Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 120739-77-7, N-((6-Chloropyridin-3-yl)methyl)ethanamine, 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, 120739-77-7, blongs to pyridine-derivatives compound. category: pyridine-derivatives

1, In the 5000L stainless steel reactor,put disodium hydrogenphosphate 284kg, sodium dihydrogen phosphate, 67.9kg,720kg of tap water was added. Stirred solution becomes clear. At 25 deg.C, then 1500kg of methylene chloride was added, as well as N- (6-chloro – 3-pyridylmethyl) -N- ethylamine 341kg. Cooled 0 deg. C;2, was added dropwise 325 kg of 1,1-dichloro-2-nitroethylene, about 2 ~ 3h, temperature 5 ~ 10 deg.C;3, addition was complete at 5 ~ 10 deg.C. Maintain temperature for 2h; 4, then dropping 40% monomethylamine 390kg,about 2 ~ 3h, and maintain temperature for 2h at 5 ~ 10 deg.C ;5, then heated to 30 deg.C and hold temperature 1h; 6, still 30min, separated and the aqueous layer was further 500kg, extracted once with methylene chloride; 7, the combined organic phases, first at atmospheric pressure and then vacuum recovery methylene chloride, ethyl acetate500kg;8, 0 ~ 5 deg.C cooling crystallization 2h, centrifugal drying drying material, was 494.1kg, HPLC?99.5%,external standard content ?98%, a yield of 0.92.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,120739-77-7, its application will become more common.

Reference:
Patent; Shanghai Jinjing Chemical Co., Ltd.; Long, Congwei; Ma, Jun; Zhou, Xianpei; Tang, Songqing; Lv, Yejun; (9 pag.)CN105330593; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 130473-26-6, 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 130473-26-6 as follows.

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 RL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5C. 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 HC1. 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 CGH6N202+H : 163.0508, found 163.0507 (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,130473-26-6, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/39815; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 896139-85-8, Adding some certain compound to certain chemical reactions, such as: 896139-85-8, name is Imidazo[1,2-a]pyridin-7-ol,molecular formula is C7H6N2O, 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 896139-85-8.

A solution of imidazo [1,2-a] pyridine-7-ol (218 mg, 1.63 mmol)N-Boc-4-hydroxypiperidine (654 mg, 3.25 mmol) and Ph3P (1.71 g, 6.52 mmol) were dissolved in THF (30 mL)Then DBAD (748 mg, 3.25 mmol) dissolved in THF (10 mL) was added dropwise to the reaction solution at 0 C,After the room temperature reaction is complete,The product was quenched by the addition of water to give the product 7 (250 mg, 48%) by vacuum spin column chromatography.

According to the analysis of related databases, 896139-85-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; East China Normal University; Hu Wenhao; Xi Jianbei; Lei Ruirui; Zhu Mengli; Ma Mingliang; Xiao Guolan; Zhang Xiongwen; Fang Yanfen; Li Hongyu; (28 pag.)CN106496222; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 116308-38-4, Adding some certain compound to certain chemical reactions, such as: 116308-38-4, name is 2-Formylisonicotinonitrile,molecular formula is C7H4N2O, 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 116308-38-4.

Triethylamine (2.2 ml, 15 mmol) was added to a mixture of (3-oxo-1,3-dihydro-isobenzofuran-1-yl)-phosphonic acid dimethyl ester (i)(2.4 g, 10.2 mmol) and (iid) (10.2 mmol) in tetrahydrofuran (10 ml). The reaction mixture was stirred for over 12 hours at 25C and concentrated in vacuo to yield 2-[3-oxo-3H-isobenzofuran-(1£,Z)-ylidenemethyl]-isonicotinonitrile (iii-int) as a red solid which was taken towards the next step without purification. (c) 2-(3-Oxo-3H-isobenzofuran-1-ylidenemethyl)-isonicotinonitrile (iii-int)To a cooled suspension (ca 0C) of [(3-Oxo-1,3-dihydro-isobenzofuran-1-yl)-phosphonic acid dimethyl ester] phosphonate (i)(8.0g, 33.0mmol) in THF (400mL) was added crude 2-formyl-isonicotinonitrile (iid)(30.0mmol) followed by triethylamine (6.2mL, 33.0mmol). The mixture was stirred for 30 minutes at 0C and then allowed to warm overnight.The reaction mixture was then evaporated in vacuo, the resultant solid was then washed with ethyl acetate (2 x 50ml_), methanol (1x 15mL) and then diethyl ether (2x 20mL). Two peaks were detected in LC-MS analysis, the desired product; m/z (LC-MS, ESP), RT=4.27mins, (M+H)=249.0, and an impurity peak (approx 40%)RT=4.47mins M+H 194). This material used without need for any purification.

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. 116308-38-4, 2-Formylisonicotinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2006/21801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13472-56-5, 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 13472-56-5, name is 2-Methoxy-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-Methoxy-5-methylpyridine (50 g, 0.4 mol) was mixed with urea peroxide (330 g, 3.5 mol) in solvent trifluoroacetic anhydride (250 mL) and reacted at 120 C for 15 h After the reaction was completed, the reaction solution was poured into crushed ice and stirred continuously. After extraction with methylene chloride, the organic phase was concentrated to give 56 g of a white solid product, i.e., the 2-methoxy-5-methylpyridine -N-oxide (yield 99%, content 97%)

According to the analysis of related databases, 13472-56-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wuxi Jiehua Pharmaceutical Technology Co., Ltd.; Li Huan; Bao Liang; (6 pag.)CN106928130; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5006-66-6, 6-Oxo-1,6-dihydropyridine-3-carboxylic 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, Safety of 6-Oxo-1,6-dihydropyridine-3-carboxylic acid, blongs to pyridine-derivatives compound. Safety of 6-Oxo-1,6-dihydropyridine-3-carboxylic acid

Stage 1.-Preparation of 6-Hydroxynicotinamide A solution of 6-hydroxynicotinic acid (1.00 g, 7.19 mmol) and concentrated sulfuric acid (0.47 ml) in methanol (80 ml) was refluxed for 10 hours then poured into water and sodium bicarbonate (1.45 g) was added. The solvents were evaporated in vacuo and the residue was purified by flash chromatography on silica gel (eluding with 10% -20% methanol in dichloromethane) to give 6-hydroxynicotinic acid, methyl ester as a colourless solid (996 mg, 90%). The product was dissolved in concentrated aqueous ammonia solution and heated at 60 C. for 10 hours.

The synthetic route of 5006-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHRAMM, VERN L.; FURNEAUX, RICHARD HUBERT; TYLER, PETER CHARLES; CLINCH, KEITH; US2001/19823; (2001); 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.884494-82-0, name is 5-Fluoro-2-methoxynicotinic acid, molecular formula is C7H6FNO3, molecular weight is 171.13, as common compound, the synthetic route is as follows.Quality Control of 5-Fluoro-2-methoxynicotinic acid

PREPARATION 45-Fluoro-2,N-dimethoxy-N-methyl-nicotinamideTo a solution of 5-fluoro-2-methoxynicotinic acid (1 g, 5.8 mmol) in tetrahydrofuran (10 mL) was added 1 , 1 ‘-carbonyldiimidazole (1.4 g, 8.77 mmol, 1.5 eq.) portionwise over a 5 min period. The resulting solution was stirred at room temperature for 20 min before adding O, N-Dimethyl-hydroxylamine hydrochloride (0.63 g, 6.43 mmol, 1.1 eq.) and then stirred for a further 72 hr. The resulting mixture was then partitioned between ethyl acetate (30 mL) and 2M aqueous hydrochloric acid (30 mL). The organic phase was washed with 1 M aqueous sodium hydrogen carbonate (30 ml_), followed by brine (30 ml_) and then dried over magnesium sulphate. The resulting mixture was filtered and concentrated under reduced pressure to produce the title compound as a colourless oil (0.53 g, 43%).1H NMR (400 MHz, CDCI3): delta ppm 3.36 (br. s., 3 H) 3.55 (br. s., 3 H) 3.97 (s, 3 H) 7.33 – 7.44 (m, 1 H) 8.06 (d, J=2.73 Hz, 1 H).LRMS: APCI, m/z = 215 [M+H]+

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; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1072-98-6 , The common heterocyclic compound, 1072-98-6, name is 2-Amino-5-chloropyridine, molecular formula is C5H5ClN2, 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. Ethyl 6-Chloroimidazo[1,2-a]pyridine-2-carboxylate To 2-amino-5-chloropyridine (Aldrich; 2.19 g) in dimethoxyethane (Aldrich; 25 mL) is added ethyl 2-bromopyruvate (Aldrich; 2.37 mL). After stirring overnight, the solid is collected and washed with diethyl ether. The solid is dried under reduced pressure at 45 C. and then is partitioned between dichloromethane and aqueous sodium bicarbonate. The organic phases are dried over sodium sulfate and concentrated to give 3.05 g of ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate. 1 H NMR (CDCl3) delta1.44, 4.46, 7.23, 7.64, 8.16, 8.21.

The synthetic route of 1072-98-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmacia & Upjohn Company; US5912246; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59290-81-2, 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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid, molecular formula is C7H6N2O4, 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.

REFERENTIAL EXAMPLE 12 synthesis of N,N-diethyl 2-bromomethyl-5-nitronicotinamide To a solution of 0.6 g of 2-methyl-5-nitronicotinic acid and 3 ml of diethylamine in 100 ml of chloroform was added 20 g of phosphorus pentachloride and the resulting mixture was stirred at 60 C. for 3 hours. After cooling, the chloroform layer was separated, the solvent was distilled off under reduced pressure, the residue was mixed with water, neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was dried, concentrated and chromatographed over silica gel to give 0.4 g of the desired product as oil. Analysis for C11 H15 N3 O3: Calcd. (%): C, 55.68; H, 6.37; N, 17.71. Found (%): C, 55.57; H, 6.43; N, 17.56. To a solution of 0.4 g of N,N-diethyl-2-methyl-5-nitronicotinamide in 1.5 ml of acetic acid was added a solution of 0.27 g of bromine in 1.0 ml of acetic acid and the resulting mixture was stirred at 120 C. for 1.5 hours. The reaction mixture was poured into ice-water, made alkaline with sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off to give brown oily substance. This substance was chromatographed over silica gel to give 0.1 g of unreacted starting material and 0.28 g of N,N-diethyl 2-bromomethyl-5-nitronicotinamide. mp 62 – 64 C.

According to the analysis of related databases, 59290-81-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sankyo Company Limited; US4053608; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59942-87-9, 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. 59942-87-9, name is Pyrazolo[1,5-a]pyridin-2(1H)-one, molecular formula is C7H6N2O, 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.

A solution of pyrazolo[1,5-a]pyridin-2-ol (776 mg, 5.78 mmol), K2CO3 (2.4 g, 17.3 mmol), 1-bromo-4-chlorobutane (1.35 mL, 11.6 mmol) and sodium iodide (catalytic amount) in 20 mL of DMF was stirred for 18 h at room temperature. The resulting mixture was filtered, the solid washed with DMF and the organic filtrate concentrated. The residue was poured into diethyl ether and the generated precipitate filtered and discarded. The organic filtrate was washed with water and the organic layer dried (Na2SO4) and concentrated under vacuum to afford 1.35 g (quantitative) of brown oil.

According to the analysis of related databases, 59942-87-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laboratorios del. Dr. Esteve, S.A.; Diaz-Fernandez,Jose-Luis; Cuberes-Altisent,Mª Rosa; EP2631236; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem