Month: April 2022

Application of 112006-57-2, 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 112006-57-2, name is 2-(Benzylthio)-N,N-dimethylnicotinamide. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 N,N-Dimethyl-2-aminosulfonyl-3-pyridinecarboxamide A mixture of 4.4 ml of concentrated hydrochloric acid, 66 ml of methylene chloride, 34 ml of water and 4.0 g (14.7 mmol) of the N,N-dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide was cooled to 0 C. Maintaining a temperature of -5 to 3 C., 60 ml (40.5 mmol) of 5% sodium hypochlorite was added dropwise over 15 minutes. The resulting yellow emulsion was stirred at 0 C. an additional 20 minutes. The reaction mixture was then poured into water and extracted with methylene chloride. The combined organic extracts were kept at 0 C. and washed with a saturated sodium bisulfite solution and dried over sodium sulfate. After 30 minutes, the yellow solution was filtered into a reaction flask and cooled to -78 C. and 5 ml (431 mmol) of dry ammonia added. The reaction mixture was allowed to warm to room temperature and the solvent removed under reduced pressure. The resulting solid was slurried with 5 ml of water and the insoluble white solid collected by filtration to provide 2.0 g of the subject compound, m.p. 198-209 C.(d). NMR (DMSO): delta 2.70 (s, 3H, NCH3); 2.93 (s, 3H, NCH3); 7.60-7.75 (m, 1H); 7.90 (m, 1H); and 8.75 (m, 1H).

According to the analysis of related databases, 112006-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4789393; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 936342-91-5, name is 5-Bromo-2-(chloromethyl)pyridine hydrochloride, the common compound, a new synthetic route is introduced below. Recommanded Product: 5-Bromo-2-(chloromethyl)pyridine hydrochloride

To an N,N-dimethylformamide (40.0 mL) solution of 4-fluorophenol (3.00 g, 26.8 mmol) was added sodium hydride (1.00 g, 25.0 mmol, 60percent in oil) on an ice bath (0° C.) under nitrogen atmosphere, which was stirred for 20 minutes at room temperature. To the reaction solution was then added a mixture of 5-bromo-2-chloromethyl-pyridine hydrochloride (4.6 g, 22.3 mmol) described in Manufacturing Example 54-1-2 and triethylamine (30.6 mL, 20.4 mmol), which was stirred for 10 minutes at room temperature. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. This organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated from the filtrate under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate_heptane=1:4) to obtain the title compound (4.0 g, 63.6percent). 1H-NMR Spectrum (CDCl3) delta (ppm): 5.10 (2H, s), 6.88-6.91 (2H, m), 6.95-6.99 (2H, m), 7.40-7.42 (1H, m), 7.81-7.84 (1H, m), 8.64-8.65 (1H, m).

The synthetic route of 936342-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 66909-38-4, 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 66909-38-4 as follows.

An aqueous solution of sodium, nitrite (0.5M, 50.5 mL) was added to a cold (0- 5C) solution of 6-chloro-4-methylpyridin-3-amine (3 g, 21.04 mmol) in.50% aqueous H2SO4 (75 mL) over 1 h, maintaining a temperature of 0-5C. The reaction mixture was allowed to stir for 20 minutes, then added to acetic acid (60 ml. ) at 1 ()0″C over 30 minutes. Stirring was continued for 2 h, then the reaction mixture was cooled and neutralised with saturated aqueous NaHC03 solution, followed by solid NaHCOa, to pH 7. The residue was extracted with EtOAc (4 x 200 ml.) and dried (Na2S04), then filtered and concentrated. Purification by Biotage (eluent 0-100% EtOAc:heptanes; RF 0.33 in 1 :1 EtOAciheptane) afforded the title compound (1.47 g, 48.8%). deltaEta (500 MHz, DMSO- d6) 10.05 (s, 1H), 7.83 (s, GammaEta), 7.23 (s, 1H), 2.14 (s, 3H). Method B HPLC-MS: MH+ mlz 143.9/145.9, RT 1.48 minutes (100%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,66909-38-4, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHOVATIA, Prafulkumar Tulshibhai; FOULKES, Gregory; JOHNSON, James Andrew; JONES, Severine Danielle; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LOKE, Pui Leng; LOWE, Martin Alexander; MANDAL, Ajay; NORMAN, Timothy John; PALMER, Christopher Francis; PEREZ-FUERTES, Yolanda; PORTER, John Robert; SMYTH, Donald; TRANI, Giancarlo; UDDIN, Muhammed; ZHU, Zhaoning; (207 pag.)WO2016/198400; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 914942-88-4 ,Some common heterocyclic compound, 914942-88-4, molecular formula is C13H18IN5O2, 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.

Copper iodide (5.0mg, 0.025mmol) and dichlorobis(triphenylphosphine) palladium (4.0mg, 0.050mmol) were each added in one portion to a mixture of Al.12 (lOOmg, 0.25mmol), phenylacetylene (28mg, 0.28mmol) and triethylamine (0.11ml, 0.75mmol) in dichloromethane (0.5ml) at room temperature under a nitrogen atmosphere. The resulting mixture was heated to 40 0C for 24hrs before cooling to room temperature and evaporating in vacuo. The residue was purified by column chromatography using ethyl acetate as eluent to give 62mg of A1.13. LC/MS Phenomenex S5 4.6x30mm (2min gradient) Found: M+H = 378.27 at 1.51 min

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. 914942-88-4, tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 27652-89-7, (4-Chlorophenyl)(pyridin-2-yl)methanol, 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, 27652-89-7, blongs to pyridine-derivatives compound. category: pyridine-derivatives

The compounds of the present invention were synthesized according to the procedure, which is illustrated schematically in FIG. 1 for three MPH alkyl analogs. Referring to FIG. 1, para-bromochlorobenzene 1 was converted into a Grignard reagent with Mg/THF which was then reacted with the pyridine-2-carboxaldehyde 2 to produce the alcohol 3. The alcohol 3 was oxidized with pyridinium chlorochromate in CH2Cl2 to produce the ketone 4. The ketone 4 was then reacted with a Grignard reagent that contains the required R group to produce the alcohol 5. After dehydration with refluxing HCl, the resulting Z and E olefin mixture 6 was hydrogenated with 10% Pt/C in HOAc containing 3% CF3COOH to produce the final compounds 7 with a ratio of about 40:60 of the R,R/S,S and R,S/S,R racemates for the ethyl compound. The racemates were separated by column chromatography and their relative configurations were determined by x-ray crystallography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,27652-89-7, its application will become more common.

Reference:
Patent; Froimowitz, Mark; Kelley, Charles J.; US2006/100243; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 603311-76-8, 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 603311-76-8 as follows.

Add 0. 5M diisobutylaluminum hydride in toluene (4.6 mL, 2.29 mmol) to a solution of (6-bromo-imidazo [1, 2-a] pyridin-3-yl) -acetic acid ethyl ester (0.65 g, 2.29 mmol) and morpholine (5 mL) in THF (40 mL) AT-78 C. Gently warm the reaction to room temperature and dilute carefully with methanol. Filter and concentrate the filtrate. Flash chromatography gives the subtitled compound (0.24 g, 32percent) as a white solid. MS ES+m/e 324.0, 326.0 (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,603311-76-8, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/50659; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1156542-25-4, 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. 1156542-25-4, name is 6-Chloro-4-(trifluoromethyl)picolinonitrile. A new synthetic method of this compound is introduced below.

A 2 dram vial containing (S)-N-((1R,2R,4S)-7-cyano-7-azabicyclo[2.2.1]heptan-2-yl)pyrrolidme- 3 -carboxamide hydrochloride (0 2 mmol) was added 6-chloro-4-(trifluoromethyl)picolitionitrile (62.0 mg, 0 300 mmoi), acetonitrile (667 m) and DIPEA (140 m, 0.800 mmol). The suspension was stirred at 60 C for 2h when LC-MS showed good conversion (80%). The reaction was purified via RP- HPLC with 0.1% NH40H in ACN and water as mobile phase to afford (S)-l-(6-cyano-4- (trifluoromethyl)pytidin-2-yl)-N-((lR,2R 4S)-7-cyano-7-azabicyclo[2.2.1]heptan-2-yl)pyirolidine-3- carboxamide in 41% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1156542-25-4, 6-Chloro-4-(trifluoromethyl)picolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; CARMOT THERAPEUTICS, INC.; BUTLER, John R.; ERLANSON, Daniel; GRACEFFA, Russell; IWIG, Jeffrey; JEONG, Joon Won; WHITE, Ryan D.; WU, Yongwei; YI, Shuyan; BANERJEE, Abhisek; MCFARLAND, Jesse M.; ZHENG, Xiao Mei; (307 pag.)WO2020/36940; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1097264-89-5, name is 2-Chloro-5-fluoro-3-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a solution of 2-chloro-5-fluoro-3-(methyloxy)pyridine D47 (0.11 g, 0.70 mmol) in dry toluene (3 ml), sodium t-butoxide (0.094 g, 0.98 mmol), Pd2(dba)3 (0.064 g, 0.07 mmol), BINAP (0.131 g, 0.21 mmol) and benzophenone imine (0.14 ml, 0.84 mmol) were added. The resulting mixture was degassed (3×pump/N2) and then heated to 80 C. After 1 h stirring, the mixture was cooled down to room temperature, diluted with Et2O (80 ml) and filtered through a celite pad. Volatiles were evaporated, the resulting oil was dissolved in THF (8 ml) and HCl (0.35 ml of a 2 M aqueous solution, 0.70 mmol) was added. The mixture was stirred at room temperature for 1.5 h, then neutralized with a saturated NaHCO3 aqueous solution and diluted with DCM (40 ml). The phases were separated and the aqueous one back-extracted with DCM (2×10 ml). The collected organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (Biotage SP4 12M, Cy/EtOAc 60/40) to give the title compound D48 (0.071 g, 0.49 mmol, 70% yield from D47, two steps) as a yellow solid. UPLC: rt=0.28 min, peak observed: 143 (M+1). C6H7FN2O requires 142.

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, 1097264-89-5, 2-Chloro-5-fluoro-3-methoxypyridine.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 887266-57-1, Adding some certain compound to certain chemical reactions, such as: 887266-57-1, name is 3-Fluoro-2-hydrazinylpyridine,molecular formula is C5H6FN3, 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 887266-57-1.

A solution of methyl 2- {3 -(4-chlorophenyl)-5-oxo-4- [(2-3,3 ,3 -trifluoro-2-hydroxypropyl] -4,5-dihydro-1H-1,2,4-triazol-1-yl}ethanimidate (Example 7A, 1.00 g, 2.64 mmol) in tetrahydrofuran(20 ml) was cooled to 0C and treated with methyl chloro(oxo)acetate (270 jil, 2.9 mmol). Theresulting mixture was stirred for 30 mm. 3 -Fluoro-2-hydrazinylpyridine (369 mg, 2.90 mmol) andN,N-diisopropylethylamine (510 jil, 2.9 mmol) were added, the reaction mixture was warmed up toroom temperature and stirred for 1 h, followed by 1 h at 120C in a sealed vial under microwave irradiation. The crude product was purified by preparative HPLC (Method 5). Lyophilisation of the product containing fractions afforded 680 mg (48% of th.) of the title compound.LC-MS (Method 3): R = 1.78 mm; MS (ESIpos): mlz = 542 [M+H]1H-NMR (400 MHz, DMSO-d6) [ppm]: 3.808 (16.00), 3.821 (1.05), 3.844 (0.95), 3.857 (1.15),3.881 (1.24), 3.990 (1.20), 3.998 (1.28), 4.027 (0.81), 4.035 (0.78), 5.217 (8.13), 6.907 (2.33),6.923 (2.34), 7.614 (3.78), 7.618 (1.47), 7.630 (1.62), 7.635 (5.20), 7.751 (5.36), 7.756 (1.78),7.768 (1.53), 7.773 (3.96), 7.794 (0.74), 7.806 (1.20), 7.816 (1.57), 7.827 (1.42), 7.837 (0.87), 8.135 (0.90), 8.138 (0.95), 8.156 (1.02), 8.159 (1.71), 8.162 (1.23), 8.180 (0.81), 8.184 (0.82),8.485 (1.74), 8.496 (1.69).

According to the analysis of related databases, 887266-57-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; COLLIN-KROePELIN, Marie-Pierre; KOLKHOF, Peter; NEUBAUER, Thomas; FUeRSTNER, Chantal; POOK, Elisabeth; TINEL, Hanna; SCHMECK, Carsten; WASNAIRE, Pierre; SCHIRMER, Heiko; LUSTIG, Klemens; (205 pag.)WO2019/81299; (2019); A1;,
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. 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine, molecular formula is C8H7BrN2, 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. Recommanded Product: 116355-18-1

Step 2: To a solution of 6-bromo-7-methylimidazo(l,2-a)pyridine (9 g, 43.0 mmol) and anhydrous sodium acetate (9.52 g, 116.1 mmol) in MeOH (100 mL) at 0 C was added iodine (12.0 g, 47.3 mmol). The reaction mixture was stirred at rt for 20 h. The precipitate was collected by filtration and washed with MeOH to afford 6-bromo-3-iodo-7- methylimidazo[l,2-a]pyridine (6 g, 41%) as a light grey solid. 1H NMR (400 MHz, CDC13) delta 8.30 (s, 1H), 7.64 (s, 1H) 7.49 (s, 1H) 2.50 (s, 3H); MS (ESI) m/z 336.7 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 116355-18-1.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem