Pyridine-derivatives

Related Products of 90145-48-5, 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. 90145-48-5, name is 5-Bromopyridine-2-carboxamide, molecular formula is C6H5BrN2O, 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.

(i) (S)-tert-Buty l-(2-(4-(6-carbamoylpyridin-3-yl)phcyanoethylcarbamoyl)cyclohexylcarbamateA solution of (S)-tert-butyl l-(l-cyano-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate (Example 23 step (i),300 mg), potassium acetate (178mg) and 4-bromopicolinamide (121mg) in mixture of acetonitrile (15 mL) and water (5 mL), was stirred under an atmosphere of nitrogen. 1,1 ¾z’5(di-tert-butylphosphino)ferrocene palladium dichloride (12 mg) was added and the mixture heated at 90 C for 4h. After standing at rt for 24h the reaction mixture was concentrated to dryness and the residue purified on silica gel using ethyl acetate as eluant to afford the subtitled comound (450 mg). m/e (APCI+) 492 [M+H]+

According to the analysis of related databases, 90145-48-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; KINCHIN, Elizabeth; MATHER, Andrew; METE, Antonio; MILLICHIP, Ian; STANIER, Andrew Geoffrey; WO2011/154677; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16744-81-3, Adding some certain compound to certain chemical reactions, such as: 16744-81-3, name is 4-Methoxypicolinaldehyde,molecular formula is C7H7NO2, 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 16744-81-3.

General procedure: A mixture of 6-(3 -hydroxypropoxy)-4-(6-(piperazin- 1 -yl)pyridin-3 -yl)pyrazolo[ 1,5 -a]pyridine-3 -carbonitrile hydrochloride (Intermediate P51; 12.1 mg, 0.0292mmol), 5-chloropicolinaldehyde (8.26 mg, 0.0583 mmol) and NaBH(AcO)3 (18.5 mg, 0.0875mmol) in DCE (583 tL) was stirred for 1 day at ambient temperature. The mixture was purified directly by C18 reverse phase (5-95percent ACN/ water with 0.1percent TFA as the gradient eluent) to afford the title compound (17.1 mg, 95percent yield). MS (apci) m/z = 504.2 (M+H).

According to the analysis of related databases, 16744-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19235-89-3, 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 19235-89-3 as follows.

Step 3. Preparation of 4-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yloxy)picolinonitrile To the reaction mixture of 2-(cyclohexylmethylamino)benzo[d]thiazol-6-ol (18 mg, 0.068 mmol) in 0.4 ml of NMP was added Cesium Carbonate (56 mg, 0.171 mmol) and stirred at RT for 1-3 minutes. To this mixture was added 4-chloropicolinonitrile (19 mg, 0.136 mmol). The reaction mixture was stirred at 60 C. for 5 hours or until done by LC. The crude reaction mixture was filtered, purified on prep HPLC and lyophilized to give 4-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yloxy)picolinonitrile as TFA salt (9.8 mg). ES/MS m/z 365.1 (MH+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19235-89-3, its application will become more common.

Reference:
Patent; Novartis AG; US2008/45528; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 109613-90-3, 2-Chloro-3-fluoro-4-nitropyridine, 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, Recommanded Product: 2-Chloro-3-fluoro-4-nitropyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-3-fluoro-4-nitropyridine

A solution of 2-aminoethanol (0.67 mL; 11 mmol) cooled to 0 C was treated with 2-chloro-3-fluoro-4- nitropyridine (2.00 g; 11 mmol) and stirred for 0.5 h. A solid was formed, which was then purified by column chromatography (silica gel; PE : EA; 1 :1 to 0:1 ; v/v) to afford 2-[(2-chloro-4-nitro-3- pyridyl)amino]ethanol (1.68 g) as an orange solid. ‘H-NMR (400 MHz, CDC13) delta ppm: 7.85 (d, J= 5.6 Hz, 1H), 7.68 (d, J= 5.6 Hz, 1H), 3.89 – 3.85 (m, 2H), 3.56 – 3.52 (m, 2H).

The synthetic route of 109613-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; RICHALET, Florian; WEILER, Sven; EL SHEMERLY, Mahmoud; LANE, Heidi; (131 pag.)WO2019/72978; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75893-75-3, 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. 75893-75-3, name is 6-Cyclopropylnicotinic acid. A new synthetic method of this compound is introduced below.

Example 56 6-Cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide (56) In a 10-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, [2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methanamine (100 mg, 0.31 mmol, 1.00 equiv) and 6-cyclopropylpyridine-3-carboxylic acid (60.7 mg, 0.37 mmol, 1.20 equiv) were dissolved in N,N-dimethylformamide (2 mL), to which were added HATU (176.9 mg, 0.47 mmol, 1.50 equiv) and DIEA (120.3 mg, 0.93 mmol, 3.00 equiv) in sequence at room temperature. The resulting solution was stirred for 16 h at room temperature. When the reaction was done, it was quenched by the addition of 5 mL water and the mixture was extracted with dichloromethane (3*10 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-HPLC using the following conditions: column, X Bridge C18, 19*150 mm, 5 um; mobile phase, acetonitrile in water (with 0.05% TFA), 30% to 70% gradient in 10 min; detector, UV, 254 nm. 6-cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide (20 mg, 13%) was obtained as white solid. HPLC: 97.7% purity. MS: m/z=468.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 6 13.39 (br s, 1H), 9.20-9.17 (m, 1H), 8.91 (d, J=2.0 Hz, 1H), 8.44 (s, 1H), 8.29-8.20 (m, 2H), 8.14-8.11 (m, 3H), 7.56-7.52 (m, 2H), 7.42 (d, J=8.0 Hz, 1H), 4.60 (s, 2H), 3.94 (s, 3H), 2.33-2.15 (m, 1H), 1.05-1.01 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75893-75-3, 6-Cyclopropylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 201937-23-7 ,Some common heterocyclic compound, 201937-23-7, molecular formula is C6H7Cl2N3, 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.

Compound 88 (1.08 g, 3.14 mmol), 6-chloropyridine-3-carboxirnidamide hydrochloride (900 mg, 4.69 mmol) and K2CO3 (1.30 g, 9.42 mmol) in EtOH (15 mL) were heated in a Biotage microwave synthesizer at 120 C for 3 h. After the reaction was cooled to room temperature, EtOAc was added. The mixture was washed with water. The organic extract was dried with Na2S04and concentrated. The crude product was dissolved in CH2CI2 (31 mL) and treated with DDQ (713 mg, 3.14 mmol). After the reaction was stirred at room temperature for 1 h, aq. sat. NaHCCb was added. The mixture was stirred at room temperature for 10 min; filtered through a pad of Celite; and eluted with CH2CI2. The organic phase of the filtrate was separated. The aqueous phase was extracted with CH2CI2. The combined organic extract was dried with Na2S04 and filtered and concentrated. The residue was purified by flash chromatography (silica gel, eluting with 0% to 5% EtOAc in CH2CI2) to give compound 363 (902 g, 60% yield) as a white foamy solid, m/z = 480 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,201937-23-7, its application will become more common.

Reference:
Patent; REATA PHARMACEUTICALS, INC.; JIANG, Xin; BENDER, Christopher, F.; VISNICK, Melean; HOTEMA, Martha, R.; SHELDON, Zachary, S.; LEE, Chitase; CAPRATHE, Bradley, William; BOLTON, Gary; KORNBERG, Brian; (497 pag.)WO2018/111315; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 17570-98-8, Adding some certain compound to certain chemical reactions, such as: 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide,molecular formula is C7H7Br2NO, 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 17570-98-8.

EXAMPLE 17 2-Pyridin-4-yl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (alternative method) Bromoacetylpyridine hydrobromide (3.3 g, 11.78 mmol), piperidindione (2 g, 17.68 mmol) and ammonium acetate (3.63 g, 47.1 mmol) were dissolved in anhydrous ethanol (54 mL) and stirred at RT overnight. Ethyl acetate (200 mL) was added (precipitate formed) and the mixture was stirred at RT for 30′. The solid was filtered off and discarded, while the solution was concentrated under reduced pressure. The residue (orange-red solid, 4.8 g) was purified by flash chromatography (eluant DCM/MeOH 6:1). To the obtained pink solid (1.34 g, 6.28 mmol), dissolved in MeOH (140 mL), 4N HCl in dioxane (3.14 mL, 12.56 mmol) was added. The mixture (precipitate) was stirred for 30′, then concentrated under reduced pressure to half of the volume, stirred 30′ and filtered to yield the first crop (1.3 g). The mother liquor was concentrated to 20 mL and the second crop filtered out (0.12 g). The two crops were joined and washed twice with 95% EtOH: first with 35 mL and 2 hours stirring, the second with 25 mL of ethanol. The collected solid was dried to yield 1.21 g of desired compound (41.1% yield, purity>90%). By working in an analogous way and starting from the corresponding bromoketoheteroaryl the following compounds were also obtained:

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. 17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142414; (2007); 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. 69422-72-6, name is 2,4,6-Trichloronicotinic acid, molecular formula is C6H2Cl3NO2, 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. Application In Synthesis of 2,4,6-Trichloronicotinic acid

A solution of the product of EXAMPLE 14C (1.5 g, 6.7 mmol) in dichlorom ethane (50 mL) was treated at room temperature with 2 drops of N,N-dimeth lformamide. O alyl chloride (1.27 g, 10 mmol) was added dropwise over 15 minutes and stirring was continued for 2 hours. The solution was concentrated and dried under vacuum to give the crude acid chloride. Ammonium (gas) was passed through a solution of the acid chloride in tetrahydrofuran (20 mL) and the mixture stirred at room temperature for 0.5 hours. The mixture was concentrated under vacuum and the residue purified by flash chromatography on silica gel (200-300 mesh) eluting with 100/1 dichloromethane/methanol to give the title compound. MS: 225 (M+H+).

With the rapid development of chemical substances, we look forward to future research findings about 69422-72-6.

Reference:
Patent; ABBOTT LABORATORIES; VASUDEVAN, Anil; PENNING, Thomas, Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97479; (2012); A1;,
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. 630395-95-8, name is 1H-Pyrrolo[3,2-c]pyridine-2-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 1H-Pyrrolo[3,2-c]pyridine-2-carbaldehyde

To a solution of lH-pyrrolo[3,2-c]pyridine-2-carbaldehyde (3.24 g, 22.19 mmol) in MeOH at 0C under argon is added sodium cyanide (5.44 g, 111 mmol) and manganese dioxide (9.65 g, 111 mmol). The reaction mixture is stirred for 5h after which time it is filtered through Celite and diluted with EtOAc (500mL). The organic layer is washed with water (2x), brine, dried over sodium carbonate, filtered and concentrated to yield 3.27 g ( 84%) of desired product. 1H NMR (DMSO-dtf, 300 MHz) delta 12.3 (bs, 1H), 9.0 (s, 1H), 8.3 (d, 1H), 7.4 (d, 1H), 7.3 (s, 1H), 4.0 (s, 3H). LCMS m/z 177 (M+H).

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, 630395-95-8, 1H-Pyrrolo[3,2-c]pyridine-2-carbaldehyde.

Reference:
Patent; SANOFI; CHOI-SLEDESKI, Yong Mi; NIEDUZAK, Thaddeus R.; POLI, Gregory B.; SHUM, Patrick Wai-Kwok; STOKLOSA, Gregory T.; ZHAO, Zhicheng; WO2011/78984; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1060810-03-8, 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. 1060810-03-8, name is 5-Chloro-2-methylisonicotinic acid. A new synthetic method of this compound is introduced below.

To a CH2Cl2 solution of acid 6-4 (0.8 g) was added EDC (1.3 eq) and aniline (2 eq) at room temperature. After 10 minutes, the reaction was diluted with CH2Cl2 and washed with dilute HCl. The organic layer was dried and concentrated to yield amide 6-5 (0.9 g, 80%) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1060810-03-8, 5-Chloro-2-methylisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; BIOTA SCIENTIFIC MANAGEMENT PTY LTD; WO2008/141385; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem