Month: February 2021

Related Products of 72830-09-2 ,Some common heterocyclic compound, 72830-09-2, molecular formula is C8H11Cl2NO2, 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 1: Preparation of Pantoprazole sodium compound of formula-la:Added a solution of 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (50 grams in 250ml of water) to a solution of 49.8 grams of 5-difluoromethoxy 2-mercaptobenzimidazole, 500 ml water and sodium hydroxide (22.5 grams of flakes in 27.5 ml of water), slowly at 25-35C. Stirred the reaction mixture for 3 hours. Extracted the reaction mixture thrice with methylene chloride. Separated the organic and aqueous layer. Washed the organic layer with water. Cooled the organic layer to -5 to 0C. Added 550 grams of 3.1% sodium hypochlorite solution having pH 8.75 and assay 3.2 to the above reaction mixture at -5 to 0C. Stirred the reaction mixture for 3 hours at -5 to 0C. Quenched the reaction mixture with 56 grams of ammonium sulphate at below 10C. Stirred the reaction mixture for 30 minutes. Separated the organic and aqueous phases. Extracted the aqueous phase twice with methylene chloride. Washed the organic layer with water. Dried the organic phase over sodium sulphate. Distilled the solvent completely under reduced pressure at below 45C. Added 37.5 ml of acetone to the above crude and distilled the solvent completely under reduced pressure at below 45C. Dissolved the residue in 375 ml of acetone at 25-35C. Heated the reaction mixture to reflux temperature. Stirred the reaction mixture for 30 minutes at reflux temperature. Cooled the reaction mixture to 18-23C. Added aqueous sodium hydroxide solution (8.5 grams in 10 ml of water) at 18-23C. Stirred the reaction mixture for 1 hour at 18-23C. Cooled the reaction mixture to 0-5C. Stirred the reaction mixture for 3 hours. Filtered the solid and washed with acetone followed by washed with methylene chloride. The obtained solid is purified in acetone to get pure compound.The amount of sulfone compound of formula-6 and compound of formula- 1 present in the obtained solid was measured using HPLC and the results are as follows. Yield: 65 grams Example-3: Preparation of pantoprazole sodium sesquihydrate compound of formula-la:Added a solution of 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (50 grams in 250ml of water) to a solution of 49.8 grams of 5-difluoromethoxy-2- mercaptobenzimidazole, 500 ml of water and aqueous sodium hydroxide (22.5 grams of flakes in 27.5ml of water), slowly at 25-350C. Stirred the reaction mixture for 3 hours. Extracted the reaction mixture thrice with methylene chloride. Separated the organic and aqueous layer. Washed the organic layer with water. Added 550 grams of 3.1% sodium hypochlorite having pH 8.75 and assay 3.2 to the above reaction mixture at 25-300C for 2 hours. Stirred the reaction mixture for 10 hours at 25-3O0C. Quenched the reaction mixture with water at 25-300C. Stirred the reaction mixture for 30 minutes at 25-300C. Separated the organic and aqueous phases. Extracted the aqueous layer with methylene chloride. Washed the organic phase twice with aqueous sodium hydroxide solution. Separated the phases. Cooled the aqueous layer to 10-150C. Adjusted the pH of the reaction mixture to 9.3 with aqueous acetic acid. Added 250 ml of methylene chloride. Stirred the reaction mixture for 15 minutes. Separated the organic phase. Extracted the reaction mixture with methylene chloride. Washed the organic layer with water. Distilled the solvent completely from organic layer at below 45C under reduced pressure. Added 37.5 ml of acetone to the crude and distilled the solvent completely under reduced pressure at below 45C. Dissolved the residue in 375 ml of acetone at 25-35C. Heated the reaction mixture to reflux temperature. Stirred the reaction mixture for 30 minutes at reflux temperature. Cooled the reaction mixture to 18-23C. Added aqueous sodium hydroxide solution (8.5 grams in 10 ml of water) at 18-23C. Stirred the reaction mixture for 1 hour at 18-23C. Cooled the reaction mixture to 0-50C and 35 ml of methylene chloride was added. Stirred the reaction mixture for 3 hours. Filtered the solid and washed with methylene chloride. The above obtained compound can optionally purified as follows.Acetone (400 ml) was added to the above obtained wet compound and heated to reflux. The obtained solution was treated with carbon and cooled the filtrate to 0-5C. Stirred for 2 hours. Filtered the precipitated solid and washed with 30 ml of chilled acetone followed by washing with 50 ml of methylene chloride. Methylene chloride (250 ml) was added to the obtained wet compound at 25-35C. Stirred the reaction mixture for 90 minutes at 25-350C. Filtered the precipitated solid and washed with 25 ml of methylene chloride. Dried the compound at 40-500C for 10 hours.Yield: 70 grams W.C : 5.9 %HPLC : 99.93 %; 0.02 % (Sulfone Impurity) PSD : before micronization : D (v, 0.1) is 0.4 mum ; D (v, 0.5) is 8.73 mum; D (v, 0.9) is 27.7 mum andD(4,3) is 12.02 mum.PSD : after micronization 😀 (v,0.1) is 1.75 mum; D (v,Q.5) is 4.92 mum; D (v,0.9) is 13.10 mum andD(4,3) is 6.35 mum.Exam…

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. 72830-09-2, 2-Chloromethyl-3,4-dimethoxypyridinium chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MSN LABORATORIES LIMITED; WO2008/1392; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 122368-54-1, 2-((4-Chlorophenyl)(piperidin-4-yloxy)methyl)pyridine, 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, 122368-54-1, blongs to pyridine-derivatives compound. Product Details of 122368-54-1

To 10 mL of DMF were added 0.5 g of vanillic acid, 0.51 g of EDC, 0.44 g of HOBt, 1.44 mL of TEA and 0.99 g of 2-[(4-chlorophenyl)(4-piperidinyloxy)methyl]pyridine, and the mixture was stirred at 60 to 80C for 4 hours. 10 mL of EtOAc and 10 mL of purified water were added to the reaction mixture and the layers were separated. The aqueous layer was extracted once with 10 mL of EtOAc and the aqueous layer was discarded. The organic layer was washed three times with 10 mL of purified water, dried over Na2SO4 and filtered. The filtrate was distilled under reduced pressure and purified by flash column chromatography to obtain 0.40 g of the title compound as a pale yellow solid. Yield: 31.6% 1H NMR (400MHz, DMSO-d6) delta 9.41 (brs, 1H), 8.47 (d, J = 4.0 Hz, 1H), 7.81 (t, J = 7.0, 1H), 7.57(d, J = 8.0 Hz, 1H), 7.44?6.94(m, 6H), 6.84?6.67(m, 3H), 5.71(s, 1H), 3.87(s, 3H), 3.74?3.69(m, 2H), 3.37(brs, 2H), 1.85(brs, 2H), 1.72(brs, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,122368-54-1, its application will become more common.

Reference:
Patent; Shin Poong Pharmaceutical Co., Ltd.; RYU, JeiMan; LEE, Dong Won; LEE, Kang Hyeok; PARK, Jin Hun; CHO, Geum Sil; LEE, Ki Sung; CHUNG, Jin Ho; PARK, Woo Ile; LEE, Jae Young; (35 pag.)EP3345910; (2018); 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. 914358-73-9, name is 5-Bromo-2-methylpyridin-3-amine, molecular formula is C6H7BrN2, 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. Formula: C6H7BrN2

c) N-(5-bromo-2-methyl-3-pyridinyl)cyclopropanesulfonamide; In an oven dried round bottom flask under nitrogen, a solution of 5-bromo-2-methyl-3-pyridinamine (150 mg, 0.802 mmol) in anhydrous pyridine (4 mL) was treated with cyclopropanesulfonyl chloride (0.098 mL, 0.962 mmol) and the resultant reaction mixture stirred at room temperature for 18.75 hours. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate (100 mL) and water (30 mL), neutralized with saturated ammonium chloride (aq) and the product extracted into the organic layer. The aqueous layer was back-extracted with ethyl acetate (40 mL) and the combined organic layers washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to give a yellow-brown solid. Purification by silica gel chromatography (0-50% ethyl acetate in hexanes) provided the title compound (218 mg, 93%) as an off-white solid. MS (ES)+ m/e 290.9, 292.8 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 914358-73-9.

Reference:
Patent; CHAUDHARI, Amita; DHANAK, Dashyant; DONATELLI, Carla Ann; FAITG, Thomas H.; FENG, Yanhong; KNIGHT, Steven David; PARRISH, Cynthia A.; RALPH, Jeffrey M.; US2008/293706; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6602-32-0, 2-Bromo-3-hydroxypyridine, 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, COA of Formula: C5H4BrNO, blongs to pyridine-derivatives compound. COA of Formula: C5H4BrNO

6 g (87.25 mmol) of 1H-pyrazole (1H-pyrazole, a1) 16.86 g (95.98 mmol) of 2-bromopyridin-3-ol, b,25.685 g (185.843 mmol) of K2CO3,0.72 g (3.75 mmol) CuI,L-proline(L-proline) 0.94 g (8.16 mmol)And dimethyl sulfoxide (DMSO) And the mixture was stirred in a nitrogen atmosphere for two days.As a result, 5.6 g (40% yield) of ligand (III) was obtained as a white solid.

The synthetic route of 6602-32-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dankook UniversityAcademicCooperation; Lee, Jun Yeop; Oh, Chan Suk; (18 pag.)KR101627893; (2016); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13091-23-1, 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 13091-23-1, name is 4-Chloro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-enone (1.0 equiv.) in degassed dioxane and 2M Na2CO3 was added 4-chloro-3-nitropyridine (1.2 equiv.) and Pd(PPh3)4 (0.05 equiv.). The reaction was heated in an oil bath to 120 C. for 30 min. (reaction can also be carried out in the microwave for 10 min at 120 C.). Cooled to room temperature, then diluted with EtOAc, added H2O-dark solution, lots of emulsions. Filtered to get rid of the solids, then extracted the organic phase, dried with Na2SO4, and concentrated. The crude was purified via silica gel chromatography to yield 3-(3-nitropyridin-4-yl)cyclohex-2-enone (64%, 2 steps). LC/MS=219 (M+H), LC=2.29 min.

According to the analysis of related databases, 13091-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Burger, Matthew; Lan, Jiong; Lindvall, Mika; Nishiguchi, Gisele; Tetalman, Michelle; US2010/216839; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 67443-38-3, 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.67443-38-3, name is 5-Bromo-2-chloro-3-nitropyridine, molecular formula is C5H2BrClN2O2, molecular weight is 237.44, as common compound, the synthetic route is as follows.

Compound A (30.0 g), glycine-tert-butyl ester hydrochloride(23.3 g) and DMA (250 mL) was added triethylamine(38.4 mL) was added dropwise at 50 C. After completion of the dropwise addition,Followed by stirring at 50 C. for 2 hours. To the reaction mixture was added toluene (400 mL)And the mixture was washed with water, 1% hydrochloric acid and water in this order. After drying over sodium sulfate,A toluene solution of compound B was obtained.

Statistics shows that 67443-38-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloro-3-nitropyridine.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA COMPANY LIMITED; LEE, SHOUKOU; IWAMOTO, KOHEI; (57 pag.)JP2016/132649; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13466-38-1, 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. 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, 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.

Compound SM (1.73 g, 10 mol), 1-bromocyclopentane (1.79 g, 12 mmol) and cesium carbonate (6.52 g,20 mmol) was dissolved in 10 mL of DMF and reacted at 90 C overnight. The reaction is completed,Diluted with water and extracted three times with ethyl acetate. The organic phases were combined and washed three times with water.Wash once with saturated brine, dry over anhydrous sodium sulfate, and filter.The solvent was evaporated under reduced pressure, and the obtained oil was purified to give 5-bromo-1-cyclopentylpyridine-2(1H)-one (459 mg, yield 20%,White solid).

According to the analysis of related databases, 13466-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Gang; Luo Xiaoyong; Dong Zhenwen; Li Xiaoyong; Yu Hua; Zeng Hong; Song Hongmei; Wang Ying; Wang Lichun; Wang Jingyi; (49 pag.)CN109293652; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 149806-06-4, 6-Bromonicotinaldehyde, 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, Quality Control of 6-Bromonicotinaldehyde, blongs to pyridine-derivatives compound. Quality Control of 6-Bromonicotinaldehyde

To a solution of compound 5 (10 g, 54 mmol, 1 eq) in DCM (170 mL) was added compound 6 (7.4 g, 65 mmol, 1.2 eq). The mixture was stirred at rt for 30 minutes, then NaBH(OAc)3 (17.1 g, 81 mmol, 1.5 eq) was added portion wise. The mixture was stirred at rt for 12 h. After completion, the mixture was diluted with DCM (300 mL) and 2N NaOH (100 mL). The organic layer was separated and the aqueous layer was extracted with DCM (100 mL). The combined organic layers were dried over sodium sulfate, concentrated and purified by silica column chromatography to give the desired product (7 g, 46%). NMR (300 MHz, CDCb) delta 8.30 (s, 1 H), 7.55 (d, J= 8.1 Hz, 1 H), 7.44 (d, J= 8.1 Hz, 1 H), 3.49 (s, 2 H), 2.55- 2.48 (m, 10 H), 1.12 (t, J= 7.2 Hz, 3 H). LCMS: (M+H)+: 283.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,149806-06-4, 6-Bromonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BEIJING XUANYI PHARMASCIENCES CO., LTD.; SONG, Yuntao; CHEN, Xiaoqi; (188 pag.)WO2019/35008; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1620-76-4, 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 1620-76-4, name is 4-Methylpicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

II-3-2: Synthesis of 4-methylpicolinic acid A solution of 0.80 g (6.8 mmol) of 2-cyano-4-methylpyridine dissolved in 10.0 g of sulfuric acid was stirred under heating at 120 C. for 2 hours and then cooled to 20 C. A solution of 4.00 g of sodium sulfite in 8 ml of water was dropwise added at 20 to 25 C., and heated at the same temperature for 1.5 hours, and further, at 75 to 85 C. for 1.5 hours. After cooling, sodium carbonate was added to adjust the pH to about 3, and the mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the extract was concentrated under a reduced pressure and the residue recrystallized from an ethyl acetate hexane mixture to give 0.50 g of crystals (yield 53.8%). m.p.: 127-128 C. IR (KBr): 3400, 3150, 2600, 2150, 1590, 1515 cm-1.

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 1620-76-4, 4-Methylpicolinonitrile.

Reference:
Patent; Shiseido Company, Ltd.; US5219847; (1993); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 626-55-1, 3-Bromopyridine, 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, 626-55-1, blongs to pyridine-derivatives compound. Recommanded Product: 626-55-1

A mixture of 264 3-bromopyridine (0.38 mL, 4.0 mmol), 265 (4-methoxyphenyl)boronic acid (500 mg, 3.3 mmol), Pd(dppf)Cl2 (69 mg, 0.094 mmol), 105 K2CO3 (720 mg, 5.2 mmol), 31 dioxane (10 mL), and 18 water (5 mL), was bubbled with N2 for 1 min and then stirred at 110 C. for 12 h. After cooling to rt, the mixture was diluted with EtOAc, filtered through Celite, the filtrate washed with water, brine, dried (MgSO4), the solvent was removed by evaporation and the residue was purified (FCC, SiO2, 0-100% EtOAc/heptanes) to provide the 266 title compound (350 mg, 57%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta 8.8 (d, 1H, J=2.1 Hz), 8.5 (q, 1H, J=1.2, 3.3 Hz), 7.85-7.81 (m, 1H), 7.55-7.50 (m, 2H), 7.35-7.26 (m, 1H), 7.04-6.99 (m, 2H), 3.86 (s, 1H). [M+H]=186.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,626-55-1, its application will become more common.

Reference:
Patent; Dart NeuroScience, LLC; Bookser, Brett; Botrous, Iriny; Branstetter, Bryan; Dyck, Brian; Weinhouse, Michael; US2019/177327; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem