Category: pyridine-derivatives

Application of 18206-06-9, 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 18206-06-9, name is 2,6-Dimethylisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,6-dimethylpyridine-4-carbaldehyde (0.14 g, 1.00 mmol) in N,N-dimethyl acetamide (8 mL) were added 2-amino-5-(4-methyl-piperazin-1-ylmethyl)benzamide (0.25 g, 1.00 mmol), sodium hydrogensulfite (0.18 g, 1.20 mmol), and p-toluenesulfonic acid (0.057 g, 0.30 mmol). The reaction mixture was stirred at 115° C. for 20 hours under nitrogen, then cooled to room temperature. Solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane, washed with sat. NaHCO3, water, then brine, and dried over anhydrous sodium sulfate. Solvent was evaporated and the residue was purified by column chromatography (silica gel 230-400 mesh; 2-3percent 7 M ammonia in methanol and dichloromethane as eluent) to give the title compound. Yield: 0.035 g (9.6percent). MP 229-230° C. 1H NMR (400 MHz, CDCl3): delta 8.30 (br s, 1H), 7.88 (s, 2H), 7.84 (m, 2H), 3.66 (s, 2H), 2.72 (s, 6H), 2.50 (br s, 8H), 2.30 (s, 3H). MS (ES) m/z: 364.17 (M+1), 182.67 (100percent).

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 18206-06-9, 2,6-Dimethylisonicotinaldehyde.

Reference:
Patent; Resverlogix Corp.; Hansen, Henrik C.; (96 pag.)US9238640; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 96530-81-3, 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 96530-81-3 as follows.

To 3-iodo-lH-pyrazole (763 mg, 3.93 mmol) in DMSO (15 mL) at 0 C, was added sodium hydride (60% in mineral oil, 189 mg, 4.72 mmol). The reaction was warmed to 25 C and stirred for 60 min before 4-fluoro-2-methoxypyridine (500 mg, 3.93 mmol) was added. The reaction mixture was stirred at 90 C for 4.5 h before quenching by the addition of water. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 0-30% EtOAc in hexanes) to afford 4-(3- iodo-lH-pyrazol-l-yl)-2-methoxypyridine, as a white solid. LCMS calc. = 301.97; found = 302.02 (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,96530-81-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; HIRABAYASHI, Tomokazu; KATSUNO, Mika; SMITH, Cameron James; SHERER, Edward; CAMPEAU, Louis-Charles; BALKOVEC, James; GREENLEE, William John; LI, Derun; GUO, Liangqin; CHAN, Tin Yan; CHEN, Yi-Heng; CHEN, Yili; CHACKALAMANNIL, Samuel; TAN, John Qiang; WO2014/99694; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 131747-69-8 , The common heterocyclic compound, 131747-69-8, name is 2-Fluoroisonicotinaldehyde, molecular formula is C6H4FNO, 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.

Example 132Preparation of 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a-((2-fluoropyridin- 4-yl)methylamino)-5a,5b,8,8,lla-pentamethyl-l-(prop-l-en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,ll,lla,llb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoic acid. Step 1. Preparation of methyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- ((2-fluoropyridin-4-yl)methylamino)-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate.To a solution of methyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- amino-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate, HCl (318 mg, 0.548 mmol) in DCE (10 mL) was added glacial acetic acid (0.314 mL, 5.48 mmol), sodium acetate (67.4 mg, 0.822 mmol), 2-fluoropyridine-4-carboxaldehyde (206 mg, 1.644 mmol) and 4A molecular sieves. The reaction mixture was heated to 65 C for 18 h. To the reaction mixture was added sodium triacetoxyhydroborate (581 mg, 2.74 mmol) and the resulting mixture was heated to 65 C for 7.5 h, then the mixture was left at rt for 48 h. The reaction was diluted with DCM (50 mL) and washed with saturated aHC03 (20 mL). The aqueous layer was extracted with DCM (2 x 25 mL). The combined organic layer was dried over MgS04, filtered and concentrated. The resulting dark brown residue was dissolved in THF (3 mL) and MeOH (0.6 mL), filtered and purified by reverse phase preparative HPLC using HPLC method 3 to give methyl 4- ((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a-((2-fluoropyridin-4- yl)methylamino)-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate, TFA (218.4 mg, 0.285 mmol, 52.0% yield) as a white solid. LCMS: m/e 653.4 (M+H)+, 2.69 min (method 6).

The synthetic route of 131747-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; REGUEIRO-REN, Alicia; LIU, Zheng; SWIDORSKI, Jacob; SIN, Ny; VENABLES, Brian Lee; SIT, Sing-Yuen; CHEN, Yan; CHEN, Jie; MEANWELL, Nicholas A.; WO2012/106190; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89284-11-7, 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 89284-11-7, name is 5,6-Dibromopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5,6-dibromo-pyridin-2-ylamine (10 kg, 39.7 mol) A and methylcyclohexane (40 L) is heated to 65 C. At this temperature is added N,N- dimethylformamide dimethyl acetal (4.97 kg, 41.7 mol) over a period of 30 min rinsing with methylcyclohexane (10 L). The reaction mixture is heated to 100 C for 1 h or until the reaction is complete while removing 10 L of solvent under reduced pressure. Then, methylcyclohexane (20 L) is added and the mixture is cooled to about 60-55 C. Crystallization is initiated by addition of seeding crystals and the resulting suspension is cooled to 20 C over a period of 4 h and then stirred for additional 15 min at this temperature. The title product B is isolated by filtration, washed with methylcyclohexane (2 x 15 L) and dried under vacuum at 50 C. Yield 80 %. MS (ESI+) m/z = 306/308/310 [M+H]+.

According to the analysis of related databases, 89284-11-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LU, Guanghua; HUCHLER, Guenther; KRUEGER, Thomas; PANGERL, Michael; SANTAGOSTINO, Marco; DESROSIERS, Jean-Nicolas; (71 pag.)WO2017/198734; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 896722-50-2, 6-Chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, 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, 896722-50-2, blongs to pyridine-derivatives compound. HPLC of Formula: C13H9ClN2O2S

A solution of methylzinc chloride in THF (2 M) (9 mL, 12 mmol) was added to 6-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.600 g, 2.05 mmol) and Pd(PPh3)4 (0.095 g, 0.08 mmol) in THF (30 mL). The mixture was refluxed for 40 h, cooled to 0 C., quenched with water and extracted with Et2O. The organic layer was concentrated and the residue was purified over a silica gel column eluting with EtOAc/hexane (1:5) to give N-protected 6-methyl-7-azaindole (0.495 g, 88%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,896722-50-2, its application will become more common.

Reference:
Patent; Hsieh, Hsing-Pang; Chao, Yu-Sheng; Liou, Jing-Ping; Chang, Jang-Yang; Tung, Yen-Shih; US2006/148801; (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.923169-37-3, name is 4-(Hydroxymethyl)picolinic acid, molecular formula is C7H7NO3, molecular weight is 153.14, as common compound, the synthetic route is as follows.Quality Control of 4-(Hydroxymethyl)picolinic acid

To a stirred solution of 4-(hydroxymethyl)picolinic acid 1 (461 mg, 3.012 mmol) in DMF (10 mL) was added diisopropylethylamine (0.8 mL, 4.518 mmol) and HATU (1.14 g, 3.012 mmol) at 0 C. After 20 min (1S,3R)-N1-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3- b]pyridin-3-yl)pyrimidin-4-yl)cyclohexane-1,3-diamine (Intermediate 12, enantiomer 2 (Ent- 2)) (750 mg, 1.506 mmol) was added and stirred the reaction mixture at room temperature for 16 h. After completion of the reaction, the mixture was diluted with ice cold water (100 mL) and filtered the precipitated solid to afford pure compound N-((1R,3S)-3-((5-fluoro-2-(5- fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)cyclohexyl)-4- (hydroxymethyl)picolinamide (Intermediate 23) (950 mg with 75% LCMS purity) as a brown solid. TLC system: 10% MeOH in dichloromethane; Rf: 0.6; LCMS (ESI): m/z 634.31(M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,923169-37-3, 4-(Hydroxymethyl)picolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina, C.; LEE, Sam SK; FEESE, Michael, David; (206 pag.)WO2020/23813; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 944401-77-8, 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.944401-77-8, name is 2-Amino-4-fluoropyridine, molecular formula is C5H5FN2, molecular weight is 112.105, as common compound, the synthetic route is as follows.

To a solution of 4-fluoropyridin-2-amine (2.5 g, 22.3 mmol) in acetonitrile (25 niL) was added TFA (0.85 mL, 11.16 mmol), S (5.5 g, 24.55 mmol) at 0 C and the reaction mixture was stirred at rt for 4 hours. After completion of the reaction, the reaction mixture was diluted with EtOAc (75 mL). The organic layer was washed with water (20 mL), dried (anhydrous NaPatent; RICHTER GEDEON NYRT.; ORION CORPORATION; HAIKARAINEN, Anssi; JOUBERT, Muriel; KAROLYI, Benedek; KAeSNAeNEN, Heikki; PASSINIEMI, Mikko; POHJAKALLIO, Antti; SZANTO, Gabor; VAISMAA, Matti; (97 pag.)WO2019/43635; (2019); 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.849937-96-8, name is 5-Bromo-2,4-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.8861, as common compound, the synthetic route is as follows.Recommanded Product: 5-Bromo-2,4-dichloropyridine

A solution of sodium methylate in methanol (0.95 ml, 0.90 mmol, 21%) was added dropwise to a flask containing 5-bromo-2,4,-dichloro-pyridine (0.75 g, 3.31 mmol) at 0 C. The reaction mixture was stirred at rt for 4 hours after which it was poured into ice-cold water and extracted with EtOAc. Organic phases were combined, washed with brine, dried (Na2S04), filtered and evaporated to dryness yielding 0.68 g of 5-bromo-2-chloro-4- methoxypyridine, NMR (DMSO-d6) delta: 8.43 (s, 1H), 7.32 (s, 1H), 3.99 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,849937-96-8, 5-Bromo-2,4-dichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; ORION CORPORATION; HAIKARAINEN, Anssi; JOUBERT, Muriel; KAROLYI, Benedek; KAeSNAeNEN, Heikki; PASSINIEMI, Mikko; POHJAKALLIO, Antti; SZANTO, Gabor; VAISMAA, Matti; (97 pag.)WO2019/43635; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16063-70-0, 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 16063-70-0, name is 2,3,5-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydride (60% in oil, 0.2 g, 5.5 mmol) was added to a solution of 3-hydroxy-5-methylpyrazole (0.49 g, 5.0 mmol) in DMF (10 ml) at 0C, and the mixture was stirred for 30 minutes while it was allowed to have room temperature gradually. Then, 2,3,5-trichloropyridine (0.9 g, 5.0 mmol) was added, and the mixture was stirred under heating at 70C for 2 days. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid (20 ml) and extracted with ethyl acetate (10 ml x 3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane = 1/7 ? 1/2), to give a white solid of 3-(3,5-dichloropyridin-2-yloxy)-5-methylpyrazole (0.7 g, yield: 57.4 %). mp: 109-111C; 1H-NMR(CDCl3, TMS, ppm): delta 2.32(s, 3H), 5.86(s, 1H), 7.77(d, J=2.3Hz, 1H), 8.03(d, J=2.3Hz, 1H), 9.40-11.50(br s, 1H).

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 16063-70-0, 2,3,5-Trichloropyridine.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH CENTER; Kaken Pharmaceutical Co., Ltd.; EP1362852; (2003); A1;,
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. 106447-97-6, name is 2-Amino-4-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., Quality Control of 2-Amino-4-(trifluoromethyl)pyridine

To a solution of 2-amino^l- trifluoromethyl-pyridine (2.00 g, 0.0123 mol) in DMF (4 mL, 0.05 mol) was added a solution of 1,3-dichloro-5,5- dimethylhydantoin (1.4 g, 0.0074 mol) in DMF (4 mL) dropwise. The reaction was stirred at room temperature for 2 hr, whereupon the reaction mixture was diluted with ether (80 mL) and washed with water (10 mL). The organic phase was dried and concentrated to give the crude product, which was purified on combiflash (0-20% EtOAc/Hexanes) to give compound G.5 as light yellow oil. (65% yield); 1H NMR: (DMSO-d6) delta 8.16 (s, 1H), 6.87 (s, 1H), 6.76 (brs, 1H); LCMS: m/z 197 [M+l].

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, 106447-97-6, 2-Amino-4-(trifluoromethyl)pyridine.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; CHUAQUI, Claudio; COSSROW, Jennifer; DOWLING, James; GUAN, Bing; HOEMANN, Michael; ISHCHENKO, Alexey; JONES, John, Howard; KABIGTING, Lori; KUMARAVEL, Gnanasambandam; PENG, Hairuo; POWELL, Noel; RAIMUNDO, Brian; TANAKA, Hiroko; VAN VLOTEN, Kurt; VESSELS, Jeffrey; XIN, Zhili; WO2010/78408; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem