Day: April 21, 2022

Related Products of 1074-98-2, 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.1074-98-2, name is 3-Methyl-4-nitropyridine 1-oxide, molecular formula is C6H6N2O3, molecular weight is 154.13, as common compound, the synthetic route is as follows.

A suspension of 3-methyl-4-nitropyridine N-oxide (2.0 g, 13 mmol) and palladium hydroxide on carbon (0.4 g) in ethanol (30 mL) was heated to 60 C. Ammonium formate (3.3 g, 52 mmol) was then added portionwise and the mixture heated at 60 C for three hours. The cool reaction mixture was filtered through Arbocel and the filtrate evaporated under reduced pressure to afford the title compound as a colourless oil, 1.81 g. LRMS (APCI+): m/z [M+H]+ 125

The chemical industry reduces the impact on the environment during synthesis 1074-98-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/121094; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 112110-07-3, 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.112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.

General procedure: l-methyl-4-[(3-methyloxetan-3-yl)sulfamoyl]-lH-pyrrole-2-carboxylic acid (200 mg, (0182) 0.729 mmol) was dissolved in DMF (1.7 mL) and triethylamine (0.41 mL, 2.9 mmol) and HATU (360 mg, 0.95 mmol) were added. After 10 minutes 4-aminopyridine-2-carbonitrile (174 mg, 1.46 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and heated at 65C for 42 hours. The mixture was poured into water (50 mL) and the organics were extracted with ethyl acetate (3 x 40 mL). The combined organic layers were dried (Na2S04) and concentrated to dryness. The residue was purified using silica gel column chromatography (ethyl acetate in heptane from 0 to 100%) followed by prep. HPLC (Stationary phase: RP SunFire Prep C18 OBD-IotaOmicronmuiotaeta, 30 x 150mm), Mobile phase: 0.5% NH4OAc solution in water + 10% CH3CN, MeOH), resulting in compound 1 (4.6 mg). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.54 (s, 3 H), 3.94 (s, 3 H), 4.14 (d, J=6.4 Hz, 2 H), 4.60 (d, J=5.9 Hz, 2 H), 7.43 (s, 1 H), 7.66 (d, J=1.3 Hz, 1 H), 7.86 – 8.12 (m, 2 H), 8.26 (d, J=2.0 Hz, 1 H), 8.60 (d, J=5.7 Hz, 1 H), 10.68 (br. s., 1 H). Method A; Rt: 1.22 min. m/z : 374.0 (M-H)- Exact mass: 375.1. Compound 2 was prepared similarly as described for compound 1, using 5-(trifluoromethyl)-3- aminopyridine instead of 4-aminopyridine-2-carbonitrile. The reaction mixture was stirred at room temperature for 1 hour and heated at 65C for 4 hours. The mixture was poured into water (50 mL), the formed precipitate was filtered and the solids were washed with water and recrystallised from methanol/ethyl acetate (10 mL, 1 : 1). The white solids were filtered, washed with methanol (2 x 3 mL) and dried overnight in vacuum oven resulting in compound 2 (74 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.55 (s, 3 H), 3.94 (s, 3 H), 4.14 (d, J=6.2 Hz, 2 H), 4.60 (d, J=5.9 Hz, 2 H), 7.41 (s, 1 H), 7.63 (s, 1 H), 8.01 (br. s., 1 H), 8.56 (s, 1 H), 8.66 (s, 1 H), 9.13 (s, 1 H), 10.55 (br. s., 1 H). Method B; Rt: 0.84 min. m/z : 417.1 (M-H)~ Exact mass: 418.1.

Statistics shows that 112110-07-3 is playing an increasingly important role. we look forward to future research findings about 5-(Trifluoromethyl)pyridin-3-amine.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 20970-75-6, Adding some certain compound to certain chemical reactions, such as: 20970-75-6, name is 2-Cyano-3-methylpyridine,molecular formula is C7H6N2, 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 20970-75-6.

General procedure: General Procedure for the Preparation of 7-Aza-5,6-dihydro-5-oxo-11H-indeno[1,2-c]isoquinolines 12-14 [0111] 3-Methylpicolonitrile (10, 3.0-4.0 g, 25.4-33.9 mmol, 1 equiv), NBS (6.78-9.04 g, 38.1-50.8 mmol, 1.5 equiv), and AIBN (0.42-0.56 g, 2.5-3.4 mmol, 0.1 equiv) were diluted with 1,2-dichloroethane (80-100 mL), and the reaction mixture was heated at reflux for 2 h. The reaction mixture was concentrated to half its original volume, filtered, and the filtrate was concentrated to dryness to provide crude 11. Compound 11 was diluted with acetonitrile (100-125 mL). The appropriate homophthalic anhydride (5, 6, or 7, 6.8-12.4 g, 41.9-55.9 mmol, 1.65 equiv) was added, followed by triethylamine (18-24 mL, 127.0-169.5 mmol, 5 equiv), and the solution was heated at reflux for 10 h. The solution was allowed to cool to room temperature, and the precipitate was filtered and washed with hot acetonitrile (2×35 mL) to provide the described compound.

According to the analysis of related databases, 20970-75-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CUSHMAN, Mark S.; KISELEV, Evgeny A.; MORRELL, Andrew E.; US2014/18360; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1443-42-1, 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 1443-42-1, name is (4-Methylpyridin-3-yl)methanamine. This compound has unique chemical properties. The synthetic route is as follows.

In a sealed tube, a mixture of intermediate 5 (0.5 g, 1.01 mmol), (4-Methylpyridin- 3-yl)methylamine (0.108 mL, 1.21 mmol) and cesium carbonate (0.66 g, 2.02 mmol) in tert-amyl alcohol (5mL) was degazed with N2. 2-Dicyclohexyphosphino-2′,6′- diisopropoxy-l,l ‘-biphenyl (23.544 mg, 0.0505 mmol) and BrettPhos Precatalyst First Gen (40.305 mg, 0.0505 mmol) were added, the reaction mixture was purged with N2and heated at 100C for 18 h. Water and Ethyl acetate were added. The aqueous layer was extracted and the organic layer was separated, dried over MgS04, filtered and concentrated. This crude (578 mg) was purified by silica gel chromatography (25g of SiOH, 15muiotaeta, gradient from 100% DCM to 90/10/0.1 DCM/MeOH/NH4OH). The fractions containing the product were collected and evaporated until dryness to afford 405 mg (74%) of intermediate 6 which was used in the next step without any further purification.

According to the analysis of related databases, 1443-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; JOUSSEAUME, Thierry, Francois, Alain, Jean; (114 pag.)WO2018/178280; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19346-44-2, 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 19346-44-2 as follows.

[0205] A solution of 2-fluoro-5-methyl-3-nitropyridine (1 g, 6.41 mmol), 4~(2,4~ difluorophenoxy)piperidine hydrochloride (1.919 g, 7.69 mmol) and K2CO3 (2.66 g, 19.22 mmol) in ACN (16.01 mL) was stirred at 80C for 5 hours. The reaction mixture was poured into water and extracted with EtOAc (3 x 50 mL). The organic layers were combined, dried over Na,2S(>4, and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography (I SCO column) eluiing with a gradient of 0-100% EtOAc in heptane to give the title compound as a yellow solid (2.21 g, 99%). NMR (500 MHz, DMSQ-<:) delta ppm 1.66 - 1.73 (m, 2 H), 2.00 (d, J=12.20 Hz, 2 H), 2.25 (s, 3 H), 3.19 - 3.25 (m, 2 H), 3.52 - 3.57 (m, 2 H), 4.58 (dt, J=7,69, 3.72 Hz, 1H), 6,98 - 7.04 (m, 1H), 7.26 - 7.34 (m, 2 H), 8.1 1 (s, 1H), 8.28 -MS m/z [M+H 350.2, These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19346-44-2, its application will become more common. Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); 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. 94170-15-7, name is 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde, the common compound, a new synthetic route is introduced below. Safety of 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde

Intermediate 2-11 (30 mg, 0.087 mmol) was dissolved in DCM (2 mL)4-Aldehyde-1-methylpyridine-2(1H)-one (14.3 mg, 0.104 mmol), NaBH (OAc) 3 (46.1 mg, 0.218 mmol).Stir at room temperature overnight.TLC monitors the reaction,Add saturated aqueous sodium bicarbonate (5 mL),Extracted with DCM (3 x 10 mL),Combine the organic phase,Wash with water (2 × 5mL),Dry over anhydrous sodium sulfate,filter,concentrate,The crude product was purified by silica gel column chromatography (DCM: MeOH=200:1-20:1)White solid (5.8 mg, yield: 14.5%).

The synthetic route of 94170-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Wang Lin; Yang Xiaoju; Tian Yuwei; (46 pag.)CN108341819; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54718-39-7, 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.54718-39-7, name is 2,5,6-Trichloronicotinic acid, molecular formula is C6H2Cl3NO2, molecular weight is 226.4446, as common compound, the synthetic route is as follows.

Step 1: 2,5,6-trichloronicotinamide (Intermediate P) 1,1′-Carbonyldiimidazole (40 g, 247 mmol) was added in portions to 2,5,6-trichloronicotinic acid (50.7 g, 224 mmol, Combi-Blocks, San Diego, Calif., USA) in THF (400 mL), allowing gas evolution to cease between additions. The resulting mixture was stirred for 5 min and then was degassed with house vacuum and flushed with nitrogen (*2). The resulting mixture was heated to 50 C. for 60 min, then diluted with toluene (100 mL) and concentrated to half volume. The resulting mixture was cooled to 0 C. and ammonium hydroxide (60 mL, 437 mmol) was added slowly via syringe. The reaction was stirred for 10 min at room temperature, diluted with EtOAc (200 mL) and washed with water (3*100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was suspended in 9:1 heptane/EtOAc (300 mL) and filtered. The filtered solids were collected and the remaining mother liquor was partially evaporated to half volume, cooled to 0 C., and filtered. The two crops of filtered solids were combined to provide 2,5,6-trichloronicotinamide.

Statistics shows that 54718-39-7 is playing an increasingly important role. we look forward to future research findings about 2,5,6-Trichloronicotinic acid.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; KOPECKY, David John; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; BOOKER, Shon; NISHIMURA, Nobuko; SHIN, Youngsook; TAMAYO, Nuria A.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; (266 pag.)US2018/334454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 51173-05-8, 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. 51173-05-8, name is 5-Fluoro-2-hydroxypyridine. A new synthetic method of this compound is introduced below.

The solid from above containing (4-80) was divided in 4 batches and treated with H2SO4 and fuming HNO3 as shown below. The amounts used were: Compound 4-80 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM? showed 4-80 and something else (discarded)). [1493] The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford 5-80 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of 5-80; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product 5-80 [1494] Total:117.0+3.6+6.23 =126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). [1495] Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min. [1496] Note: A portion of the aqueous acidic solution was taken and neutralized with Na2CO3 until effervescence stopped and then it was extracted with AcOEtA different product was obtained. No desired product in these extracts.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51173-05-8, 5-Fluoro-2-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; Kadow, John F.; Yin, Zhiwei; Xue, Qiufen May; Regueiro-Ren, Alicia; Matiskella, John D.; Ueda, Yasutsugu; US2004/110785; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1450634-01-1, 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 1450634-01-1 as follows.

To a solution of 3-(prop-1-en-2-yl)picolinonitrile in acetic acid was added 10% Pd/C. The parr shaker bottle was evacuated/H2 purged 3x, and then shaken at Sopsi until starting material was consumed (typically Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore; JIANG, Rong; SONG, Xinyi; WO2013/119639; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 26163-03-1, 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 26163-03-1, name is 3-Bromo-5-chloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-bromo-5-chloro-2-pyridinamine (5.0 g), bromoacetoaldehyde diethyl acetal (7.3 mL), p-toluenesulfonic acid monohydrate (498 mg) and ethanol (20 mL) was stirred at 80 C. overnight. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give a residue. The obtained residue was washed with ethyl acetate/IPE to give the title compound (4.71 g). (1141) 1H NMR (300 MHz, DMSO-d6) delta 7.68 (1H, d, J=1.2 Hz), 7.75 (1H, d, J=1.8 Hz), 8.06 (1H, d, J=1.2 Hz), 8.91 (1H, d, J=1.8 Hz).

According to the analysis of related databases, 26163-03-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem