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.72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.Quality Control of 2-Chloro-5-(trifluoromethyl)pyridin-3-amine

240 mg (1.19 mmol) of 2-chloro-5-(trifluoromethyl)pyridin-3-amine and 357 mg (1.31 mmol) of 3-ethylsulphanylquinoline-2-carboxylic acid were dissolved together with 0.39 ml (4.78 mmol) of pyridine in 20 ml of dioxane, 367 mg (2.39 mmol) of phosphoryl chloride were added, and the mixture was stirred at reflux for 90 min. The mixture was concentrated, the residue was taken up in ethyl acetate and washed with water, and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography purification with a cyclohexane/ethyl acetate gradient (80:20 to 40:60) as eluent. (log P (neutral): 5.71; MH+: 412; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 1.37 (t, 3H), 3.12 (q, 2H), 7.74-7.84 (m, 2H), 8.07-8.14 (m, 2H), 8.49 (s, 1H), 8.70 (s, 1H), 9.02 (s, 1H), 11.12 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, Ruediger; HAGER, Dominik; HOFFMEISTER, Laura; KAUSCH-BUSIES, Nina; WILCKE, David; WILLOT, Matthieu; GOeRGENS, Urich; ILG, Kerstin; MOSRIN, Marc; PORTZ, Daniela; TURBERG, Andreas; US2018/305353; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1083057-12-8, 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 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate. This compound has unique chemical properties. The synthetic route is as follows.

The 3-butyl 3-(3-methylpyridin-2-yl)benzoate (1.0 eq.) was dissolved in EtOAc (6 EtOAc). Water (0.3 vol) and hydrogen peroxide urea (3 eq.) were added in that order. Phthalic anhydride (3 equivalents) was then added portionwise to the mixture in solid form at a rate to maintain the temperature in the reactor below 45 C. After the addition of phthalic anhydride was completed, the mixture was heated to 45 C. After stirring for another 4 hours, the heater was turned off. A 10% w/w aqueous Na2SO3 solution (1.5 eq.) was added via an addition funnel. After the addition of Na2SO3 was completed, the mixture was stirred for additional 30 min and the layers were separated. The organic layer was stirred and a 10% wt/wt aqueous Na2CO3 solution (2 eq.) was added. After stirring for 30 minutes, the layers were separated. The organic phase was washed with a 13% w/v NaCl aqueous solution. The organic phase was then filtered and concentrated to give crude 2-(3-(t-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) which was used directly in the next step .

According to the analysis of related databases, 1083057-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VERWIJS, MARINUS JACOBUS; ALARGOVA, ROSSITZA GUEORGUIEVA; KAUSHIK, RITU ROHIT; KADIYALA, IRINA NIKOLAEVNA; YOUNG, CHRISTOPHER; (118 pag.)TWI636051; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256785-86-0, 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.1256785-86-0, name is 1-(4-Aminopyridin-2-yl)ethanone, molecular formula is C7H8N2O, molecular weight is 136.15, as common compound, the synthetic route is as follows.

Example 20 (2R,5S)-N-(2-Acetyl-4-pyridyl)-4-(4-cyano-3-trifluoromethylphenyl)-2,5-dimethylpiperazine-1-carboxamide While stirring with ice-cooling, 12.5 ml of trifluoroacetic acid was added to 12.5 ml of chloroform solution containing 1.41 g of 2-acetyl-4-pyridinylcarbamic acid t-butyl ester.. The mixture was immediately warmed up to room temperature and stirred for 2 hours and 40 minutes.. The solvent was evaporated under reduced pressure to obtain a crude amine.. This compound was dissolved in 25 ml of pyridine, and the solution was mixed with 0.83 ml of phenyl chloroformate while stirring with ice-cooling and then immediately warmed up to room temperature.. After 8 hours and 30 minutes, this was mixed with 10 ml of pyridine solution containing 1.4 g of (2S,5R)-4-(2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile and heated under reflux for 1 hour.. The reaction mixture cooled to room temperature was mixed with water and extracted with chloroform.. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure.. The residue was purified by a silica gel column chromatography to obtain 1.03 g of the title compound from methanol-chloroform (1:99, v/v) elude. NMR: 1.10 (3H, d, J=7), 1.20 (3H, d, J=7), 2.61 (3H, s), 3.34-3.52 (2H, m), 3.75 (1H, d, J=14), 3.92 (1H, d, J=14), 4.28-4.45 (1H, m), 4.46-4.62 (I H, m), 7.20-7.35 (2H, m), 7.78-7.91 (2H, m), 8.12 (1H, d, J=2), 8.48 (1H, d, J=6), 9.24(1H, s)

The chemical industry reduces the impact on the environment during synthesis 1256785-86-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamanouchi Pharmaceutical Co. Ltd.; US6673799; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90395-45-2 ,Some common heterocyclic compound, 90395-45-2, molecular formula is C13H11NO, 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.

1-(4-Pyridin-3-ylphenyl)-ethanone (33 g, 166.8 mmole),3,5-Dibromo-benzaldehyde (42.06 g, 159.34 mmole), and 840 ml of ethanol were added to the reaction flask for stirring.Finally, sodium tert-butoxide (22.94 g, 239 mmole) was added and stirred at room temperature.After the reaction has been completed, 200 ml of deionized water is added and stirred for filtration. The solid is filtered and washed with deionized water and methanol. The solid is then filtered with 100 ml of deionized water and 200 ml of methanol for 30 minutes, and repeated twice. Dry the solid to give 55 g of pale yellow solid 3-(3,5-dibromophenyl)-1-(4-pyridin-3-ylphenyl)-acetone(3-(3,5-Dibromo-phenyl)-1-(4-pyridin-3-yl-phenyl)-propanone),The yield was 77.89%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90395-45-2, its application will become more common.

Reference:
Patent; E-ray Optoelectronics Technology Co Ltd; Huang, Heh Lung; Guo, Huang Ming; Chao, Teng Chih; Lin, Chi Jen; Chang, Min Jong; (53 pag.)TW2019/30287; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1093879-46-9 , The common heterocyclic compound, 1093879-46-9, name is 2-(6-Bromopyridin-2-yl)acetic acid, molecular formula is C7H6BrNO2, 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 1 : to a solution of 2-(6-bromopyridin-2-yl)acetic acid (266 mg, 1 .23 mmol) in DMF (5 ml.) were added DMAP (150 mg, 1.23 mmol), EDCl.HCl (279 mg, 1 .35 mmol) and [4-methyl- 2-(piperidin-1 -yl)phenyl](5-methylfuran-2-yl)methanamine Ex.2 (350 mg, 1.23 mmol). The reaction mixture was stirred at rt. After completion of the reaction (monitored by TLC), sat. NH4CI was added and the solution was extracted with EtOAc. The organic layer was washed with sat. NH4CI, dried over MgS04, filtered and evaporated to dryness under reduced pressure. The crude material was purified by column chromatography on silica gel using Cyclohexane/EtOAc (70:30) as eluent to afford 2-(6-bromopyridin-2-yl)-N-{[4-methyl-2- (piperidin-1 -yl)phenyl](5-methylfuran-2-yl)methyl}acetamide (470 mg, 79%) as yellow oil. 1H NMR (300 MHz, DMSO-d6, d in ppm): 1.39-1 .59 (m, 6H), 2.17 (s, 3H), 2.26 (s, 3H), 2.52- 2.63 (m, 2H), 2.73-2.87 (m, 2H), 3.66 (s, 2H), 5.91 (d, 1 H, J=3.3Hz), 5.94 (dd, 1 H, J=3.0Hz, J=0.9Hz), 6.49 (d, 1 H, J=8.4Hz), 6.91 (d, 1 H, J=7.9Hz), 6.95 (s, 1 H), 7.20 (d, 1 H, J=7.8Hz), 7.35 (dd, 1 H, J=7.5Hz, J=0.6Hz), 7.49 (dd, 1 H, J=7.9Hz, J=0.7Hz), 7.68 (t, 1 H, J=7.4Hz), 8.86 (d, 1 H, J=8.4Hz).

The synthetic route of 1093879-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (76 pag.)WO2018/138356; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884494-82-0, 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. 884494-82-0, name is 5-Fluoro-2-methoxynicotinic acid. A new synthetic method of this compound is introduced below.

[0361] To a solution of 5-fluoro-2-methoxynicotinic acid (372 mg, 2.172 mmol) in DCM (18.3 mL) was added oxalyl chloride (380 xL, 4.34 mmol) and DMF (8.41 mu, 0.109 mmol) at 0C. After stirring at 20C for 1 hour, the mixture was concentrated in vacuo. The residue was taken up in THF (1 mL) and added dropwise to a mixture of 5-amino-4-(4-(2,4- difluorophenoxy)piperidin-l-yl)-NJV-dimethylpicolinamide (545 mg, 1.448 mmol) and DIPEA (759 xL, 4.34 mmol) in THF (11 mL). The reaction mixture was stirred at 60C for 1 hour, then cooled to RT, and filtered. The filtrate was purified by HPLC, eluting with ACN in water. The solid product was recrystallized from 3: 1 MeOH/water solution and filtered. The solids were placed in a 70C vacuum oven overnight to give the title compound as an off-white solid (487 mg, 63.5%). NMR (500 MHz, DMSG-cfe) delta ppm 1.81 – 1.87 (m, 2 H), 2.06 – 2.10 (m, 2 H), 2.94 – 2.98 (m, 2 H), 2.99 (d, J=6,83 Hz, 6 H), 3.27 (dd,,1=1.96, 7.08 Hz, 2 H), 4.12 (s, 3 H), 4.55 (di,./ 7.93. 4.09 Hz, 1H), 6.99 – 7.05 (m, 1H), 7.27 – 7.34 (m, 3 H), 8.25 (dd,./ K.54. 3.17 Hz, 1H), 8.46 (d,./ 3.42 Hz, 1H), 9.15 is. 1H), 10.17 (s, 1H); ES1-MS m/z j M 1 .] 530.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-82-0, 5-Fluoro-2-methoxynicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 21427-61-2, 5-Chloro-2-hydroxy-3-nitropyridine, 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, 21427-61-2, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3ClN2O3

Intermediate 4; 3-amino-5-chloropyridin-2-ol; To a 500 mL round bottom flask charged with 5-chloro-2-hydroxy-3-nitro pyridine (4.9 g, 28.7 mmol), Fe (7.2 g, 129.7 mmol) and CaCI2 (2.86 g, 25.8 mmol) was added 4:1 EtOHiH2O (50 mL) and the mixture was heated at reflux for 2h. After cooling to room temperature the mixture was filtered through a celite pad and washed with ethanol/water. EPO The dark filtrate was evaporated and dried in vacuum for 2h to afford 3-amino-5-chloropyridin- 2-ol. LCMS: m/e 145 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21427-61-2, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2006/51410; (2006); 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 36936-23-9, name is 5-Chloro-6-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Chloro-6-methylpyridin-2-amine

Intermediate IXc 3 ,6-dichloro-2-methylpyridine To a suspension of 5-chloro-6-methylpyridin-2-amine (7.5 g, 52.60 mmol, Combi- Blocks) in DCM (200 niL) was added copper(II) chloride (9.19 g, 68.38 mmol) and stirred at for 10 min. tert-butyl nitrite (12.50 mL, 105.20 mmol) was added and the stirring was continued further 30 min at RT. The colour was changed to dark blue. The reaction was monitored by LCMS. LCMS showed the completion of reaction. The reaction mixture was washed with water, brine solution, and organic layer was dried on sodium sulphate and concentrated under vacuum to get crude. The product was purified by column chromatography using 5 % ethyl acetate :hexane mixture to get 3,6-dichloro- 2-methylpyridine (3.80 g, 44.6 %) as a yellow liquid. MS (ES+), (M+H)+ = 162.15 for C6H5C12N.

With the rapid development of chemical substances, we look forward to future research findings about 36936-23-9.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; HAMEED PEER MOHAMED, Shahul; PATIL, Vikas; MURUGAN, Kannan; VITHALRAO BELLALE, Eknath; RAICHURKAR, Anandkumar; LANDGE, Sudhir; PUTTUR, Jayashree; ROY CHOUDHURY, Nilanjana; SHANBHAG, Gajanan; KOUSHIK, Krishna; IYER, Pravin; KIRTHIKA SAMBANDAMURTHY, Vasan; SOLAPURE, Suresh; NARAYANAN, Shridhar; WO2015/165660; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 880870-13-3, Adding some certain compound to certain chemical reactions, such as: 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine,molecular formula is C6H5BrClNO, 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 880870-13-3.

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged nitrogen for 15 min. Next, 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 95C for 12 h 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. 1HNMR (500 MHz, DMSO- 6) delta 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC/MS: [(M+l)]+ = 169.

According to the analysis of related databases, 880870-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 175204-80-5, 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 175204-80-5, name is 3-Amino-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Oxalylchloride (132 muL, 1.5 mmol) was added dropwise to a stirred suspension ofbenzoic acid 124 (350 mg, 1.0 mmol) and DMF (1 drop) in dry THF (20 mL) and thesolution was stirred at 20 C. for 2 h, then at 66 C. for 1 h. The solutionwas cooled to 20 C., then the solvent was evaporated and the residue dissolvedin dry pyridine (10 mL). 4-Trifluoromethyl-3-pyridinylamine (180mg, 1.1 mmol) was added and the solution stirred at 20 C. for 16 h. Thesolvent was evaporated and the residue suspended in ice/water (50 mL) for 1 h.The precipitate was filtered, washed with water (5 mL) and dried. The crudesolid was purified by column chromatography, eluting with EtOAc, to givebenzamide 140 (265 mg, 53%)

According to the analysis of related databases, 175204-80-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THEBOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLANDUNISERVICES LIMITED; SUTPHIN, PATRICK; CHAN, DENISE; TURCOTTE, SANDRA; DENNY, WILLIAMALEXANDER; HAY, MICHAELPATRICK; GIDDENS, ANNACLAIRE; BONNET, MURIEL; GIACCIA, AMATO; (181 pag.)JP5789603; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem