Month: April 2022

Reference of 169205-95-2, 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. 169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine. A new synthetic method of this compound is introduced below.

Example 17 Production of 6-(oxazolo[4,5-b]pyridin-2-ylamino)-N-(2,6-diisopropylphenyl)hexanamide 2-Methylthiooxazolo[4,5-b]pyridine (65.0 mg, 0.39 mmol) and 6-amino-N-(2,6-diisopropylphenyl)hexanamide (114 mg, 0.39 mmol) were mixed together and stirred at 90 C. for 2 hours. The reaction mixture was purified by preparative thin layer chromatography (elution solvents: hexane_acetone=5:3). The resulting crude crystal was recrystallized from dichloromethane-ether-hexane, to recover the objective compound as a colorless needle-like crystal. Melting Point: 152-153 C. IR (KBr) cm-1: 3416, 2964, 1656, 1571, 1413. 1H-NMR (d6-DMSO) delta: 1.11 (12H, d, J=6.8 Hz), 1.43-1.57 (2H, m), 1.64-1.77 (4H, m), 2.35 (2H, t, J=7.3 Hz), 3.08 (2H, sept, J=6.8 Hz), 3.38 (2H, dd, J=12.9, 6.8 Hz), 6.89 (1H, dd, J=7.8, 5.1 Hz), 7.09 (1H, d, J=8.3 Hz), 7.09 (1H, d, J=7.1 Hz), 7.19 (1H, dd, J=8.3, 7.1 Hz), 7.53 (1H, dd, J=7.8, 1.5 Hz), 7.87 (1H, br s), 8.06 (1H, dd, J=5.1, 1.5 Hz), 8.65 (1H, br s). EIMS m/z (relative intensity): 408 (M+, 100). Elementary Analysis: C24H32N4O2 Required: C, 70.56; H, 7.89; N, 13.71. Found: C, 70.70; H, 7.87; N, 13.51.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,169205-95-2, its application will become more common.

Reference:
Patent; Kowa Company, Ltd.; US6362208; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1227594-89-9, 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. 1227594-89-9, name is 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, molecular formula is C6H3F4NO, 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.

[00602] Step A: A solution of triphenylphosphine (1.34 g, 5.1 mmol) in THF (25 mL) was cooled to 0 C and treated with DIAD (1.0 mL, 5.12 mmol). The mixture was stirred for 15 min, then tert-butyl (3-bromo-1-((1r,4r)-4-hydroxycyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(ethyl)carbamate (1.5 g, 3.41 mmol) was added as a solid, followed by a solution of 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (1.24 g, 6.83 mmol) in THF (10 mL) over 5 min. The mixture was allowed to warm slowly to room temperature overnight. The mixture was partitioned between water (100 mL) and EtOAc (100 mL) and the aqueous layer was extracted with EtOAc (2 x 30 mL). The combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (10-40% EtOAc/hexanes) to afford tert-butyl (3-bromo-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(ethyl)carbamate (1.07 g, 52 % yield).

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 1227594-89-9, 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13269-19-7, 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. 13269-19-7, name is 2-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 2-nitropyridin-3-amine (4 g, 28.8 mmol) in AcOH (40 mL) was added potassium acetate (2.82 g, 28.8 mmol) and the mixture stirred for 1 h at room temperature. Br2 (1.481 mL, 28.8 mmol) was added slowly to the reactionmixture and the mixture stirred at room temperature for 16 h. The solid formed wascollected by vacuum filtration, washed with diethyl ether (2×10 mL) and dried underhigh vacuum to afford 4-bromo-2-nitropyridin-3-amine (6 g, 27.5 mmol, 96% yield) as a yellow solid. LCMS (ESI)m/e 218.0 [(M+H), calcd for C5H5BrN3O2 218.01; LC/MS retention time (method B): tR = 0.61 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13269-19-7, 2-Nitropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1142363-52-7, 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. 1142363-52-7, name is JNJ-40346527, molecular formula is C27H35N5O2, 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.

Example 31 4-Cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide sulfate salt A suspension of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (24.8 mg, 0.0537 mmol), as prepared in Example 15, in acetonitrile (1.0 mL) was heated to yield a solution. To the solution was added a solution of concentrated sulfuric acid (0.0062 mL) in water (0.5 mL) at room temperature. The solution was reduced via evaporation with flowing nitrogen gas (approximately 1.0 mL). The solution was then allowed to sit overnight at room temperature in a sealed vial. The resulting crystals were then collected via filtration and air-dried. The white solid was characterized by Powder X-Ray Diffraction (PXRD), Differential Scanning Calorimetry (DSC), Thremogravimetric Analysis (TGA), and single-crystal X-ray diffraction. The DSC for the sulfate salt showed a 241 degree Celsius endotherm maximum. The PXRD of the sulfate salt product is shown in and the prominent peaks are shown in the table below. Representative 2-Theta peaks of the sulfate salt product are shown below:

According to the analysis of related databases, 1142363-52-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Illig, Carl R.; Chen, Jinsheng; Meegalia, Sanath K.; Wall, Mark J.; US2009/105296; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 90145-48-5 ,Some common heterocyclic compound, 90145-48-5, molecular formula is C6H5BrN2O, 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) tert-Butyl 2-(6-carbamoylpyridin-3-yl)-lH-indole-l-carboxylatel-(tert-butoxycarbonyl)indole-2-boronic acid (1 mmol), 5-bromopyridine-2-carboxamide (lmmol), Pd(dppf)Cl2 (0.05 mmol) and aq 2M Na2CO3 (1.5 mL) solution were mixed in THF/water 5:1 (10 mL) in a 20 mL microwave vial. The reaction mixture was stirred at 1200C in the microwave reactor for 15 min. Water was added and the solution was extracted with EtOAc. The organic extracts were dried over Na2SO4, filtered and concentrated. The crude mixture was purified by flash chromatography (Heptane/EtOAc gradient) to afford the title intermediate (172 mg). MS m/z (M+H) 338.

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. 90145-48-5, 5-Bromopyridine-2-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2008/108729; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 823221-93-8, 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.823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrClF3N, molecular weight is 260.44, as common compound, the synthetic route is as follows.

Step C. (1 S, 1 aS,6aR)-4-((5-(6-chloro-4-(trifluoromethyl)pyridin-3-yl)-2-fluorobenzyl)oxy)- l, la,6,6a-tetrahvdrocyclopropara1indene-l -carboxylic acid, ethyl ester 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine (974 mg, 3.74 mmol) was added to a solution of (l S,laS,6aR)-4-((2-fluoro-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)benzyl)oxy)-l, la,6,6a-tetrahydrocyclopropa[a]indene-l -carboxylic acid, ethyl ester (1.583 g, 3.5 mmol) in DME (20 ml) under N2, followed by potassium carbonate (2.43 g, 17.58 mmol) and l,l’-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride dichloromethane complex (35 mg, 0.043 mmol). The mixture was heated at 90C overnight. It was poured into saturated NH4CI solution and extracted with EtOAc (lx). The organic phase was washed with brine, dried (MgS04), filtered and the solvent evaporated. The residue was purified on silica gel using hexane and to give the title compound. MS m/e: (M+H)+ 506, 508.

The chemical industry reduces the impact on the environment during synthesis 823221-93-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William, K.; LI, Bing; SZEWCZYK, Jason, W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi, P.; PIO, Barbara; DANG, Qun; LIN, Linus, S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/95256; (2015); 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 62150-47-4, name is Ethyl 4-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C8H8BrNO2

To a stirring solution of compound 2.3 (32.4 g,. 0.14 mol). compound 2,4 (32.2 g, 0.17 mol) and Pd(PPh2)4 (8.08 g, 7 ram of) in 1 ,4-dioxane/nrietrianoi (800 rnL 1 :1) was added Na2COs (22.3 g,u.21 mol) under an argon atmosphere and the mixture was stirred at 80C for 15 nr. The solvent was removed under reduced pressure and the resulting residue was diluted with wafer (500 rnL) and extracted with EtOAc (3 x 500 ml). The combined organic layers were dried and concentrated under reduced pressure to give a crude, which was purified by flash chromatography (silica gel/ RhoEpsilon.Alpha 2: 1) to give ethyl 4-(4-formylphenyl picolinate (2.5, 14.2 g, 40%) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 62150-47-4.

Reference:
Patent; ACHAOGEN, INC.; PATTERSON, Brian D.; LU, Qing; AGGEN, James Bradley; DOZZO, Paola; KASAR, Ramesh Annasaheb; LINSELL, Martin Sheringham; KANE, Timothy Robert; GLIEDT, Micah James; HILDEBRANDT, Darin James; MCENROE, Glenn A.; COHEN, Frederick; WO2013/170165; (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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-2-chloro-4-methoxypyridine

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 minutes. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 C for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product. 1H NMR (500 MHz, DMSO- , 5 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC MS (M+l)+ – 169.

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, 880870-13-3, 5-Bromo-2-chloro-4-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; PASTERNAK, Alexander; SHI, Zhi-Cai; CATO, Brian; KIM, Esther, Y.; WO2013/66718; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62002-31-7, 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.62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, molecular formula is C6H11Cl2N3, molecular weight is 196.08, as common compound, the synthetic route is as follows.

To a suspension of 3,3-diphenylpropionic acid (14 mg, 0.06 mmol) and HOBt (9 mg, 0.07 mmol) in ethyl acetate (1.5 mL) a solution of EDC (12 mg, 0.06 mmol) in ethyl acetate (0.5 mL) was added. The resulting mixture was shaken for 20 min at room temperature and then 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (12 mg, 0.06 mmol) and triethylamine (0.02 mL) were added. After shaking for 16 h the mixture was washed with brine (2*2 mL), and the organic phase was concentrated. 12 mg (60%) of the title amide was obtained. HPLC (214 nm): elution at 8.71 min. LC-MS: Calcd. for MH+: 332; found: 332. 1H NMR (300 MHz, CDCl31 two rotamers, 1:1): delta2.55 (m, 2H), 3.15 (t, J=7 Hz, 2H), 3.61 (t, J=5 Hz, 1H), 3.80 (t, J=5 Hz, 1H), 4.41 (s, 1H), 4.57 (s, 1H), 4.67 (m, 1H), 7.06-7.30 (m, 10H), 7.39 (s, 0.5H), 7.43 (s, 0.5H).

The chemical industry reduces the impact on the environment during synthesis 62002-31-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1440519-73-2, name is 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, molecular formula is C15H13ClN2O2, 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. SDS of cas: 1440519-73-2

To a solution of 2-chloro-6-(4-methoxy-benzyl)-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one (5.8 g, 20.0 mmol) in THF (50 mL) was added sodium hydride (60% in mineral oil, 1.7 g, 42.0 mmol) at room temperature. The resulting reaction mixture was stirred for 30 min before iodomethane (6.0 g, 42.0 mmol) was added. After stirring at room temperature over night, the mixture was quenched with water and extracted with EtOAc. The organic layer was then washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give the crude product which was then purified by flash column chromatography (silica gel 20 g, 5% to 20% ethyl acetate in DCM). The title compound was obtained (3.8 g, 57%) as a white solid. MS: 316.2 (M+H+).

With the rapid development of chemical substances, we look forward to future research findings about 1440519-73-2.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem