Month: March 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.847729-27-5, name is Methyl 2-chloro-5-fluoronicotinate, molecular formula is C7H5ClFNO2, molecular weight is 189.57, as common compound, the synthetic route is as follows.Safety of Methyl 2-chloro-5-fluoronicotinate

A mixture of methyl 2-chloro-5-fluoronicotinate (D69) (199.85 mg, 1.054 mmol) and potassium carbonate (291 mg, 2.108 mmol) in tetrahydrofuran (2 ml) was stirred under N2 nitrogen 15 min at room temperature. N-(4-fluoro-2-methylphenyl)azetidin-3-amine (D55) (190 mg, 1.054 mmol) was added and the resulting mixture was stirred 1 day at room temperature. The residue obtained after solvent evaporation was purified by Biotage SNAP-Si column eluting with a mixture cyclohexane/ethyl acetate from 100/0 to 80/20. Collected fractions after solvent evaporation afforded the title compound (D90)(155 mg)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,847729-27-5, Methyl 2-chloro-5-fluoronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Borriello, Manuela; Rovati, Lucio; Stasi, Luigi Piero; Buzzi, Benedetta; Colace, Fabrizio; US2013/261100; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 107867-51-6, 5-(Trifluoromethyl)pyridine-2,3-diamine, 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, Formula: C6H6F3N3, blongs to pyridine-derivatives compound. Formula: C6H6F3N3

General procedure: Step 1: To a solution of compound 47 (35 mg, 0.097 mmol) in 3% HOAc/DMF (2 mL) wasadded 4, 5-difluorobenzene-1, 2-diamine (28 mg, 0.194 mmol) and potassiumperoxymonosulfate (Oxone, 60 mg, 0.097 mmol). The reaction was stirred at 80C for 16 hr. Thesolution was cooled to ambient temperature and neutralized with K2CO3 (30 mg). The mixturewas patitioned between EtOAc (6 mL) and water (2 mL). The organic phase was isolated andevaporated in vacuum.

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:
Article; Yu, Yang; Wu, Zhicai; Shi, Zhi-Cai; He, Shuwen; Lai, Zhong; Cernak, Timothy A.; Vachal, Petr; Liu, Min; Liu, Jian; Hong, Qingmei; Jian, Tianying; Guiadeen, Deodial; Krikorian, Arto; Sperbeck, Donald M.; Verras, Andreas; Sonatore, Lisa M.; Murphy, Beth A.; Wiltsie, Judyann; Chung, Christine C.; Gorski, Judith N.; Liu, Jinqi; Xiao, Jianying; Wolff, Michael; Tong, Sharon X.; Madeira, Maria; Karanam, Bindhu V.; Shen, Dong-Ming; Balkovec, James M.; De Vita, Robert J.; Pinto, Shirly; Nargund, Ravi P.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 11; (2019); p. 1380 – 1385;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 867279-13-8, 4-Bromo-2-chloro-5-methylpyridine, 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, Safety of 4-Bromo-2-chloro-5-methylpyridine, blongs to pyridine-derivatives compound. Safety of 4-Bromo-2-chloro-5-methylpyridine

Step 3: To a solution 4-bromo-2-chloro-5-methylpyridine (75 g, 363 mmol) in THF (500 mL) was added isopropylmagnesium chloride lithium chloride (1397 mL of 1.3M solution in THF,1816 mmol) at 0 C, The resulting mixture stirred at 22 C for 1 h. Then, the resulting mixture was stirred at 22 C under CO2 (1 atm) for 40 mm. The mixture was quenched with H20 (1500 mL) and extracted with EtOAc (300 mL x 2). The aqueous phase was adjusted to pH 5 withM aqueous HC1 and then was extracted with EtOAc (300 mL x 3). The resulting organic layers were washed with brine (300 mL) and concentrated in vacuum to give 2-chloro-5-methylisonicotinic acid as a light yellow solid, which was used directly in next step without further purification. MS: 172 (M + 1). ?H NMR (400 MHz, DMSO-d6) 8.39 (s, 1H), 7.68 (s, 1H), 2.43 (s, 3H).

The synthetic route of 867279-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CTXT PTY. LTD.; MACHACEK, Michelle, R.; WITTER, David, J.; REUTERSHAN, Michael Hale; ALTMAN, Michael, D.; STUPPLE, Paul Anthony; (67 pag.)WO2019/94311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58539-65-4, 2-Methylnicotinamide, 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, Product Details of 58539-65-4, blongs to pyridine-derivatives compound. Product Details of 58539-65-4

The 2 – methyl nicotinic acid amide (200 mg, 1 . 47 mmol) dissolved in anhydrous tetrahydrofuran (5 ml) in, 0 C under argon conditions, dropping borane tetrahydrofuran solution (1 M, 7.4 ml, 7.4 mmol), the reaction 30 minutes, up to 60 C reaction 8 hours. Saturated ammonium chloride aqueous solution quenching, ethyl acetate extraction, anhydrous sodium sulfate drying, filtering of evaporation to dryness to obtain colourless oil of 200 mg, crude product is directly used for the next step reaction

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58539-65-4, 2-Methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Seth Ming Qiang Pharmaceutical Technology Co., Ltd.; Zhang Qiang; Liu Yansheng; Li Xingfu; Hu Chenming; (96 pag.)CN109535132; (2019); A;,
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. 72093-13-1, name is 6-Chloro-2,3-dimethylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Chloro-2,3-dimethylpyridine

To a mixture of l-Boc-4-hydroxypiperidine (CAS: 109384-19-2, 200 mg, 0.99 mmol) in DMF (3.847 mL), were added NaH (60% dispersion in mineral oil, 79.5 mg, 1.99 mmol) and l5-crown-5 (198.4 mE, 1.19 mmol). Then 6-chloro-2,3-dimethylpyridine (154.78 mg, 1.09 mmol) was added and the mixture was stirred at 80 C for 16 h. Then additional NaH (60% dispersion in mineral oil, 39.75 mg, 0.99 mmol) was added and the mixture was stirred at 80 C for 20 h. Then water was added at 0 C and the mixture was extracted with DCM. The organic layer was separated, dried, filtered and the solvents concentrated in vacuo. The crude was purified by flash column chromatography (silica, EtOAc in heptane 0/100 to 70/30). The desired fractions were collected and the solvents concentrated in vacuo to give intermediate 120 (134.1 mg, 44%) as a colourless oil

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, 72093-13-1, 6-Chloro-2,3-dimethylpyridine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana Isabel; DELGADO-JIMENEZ, Francisca; CONDE-CEIDE, Susana; VEGA RAMIRO, Juan, Antonio; (245 pag.)WO2019/243530; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13958-93-5, 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.13958-93-5, name is 3,5-Dichloroisonicotinic acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.

Preparation of (3,5-dichloro-pyridin-4-yl)-(3-hydroxymethyl-piperidin-1-yl)-methanone: To a suspension of 3,5-dichloroisonicotinic acid (250 mg, 1.30 mmol) in CH2Cl2 (6.5 mL) was added DMF (cat.) and oxalyl chloride (0.45 mL, 5.2 mmol), and the mixture was stirred at room temperature for 2 h then concentrated in vacuo. To the residue was added THF (2 mL), Et3N (0.27 mL, 1.9 mmol), and a solution of 3-piperidinemethanol (150 mg, 1.30 mmol) in THF (4.5 mL), and the mixture was stirred at room temperature for 21 h. The mixture was diluted with CH2Cl2 (50 mL) and brine (30 mL) and the phases were separated. The organic layer was washed with brine (2*50 mL) and saturated NaHCO3 (2*50 mL). The organic layer was dried (MgSO4), filtered, concentrated, and dried in vacuo to afford a crude oil. Purification of the crude material by column chromatography on silica gel (100:5:1 CH2Cl2/MeOH/NH4OH) gave a yellow oil (mixture of isomers) (147 mg, 39%). 1H NMR (CDCl3) delta 1.28-1.96 (m, 4H), 2.89-3.26 (m, 3H), 3.35-3.45 (m, 1H), 3.50-3.72 (m, 2H), 4.29-4.56 (m, 1H), 8.54 (m, 2H).

Statistics shows that 13958-93-5 is playing an increasingly important role. we look forward to future research findings about 3,5-Dichloroisonicotinic acid.

Reference:
Patent; Bridger, Gary; Kaller, Al; Harwig, Curtis; Skerlj, Renato; Bogucki, David; Wilson, Trevor R.; Crawford, Jason; McEachern, Ernest J.; Atsma, Bem; Nan, Siqiao; Zhou, Yuanxi; Schols, Dominique; Smith, Christopher D.; Di Fluri, Maria R.; US2004/19058; (2004); 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. 80862-08-4, name is 6-Methoxy-1H-pyrrolo[3,2-c]pyridine, molecular formula is C8H8N2O, 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. Safety of 6-Methoxy-1H-pyrrolo[3,2-c]pyridine

Allylpalladium(ll) chloride dimer (558 mg, 1.52 mmol) and triphenylphosphine (1.75 g, 6.68 mmol) were dissolved in dry DMF (210 ml) and stirred at room temperature for 30 min. Carbonic acid cyclohex-2-enyl ester methyl ester (9.47 g, 60.74 mmol) was added and the mixture stirred for additional 30 min. 6-Methoxy-1 H-pyrrolo[3,2- c]pyridine (4.5 g, 30.37 mmol) and cesium carbonate (19.79 g, 60.74 mmol) were added, and the reaction mixture was stirred at room temperature for 16 h. Then the mixture was partitioned between water and EA, the aqueous phase extracted with EA and the combined organic phases dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (EA/HEP) to give 5.6 g of the title compound. LC/MS (method LC4): m/z = 229

With the rapid development of chemical substances, we look forward to future research findings about 80862-08-4.

Reference:
Patent; SANOFI-AVENTIS; WO2009/95162; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884494-35-3, 2-Chloro-5-fluoropyridin-3-ol, 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, Safety of 2-Chloro-5-fluoropyridin-3-ol, blongs to pyridine-derivatives compound. Safety of 2-Chloro-5-fluoropyridin-3-ol

Example 319Synthesis of (1R,2S)-2-{{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}}-N-(5-fluoro-3-hydroxypyridin-2-yl)-2-(3-fluorophenyl)cyclopropanecarboxamide (319)(1) 2-chloro-5-fluoro-3-(methoxymethoxy)pyridine (319-1)A DMF (10 ml) solution of 2-chloro-5-fluoro-3-hydroxypyridine (500 mg) was cooled to 0 C. Sodium hydroxide (60% oil dispersion: 149 mg) was added to the reaction solution, and the obtained mixture was stirred at 0 C. for 15 minutes. Chloromethyl methyl ether (293 ul) was added to the reaction solution at the same temperature as described above, and the obtained mixture was heated to room temperature and stirred for 1 hour. Diethyl ether and water were added to the reaction solution, and the organic layer was successively washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 7:3), so as to obtain the title compound (598 mg).1H-NMR (400 MHz, CDCl3) delta (ppm): 3.52 (s, 3H), 5.28 (s, 2H), 7.32 (dd, J=9.2, 2.8 Hz, 1H), 7.95 (dd, J=2.8, 0.8 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-35-3, 2-Chloro-5-fluoropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; US2012/95031; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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 5-Bromo-N2-methylpyridine-2,3-diamine, blongs to pyridine-derivatives compound. Quality Control of 5-Bromo-N2-methylpyridine-2,3-diamine

A solution of 5-bromo-N*2*-methyl-pyridine-2,3-diamine (Stage 67,1.4, 2 09 g 10 34 mrnol) and dichloromethylene-dimethyliminium chloride (Aldrich, Buchs, Switzerland 5 04 g, 31 0 mmol) in NMP (60 ml) was stirred for 17 h at rt The reaction mixture was quenched with saturated aqueous NaHCO3 and EtOAc The aqueous layer was extracted with EtOAc and the combined organic layers washed with saturated aqueous NaHCO3 and with brine, then dned over Na2SO4, filtered and evaporated The crude product was dry loaded on silica gel and pu?fied by MPLC (DCM/MeOH 0% ? 5%) to give the title compound as a red solid (HPLC t« 2 13 mm (Method A). M+H – 255, 257 MS-ES)

The synthetic route of 89415-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1256810-26-0, 6-Bromo-3-methoxypicolinic 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, Safety of 6-Bromo-3-methoxypicolinic acid, blongs to pyridine-derivatives compound. Safety of 6-Bromo-3-methoxypicolinic acid

To a solution of (IS, 2S)- 1 -A?-(6-fluoro- 1 ,3-benzothiazol -2-yl)cyclopentane- 1 ,2-di amine hydrochloride (Intermediate 1; 343 mg, 1.19 mmol) in dry DCM (4 ml) and THF (2 ml) was added 6-bromo-3-methoxypyridine-2-carboxylic acid (CAS number 1256810-26-0; (0506) 349 mg, 1.50 mmol), HATU (680 mg, 1 .79 mmol) and tri ethyl amine (498 mu, 3.58 mmol) The reaction mixture was stirred at room temperature for 72 hours then partitioned between DCM and a saturated solution of sodium bicarbonate. The organics were filtered through a hydrophobic frit and concentrated in vacuo. The caide material was purified by column chromatography (silica, 0 – 100 % ethyl acetate / petrol then 0 – 30 % methanol / ethyl acetate) and then further purified by column chromatography (silica, 0 – 100 % ethyl acetate / petrol then 0 – 30 % methanol / ethyl acetate) to afford the title compound. (0507) 1H NMR (DMSO-t) delta ppm 1.50-1.72 (m, 2 H), 1.69-1.78 (m, 2 H), 2,05-2, 18 (m, 2 H), 3.72 (s, 3 H), 4.14-4.25 (m, 2 H), 6.99-7.08 (m, 1 H), 7.29-7.34 (m, 1 H), 7.50-7.69 (m, 3 H), 8, 13-8,21 (m, 1 H), 8,54-8,62 (m, 1 H) (0508) MS ES+: 466 / 468

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1256810-26-0, 6-Bromo-3-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; FUJIMOTO, Tatsuhiko; ROBINSON, John Stephen; WO2015/124934; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem