Month: April 2022

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.67367-24-2, name is Methyl 4-hydroxynicotinate, molecular formula is C7H7NO3, molecular weight is 153.1354, as common compound, the synthetic route is as follows.Safety of Methyl 4-hydroxynicotinate

A solution of the required alcohol (0.30 mmol; 3 eq.) in DMF (0.2 mL), in a glass vial under inert atmosphere (N2), is treated with NaH (3.3 eq.) at rt. After 10 min, it is treated with a solution of the chloride (0.10 mmol; 1 eq.) in DMF (0.8 mL) and the reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is either treated with silica gel-supported sulfonic acid (5.0 eq.; Silicycle SiliaBond Tosic Acid; SCX; R60530B; 0.8 mmol/g), shaken 1 h at rt and filtered, or loaded on a corresponding cartridge (Silicycle SiliaPrep Tosic Acid Si-SCX). In both cases, the resin is then washed with DCM, 1:1 DCM/MeOH and MeOH, and the product eventually released from the resin with 7M ammonia solution in MeOH. The solution of crude product is concentrated under reduced pressureand purification of the residue gives the desired product.Example 212 4-[3-(3-ethyl-ureido)-isoquinolin-8-ylmethoxy]-nicotinic acid methyl ester hydrochloride Starting from the compound of Preparation R and methyl 4-hydroxynicotinate and proceeding in analogy to Procedure AC, the title compound was obtained, after purification by prep-HPLC (acidic conditions) and treatment with HCl, as an amorphous solid (21% yield). MS (ESI, m/z): 381.28 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67367-24-2, Methyl 4-hydroxynicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Bur, Daniel; Gude, Markus; Hubschwerlen, Christian; Panchaud, Philippe; US2013/96119; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 76006-11-6 ,Some common heterocyclic compound, 76006-11-6, molecular formula is C6H4ClN3, 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.

General procedure: Chloro derivative 6 (490 mg, 3.19 mmol) was dissolved into concentrated sulfuric acid (9.50 mL) at 0C and then a mixture ofconcentrated sulfuric acid (0.49 mL) and nitric acid (0.49 mL)was added dropwise into this solution. This reaction mixturewas heated at 95C for 1h. Upon cooling, it was poured intocrashed ice, neutralized with an aqueous solution of NH3 andthe product was extracted with ethyl acetate (3×100 mL). Thecombined organic layers were dried over Na2SO4 and evaporated under reduced pressure to provide 600 mg of pure 7 asa yellow solid.

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. 76006-11-6, 7-Chloro-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sklepari, Meropi; Lougiakis, Nikolaos; Papastathopoulos, Athanasios; Pouli, Nicole; Marakos, Panagiotis; Myrianthopoulos, Vassilios; Robert, Thomas; Bach, Stephane; Mikros, Emmanuel; Ruchaud, Sandrine; Chemical and Pharmaceutical Bulletin; vol. 65; 1; (2017); p. 66 – 81;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56826-61-0, 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 56826-61-0 as follows.

A solution of methyl 2-methylnicotinate (0.5 g, 3.3 mmol) in THF (16 mL) at 0 C. was treated dropwise with lithium aluminum hydride in THF (6.6 mL, 1 M), stirred at 0 C. for 1.5 hours, treated with ethyl acetate (3 mL), warmed to 25 C., and partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. A solution of the residue (0.391 g) in dichloromethane (16 mL) was treated with MnO2 (2 g), stirred at 25 C. for 68 hours, filtered through celite, and the solvent was evaporated to give the title compound (0.303 g, 75% yield), which was used without further purification

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56826-61-0, its application will become more common.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; US2005/131017; (2005); 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. 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine, molecular formula is C8H7BrN2, 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. Product Details of 116355-18-1

The compound of example 146 (8 g, 37.9 mmol) was treated with 6-methylpyridin-3- ylboronic acid (5.71 g, 41 .7 mmol) in the presence of [1 ,1 ‘-Bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.495 g, 0.606 mmol) and sodium carbonate (6.03 g, 56.9 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 8.0 g (95 %); 1 H NMR (DMSO-d6, 300 MHz): delta 2.2 (s, 3H, CH3), 2.54 (s, 3H, CH3), 7.35-7.37 (d, 1 H, J=8.1 Hz, Ar), 7.50-7.53 (d, 1 H, J=8.7 Hz Ar), 7.53 (s, 1 H, Ar), 7.76-7.80 (dd, 1 H, J=2.4 Hz & J=5.7 Hz, Ar Ar), 7.8 (s, 1 H, Ar), 8.4 (s, 1 H, Ar), 8.49-8.50 (d, 1 H, J=1 .8 Hz, Ar); MS (ES+): m/e 224.1 (M+1 ).

With the rapid development of chemical substances, we look forward to future research findings about 116355-18-1.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GHOSH, Usha; MORE, Tulsidas; KULKARNI, Mahesh; BAJAJ, Komal; BURUDKAR, Sandeep; RIZVI, Zejah; WO2014/80241; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22282-96-8, 2-Bromo-6-methyl-5-nitropyridine, 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, 22282-96-8, blongs to pyridine-derivatives compound. Product Details of 22282-96-8

To a stirred solution of 6-bromo-2-methyl-3-nitropyridine (15 g, 69.12 mmol) in ethanol (280 mL) was added iron powder (57.9 g, 1036 mmol) followed by conc HCl (30 mL). The reaction mixture was stirred for 6 h at 100 C., after completion of reaction (monitored by TLC), reaction mixture was cooled to room temperature, filtered through celite. Filterate was basified with saturated NaHCO3 solution, extracted with EtOAc. Organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product was used in next step without further purification to afford desired compound (5.6 g, 65%) as an off-white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-96-8, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; BOCK, Mark; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (141 pag.)US2016/347717; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 107867-51-6, 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. 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine. A new synthetic method of this compound is introduced below.

B. 6-Trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one Add 1,1′-carbonyldiimidazole (1.0 g, 6.17 mmol)to a solution of 5-trifluoromethyl-pyridine-2,3 diamine (0.90 g, 5.08 mmol) in CH2Cl2 (10 mL) and stir at room temperature for 18 hours. Heat the solution to reflux for 2 hours and filter the precipitate to obtain 6-trifluoromethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,107867-51-6, 5-(Trifluoromethyl)pyridine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROGEN CORPORATION; US2003/36652; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 10177-08-9, 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 10177-08-9, name is 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-Oxo-5-phenyl-l,2-dihydro-pyridine-3-carboxylic acid (44 g, 0.20 mmol) in tetrahydrofuran (5 mL) were successively added aniline (20 muL, 0.23 mmol), hydroxybenzotriazole (30 mg, 0.23 mmol), dimethylaminopyridine (27 mg, 0.23 mmol) and EDC (43 mg, 0.23 mmol). The reaction mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with DCM containing 10percent of MeOH to afford the title compound as a white solid (20 mg, 34percent yield). MS (ES+) 291. deltaH (DMSOd6) 7.2 (3H, m), 7.9 (IH, t), 8.5 (IH, d), 8.6 (2H, m), 9.3 (IH, s).

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 10177-08-9, 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/65946; (2006); 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.1142197-14-5, name is 2-Bromo-5-cyclopropylpyridine, molecular formula is C8H8BrN, molecular weight is 198.06, as common compound, the synthetic route is as follows.category: pyridine-derivatives

n-Butyllithium solution (1.6 M in hexane, 0.61 mL, 0.98 mmol) was added to a flask with diethyl ether (2.2 mL) at -78 C, followed by the dropwise addition of 2-bromo-5-cyclopropylpyridine (213 mg, 1.07 mmol), and the resulting mixture was stirred at -78C for 45 min. To the prepared aryllithium solution was added a solution of (7h) (100 mg, 0.244 mmol) in THF (1.1 mL) dropwise and the mixture was stirred at -78 C for 10 min. The reaction was quenched by the addition of water. The dry ice bath was removed and then saturated aq. NLLCl solution was added. The resulting mixture was warmed to rt and the solution was extracted (EtOAc). The combined organic layer was washed (brine), dried (Na2SC>4), and concentrated under reduced pressure. Purification of the residue by column chromatography (30% to 60% (0610) acetone/hexanes, a gradient elution) provided the title compound (7i) (99 mg, 77%) as a yellow solid m/z (ESI, +ve ion) 529.2 = [M+H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1142197-14-5, 2-Bromo-5-cyclopropylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; DU, Xiaohui; EKSTEROWICZ, John; FANTIN, Valeria R.; REW, Yosup; SUN, Daqing; YE, Qiuping; ZHOU, Haiying; KAWAI, Hiroyuki; MOORE, Jared; PHAM, Johnny; WU, Kejia; ZHU, Liusheng; (116 pag.)WO2020/76999; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 66909-38-4, Adding some certain compound to certain chemical reactions, such as: 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine,molecular formula is C6H7ClN2, 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 66909-38-4.

A mixture of 6-chloro-4-methyl-pyridin-3-ylamine (1.53 g, 11 mmol), sodium methanesulfinate (1.60 g, 16 mmol), copper catalyst (0.50 g, 0.99 mmol), and N1,N2-dimethylethane-1,2-diamine (0.214 mL, 2.0 mmol) in 20 mL DMSO was heated under microwave irradiation at 150 C. After 2 h, mixture was poured into ca. 200 mL water and extracted five times with ca. 200 mL AcOEt. Organic phases were dried over MgSO4, filtered, and concentrated. Residue was purified by column chromatography (AcOEt/hexane 5:1?AcOEt) to give 6-methanesulfonyl-4-methyl-pyridin-3-ylamine as a white solid (0.534 g, 27%). 1HNMR (DMSO-d6, 400 MHz) delta 2.4 (s, 3H), 3.08 (s, 3H), 6.08 (s, 2H), 7.59 (s, 1H), 7.97 (s, 1H). Exact mass calculated for C7H10N2O2S 186.05, found 187.0 (MH+).

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. 66909-38-4, 6-Chloro-4-methylpyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jones, Robert M.; Lehmann, Juerg; Wong, Amy Siu-Ting; Hurst, David; Shin, Young-Jun; US2006/155128; (2006); 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.1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.COA of Formula: C6H4ClF3N2

To a solution of S.6 (205 mg, 0.64 mmol) in methylene chloride (4 mL) at RT was added oxalyl chloride (160 muL, 0.0019 mol) followed by the addition of DMF (50 muL) and stirred at RT for 1 hr. Separately a solution of A.6 (132 mg, 0.000672 mol), acetonitrile (2 ml) and pyridine (520 muL, 0.0065 mol) was stirred at RT followed by the addition of chlorotrimethylsilane (100 muL, 0.0008 mol). The acid chloride was concentrated under reduced pressure to a tan solid and redissolved in acetonitrile (2 mL). To the acid chloride solution was added the activated aniline. After 3 hr, the reaction mixture was diluted with ethyl acetate (75 mL) and washed with dilute citric acid (50 mL), aqueous sodium bicarbonate (50 mL) and water. The organic layer was dried over sodium sulfate and concentrated to a residue which was purified by to give compound S.7. LCMS m/z: 498.95 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem