Category: 669066-91-5

Reich, Siegfried H. et al. published their research in Journal of Medicinal Chemistry in 2018 | CAS: 669066-91-5

5-Bromo-3-fluoropicolinic acid (cas: 669066-91-5) 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. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Formula: C6H3BrFNO2

Structure-based Design of Pyridone-Aminal eFT508 Targeting Dysregulated Translation by Selective Mitogen-activated Protein Kinase Interacting Kinases 1 and 2 (MNK1/2) Inhibition was written by Reich, Siegfried H.;Sprengeler, Paul A.;Chiang, Gary G.;Appleman, James R.;Chen, Joan;Clarine, Jeff;Eam, Boreth;Ernst, Justin T.;Han, Qing;Goel, Vikas K.;Han, Edward Z. R.;Huang, Vera;Hung, Ivy N. J.;Jemison, Adrianna;Jessen, Katti A.;Molter, Jolene;Murphy, Douglas;Neal, Melissa;Parker, Gregory S.;Shaghafi, Michael;Sperry, Samuel;Staunton, Jocelyn;Stumpf, Craig R.;Thompson, Peggy A.;Tran, Chinh;Webber, Stephen E.;Wegerski, Christopher J.;Zheng, Hong;Webster, Kevin R.. And the article was included in Journal of Medicinal Chemistry in 2018.Formula: C6H3BrFNO2 This article mentions the following:

Dysregulated translation of mRNA plays a major role in tumorigenesis. Mitogen-activated protein kinase interacting kinases (MNK)1/2 are key regulators of mRNA translation integrating signals from oncogenic and immune signaling pathways through phosphorylation of eIF4E and other mRNA binding proteins. Modulation of these key effector proteins regulates mRNA, which controls tumor/stromal cell signaling. Compound 23 (eFT508, 6′-((6-aminopyrimidin-4-yl)amino)-8′-methyl-2’H-spiro-[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione hydrochloride), an exquisitely selective, potent dual MNK1/2 inhibitor, was designed to assess the potential for control of oncogene signaling at the level of mRNA translation. The crystal structure-guided design leverages stereoelectronic interactions unique to MNK culminating in a novel pyridone-aminal structure described for the first time in the kinase literature. Compound 23 has potent in vivo antitumor activity in models of diffuse large cell B-cell lymphoma and solid tumors, suggesting that controlling dysregulated translation has real therapeutic potential. Compound 23 is currently being evaluated in Phase 2 clin. trials in solid tumors and lymphoma. Compound 23 is the first highly selective dual MNK inhibitor targeting dysregulated translation being assessed clin. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-fluoropicolinic acid (cas: 669066-91-5Formula: C6H3BrFNO2).

5-Bromo-3-fluoropicolinic acid (cas: 669066-91-5) 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. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Formula: C6H3BrFNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The important role of 5-Bromo-3-fluoropicolinic acid

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. 669066-91-5, 5-Bromo-3-fluoropicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference of 669066-91-5 ,Some common heterocyclic compound, 669066-91-5, molecular formula is C6H3BrFNO2, 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.

A solution of 5-bromo-3-fluoropyridine-2-carboxylic acid (2.7 g, 12.27 mmol, 1 equiv.) and H2S04 (5 mL) in MeOH (10 mL) was stirred at 85 C for 1 hour. The mixture was basified to pH 7 with saturated NaHCO3. The resulting mixture was extracted with EA (3x) and evaporated to afford the title compound (2.3 g) as off white solid. ESI-MS m/z= 233.90[M+Hjt

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. 669066-91-5, 5-Bromo-3-fluoropicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; OR, Yat, Sun; BLAISDELL, Thomas, P.; SHOOK, Brian, C.; KIM, In, Jong; (98 pag.)WO2018/226801; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Analyzing the synthesis route of 669066-91-5

According to the analysis of related databases, 669066-91-5, the application of this compound in the production field has become more and more popular.

Related Products of 669066-91-5, Adding some certain compound to certain chemical reactions, such as: 669066-91-5, name is 5-Bromo-3-fluoropicolinic acid,molecular formula is C6H3BrFNO2, 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 669066-91-5.

N,N-Diisopropylethylamine (200 mu, 1 mmol) was added to a mixture of 2- methylbiphenyl-3-amine (70 mg, 0.4 mmol), 5-(methoxycarbonyl)pyridine-2-carboxylic acid (Oakwood Chemical, cat017196, 75 mg, 0.42 mmol), and N,N,N’,N’-tetramethyl-0-(7- azabenzotriazol-l -yl)uronium hexafluorophosphate (220 mg, 0.57 mmol) in N,N- dimethylformamide (2 mL, 20 mmol). The reaction mixture was allowed to stir at room temperature (rt) overnight. The reaction mixture was quenched with saturated aqueous NaHCC , and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with brine, dried over MgSCn, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-35%) to afford the desired product. LC-MS calculated for C21H19N2O3 (M+H)+: m/z = 347.1 ; found 347.1. This compound was prepared using a similar procedure as described for Example 1, Step 2, with 5-bromo-3-fluoropyridine-2-carboxylic acid (Aldrich, cat753483) replacing 5- (methoxycarbonyl)pyridine-2-carboxylic acid and prolong the reaction time to 3 days. LC-MS calculated for C19H15BrFN2O (M+H)+: m/z = 385.0; found 385.0.

According to the analysis of related databases, 669066-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; YU, Zhiyong; ZHANG, Fenglei; YAO, Wenqing; (173 pag.)WO2017/106634; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem