Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 72093-13-1, 6-Chloro-2,3-dimethylpyridine, 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, 72093-13-1, blongs to pyridine-derivatives compound. Recommanded Product: 6-Chloro-2,3-dimethylpyridine

A mixture of 6-chloro-2,3-dimethylpyridine (400 mg), N-(czs-4-aminocyclohexyl)-3-chloro- 4-fluorobenzamide obtained in step A of example 1 (841 mg), and BuOH (0.8 mL) was heated in a microwave synthesizer at 180 0C for 20 min and 230 0C for 50 min. The mixture was diluted with CHCl3 and added to aqueous saturated NaHCO3. The aqueous layer was extracted with CHCl3 three times. The combined organic layer was dried over MgSO4, filtrated, concentrated under reduced pressure, and purified by medium-pressure liquid chromatography (NH-silica gel, 20% to 99% EtOAc EPO in hexane and silica gel, 3% to 5% MeOH in CHCl3) to give 3-chloro-N-{c/s-4-[(5,6- dimethylpyridin-2-yl)amino]cyclohexyl}-4-fluorobenzamide. To a solution of the above material in EtOAG (3 mL) was added 4 M hydrogen chloride in EtOAc (0.18 mL). The mixture was stirred at ambient temperature for 4 h and concentrated under reduced pressure. The residue was suspended in Et2O and the suspension was stirred at ambient temperature. The precipitate was collected by filtration, washed with Et2O, and dried at 80 0C under reduced pressure to give 3-chloro-N-{c-4- [(5,6-dimethylpyridin-2-yl)amino]cyclohexyl}-4-fluorobenzamide hydrochloride (112 mg) as a colorless powder.1H NMR (300 MHz, CDCl3, delta): 1.70-2.01 (m, 8H), 2.19 (s, 3H), 2.53 (s, 3H), 3.74-3.84 (m, IH), 4.04-4.20 (m, IH), 6.56 (d, J= 9.0 Hz, IH), 6.63 (d, J= 8.9 Hz, IH), 7.18 (t, J= 8.6 Hz, IH), 7.59 (d, J= 8.9 Hz, IH), 7.67-7.74 (m, IH), 7.94 (dd, J= 7.1, 2.3 Hz, IH), 8.71 (d, J= 8.6 Hz, IH), 14.74 (brs, IH); ESI MS m/z 376 [M (free)++l, 100%].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72093-13-1, its application will become more common.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; ARENA PHARMACEUTICALS, INC.; WO2006/35967; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 92992-85-3, 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. 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. A new synthetic method of this compound is introduced below.

To (2S,4S)-4-amino-2-methoxymethylpyrrolidine-1-carboxylic acid tert-butyl ester (300 mg) were added 2-bromo-3,5-dimethylpyridine (291 mg),tris(dibenzylideneacetone)dipalladium(O)(30 mg),2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (41 mg),sodium tert-butoxide (188 mg) and toluene (6 mL) and the mixture was stirred at 80c for 6 hr. The reaction mixture was purified by column chromatography (hexane:ethyl acetate)to give (2S,4S)-4-(3,5-dimethylpyridin-2-ylarnino)-2-methoxymethylpyrrolidine-1-carboxylic acid tert-butyl ester (489 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,92992-85-3, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131747-62-1, 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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, molecular formula is C7H4F3NO, 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.

To a solution of 214 (110 mg, 0.322 mmol)) in toluene 15 ml was added 66 (84.9 mg, 0.483 mmol). PTSA (122.4 mg, 0.644 mmol) was added to the reaction mass, which was stirred at 120 C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude 215, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 10% ethyl acetate in hexane to afford yellow coloured solid 215.

According to the analysis of related databases, 131747-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; US2015/72980; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 24195-07-1, 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. 24195-07-1, name is 2-(Methoxycarbonyl)nicotinic acid. A new synthetic method of this compound is introduced below.

2-(Methoxycarbonyl)pyridine-3-carboxylic acid (3 g, 16.57 mmol) was dissolved in 50 mL of t-ButOH and 4 mL of TEA were added. The solution was stirred for 5 min at room temperature, then diphenylphosphorylazide (3.6 mL, 16.57 mmol) was added and the reaction was refluxed for 3 hours. The mixture was concentrated and the residue purified flash chromatography (silica) eluting with ethyl acetate in cyclohexane from 20 to 50%. The fractions containing the product were collected and concentrated in vacuo to give methyl 3-{[(tert- butoxy)carbonyl]amino}pyridine-2-carboxylate (1.6 g, 38.5% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24195-07-1, 2-(Methoxycarbonyl)nicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89466-17-1, Adding some certain compound to certain chemical reactions, such as: 89466-17-1, name is 6-Bromo-5-methylpyridin-2-amine,molecular formula is C6H7BrN2, 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 89466-17-1.

To a stirred solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (250 mg, 1.07 mmole) in 10 mL of CH2Cl2, was added 1-methyl imidazole (0.21 mL, 2.5 equiv.) at 0-5 C. under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0-5 C. and then added methane sulfonyl chloride (0.1 mL, 1.2 equiv) at the same temperature. It was stirred for 1 h at 0-5 C. Then 6-bromo-5-methylpyridin-2-amine (200 mg, 1 equiv) was added, and stirred for 18h at room temperature. Water (10 mL) was added to the reaction mixture, layers were separated and aqueous layer was extracted with DCM (3×10 mL). The combined organic layer was washed with 1N HCl (10 mL), followed by Sat NaHCO3 (10 mL) and then with brine (10 mL). Combined organic layer was dried over Na2SO4, concentrated and to obtain titled compound 404 mg (quantitative yield).

According to the analysis of related databases, 89466-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 98353-08-3, 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. 98353-08-3, name is 5-Ethoxypicolinic acid. A new synthetic method of this compound is introduced below.

5-Ethoxypicolinic acid (53.6 mg, 320 muiotaetaomicron) was suspended in dichloromethane (5 mL), the suspension was cooled to 0-5C (ice bath) and oxalyl chloride (56.9 mg, 39.3 mu, 448 muiotaetaomicron) as well as dimethylformamide (0.308 M in toluene, 51.9 mu, 16 muiotaetaomicron) were added. The mixture was stirred for 2.5 h at room temperature. Then, it was concentrated in vacuo (40C, 5 mbar) and dried azeotropically by two cycles of addition of toluene (3 mL) followed by concentration in vacuo to afford 5-ethoxypicolinoyl chloride as purple oil (59 mg, quant.). After that, tert-butyl ((3aS,4R,8R)-4-(5-amino-2-fluorophenyl)-4,7,7-trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H- isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int-16ABp, 80 mg, 188 muiotaetaomicron) was dissolved in dichloromethane (5 mL), the solution cooled to 10C and N,N-diisopropylethylamine (36.5 mg, 49.4 mu, 283 muiotaetaomicron) was added, followed by a solution of 5-ethoxypicolinoyl chloride (vide supra, 47.5 mg, 256 muiotaetaomicron) in dichloromethane (4 mL). The reaction mixture was stirred for 15 min at 10C. Then, methanol (2 mL) was added, the mixture was stirred for 5 min at room temperature and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 24 g, eluting with 2 M ammonia in methanol / dichloromethane, gradient 1:99 to 3:97) to yield, after drying in vacuo (40C, 5 mbar), the title compound as a colorless viscous oil (95 mg, 88% yield). HPLC (method LCMS_fglm) tR = 1.36 min. MS (ES+) m/z 574.4 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98353-08-3, 5-Ethoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; OBST SANDER, Ulrike; VIFIAN, Walter; WOLTERING, Thomas; (89 pag.)WO2017/25491; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 39856-58-1, name is 2-Bromopyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Bromopyridin-3-amine

1.22 ml 2-oxo-propionic acid, 0.26 g palladium acetate and 3.20 ml triethylamine were added to a solution of 1.00 g 2-bromo-pyridin-3-yl amine and 1.21 g triphenyl-phosphine in 10 ml N,N-dimethylformamide. The reaction mixture was stirred for 4 hours at 100C. After removal of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel with dichloromethane/ methanol as eluent. Yield: 260 mg MS(ES+): m/e=163. 1H-NMR (400 MHz, DMSO/TMS): delta = 13.30 (s, 1H); 12.00 (s, 1H); 8.45 (d, 1H); 7.82 (d, 1H); 7.25 (dd, 1H); 7.14 (s, 1H)

With the rapid development of chemical substances, we look forward to future research findings about 39856-58-1.

Reference:
Patent; Aventis Pharma Deutschland GmbH; EP1479680; (2004); 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. 1064783-29-4, name is 5-Chloro-3-fluoro-2-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Chloro-3-fluoro-2-nitropyridine

To the solution of 229 (100 mg, 0.39 mmol) in dried THF (10mL) was added t-BuOK (44 mg, 0.39 mmol) . The mixture was stirred at room temperature for 10min, then was added 2-nitro-3-fluoro-5-chloropyridine (69 mg, 0.39 mmol) and continued to stirred at room temperature for 1h. The reaction was quenched with silica gel (1g) , and purified by column chromatography to give the desired product (153 mg, 95%) .

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, 1064783-29-4, 5-Chloro-3-fluoro-2-nitropyridine.

Reference:
Patent; FUJIAN HAIXI PHARMACEUTICALS CO., LTD; FENG, Yan; WANG, Ruyong; LI, Junqing; ZHENG, Jianjia; LIAN, Xin; GONG, Xuan; FU, Yueli; KANG, Xinshan; (144 pag.)WO2019/174601; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 885588-17-0, Adding some certain compound to certain chemical reactions, such as: 885588-17-0, name is 5-Fluoro-2-methylisonicotinic acid,molecular formula is C7H6FNO2, 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 885588-17-0.

A mixture of 4-(6-(4-amino-4-methylpiperidin-l-yl)pyridin-3-yl)-6-(2-hydroxy-2- methylpropoxy)pyrazolo[l,5-a]pyridine-3-carbonitrile dihydrochloride (Intermediate P48; 50 mg, 0.10 mmol), HATU (90 mg, 0.238 mmol), 5-Fluoro-2-methylisonicotinic acid (18 mg, 0.12 mmol) in DMSO (793 muIota_/) was treated with DIEA (93 mu,, 0.535 mmol) and then stirred for 18 h at ambient temperature. The reaction mixture was diluted with EtOAc and washed with water. The organic extracts were washed with brine, then dried over anhydrous Na2S04(S), filtered and concentrated in vacuo. The reaction was purified directly by silica chromatography (1-10% MeOH in DCM as the gradient eluent) to cleanly provide the title compound (41.9 mg, 63.2% yield) MS (apci) m/z= 558.3 (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. 885588-17-0, 5-Fluoro-2-methylisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 116308-38-4, 2-Formylisonicotinonitrile, 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, blongs to pyridine-derivatives compound. Recommanded Product: 2-Formylisonicotinonitrile

General procedure: The E isomer of hydrazones 1-15 all can be easily to get by similar procedures. The corresponding aldehydes and hydrazine hydrochloride were added to the methanol solution, then the reaction mixture was heated under reflux for 10 h. After the reaction was finished, removed the solvent in vacuo. The residue was dissolved in water and neutralized with saturated NaHCO3 solution. Afterwards, extracted with dichloromethane and collected the organic layer. The organic layer were dried over by Na2SO4, filtered and concentrated. The residue was recrystallized by methanol to give the pure product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116308-38-4, its application will become more common.

Reference:
Article; Lu, Chaocao; Htan, Bu; Fu, Shitao; Ma, Chunmiao; Gan, Quan; Tetrahedron; vol. 75; 30; (2019); p. 4010 – 4016;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem