Month: April 2022

Reference of 1196152-34-7 ,Some common heterocyclic compound, 1196152-34-7, molecular formula is C6H7BrN2O, 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.

[00237] A solution of 5-bromo-2,3-dihydro-benzo[1,4]dioxine (1.0 eq, 4.65 mmol), PdCl2(dtbpf) ([1, 1 ‘-bis(di-fe/f-butylphosphino)ferrocene] dichloropalladium(ll)) (0.1 eq, 0.46 mmol), KOAc (2.5 eq, 1 1.6 mmol), and bis(pinacolato)diboron (1.5 eq, 10.2 mmol) in dioxane (10 ml_) was purged with N2 for 10 min and the mixture was heated to 120 C for 3 h. Then, 2-bromo-6-methoxy-pyridin-4-amine (1.0 eq, 4.65 mmol), Pd(PPh3)4 (0.1 eq, 0.46 mmol), K2CO3 (2.0 eq, 9.30 mmol) and H2O (1 ml_) were added. The reaction was purged with N2 for 10 min and the mixture was heated to 110 C for 2.5 h. the mixture was cooled to RT then the solvent was removed. The dark residue was dissolved in ethyl acetate and filtered over celite. The compound in this organic layer was directly washed with water, brine, dried over magnesium sulphate, filtered and the reaction was concentrated in vacuo. The compound was purified by column chromatography eluting with dichloromethane then increasing the polarity with 0-5 % MeOH. Then the compound was purified by preparative HPLC-MS to afford 2-(2,3- dihydro-1,4-benzodioxin-5-yl)-6-methoxy-pyridin-4-amine (780 mg, 65 %) as a white solid. AnalpH2_MeOH_QC_V1, Rt: 3.93 min, m/z 259.3 [M+H]+ AnalpH9_MeOH_QC_V1, Rt: 6.46 min, m/z 259.3 [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,1196152-34-7, its application will become more common.

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; RABBITTS, Terrence; QUEVEDO, Camilo; CRUZ, Abimael; PHILIPS, Simon; FALLON, Philip Spencer; DUNN, Jonathan Neil; FREEM, Joshua Robert; LEE, Lydia Yuen-Wah; TRAORE, Tenin; WILLIAMS, Sophie Caroline; (219 pag.)WO2019/145718; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54718-39-7, 2,5,6-Trichloronicotinic acid, 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 54718-39-7, blongs to pyridine-derivatives compound. Product Details of 54718-39-7

1,1 ?-Carbonyldiimidazole (40 g, 247 mmol) was added in portions to 2,5,6- trichloronicotinic acid (50.7 g, 224 mmol, Combi-Blocks, San Diego, Calif.) in THF (400 mE), allowing gas evolution to cease between addition. The resulting mixture was stirred for 5 mm and then was degassed with house vacuum and flushed with nitrogen. The resulting mixture was heated to 50 C. for 60 mm, then diluted with toluene (100 mE) and concentrated to half the initial volume. The resulting mixture was cooled to 0 C. and ammonium hydroxide (60 mE, 437 mmol) was added slowly via syringe. The reaction was stirred for 10 mm at it, diluted with EtOAc (200 mE) and washed with water (3×100 mE). The organic layer was dried over anhydrous Na2504 and concentrated in vacuo. The residue was suspended in 9:1 heptane/EtOAc (300 mE) and filtered. The filtered solids were collected and the remaining mother liquor was partially evaporated to half the initial volume, cooled to 0 C., and filtered. The two crops of filtered solids were combined to provide 2,5,6-trichloroni- cotinamide.

The synthetic route of 54718-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; BOOKER, Shon; GOODMAN, Clifford; REED, Anthony B.; LOW, Jonathan D.; WANG, Hui-Ling; CHEN, Ning; MINATTI, Ana Elena; WURZ, Ryan; CEE, Victor J.; (88 pag.)US2019/77801; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84539-34-4, Adding some certain compound to certain chemical reactions, such as: 84539-34-4, name is 4-Amino-3,5-dibromopyridine,molecular formula is C5H4Br2N2, 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 84539-34-4.

Into a 500-mL round-bottom flask, was placed 3,5-dibromopyridin-4-amine (5 g, 19.85 mmol, 1.00 equiv), dioxane (150 mL), water(l5 mL), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (10.08 g, 59.99 mmol, 3.00 equiv), CS2CO3 (19.56 g, 60.03 mmol, 3.00 equiv), and Pd(dppf)Cl2 (1.46 g, 2.00 mmol) under an atmosphere of nitrogen. The resulting solution was stirred for 15 h at 90C in an oil bath, after which it was concentrated under vacuum. The residue thus obtained was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :3). This resulted in 3.0 g (87%) of 3,5-bis(prop-1-en-2-yl)pyridin-4-amine as light yellow oil. LCMS of 3,5-bis(prop-1-en-2-yl)pyridin-4-amine (Method A): 175.1 [M+H]+, retention time 0.872 min.

According to the analysis of related databases, 84539-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS INFLAMMASOME RESEARCH, INC.; GLICK, Gary; ROUSH, William; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI, Anthony William Jr.; KATZ, Jason; (468 pag.)WO2020/10140; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6515-09-9, 2,3,6-Trichloropyridine, 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, 6515-09-9, blongs to pyridine-derivatives compound. Recommanded Product: 6515-09-9

Experiment in a volume of 100 ml in the high-pressure reactor made of steel, will be 2, 3, 6-trichloro-pyridine 4g soluble in 36g tetrahydrofuran, then added with embodiment 2 of the method for preparing the loading of 1 wt % of Pd2+/GO the catalyst dosage is 200 mg, the hydrogen pressure is 4.5 MPa, the reaction temperature is 30 C, the reaction time is 22h, after the reaction is ended, direct sampling gas phase chromatographic detection, 2,3-dichloro pyridine conversion is 75.3%, selectivity of 85.0%. After the reaction, the reaction solution is filtered to remove the catalyst, the filtrate after evaporating solvent, crystallization and purification the nitrile is heavyafter the second grade the resulting residue, to obtain the product 2,3-dichloro-pyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6515-09-9, its application will become more common.

Reference:
Patent; Zhejiang University; Wei, Zuojun; Chen, Yidong; (8 pag.)CN105418492; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73112-16-0, Adding some certain compound to certain chemical reactions, such as: 73112-16-0, name is 2,6-Dibromo-4-methylpyridine,molecular formula is C6H5Br2N, 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 73112-16-0.

[00170] A solution of n-BuLi (4.4 mL, 2.5 M in n-hexane, 11 mmol) was slowly added to a solution of 2,6-dibromo-4-methylpyridine (2.75 g, 10.9 mmol) in DCM (83 mL) at -78C under N2. After stirring for 1.5 hat -78 C, methyl 3- oxocyclopentanecarboxylate (1.54 g, 11.0 mmol) was added. The cooling bath was removed and the reaction mixture was stirred for 2 h, and then was quenched by addition of saturated aqueous NH4C1 solution. The reaction mixture was extracted with ethyl acetate, and the organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (isocratic elution, 8% ethyl acetate-petroleum ether) to give two product diastereomers. Peak 1(550 mg, yellow solid) was determined to be the 1R,3S and 1S,3R isomers, and peak 2 (350 mg, yellow oil) was determined to be the 1R,3R and 1S,3S isomers. MS (ES+) C13H16BrNO3 requires: 313, found: 314 [M+H].

According to the analysis of related databases, 73112-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; DIPIETRO, Lucian, V.; (105 pag.)WO2018/22761; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 31170-78-2, 5H-Cyclopenta[b]pyridin-7(6H)-one, 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: 5H-Cyclopenta[b]pyridin-7(6H)-one, blongs to pyridine-derivatives compound. Recommanded Product: 5H-Cyclopenta[b]pyridin-7(6H)-one

5,6-Dihydro-[1]pyrindin-7-one O-methyl-oxime: Methoxylamine hydrochloride (6.20 g, 74.23 mmol) was added to a solution of 5,6-dihydro-[1]pyrindin-7-one (4.96 g, 37.25 mmol) in MeOH and triethylamine (10.4 mL, 74.62 mmol) was added. After refluxing overnight, the reaction mixture was cooled to room temperature and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with H2O (3×200 mL), brine (1×200 mL), dried over MgSO4 and concentrated. Purification by column chromatography using hex: Et2O (4:1) as the eluant afforded 4.10 g (68% yield) of the title oxime.31 g (96.5% yield) of the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) delta 2.90-2.96 (m, 2H), 2.99-3.07 (m, 2H), 4.08 (s, 3H), 7.21 (q, J=4.69, 2.93 Hz, 1H), 7.63 (d, J=7.92 Hz, 1H), 8.55 (d, J=4.69 Hz, 1H).

The synthetic route of 31170-78-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US2008/255239; (2008); 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. 130473-26-6, name is 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde. A new synthetic method of this compound is introduced below., Formula: C8H6N2O

C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled to in an ice bath, 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5 C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL water, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67% yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+.

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, 130473-26-6, 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); 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. 716362-10-6, name is 6-Chloro-4-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H6ClNO3

Triethylamine (7.0 mL, 51 mmol) was added to a suspension of 6-chloro-4-methoxynicotinic acid (2.615 g, 13.94 mmol, Intermediate 66) in MeCN (93 mL). N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (3.74 g, 19.5 mmol), HOBt (2.64 g, 19.5 mmol), and N,O-dimethylhydroxylamine hydrochloride (2.05 g, 21.0 mmol) were added, and the resulting mixture was stirred at rt for 3 days. After this time, the mixture was concentrated, and the residue was dissolved in EtOAc and water. The layers were mixed and separated, and the aqueous layer was extracted five times with EtOAc. The organic layers were combined, dried with anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0?20% EtOAc/hexanes) to provide the title compound.

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, 716362-10-6, 6-Chloro-4-methoxynicotinic acid.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Kummer, David A.; Nishimura, Rachel T.; Fourie, Anne M.; Xue, Xiaohua; (94 pag.)US2019/382373; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 150054-50-5, 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.150054-50-5, name is (4-Chloro-3,5-dimethylpyridin-2-yl)methanol, molecular formula is C8H10ClNO, molecular weight is 171.62, as common compound, the synthetic route is as follows.

EXAMPLE 8 Synthesis 2-hydroxymethyl-4-Methoxy-3,5-Lutidine In a round bottom flask equipped with a stirrer, a condenser and a nitrogen bubbler, 4-Chloro-2-hydroxymethyl-3,5-Lutidine (1 eq.) was dissolved in Dimethylformamide (3-9 volumes) and Methanol (1.5-4.5 volumes). Sodium methoxide (4 eq.) was added and the temperature was raised to (95-100? C.). At the end of the reaction the solvent was distilled under vacuum. Water (2 volumes) was added to the residue and the product was extracted with dichloromethane (2*4 volumes). The combined organic extracts were dried over sodium sulfate, filtered and evaporated. The crude product, 2-hydroxymethyl-4-Methoxy-3,5-lutidine, was obtained in 55% yield. In another work-up method, after evaporation of the dimethylformamide/methanol, water (2 volumes was added to the residue and the product was extracted with toluene (3*4 volumes). The organic extracts were combined and while cooling and stirring HCl gas (1.2 eq.) was bubbled into solution. The product 2-hydroxymethyl-4-Methoxy-3,5-lutidine hydrochloride salt was filtered and washed with toluene. The crude product was obtained as a white solid in 50% yield.

The chemical industry reduces the impact on the environment during synthesis 150054-50-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PDi-Research Laboratories, Inc.; US6437139; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6622-91-9 ,Some common heterocyclic compound, 6622-91-9, molecular formula is C7H8ClNO2, 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.

Example 12 Synthesis of N-[(4-pyridyl)acetyl]-D,L-alanine iso-butyl ester Following General Procedure F and using 4-pyridylacetic acid hydrochloride (Aldrich) and (D,L)-alanine iso-butyl ester hydrochloride (from Example B above), the title compound was prepared as a solid having a melting point of 64-66C. The reaction was monitored by tlc on silica gel (Rf = 0.43 10% methanol/dichloromethane) and purification was by silica gel chromatography. NMR data was as follows: 1H-nmr (CDCl3): delta = 8.51 (dd, J = 1.6, 2.8, 1.6, 2H); 7.23 (dd, J = 4.3, 1.6, 4.4, 2H); 6.71 (d, J = 6.8, 1H); 4.56 (quint., J = 7.3, 7.2, 1H); 3.88 (m, 2H); 3.53 (s, 2H); 1.89 (m, 1H); 1.36 (d, J = 7.2, 3H); 0.88 (d, J = 6.7, 6H). 13C-nmr (CDCl3): delta = 173.5, 169.3, 150.5, 144.4, 125.1, 72.1, 48.9, 43.0, 28.2, 19.5, 19.5, 18.9. C14H20N2O3 (MW = 264, Mass Spectroscopy (MH+ 265)) GENERAL PROCEDURE ELow Temperature BOP Coupling of Acid and Alcohol A solution of methylene chloride containing the carboxylic acid (100M%) and N-methyl morpholine (150 M%) was cooled to -20C under nitrogen. BOP (105 M%) was added in one portion and the reaction mixture was maintained at -20C for 15 minutes. The corresponding alcohol (120 M%) was added and the reaction mixture was allowed to warm to room temperature and stirred for 12 hours. The reaction mixture was then poured into water and extracted with ethyl acetate (3x). The combined ethyl acetate portions were backwashed with saturated aqueous citric acid (2x), saturated aqueous sodium bicarbonate (2x), brine (1x), dried over anhydrous magnesium sulfate or sodium sulfate and the solvent removed under reduced pressure to yield the crude product

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. 6622-91-9, 2-(Pyridin-4-yl)acetic acid hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Elan Pharmaceuticals, Inc.; ELI LILLY AND COMPANY; EP951464; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem