189230-41-9 | Pyridine-derivatives

Hwang, Dong-Jin et al. published their research in ACS Medicinal Chemistry Letters in 2015 | CAS: 189230-41-9

2-Bromopyridine-3,4-diamine (cas: 189230-41-9) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Application of 189230-41-9

Structural Optimization of Indole Derivatives Acting at Colchicine Binding Site as Potential Anticancer Agents was written by Hwang, Dong-Jin;Wang, Jin;Li, Wei;Miller, Duane D.. And the article was included in ACS Medicinal Chemistry Letters in 2015.Application of 189230-41-9 This article mentions the following:

Diarylisoquinolines and (trimethoxyphenyl)(indolyl)imidazopyridines I (R = 2-indolyl, 3-indolyl, 4-indolyl, 6-indolyl, 7-indolyl), analogs of a previous trimethoxybenzoylphenylindole and I (R = 5-indolyl), were prepared as tubulin polymerization inhibitors acting at the colchicine binding site for potential use as antitumor agents with improved metabolic stabilities and cytotoxicities. I (R = 2-indolyl, 3-indolyl, 4-indolyl, 6-indolyl, 7-indolyl) inhibited tubulin polymerization with IC₅₀ values of 3 to 175 nM against a panel of human melanoma and prostate cancer cell lines. In particular, I (R = 6-indolyl) showed improved cytotoxic potency (average IC₅₀ of 9.75 nM vs 55.75 nM) and metabolic stability in human liver microsomes (half-life time was 56.3 min vs. 45.4 min) as compared to previously reported I (R = 5-indolyl). I (R = 6-indolyl) was effective against P-glycoprotein (P-gp) mediated multiple drug resistance (MDR) and taxol resistance. In the experiment, the researchers used many compounds, for example, 2-Bromopyridine-3,4-diamine (cas: 189230-41-9Application of 189230-41-9).

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lu, Yan et al. published their research in Journal of Medicinal Chemistry in 2014 | CAS: 189230-41-9

2-Bromopyridine-3,4-diamine (cas: 189230-41-9) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ璺痬ol閳? in pyridine vs. 150 kJ璺痬ol閳? in benzene). Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application of 189230-41-9

Design, Synthesis, and Biological Evaluation of Stable Colchicine Binding Site Tubulin Inhibitors as Potential Anticancer Agents was written by Lu, Yan;Chen, Jianjun;Wang, Jin;Li, Chien-Ming;Ahn, Sunjoo;Barrett, Christina M.;Dalton, James T.;Li, Wei;Miller, Duane D.. And the article was included in Journal of Medicinal Chemistry in 2014.Application of 189230-41-9 This article mentions the following:

To block the metabolically labile sites of novel tubulin inhibitors targeting the colchicine binding site based on SMART, ABI, and PAT templates, we have designed, synthesized, and biol. tested three focused sets of new derivatives with modifications at the carbonyl linker, the para-position in the C ring of SMART template, and modification of A ring of the PAT template. Structure-activity relationships of these compounds led to the identification of new benzimidazole and imidazo[4,5-c]pyridine-fused ring templates, represented by compounds I(X = N, CH), resp., which showed enhanced antitumor activity and substantially improved the metabolic stability in liver microsomes compared to SMART. MOM group replaced TMP C ring and generated a potent analog 15, which showed comparable potency to the parent SMART compound Further modification of PAT template yielded another potent analog 33 with 5-indolyl substituent at A ring. In the experiment, the researchers used many compounds, for example, 2-Bromopyridine-3,4-diamine (cas: 189230-41-9Application of 189230-41-9).

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some tips on 189230-41-9

At the same time, in my other blogs, there are other synthetic methods of this type of compound,189230-41-9, 2-Bromopyridine-3,4-diamine, and friends who are interested can also refer to it.

Application of 189230-41-9, 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. 189230-41-9, name is 2-Bromopyridine-3,4-diamine. A new synthetic method of this compound is introduced below.

A mixture of intermediate 22 (1.8 g, 9.57 mmol) and 4-fluoro-benzoic acid (1.34 g, 9.57 mmol) in polyphosphoric acid (25 g) was stirred and heated at 180 0C for Ih. The r.m. was cooled to r.t, and water was added. The resulting sol. was neutralized with K2CO3, and the resulting precipitate was filtered off and washed with water. Yield: 1 g of crude intermediate 23, which was used as such in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,189230-41-9, 2-Bromopyridine-3,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; VELTER, Adriana, Ingrid; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; WU, Tongfei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; PIETERS, Serge, Maria, Aloysius; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; OEHLRICH, Daniel; WO2010/89292; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some tips on 189230-41-9

At the same time, in my other blogs, there are other synthetic methods of this type of compound,189230-41-9, 2-Bromopyridine-3,4-diamine, and friends who are interested can also refer to it.

A new synthetic route of 2-Bromopyridine-3,4-diamine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Application of 189230-41-9, 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 189230-41-9 as follows.

[0355] Reference AD [0356] Synthesis of 5-chloro-N-cyclopropyl-3-(4-(2-fluoro-4-methoxyphenoxy)piperidin-l- yl)pyrido[3,4-b]pyrazin-2-amine [0358] [0359] Step 1 : 5-bromopyrido[3,4-b]pyrazine-2,3(lH,4H)-dione [0360] A solution of l,2-di(lH-imidazol-l-yl)ethane-l,2-dione (1.456 g, 7.66 mmol) and 2- bromopyridine-3,4-diamine (1.2 g, 6.38 mmol) in DMF (21.27 ml) was stirred at RT overnight. The precipitate was filtered and washed with anhydrous THF to give the title compound as a grey solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Reference:
Patent; ENVOY THERAPEUTICS, INC.; HITCHCOCK, Stephen; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; KIKUCHI, Shota; MACKLIN, Todd; HOPKINS, Maria; WO2014/28479; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A new synthetic route of 2-Bromopyridine-3,4-diamine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Reference of 189230-41-9, 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. 189230-41-9, name is 2-Bromopyridine-3,4-diamine. A new synthetic method of this compound is introduced below.

Step 2: To a solution of 2-fluoro-6-iodobenzaldehyde (1.5 g, 6.0 mmol) and 2-bromopyridine-3, 4- diamine (1.1 g, 6.0 mmol) in ethanol (20 mL), was added ferric chloride (778 mg, 4.80 mmol). The reaction mixture was stirred at 60 C under oxygen atmosphere overnight. The next day, solvent was evaporated via rotavap and theresulting residue was purified by column chromatography on silica gel eluting with petroleum/ethyl acetate (3 :1) to give the desired product (1.6 g, 64% yield) as a yellow solid. LCMS (ESI) m/z: 418 [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,189230-41-9, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LAI, Yingjie; LIANG, Jun; MAGNUSON, Steven, R.; ROBARGE, Kirk, D.; TSUI, Vickie, Hsaio-Wei; ZHANG, Birong; WO2013/41539; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

New learning discoveries about 2-Bromopyridine-3,4-diamine

According to the analysis of related databases, 189230-41-9, the application of this compound in the production field has become more and more popular.

Related Products of 189230-41-9, 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 189230-41-9, name is 2-Bromopyridine-3,4-diamine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: To a solution of 2-fluoro-6-iodobenzaldehyde (1.5 g, 6.0 mmol) and 2-bromopyridine-3,4-diamine (1.1 g, 6.0 mmol) in ethanol (20 mL), was added ferric chloride (778 mg, 4.80 mmol). The reaction mixture was stirred at 60 C. under oxygen atmosphere overnight. The next day, solvent was evaporated via rotavap and theresulting residue was purified by column chromatography on silica gel eluting with petroleum/ethyl acetate (3:1) to give the desired product (1.6 g, 64% yield) as a yellow solid. LCMS (ESI) m/z: 418 [M+H+].

According to the analysis of related databases, 189230-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Lai, Yingjie; Liang, Jun; Magnuson, Steven R.; Robarge, Kirk D.; Tsui, Vickie H.; Zhang, Birong; US2014/206702; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Brief introduction of 189230-41-9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Related Products of 189230-41-9, 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 189230-41-9 as follows.

b) Preparation of intermediate 34A mixture of intermediate 33 (1.8 g, 9.57 mmol) and 4-fluoro-benzoic acid (1.34 g, 9.57 mmol) in polyphosphoric acid (25 g) was stirred and heated for 1 h at 180 0C. The r.m. was cooled to r.t, and water was added. The resulting sol. was neutralized with K2Ctheta3, and the resulting precipitate was filtered off and washed with water. Yield: 1 g of crude intermediate 34, which was used as such in the next reaction step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; BISCHOFF, Francois Paul; ZHUANG, Wei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; MACDONALD, Gregor, James; OEHLRICH, Daniel; WO2010/94647; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Brief introduction of 189230-41-9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Brief introduction of 189230-41-9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.