Category: 81719-53-1

Synthetic Route of 81719-53-1, 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.81719-53-1, name is 3,5-Dichloropyridine-2-carboxylic Acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.

3,5-dichloro-2-(chloromethyl)pyridine; [00376] To a 0 C solution of 5-chloropicolinic acid (5.00 g, 26.0 mmol) and N,N- dimethylformamide (1 drop) in dichloromethane (20 mL) was added oxalyl chloride (3.28 g, 26.0 mmol) dropwise, after which the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for two hours. The reaction was then cooled again to 0 C, after which methanol (10 mL) was added dropwise to the reaction mixture, and the reaction was allowed to stir at room temperature for one hour where it was shown as complete by LCMS analysis. The reaction mixture was washed with saturated sodium bicarbonate solution, dried (magnesium sulfate), filtered and concentrated to afford methyl 3,5-dichloropyridine-2-carboxylate (5.36 g, 26.0 mmol, 100% yield ) as a white solid.[00377] To a 0 C solution of methyl 3,5-dichloropyridine-2-carboxylate (5.00 g, 24.3 mmol) in methanol (40 mL) was added sodium borohydride (1.80 g, 48.5 mmol), after which the reaction was warmed to room temperature and stirred at that temperature for two hours. The reaction mixture was then quenched by the addition of water (5 mL), concentrated to a residue, reconstituted in water (60 mL), extracted with ethyl acetate (2 x 60 mL), dried (magnesium sulfate), filtered and concentrated to afford (3,5-dichloropyridin-2-yl)methanol (2.90 g, 16.3 mmol, 67% yield ) as a viscous oil. This material was used in the subsequent step without any purification.[00378] To a 0 C solution of (3,5-dichloropyridin-2-yl)methanol (2.90 g, 16.3 mmol) in dichloromethane (50 mL) was added thionyl chloride (2.31 g, 19.6 mmol) dropwise, after which the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for two hours. The reaction mixture was washed by the addition of saturated sodium bicarbonate solution (1 x 40 mL) and the organic layer was separated, dried (sodium sulfate), filtered and concentrated to a residue. Purification was achieved by silica gel chromatography using 9% ethyl acetate in hexanes to afford 3,5-dichloro-2- (chloromethyl)pyridine (2.40 g, 12.2 mmol, 75% yield) as an off-white solid. NMR (300 MHz, CDC13) delta (ppm): 8.36 (s, 1H), 7.56 (s, 1H), 4.66 (s, 2H).

Statistics shows that 81719-53-1 is playing an increasingly important role. we look forward to future research findings about 3,5-Dichloropyridine-2-carboxylic Acid.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; HUDSON, Colleen; BARDEN, Timothy, C.; JIA, James; MERMERIAN, Ara; PENG, Bo; YANG, Jane; YU, Xiang, Y.; SPROTT, Kevin; WO2012/88469; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 81719-53-1, 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.81719-53-1, name is 3,5-Dichloropyridine-2-carboxylic Acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.

3,5-dichloro-2-(chloromethyl)pyridine; [00376] To a 0 C solution of 5-chloropicolinic acid (5.00 g, 26.0 mmol) and N,N- dimethylformamide (1 drop) in dichloromethane (20 mL) was added oxalyl chloride (3.28 g, 26.0 mmol) dropwise, after which the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for two hours. The reaction was then cooled again to 0 C, after which methanol (10 mL) was added dropwise to the reaction mixture, and the reaction was allowed to stir at room temperature for one hour where it was shown as complete by LCMS analysis. The reaction mixture was washed with saturated sodium bicarbonate solution, dried (magnesium sulfate), filtered and concentrated to afford methyl 3,5-dichloropyridine-2-carboxylate (5.36 g, 26.0 mmol, 100% yield ) as a white solid.[00377] To a 0 C solution of methyl 3,5-dichloropyridine-2-carboxylate (5.00 g, 24.3 mmol) in methanol (40 mL) was added sodium borohydride (1.80 g, 48.5 mmol), after which the reaction was warmed to room temperature and stirred at that temperature for two hours. The reaction mixture was then quenched by the addition of water (5 mL), concentrated to a residue, reconstituted in water (60 mL), extracted with ethyl acetate (2 x 60 mL), dried (magnesium sulfate), filtered and concentrated to afford (3,5-dichloropyridin-2-yl)methanol (2.90 g, 16.3 mmol, 67% yield ) as a viscous oil. This material was used in the subsequent step without any purification.[00378] To a 0 C solution of (3,5-dichloropyridin-2-yl)methanol (2.90 g, 16.3 mmol) in dichloromethane (50 mL) was added thionyl chloride (2.31 g, 19.6 mmol) dropwise, after which the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for two hours. The reaction mixture was washed by the addition of saturated sodium bicarbonate solution (1 x 40 mL) and the organic layer was separated, dried (sodium sulfate), filtered and concentrated to a residue. Purification was achieved by silica gel chromatography using 9% ethyl acetate in hexanes to afford 3,5-dichloro-2- (chloromethyl)pyridine (2.40 g, 12.2 mmol, 75% yield) as an off-white solid. NMR (300 MHz, CDC13) delta (ppm): 8.36 (s, 1H), 7.56 (s, 1H), 4.66 (s, 2H).

Statistics shows that 81719-53-1 is playing an increasingly important role. we look forward to future research findings about 3,5-Dichloropyridine-2-carboxylic Acid.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; HUDSON, Colleen; BARDEN, Timothy, C.; JIA, James; MERMERIAN, Ara; PENG, Bo; YANG, Jane; YU, Xiang, Y.; SPROTT, Kevin; WO2012/88469; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 81719-53-1, 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 81719-53-1 as follows.

To 4-hydrazinocarbonylpiperidine-1-carboxylic acid tert-butyl ester (500 mg) were added 3,5-dichloropyridine-2-carboxylic acid (475 mg), 1-hydroxybenzotriazole (420 mg),1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide.hydrochloride (590 mg), triethylamine (575 muL) and chloroform (10 mL) and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography (chloroform:methanol)to give 4-[N’-(3,5-dichloropyridine-2-carbonyl)hydrazinocarbonyl]piperidine-1-carboxylic acid tert-butyl ester (525 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,81719-53-1, 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

Adding a certain compound to certain chemical reactions, such as: 81719-53-1, 3,5-Dichloropyridine-2-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, name: 3,5-Dichloropyridine-2-carboxylic Acid, blongs to pyridine-derivatives compound. name: 3,5-Dichloropyridine-2-carboxylic Acid

Production Example 32 (1) [0773] 5.53 ml of thionyl chloride was added to a mixture of 4.7 g of 3,5-dichloropicolinic acid, 49 ml of toluene and 0.1 ml of DMF, and the mixture was stirred at 80C for 2 hours. The cooled reaction mixture was concentrated under reduced pressure, and 49 ml of toluene, 4.84 g of N-methyl-4-trifluoromethylsulfanylaniline and 8.05 ml of diisopropylethylamine were added, and the mixture was stirred at 80C for 2 hours. The cooled reaction mixture was poured to a saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 8.92 g of 3,5-dichloro-N-methyl-N-(4-trifluoromethylsulfanylphenyl)pi colinamide. RRN 1573,5-Dichloro-N-methyl-N-(4-trifluoromethylsulfanylphenyl)pi colinamide [0774] 1H-NMR(CDCl3)delta: 8.28(1H, d), 7.58(1H, d), 7.50(2H, d), 7.19(2H, d), 3.54(3H, s).

The synthetic route of 81719-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; MAEHATA, Ryota; MIZUNO, Hajime; SHIMIZU, Chie; NOKURA, Yoshihiko; EP2881386; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 81719-53-1, Adding some certain compound to certain chemical reactions, such as: 81719-53-1, name is 3,5-Dichloropyridine-2-carboxylic Acid,molecular formula is C6H3Cl2NO2, 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 81719-53-1.

Example B9Preparation of compound 14: rac-3,5-dichloro-pyridine-2-carboxylic acid [3-(4-amino-6- methyl-6,7-dihydro-pyrazolo[l,5-a]pyrazin-6-yl)-4-fluoro-phenyl]-amide and compound 15: (R*)-3,5-dichloro-pyridine-2-carboxylic acid [3-(4-amino-6-methyl- 6,7-dihydro-pyrazolo[l,5-a]pyrazin-6-yl)-4-fluoro-phenyl]-amide and compound 16: (S *)-3 , 5 -dichloro-pyridine-2-carboxylic acid [3 -(4-amino-6-methyl-6, 7-dihydro- pyrazolo[l,5-a]pyrazin-6-yl)-4-fluoro-phenyl]-amide3,5-Dichloro-2-pyridinecarboxylic acid (75.5 mg, 0.393 mmol) was added to a solution of 4-(4,6-dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholinium chloride (128 mg, 0.463 mmol) in MeOH (5 mL). The mixture was stirred at room temperature for 5 min. Then the mixture was cooled to 0 C and a solution of intermediate A49 (100 mg, 0.386 mmol) in MeOH (5 mL) was added. The mixture was warmed to room temperature and stirred for 4 hours. The mixture was treated with a saturated solution of Na2C03 and H20 and extracted with DCM. The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; MeOH/DCM). The desired fractions were collected and the solvents evaporated in vacuo. The crude product was triturated with Et20, sonicated, filtered and dried in vacuo at 50C. The resulting compound was purified one addition time by flash column chromatography (silica gel; MeOH/DCM) to yield, after treatment with AcOEt and DIPE, compound 14 (95 mg, 57% yield) as a white solid. This racemic compound was then further purified by preparative SFC on Chiralcel OJ-H 5 muiotaeta (250 x 20 mm), mobile phase (0.3% iPr H2, 85% C02, 15% EtOH). The desired fractions for each enantiomer were collected and concentrated in vacuo to yield compound 15 (38 mg, 23% yield). 1H MR (400 MHz, CDC13) delta ppm 1.58 (s, 3 H), 2.52 (br. s., 2 H), 4.41 (br. d, J=13.2 Hz, 1 H), 4.62 (dd, J=13.2, 0.9 Hz, 1 H), 6.43 (d, J=2.1 Hz, 1 H), 7.08 (dd, J=11.7, 8.9 Hz, 1 H), 7.52 (d, J=2.1 Hz, 1 H), 7.81 (dd, J=6.9, 2.8 Hz, 1 H), 7.89 (d, J=2.1 Hz, 1 H), 7.94 (ddd, J=8.8, 4.1, 3.0 Hz, 1 H), 8.42 (d, J=2.1 Hz, 1 H), 9.71 (br. s., 1 H) and compound 16 (40 mg, 24% yield), for which the 1H NMR was in agreement with the one of compound 15.

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. 81719-53-1, 3,5-Dichloropyridine-2-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; GIJSEN, Henricus, Jacobus, Maria; VAN GOOL, Michiel, Luc, Maria; VEGA RAMIRO, Juan, Antonio; DELGADO-JIMENEZ, Francisca; WO2012/117027; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem