocyanide (1.2 mmol), aromatic aldehyde (1.1 mmol), and 2-aminopyridine (1 mmol) and sealed in stainless steel autoclave with a Teflon-coated, and then the autoclave was put in the oven at 75oC in 2 h. The autoclave was taken out and cooled to room temperature. The reaction mixture was put into 30 mL cooled water to afford the product as a precipitate. The solid residue was filtered and crystallized from ethyl acetate to give products.

According to the analysis of related databases, 89466-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Xiaohui; Shang, Qianqian; Bo, Caiying; Hu, Lihong; Zhou, Yonghong; Arkivoc; vol. 2018; 5; (2018); p. 184 – 193;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98139-15-2, Adding some certain compound to certain chemical reactions, such as: 98139-15-2, name is 4-Aminopicolinonitrile,molecular formula is C6H5N3, 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 98139-15-2.

Into a 30-mL sealed tube, was placed 2-bromo-5-methoxy-4-[3-(pyrrolidin-l- yl)propoxy]pyridine (314 mg, 1.00 mmol, 1.00 equiv.), 4-aminopyridine-2-carbonitrile (240 mg, 2.01 mmol, 2.00 equiv.), Pd2(dba)3-chloroform (0.1 g, 0.10 equiv.), t-BuXPhos (0.085 g, 0.20 equiv.), Cs2C03 (970 mg, 2.97 mmol, 3.00 equiv.), dioxane (10 mL). The resulting solution was stirred for 16 h at 110 C in an oil bath. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic layers combined. The organic layer was washed with 1×50 mL of brine, dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The crude product (3 mL) was purified by Flash- Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, MeCN_Water=l :5 increasing to MeCN_Water=10: l within 120 min; Detector, UV 254 nm. 70 mg product was obtained. This resulted in 70 mg (20%) of 4-([5-methoxy-4-[3- (pyrrolidin-l-yl)propoxy]pyridin-2-yl]amino)pyridine-2-carbonitrile as an off-white solid.

According to the analysis of related databases, 98139-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); 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. 1042141-37-6, name is Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate. A new synthetic method of this compound is introduced below., COA of Formula: C9H7BrN2O2

A mixture of methyl delta-bromo-lJ-diazabicyclo^^.OJnona^^^jdelta-tetraene-S-carboxylate (0.39 mmol, 100 mg), (6-dimethylaminopyridin-3-yl)boronic acid (0.59 mmol, 98 mg), cesium carbonate (1.57 mmol, 510 mg) and Pd(dppf)Cl2*DCM ( 39 mumol, 32 mg) was dissolved in DMF (3 ml). The mixture was stirred at 80 0C for 1 h and filtered. The filtrate lambdavas subjected to preparative HPLC to give 20 mg of the title compound as a white solid. IH NMR (400 MHz, DMSO-^6) delta ppm 9.24 (s, 1 H) 8.69 (d, J=2.02 Hz, 1 H) 8.38 (s, 1 H) 8.02 (dd, J=8.84, 2.27 Hz, 1 H) 7.61 (s, 2 H) 6.73 (d, J=8.84 Hz, 1 H) 3.89 (s, 3 H) 3.08 (s, 6 H); MS m/z (M+H) 297

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, 1042141-37-6, Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate.

Reference:
Patent; ASTRAZENECA AB; WO2008/91195; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 195044-14-5 ,Some common heterocyclic compound, 195044-14-5, molecular formula is C9H12BrN, 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-5: Synthesis of 1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (200 mg, 0.833 mmol, 1.0 eq) and 2-bromo-6-tert-butylpyridine (214 mg, 0.999 mmol, 1.2 eq) in 1,4 dioxane (3 mL) was added potassium carbonate (230 mg, 1.666 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (31 mg, 0.666 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (30 mg, 0.333 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resultant mixture was heated at 100 C. for 5 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (150 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 95% EtOAc/Hexane to afford 1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (100 mg, 32.25%) as off white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,195044-14-5, its application will become more common.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (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.83766-88-5, name is 2-(tert-Butoxy)pyridine, molecular formula is C9H13NO, molecular weight is 151.21, as common compound, the synthetic route is as follows.Product Details of 83766-88-5

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83766-88-5, 2-(tert-Butoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
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.90145-48-5, name is 5-Bromopyridine-2-carboxamide, molecular formula is C6H5BrN2O, molecular weight is 201.02, as common compound, the synthetic route is as follows.Recommanded Product: 5-Bromopyridine-2-carboxamide

Example 10 Preparation of 5-bromo-N-(2,2,2-trichloro-1-(4- ethylcvcloheylamino)ethyl)picolinamide (Compound-46) and 5-bromo-N-(2,2,2-trichloro-1-(4- ethylcvclohexylamino)ethyl)picolinamide (Compound-47)[00144] 5-Bronnopicolinannide 112 (1.29 g, 6.4 mmol) and chloral (1.25 ml_) in dioxane (10 ml_) were heated to 100 0C. The mixture was concentrated to give 5- bromo-N-(2,2,2-trichloro-1 -hydroxyethyl)picolinamide 122 (99%). [00145] A solution of 5-bromo-N-(2,2,2-thchloro-1 -hydroxyethyl)picolinamide 122 (0.83 g, 2.39 mmol) in chloroform (20 ml_) was reacted with PCI5 (0.51 g, 2.33 mmol) at 50 0C for 30 minutes. The mixture was cooled to -78 0C and 4-ethylcyclohexanamine was added (1 g, 7.5 mmol). After 1 hour, the mixture was warmed to room temperature. The reaction mixture was subjected to an aqueous work-up and the product extracted with chloroform. The organic solution was concentrated onto silica gel and the product was eluted (flash: 97:3 hexane:ether then prep-HPLC: Phenomenex Luna column (Sitheta2), 10 micron, 250×50 mm, 150 mL/minute; 3:7 hexanes:dichloromethane) to give first eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcyclohexylamino)ethyl)picolinamide (Compound-46, 106 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.26 (d, J = 9.9 Hz, 1 H), 8.11 (dd, J = 8.4, 0.6 Hz, 1 H), 8.01 (dd, J = 8.4, 2.4 Hz, 1 H), 5.56 (t, J = 9.3 Hz, 1 H), 2.96 (brs, 1 H), 1.80- 1.71 (m, 2H), 1.59-1.21 (m, 10H), 0.85 (t, J = 7.2 Hz, 3H), and second eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4-ethylcyclohexylamino)ethyl)picolinamide (Compound- 47, 166 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.30 (d, J = 9.9 Hz, 1 H), 8.11 (dd, J = 8.4, 0.9 Hz, 1 H),8.01 (dd, J = 8.4, 2.1 Hz, 1 H), 5.50 (t, J = 8.7 Hz, 1 H), 2.68-2.58 (m, 1 H), 2.16-2.07 (m, 1 H), 1.86-1.70 (m, 4H), 1.27-1.01 (m, 6H), 0.96-.087 (m, 1 H) 0.83 (t, J = 7.5 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90145-48-5, 5-Bromopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; ALLERGAN, INC.; NGUYEN, Phong X.; HEIDELBAUGH, Todd M.; CHOW, Ken; GARST, Michael E.; WO2011/19681; (2011); 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.866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, molecular weight is 299.05, as common compound, the synthetic route is as follows.Recommanded Product: Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A step 4) (2 g, 6.69 mmol) was suspended in toluene (8 ml), then p-toluenesulfonic acid (TsOH) (0.1 15 g, 0.669 mmol) and acetonylacetone (0.941 ml, 8.03 mmol) was added. The reaction mixture was heated at reflux for 2 h and allowed to cool to RT overnight. The resulting dark red/ black solution was concentrated under reduced pressure to remove toluene and the crude residue was diluted with EtOAc (200 ml), washed with NaHC03 (50 ml), dried (MgS04) and concentrated under reduced pressure to give a brown solid; LC-MS Rt = 5.58 min [M+H]+ 377/379 (Method 10minl_C_v002). 1 H NMR (400 MHz, DMSO-d6) ? 8.50 (1 H, s), 7.77 (2H, s), 5.83 (3H, s), 1.90 (6H, s); 19F NMR (400 MHz, DMSO-d6) ? -62.26 (CF3, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,866775-18-0, Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren Mark; WO2013/38378; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem