Month: March 2022

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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid, the common compound, a new synthetic route is introduced below. Formula: C7H6N2O4

REFERENTIAL EXAMPLE 3 Synthesis of N,N-diethyl 2-methyl-5-nitronicotinamide (No. 98) In dry chloroform were dissolved 0.3 g of 2-methyl-5-nitronicotinic acid and 1.5 ml of diethylamine. After addition of 10 g of phosphorous pentaoxide, the mixture was stirred with heating at 55 – 60 C. for 3 hours. After cooling, the chloroform portion was separated and evaporated under reduced pressure. The residue was, after addition of water, neutralized with sodium hydrogen carbonate and extracted with ethyl acetate. The extract was concentrated and purified on a silica gel column to give 0.25 g of a colorless oil. Analysis for C11 H15 N3 O3:

The synthetic route of 59290-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company Limited; US4053608; (1977); A;,
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. 90610-06-3, name is Methyl 2-(6-methylpyridin-3-yl)acetate, molecular formula is C9H11NO2, 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. Application In Synthesis of Methyl 2-(6-methylpyridin-3-yl)acetate

To a stirred solution of methyl (6-methylpyridin-3-yl)acetate (60 mg, 0.36 mmol) in methanol (5 ml) was added NaOH (1.0 ml of a 2M aqueous solution, 2.0 mmol) and the resulting solution was heated at 65 0C for 2 hours. The solvent was then removed at reduced pressure and the resulting residue was dissolved in methanolic HCl (5 ml) and then reconcentrated to yield the title product (54 mg, quant, yield) that was used without further purification. LCMS data: Calculated MH+ (152); Found 100% (MH+) m/z 152, Rt = 0.79 min. Method C.

With the rapid development of chemical substances, we look forward to future research findings about 90610-06-3.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; DAVENPORT, Adam, James; HALLETT, David, James; STIMSON, Christopher, Charles; WO2010/86403; (2010); 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.188577-68-6, name is 4,5-Dichloropyridin-2-amine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.name: 4,5-Dichloropyridin-2-amine

Description 77: 2,4,5-trichloropyridine (D77); 4,5-dichloro-2-pyridinamine D76 (360 mg) was dissolved in HCl (8 ml, 96 mmol) at O0C, then sodium nitrite (305 mg, 4.42 mmol) was added portionwise, and the resulting yellow mixture was stirred at 0 0C for 1 hour and then at room temperature for 1 hour. On the basis of HPLC/MS, starting material was consumed to give the required product and the corresponding pyridone.The reaction was then poured into ammonium hydroxide (10 ml) in ice and extracted with Et2O (3×150 ml). The collected organic phases were dried over Na2SO4, then filtered and carefully concentrated (max 200 mBar) to give the title compound D77 (200 mg) as yellow oil.UPLC (Acid GEN_QC_SS): rt = 0.86 minutes, peak observed: 184 (M+2) C5H2Cl3N requires 182.1H NMR (400 MHz, CHLOROFORM- d) delta ppm 7.48 (s, 1 H) 8.43 (s, 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,188577-68-6, 4,5-Dichloropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73455-13-7, 4,5-Dichloropicolinic 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, Formula: C6H3Cl2NO2, blongs to pyridine-derivatives compound. Formula: C6H3Cl2NO2

A mixture of HATU (155 mg, 0.41 mmol), 4,5-dichloropicolinic acid (39 mg, 0.20 mmol) and (S)-2-(methoxymethyl)pyrrolidine (117 mg, 1.02 mmol) was stirred at 25C for 16h. The crude reaction mixture was directly purified by preparative HPLC (15 min gradient of 60:40 to 0:100 hhOMeOH (both modified with 0.1 % formic acid); flow rate 20 mLmin 1) affording the title compound (39 g, 66%) as a colourless oil that existed as a mixture of rotamers. Rotamer . 1 H NMR (500 MHz, Methanol-d4) d 8.71 (s, 1 H), 7.96 (s, 1 H), 4.44- 4.38 (m, 1 H), 3.82-3.75 (m, 1 H), 3.68-3.64 (m, 2 H), 3.40 (s, 3 H), 2.14-1.96 (m, 5 H). Rotamer B : 1 H NMR (500 MHz, Methanol-d4) d 8.69 (s, 1 H), 7.95 (s, 1 H), 4.85-4.78 (m, 1 H), 3.75-3.69 (m, 1 H), 3.63-3.58 (m, 2 H), 3.17 (s, 3 H), 2.14-1.96 (m, 4 H), 1.94-1.80 (m, 1 H). LCMS (Method T2) Rt = 1.39 min; m/z 289.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73455-13-7, 4,5-Dichloropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; BELLENIE, Benjamin Richard; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; HUCKVALE, Rosemary; COLLIE, Gavin; MENICONI, Mirco; BRENNAN, Alfie; LLOYD, Matthew Garth; (222 pag.)WO2019/197842; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1448428-04-3 ,Some common heterocyclic compound, 1448428-04-3, molecular formula is C24H24FN7O, 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.

Compound WXBB-16 (740.00 mg, 1.27 mmol, 1.00 eq) (a purity of 76.2%), benzylamine (420.00 mg, 3.92 mmol, 428.57 muL, 3.09 eq), and potassium carbonate (550.00 mg, 3.98 mmol, 3.13 eq) were dissolved in acetonitrile (20.00 mL). Then the reaction was stirred at 90 C. for 48 hours. The reaction solution was added with water (30 mL), and then extracted with dichloromethane (30 mL*3). The organic phases were combined and dried over anhydrous sodium sulfate (15 g). The anhydrous sodium sulfate was filtered off, and the filtrate was dried on a rotary evaporator. The crude product was separated and purified by Prep-HPLC (column: Xtimate C18 150*25 mm*5 mum; mobile phase: [water (0.225% FA)-ACN]; B %: 25%-50%, 11.5 min) to obtain compound WX011-1. MS m/z: 533.2 [M+H]+.

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. 1448428-04-3, Selonsertib, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJIAN COSUNTER PHARMACEUTICAL CO., LTD.; Wu, Chengde; Yu, Tao; Li, Ning; Chen, Shuhui; US2019/375728; (2019); 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. 670253-37-9, name is 4-Chloro-5-iodopyridin-2-amine. A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Chloro-5-iodopyridin-2-amine

In a one-neck round bottom flask, 90.7 g (357.1 mmol) of compound IF was added to 500 ml of NMP, and 21.4 g (182.1 mmol) of Zn(CN)2 was added, and 41 g (35.7 mmol) of Pd(PPh3)4 was quickly added, reacted at 135C for 5 h. After the reaction was completed, a brown oily liquid was given. The reaction mixture was slowly poured into 3 L of ice water under stirring, and a large amount of tan solid was precipitated, filtered, washed with water and dried to give compound 1G, ESI-MS m/z: 154.2 [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, 670253-37-9, 4-Chloro-5-iodopyridin-2-amine.

Reference:
Patent; Shanghai Zheye Biotechnology Limited-Liability Company; LIU, Jianyu; ZHANG, Haidong; (30 pag.)EP3564242; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 60010-03-9 ,Some common heterocyclic compound, 60010-03-9, molecular formula is C6H4Cl2N2O2, 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.

Methylamine (2M in THF, 1.5 L, 3000 mmol) was added to a solution of 2,6-dichloro-4-methyl-3- nitropyridine (Step 1 of Example 1, 295 g, 1425 mmol) THF (4.5 L) while maintaining the temperature at 20C. The reaction mixture stirred for 2 h at rt, diluted with EtOAc (3 L) andwater (5 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 L). The combined organic extracts were washed with brine (5 L), dried (Na2504), filtered and the filtrate was evaporated in vacuo at 30C to afford the title compound (285 g, purity 81%) as yellow crystals. Rt: 1.07 mm (LC-MS 1); MS mlz: 201.0 [M] (LC-MS 1).

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. 60010-03-9, 2,6-Dichloro-4-methyl-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BOLD, Guido; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUeEGER, Heinrich; VAUPEL, Andrea; WO2015/75665; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 880870-13-3, 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 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of hydrogen chloride in 1,4-dioxane (4M, 0.020ml) was added to the solution of 5-bromo-2-chloro-4-methoxypyridine (0.18 g, 0.81 mmol) and methyl hydrazinecarboxyiate (0.30 g, 3.34 mmol) in ethanol (5 mi). The reaction mixture was heated in microwave reactor at 160 C for 9 hours. The mixture was cooled and evaporated to dryness. Purification of the evaporation residue by preparative reverse phase HPLC afforded 4.8 mg of 6-bromo-7-methoxy-[l ,2,4]triazolo[4,3-a]pyridin-3(2H)-one. 1H NMR (DMSO-de) delta: 12.24 (br s, 1H), 8.08 (s, 1H), 6.63 (s, 1H), 3.87 (s, 3H).

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; RICHTER GEDEON NYRT.; ORION CORPORATION; HAIKARAINEN, Anssi; JOUBERT, Muriel; KAROLYI, Benedek; KAeSNAeNEN, Heikki; PASSINIEMI, Mikko; POHJAKALLIO, Antti; SZANTO, Gabor; VAISMAA, Matti; (97 pag.)WO2019/43635; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6945-67-1, 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.6945-67-1, name is 2-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.

Take 2-bromo-4-aminopyridine (8.651g, 50.0mmol), triethylamine (15.179g, 150mmol)And dichloromethane (50mL) placed in the reaction flask, weigh di-tert-butyl carbonate(16.369g, 75.0mmol), added to the above reaction flask at 0 , add,The reaction was stirred at 40C for 4h. After the reaction is complete, cool to room temperature,Add saturated sodium bicarbonate solution and dichloromethane to the reaction system, extract,Take the organic phase and dry with anhydrous sodium sulfate. After concentration under reduced pressure and purification by column chromatography, the title compound was obtained.

Statistics shows that 6945-67-1 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-4-nitropyridine.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Wang Yazhou; Quan Xu; Liu Haixuan; Wang Xiaowei; Zhang Yan; Li Xue; Cao Chen; Guo Zhuang; Lv Kunzhi; Wang Hai; Zheng Guochuang; (126 pag.)CN111196804; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 717843-51-1 , The common heterocyclic compound, 717843-51-1, name is 3-Bromo-2-methoxy-4-methylpyridine, molecular formula is C7H8BrNO, 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 4: To a solution of compound 95 (990 mg, 4.9 mmol) in benzene (33 mL) was added NBS (870 mg, 4.9 mmol) followed by AIBN (40 mg, 0.25 mmol). The mixture was placed in an 80 C oil bath. After six hours, the reaction was diluted with EtOAc, washed with 1 M Na2C03 and brine, dried over MgS04, filtered and concentrated. The crude product was purified by flash chromatography eluting with heptanes/EtOAc (0-10%) to afford compound 96 as an oil (669 mg, 70% pure by NMR). 1H NMR (400 MHz, DMSO-d6) delta 8.14 (d, J = 5.0 Hz, 1 H), 7.22 (d, J = 5.0 Hz, 1 H), 4.68 (s, 2 H), 3.93 (s, 3 H).

The synthetic route of 717843-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem