Tag: M.W:100-200

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. 181123-11-5, name is 5-Chloro-2-cyano-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H2ClN3O2

Step 1: 3-Amino-5-chloropicolinamide To a suspension of 5-chloro-2-cyano-3-nitropyridine (1.274 mL, 10.9 mmol) in water (22 mL) was added 28% aqueous ammonium hydroxide (3.94 mL, 28.3 mmol), and the reaction was stirred at RT for 20 minutes. Sodium hydrosulfite (2.68 mL, 32.7 mmol) was added, and the reaction mixture was stirred at RT for 70 minutes. The yellow precipitate was collected by vacuum filtration to provide the title compound (1.097 g, 6.39 mmol) as yellow solid. 1H-NMR (400 MHz, DMSO-d6): delta 7.88 (br. s, 1H), delta 7.73 (s, 1H), delta 7.39 (br. s, 1H), delta 7.23 (s, 1H), delta 7.06 (br. s, 2H). LC/MS (ESI+) m/z=172 (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, 181123-11-5, 5-Chloro-2-cyano-3-nitropyridine.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69142-64-9, 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 69142-64-9, name is Ethyl 6-aminopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Step 2. Preparation of ethyl 6-(tert-butoxycarbonylamino)picolinate (79):To a solution of ethyl 6-aminopicolinate 78 (5.5 g, 33 mmol) in £-BuOH (120 mL) and acetone (40 mL) was added 4-dimethylaminopyridine (0.08g, 0.66 mmol) and di-tert-butyl dicarbonate (10.8 g, 49.5 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was removed by concentration under reduced pressure and a mixture of hexane/dichloromethane (180 mL, 3:1) was added. The resulting mixture was cooled to -20 0C for 2 h. The resulting solids were collected by filtration and dried to afford 79 (11.O g, 91 % yield).

According to the analysis of related databases, 69142-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; OALMANN, Christopher; PERNI, Robert, B.; VU, Chi, B.; WO2010/37127; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 769-28-8, 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.769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, molecular formula is C8H8N2O, molecular weight is 148.16, as common compound, the synthetic route is as follows.

Palladium on carbon (10%) (3.24 g) was charged into a 2 L dry Parr bottle and asmall amount of acetic acid was added. Next added 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (30 g, 202.7 mmol), sodium acetate (30.75 g, 375.0 mmol),platinum oxide (0.218 g), and acetic acid (1 L) .. The bottle was capped, placed on Parrapparatus, and shaken under an atmosphere ofH2 (100 psi) for 2 days. The reaction mixture was filtered. The solvent was removed to give a residue, which was treated with150 mL of cone. HCl, and the formed solids were filtered. The yellow filtrate wasconcentrated. To the crude compound was added 30 mL of cone. HCl and 150 mL EtOH,the contents cooled to 0 C, and stirred at 0 oc for 2h. The formed solids were filtered,washed with cold EtOH, ether, and dried. The product was collected as 36 g. This batchwas combined with other batches prepared on smaller scales and triturated with ether togive 51 g of pure compound. IH NMR (400 MHz, DMSO-d6) 8 ppm 11.85 (br s,l H) 8.13(br s, 3 H) 5.93-6.01 (m, 1 H) 3.72-3.80 (m, 2 H) 2.22 (s, 3 H) 2.16 (s, 3 H).

The chemical industry reduces the impact on the environment during synthesis 769-28-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; BURGESS, Joelle, Lorraine; DUQUENNE, Celine; KNIGHT, Steven, David; MILLER, William, Henry; NEWLANDER, Kenneth, Allen; VERMA, Sharad, Kumar; WO2013/173441; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55676-22-7, 3-Acetyl-6-chloropyridine, 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 3-Acetyl-6-chloropyridine, blongs to pyridine-derivatives compound. Safety of 3-Acetyl-6-chloropyridine

To a solution of l-(6-chloropyridin-3-yl)ethanone (4.0 gm, 0.0257 mole) in DMF (15 mL), cesium carbonate (16.8 gm, 0.051 mole) was added followed by addition of methyl 2-hydroxyacetate (8.0 ml, 0.103 mmoles) at 25 C under nitrogen atmosphere and the reaction mixture was stirred at 80-90 C for 18 h. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evapourated under reduced pressure. The crude product was purified by colunm chromatography (Eluent: 16% ethyl acetate in hexane) to yield 1.25 gm (23%) of product as off white solid. NMR: DMSO-< 6,? 2.55 (s, 3H), 3.67 (s, 3H), 5.02 (s, 2H), 7.04 (dd, J = 8.8 & 0.4 Hz, 1H), 8.20 (dd, J= 8.8 & 2.4 Hz, 1H), 8.78 (d, J= 2.0 Hz, 1H). At the same time, in my other blogs, there are other synthetic methods of this type of compound,55676-22-7, 3-Acetyl-6-chloropyridine, and friends who are interested can also refer to it. Reference:
Patent; CADILA HEALTHCARE LIMITED; DESAI, Ranjit, C.; PINGALI, Harikishor; PANDYA, Vrajesh; MAKADIA, Pankaj; PATEL, Pankaj; WO2014/192023; (2014); A1;,
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. 136117-74-3, name is Imidazo[1,2-a]pyridine-8-carbaldehyde, the common compound, a new synthetic route is introduced below. COA of Formula: C8H6N2O

Preparation of ethyl imidazopyridine propenoate (According to the Literature Method: Chezal, J. M. and al. J. Org. Chem. 2001, 66, 6576-6584).Ethyl azidoacetate (1.81 g, 14.0 mmol) was added dropwise at -30 C. to a stirred solution containing sodium (0.20 g, 8.70 mmol) in dry ethanol (10 mL). To this solution was added dropwise a solution of aldehyde 4 (1.00 mmol) in dry ethanol (8 mL). The reaction mixture was returned back room temperature and stirred for 3 h (CAUTION: an exothermic reaction can take place, with gas expansion). The solution was poured into aqueous saturated ammonium chloride solution (30 mL) and then extracted with CH2Cl2. The organic layers were dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by chromatography using CH2Cl2 as eluent to afford the azide derivative 6; Example 35 Ethyl alpha-azido-beta-(imidazo[1,2-a]pyridin-8-yl)propenoate (6a) From 4a (yield: 10%); mp: 150-152 C.; IR (KBr) 2100, 1700, 1600, 1280 cm-1; 1H NMR (400 MHz, CDCl3) delta 1.41 (t, 3H, J=7 Hz), 4.39 (q, 2H, J=7 Hz), 6.83 (t, 1H, J=7 Hz), 7.57 (d, 1H, J=1 Hz), 7.61 (d, 1H, J=1 Hz), 7.76 (s, 1H), 8.06 (dd, 1H, J=7, 1 Hz), 8.17 (dd, 1H, J=7, 1 Hz). MS m/z 257 (M+, 1), 229 (61), 183 (100), 155 (31), 129 (23), 104 (14). Further elution gave 8-methylimidazo[1,2-a]pyridine (yield: 10%-Kaiser, C. and al. J. Med. Chem. 1992, 35, 4415-4424).

The synthetic route of 136117-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universite D’Auvergne Clermont 1; Universite Francois Rabelais Tours; Katholieke Universiteit Leuven; US2010/93781; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1603-40-3, 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 1603-40-3, name is 3-Methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Example 1; Synthesis of 3-amino-1-hydroxy-3,4-dihydro-1,8-naphthyridin-2(1H)-one, trifluoroacetate salt (8); 3-Methyl-2-nitropyridine (2); To a solution of H2O2 (120 g, 1.1 mol) in fuming sulfuric acid (250 mL) was added a solution of 3-methylpyridin-2-amine (1) (16 g, 0.15 mol) in concentrated sulfuric acid (50 mL) drop-wise, while keeping the reaction temperature at 0 C. After stirring for 3 h at 10-25 C., the reaction mixture was brought to pH=11-12 by adding an aqueous 40% NaOH solution at 0-5 C. The resulting mixture was extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over Na2SO4 and filtered. The solvent was removed in vacuo to give the desired compound (18.2 g, 89%) as a yellow oil.

According to the analysis of related databases, 1603-40-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2010/324043; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1072-97-5, 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 1072-97-5 as follows.

Step-1: Synthesis of ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate To a stirred solution of 5-bromopyridin-2-amine (10.0 g, 56.0 mmol, 1.0 eq.) and ethyl 3-bromo-2-oxopropanoate (12.6 g, 64.0 mmol, 1.1 eq.) in Dioxane (200 mL) was added MgSO4 (20.0 g, 150.0 mmol, 3.0 eq.) at RT. The resulting mixture heated to 80 C. for 16 h. Following this, reaction mixture cooled to RT filtered the solid and under vacuum and filtrate concentrated to get crude. The crude purified by normal phase silica-gel column to get title compound (12 g, 79%). LCMS: 269.9 [M+1]+; 1H NMR (400 MHz, DMSO-d6) delta ppm 8.91 (d, J=1.32 Hz, 1H) 8.47 (s, 1H) 7.62 (d, J=9.65 Hz, 1H) 7.47 (dd, J=9.65, 1.75 Hz, 1H) 4.31 (q, J=7.16 Hz, 2H) 1.31 (t, J=7.02 Hz, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1072-97-5, its application will become more common.

Reference:
Patent; INTEGRAL BIOSCIENCES PRIVATE LIMITED; CHAKRAVARTY, Sarvajit; PENDHARKAR, Dhananjay; RAMACHANDRAN, Sreekanth A.; BATHULA, Chandramohan; SONI, Sanjeev; KUMAR, Vivek; SAEED, Uzma; DANODIA, Abhinandan Kumar; SHARMA, Ankesh; JADHAVAR, Pradeep S.; US2020/206233; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 850349-02-9, 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.850349-02-9, name is 8-Bromoimidazo[1,2-a]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.

l-Iodo-2,5-pyrrolidinedione (2.28 g, 10.15 mmol) was added to a solution of 8-bromo- imidazo[l,2-a]pyridine (2 g, 10.15 mmol) in CH3CN (8 ml). The r.m. was stirred at r.t. for 30 min. The mixture was concentrated in vacuo and the residue was purified by flash chromatography over silicagel (eluent: DCM/MeOH(NH3) from 100/0 to 99/1). The product fractions were collected and the solvent was evaporated in vacuo. Yield: 2.89 g of intermediate 5 (84.6 %).

Statistics shows that 850349-02-9 is playing an increasingly important role. we look forward to future research findings about 8-Bromoimidazo[1,2-a]pyridine.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; TRESADERN, Gary, John; TRABANCO-SUAREZ, Andres, Avelino; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2010/70008; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18653-75-3, 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 18653-75-3, name is 2-(1H-Imidazol-2-yl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Na2MoO4·2H2O (0.847g, 3.5mmol), 2-pyim (0.0065g, 0.040mmol), Mo powder (0.06g, 0.60mmol), ZnCl2 (0.136g, 1mmol), H3PO3 (0.02g, 0.25mmol), tetrabutylammonium hydroxide (TBAOH, 0.2mL, 0.3mmol) and distilled water (9.0mL) were stirred for 1h under the room temperature. An aqueous solution of 2molL-1 HCl was added into the mixture and the pH value was adjusted to 3.8. After that, the mixture continues to stir for an another 2h. Finally, the product was transferred to 25 Teflon-lined antoclave and was heated to 180C for 3days before cooled down to the room temperature. In the end, dark-red crystals 2 were collected and dried in air (yield: 62.45%). Elemental analysis: calculated: C, 14.11; H, 1.36; N, 6.17; found: C, 14.01; H, 1.28; N, 6.58.

According to the analysis of related databases, 18653-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Han, Ye-Min; Cheng, Wei-Wei; Cao, Jia-Peng; Yang, Mu-Xiu; Hong, Ya-Lin; Kang, Run-Kun; Xu, Yan; Inorganica Chimica Acta; vol. 498; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14150-94-8, Adding some certain compound to certain chemical reactions, such as: 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one,molecular formula is C6H5N3O5, 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 14150-94-8.

A mixture ofbenzyl (3-oxocyclohexyl)carbamate (247 mg, 0.999 mmol) and 1-methyl- 3,5-dinitropyridin-2(1H)-one (300 mg, 1.507 mmol) in ammonia/MeOH (1M, 6 mL) was microwaved at 90 C for 30 mm to provide a blackish-red solution. Eleven more samples of the same composition were run under the same conditions. The twelve samples were combined and evaporated under reduced pressure. The residue was partitioned between DCM (300 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was washed with brine (100 mL), dried (MgSO4), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 50% EtOAc in hexanes) provided a mixture of benzyl (3-nitro- 5,6,7, 8-tetrahydroquinolin-7-yl)carbamate and undesired regioi somer benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-5-yl)carbamate as a pale yellow gum. The mixture was used without further purification. MS (ESI, m/z): 213 [M+H]t; j00424J A solution of benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (2.64 g, 8.07 mmol) in ethanol (110 mL) was treated with tin(II) chloride dihydrate (9.10 g, 40.3 mmol) and conc. HC1 (1 mL), then stirred at 80 C for 75 mm. The solution was allowed to cool, then was concentrated under reduced pressure to about 15 mL. The sample was made basic (pH 9) by addition of saturated aqueous NaHCO3; about midway through, the sample was diluted with DCM (100 mL). The mixture was triturated, then filtered, and the filter cake was washed with DCM (50 mL). The filter cake was triturated and sonicated in MeOH (200 mL), then the mixture was filtered. The slightly cloudy filtrate was filtered through Celite 545, then concentrated to provide a yellow solid. Purification by silica gel chromatography (0 to 15% MeOH in DCM) provided a mixture of benzyl (3-amino-5,6,7,8-tetrahydroquinolin-7-yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification. MS (ESI, m/z):298 [M+H]t; 1004251 A sample of benzyl (3-amino-S ,6, 7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (1.25 g, 4.22 mmol) was treated with ACN (17 mL). The material was cooled on a dry ice / ethylene glycol bath (approximately -10 to -15 C) and PTSA monohydrate (1.61 g, 8.45 mmol) was added. After stirring 10 mm, a solution of potassium iodide (1.05 g, 6.33 mmol) and sodium nitrite (0.436 g, 6.32 mmol) in water (3.4 mL) was added dropwise over 20 mm. The dry ice bath was replaced with an ice bath, and the reddish-brown mixture was stirred at 0 C for 3 h 40 mm. The solution was diluted with EtOAc (50 mL), cooled on an ice bath and treated with saturated aqueous NaHCO3 until basic (pH 8-9). The organic layer was removed and the aqueous layer was extracted once more with EtOAc (50 mL). The combined organics were washed sequentially with water and brine (50 mL each), dried (Na2504), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 23% EtOAc in hexanes) provided a mixture of benzyl (3-iodo-S,6,7,8-tetrahydroquinolin-7- yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification.MS (ESI, m/z): 409 [M+H]; 1004261 A mixture of t-BuXPhos Pd G4 (76.3 mg, 94.4 tmole), benzyl (3-iodo-5,6,7,8- tetrahydroquinolin-7-yl)carbamate and regioisomer (605.0 mg, 1.482 mmol), tert-butyl piperazine-1-carboxylate (553.5 mg, 2.97 mmol), and sodium tert-butoxide (257.1 mg, 2.68 mmol) was sealed in a 40-mL vial. The atmosphere was evacuated and replaced with nitrogen, three times. Dioxane (15 mL) was added and the solution was stirred at ambient temperature for three days. Material at the same stage from a previous run (from 40.7 mg, 0.100 mmol iodo starting material) was added. The mixture was diluted with EtOAc (100 mL), treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 87% EtOAc in hexanes) provided a mixture of tert-butyl 4-(7-(((benzyloxy)carbonyl)amino)-5 ,6,7, 8-tetrahydroquinolin-3 – yl)piperazine-1-carboxylate and regioisomer as a yellow foam. The mixture was used without further purification. MS (ESI, m/z): 467 [M+H].

According to the analysis of related databases, 14150-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem