Category: pyridine-derivatives

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.73781-91-6, name is Methyl 6-chloronicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.COA of Formula: C7H6ClNO2

Example 7. Preparation of 0-(6-pyrazol-l-yl-pyridin-3-almethel)-hadroxylamine (Compound of formula (Xl)); Step 7a. Preparation of 6-Pyrazol-1-vl-nicotinic acid methyl ester (Compound of formula (XI-a)); To a solution of pyrazole (19.4g, 0. 28mol) in 100 mL anhydrous DMSO, which was at a temperature of 0C, was added NaH (7. 5g, 0. 3mol) gradually over a period of 30 min. The resulting reaction mixture was allowed to warm to room temperature, at which the mixture continued to agitate for an additional 30 min. Methyl 6- chloronicotinate (35g, 0. 2mol) was added to the stirring reaction mixture and agitated vigorously for a period of 6 hr. The reaction mixture was subsequently cooled to a temperature of about 0C and poured into a saturated aqueous, 0C NH4C1 solution. The resulting precipitate was filtered, washed with water, and dried to give a compound of formula (XI-a) (38.3g, 93% yield) as an off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73781-91-6, Methyl 6-chloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WO2005/70918; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 94166-64-0, 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 94166-64-0 as follows.

In a 20 ml microwave vial, 2-chloro-6-nitropyridine (1.0 g, 6.3 mmol) was dissolved in dioxane (10 ml) and piperidine-4-carboxamide (1.05 g, 1.3 eq) was added followed by Hunig’s base (3.3 ml, 3 eq). The reaction was subjected to in the microwave for 2.5 h at 180 C. The reaction mixture was diluted with water, the mixture was extracted twice with hot ethyl acetate, treated with brine, dried with MgS04, filtered and the solvent was removed in vacuo to give the crude product. The crude product was refluxed with DCM (10 ml), the solution was allowed to cool and washed with DCM to give the purified crude product as a solid. The solid was recrystallized from 2% hexane/ ethyl acetate to give [l-(6-nitropyridin-2-yl)piperidine-4-carboxamide (0.53 g solid, 33% yield, HPLC Rf 2.18 min, MS m/z (M+l) 251.3, (M-l) 249.2). TLC ethyl acetate Rf 0.26.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,94166-64-0, its application will become more common.

Reference:
Patent; KARIN & STEN MORTSTEDT CBD SOLUTIONS AB; SOHN, Daniel Dungan; (185 pag.)WO2019/197502; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6302-02-9, 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 6302-02-9 as follows.

EXAMPLE 19 2-Guanidino-4-methyl-5-(2-pyridyl)thiazole (0.16 g) was obtained according to substantially the same manner as that of Example 17 from 1-(2-pyridyl)acetone (2.8 g) and N-amidinothiourea (1.18 g). mp 166-168 C. IR (Nujol): 3440, 3400, 3270, 3080, 1630, 1600, 1580, 1540, 1520, 1420, 1320, 1240 cm-1 NMP (DMSO-d6, delta): 2.42 (3H, s), 6.8-7.1 (1H, m), 7.36 (1H, d, J=7 Hz), 7.5-7.8 (1H, m), 8.33 (1H, d d., J=2 Hz, 7 Hz) Mass. 233 (M+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6302-02-9, its application will become more common.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4649146; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 71701-92-3, name is 3-Bromo-2-chloro-5-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H2BrClF3N

n-BuLi (1.57M solution in hexane; 64 ml_, 0.10 mol) is added dropwise to a solution of 3- bromo-2-chloro-5-trifluoromethylpyridine (20.00 g, 0.077 mol), DMF (7.72 ml_, 0.10 mol) in toluene (400 ml_) at -650C. After stirring at the same temperature for 30 min, the mixture is quenched by addition of 1 N HCI and extracted with ethyl acetate. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered and concentrated to give crude 2-chloro-5-trifluoromethylpyridine-3-carbardehyde.

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, 71701-92-3, 3-Bromo-2-chloro-5-(trifluoromethyl)pyridine.

Reference:
Patent; NOVARTIS AG; WO2008/58967; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 934-37-2 ,Some common heterocyclic compound, 934-37-2, molecular formula is C8H8N2, 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.

2-methylimidazo[1,2-a]pyridine-3-carbaldehyde: Over excess of anhydrous DMF at 0 C are added slowly 2.5 equivalents of POCl3 and the mixture is mixed during 15 min. Posterior, one equivalent of compound 2-methylimidazo[1,2-a]pyridine is added and the reaction mixture is stirred vigorously by 1 h. Then the reaction is warmed at 60 C. Chopped ice was added and the mixture is neutralized with ammonium hydroxide. Oil was obtained which was solubilized in hot hexane, after cooling a solid was formed. Recrystallized from hexane to obtain a white solid. Yield 59 %; m.p. 118-119 C. 1H NMR (300 MHz, CDCl3) ppm 2.73 (s, 3 H), 7.07 (dd, J = 1.2 Hz, 6.8 Hz, 1 H), 7.52 (ddd, J = 1.2 Hz, 6.8 Hz, 9.0 Hz, 1 H), 7.68 (dd, J = 1.2 Hz, 9.0 Hz, 1 H), 10.01 (s, 1 H). 13C NMR (75 MHz, CDCl3) ppm 114.5, 114.8, 116.6, 121.2, 128.3, 130.0, 147.7, 157.1, 177.0. MS (EI, 70 eV): m/z [%] = 160[M]+ (100), 159[M-H]+ (98), 131[M-CHO]+ (25).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934-37-2, its application will become more common.

Reference:
Article; Garcia-Carrillo, Mario Alfredo; Guzman, Angel; Diaz, Eduardo; Tetrahedron Letters; vol. 58; 20; (2017); p. 1952 – 1956;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 93-60-7, Methyl nicotinate, 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, Computed Properties of C7H7NO2, blongs to pyridine-derivatives compound. Computed Properties of C7H7NO2

To a stined solution of methyl nicotinate (500gm) in isopropyl alcohol was addedhydrazine hydrate (80%) (460m1). Resultant mixture was heated and stined at 80-85C for 4hrs. Reaction mixture was cooled to RT. Separated solid was filtered, washed with isopropyl alcohol and dried to give title compound as off white solid.?H NMR (DMSO-d6, 400 MHz, ppm): 9.967(1H, singlet), 8.967-8.961(1H, singlet), 8.699- 8.683(1H, doublet), 8.167-8.138(1H, doublet), 7.512-7.479(1H, triplet), 4.567(2H, Singlet) Mass (mlz):138 (M + 1)

The synthetic route of 93-60-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TORRENT PHARMACEUTICALS LIMITED; DUTT, Chaitanya; GUPTA, Rameshchandra; PATEL, Manish; ABRAHAM, Jaya; MISHRA, Vivek; KESARWANI, Amit; DESHPANDE, Shailesh; ZAMBAD, Shital, Kumar; MATHUR, Anoop; KOTECHA, Jignesh; LATAD, Sachin; CHAUDHARI, Anita; (45 pag.)WO2016/162785; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1289197-78-9, 2-Bromo-4-chloronicotinaldehyde, 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, Quality Control of 2-Bromo-4-chloronicotinaldehyde, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-4-chloronicotinaldehyde

Example 193f 4-Chloro-2-(1-oxo-6,7,8,9-tetrahydropyridazino[4,5-b]indolizin-2(1H)-yl)nicotinaldehyde 193f A 100-mL single-neck round-bottomed flask equipped with a reflux condenser was charged with 1,4-dioxane (40 mL), 193e (800 mg, 3.6 mmol), 2-bromo-4-chloronicotinaldehyde (2.8 g, 12.6 mmol), and potassium carbonate (1.2 g, 8.4 mmol). After bubbling nitrogen through the resulting mixture for 30 minutes, copper(I) iodide (800 mg, 4.2 mmol) and 4,7-dimethoxy-1,10-phenanthroline (1.0 g, 4.2 mmol) were added, and the reaction mixture was heated at 90C for 12 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was partitioned between methylene chloride (60 mL) and water (40 mL). The aqueous layer was separated and extracted with methylene chloride (3 x 40 mL). The combined organic layer was washed with brine (30 mL) and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with1:1 ethyl acetate/petroleum ether to afford 193f as a brown solid (513 mg, yield 37%). MS-ESI: [M+H]+ 329.1.

The synthetic route of 1289197-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
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. 1594-58-7, name is N-Hydroxynicotinimidamide, the common compound, a new synthetic route is introduced below. Safety of N-Hydroxynicotinimidamide

To a solution of 5-(lH-pyrrol-l-yl)nicotinic acid (Maybridge, 188 mg, 1.00 mmol) in dimethylformamide (anhydrous, 5 mL) was added N-(3-methylaminopropyl)-N’- ethylcarbodiimide hydrochloride (EDC) (Aldrich, 192 mg, 1.00 mmol) and 1- hydroxybenzotriazole (HOBT) hydrate (Fluka, 153 mg, 1.00 mmol). The mixture was stirred at ambient temperature for 20 minutes. lambdaf’-Hydroxynicotinimidamide (137 mg, 1.0 mmol) was added and the mixture was stirred for 6-10 hours, and then warmed to 140 0C for 2-4 hours. The reaction was cooled to ambient temperature and triturated with water (10 mL). The precipitate was filtered and dried under vacuum to give the titled compound. 1H NMR (300 MHz, DMSO-J6) delta 6.34 – 6.44 (m, 2 H), 7.60 – 7.82 (m, 3 H), 8.50 (dt, J=8.1, 1.9 Hz, 1 H), 8.71 (dd, J=2.5, 1.9 Hz, 1 H), 8.84 (dd, J=4.6, 1.5 Hz, 1 H), 9.21 (d, J=1.7 Hz, 1 H), 9.26 (d, J=2.4 Hz, 1 H), 9.31 (d, J=I .7 Hz, 1 H) ppm; MS (DCI/NH3) m/z 290 (M+H)+.

The synthetic route of 1594-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/148452; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1180132-17-5, 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. 1180132-17-5, name is 5-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine. A new synthetic method of this compound is introduced below.

Add 5-(4-ethyl-piperazine-1 -yl methyl)-2-amin- opyridine (VIII) (2.2 g, 10 mmol) and anhydrous ethyl alcohol 25 mL into the reaction flask, low the temperature to 0 C., and add 65% nitric acid 0.45 mL and 50% cyanamide aqueous solution (1 mL, 12 mmol) in sequence, and then, raise the temperature slowly to 80 C., and conduct stirring reaction for 8-12 hours. Lower the temperature to 0 C., and again add 65% nitric acid 0.45 mL and 50% cyanamide aqueous solution (1 mL, 12 mmol), and then raise the temperature slowly to 80 C., and conduct stirring operations again for 6-8 hours, and detect completion of the reaction with TLC sampling. Lower the temperature to room temperature, and there will be precipitation. Make filtration, and recrystallize the filter cake with ethyl acetate and n-hexane (2:1, V/V) mixed solvent, and make vacuum drying to obtain luminous yellow solid N-[5-(4-ethyl-pip- erazine-1 -yl methyl) pyridine-2-yl]guanidine nitrate (IX) 2.8 g, the yield rate is 86.2%; mass spectrum (El): mlz 326 (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,1180132-17-5, its application will become more common.

Reference:
Patent; SUZHOU MIRACPHARMA TECHNOLOGY CO., LTD.; Xu, Xuenong; (9 pag.)US2017/305884; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73027-79-9, 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 73027-79-9 as follows.

Oxalic dichloride (2.8 g, 22.1 mmol) was added dropwise to a pre-cooled mixture at 0 C of 4,6- dichloronicotinic acid (1.40 g, 7.29 mmol) and NN-dimethylformamide (0.10 mL, 1.29 mmol) in dichloromethane (20 mL). The resulting mixture was stirred for 3 h at room temperature. After the reaction was completed, the resulting mixture was concentrated in vacuo to afford the title compound (1.8 g ) as a yellow solid, which was carried forward without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73027-79-9, its application will become more common.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; DIEDERICH, Francois; DOTSON, Jennafer; HANAN, Emily; HEFFRON, Timothy; LAINCHBURY, Michael; HEALD, Robert; SEWARD, Eileen M.; WO2014/210354; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem