2-((2-fluoro-4-iodophenyl)amino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Base Information

• Chemical Name: 2-((2-fluoro-4-iodophenyl)amino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide
• CAS No.: 869357-68-6
• Molecular Formula: C16H17FIN3O4
• Molecular Weight: 461.232
• Hs Code.: 2933998090
• European Community (EC) Number: 642-441-7
• UNII: G4990BOZ66
• ChEMBL ID: CHEMBL3182621
• DSSTox Substance ID: DTXSID50235986
• Metabolomics Workbench ID: 149617
• NCI Thesaurus Code: C69143
• Pharos Ligand ID: VXP4LG28PLAJ
• Wikidata: Q27074802
• Mol file: 869357-68-6.mol

Synonyms:2-(2-fluoro-4-iodophenylamino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide;ARRY-424704;ARRY-704;AZD8330

Chemical Property of 2-((2-fluoro-4-iodophenyl)amino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Chemical Property:

• PSA: 96.08000
• Density: 1.732 g/cm³
• LogP: 2.48250
• Solubility.: ≥23.05 mg/mL in DMSO; insoluble in H2O; ≥46.1 mg/mL in EtOH
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 461.02478
• Heavy Atom Count: 25
• Complexity: 596

Purity/Quality:

99% ^*data from raw suppliers

AZD 8330 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(N(C1=O)C)NC2=C(C=C(C=C2)I)F)C(=O)NOCCO
• Recent ClinicalTrials: AZD8330 First Time in Man in Patients With Advanced Malignancies
• Description: AZD 8330 is a selective allosteric inhibitor of MEK1/2 (IC50 = 7 nM). It blocks phosphorylation of ERK1/2 and inhibits proliferation of certain cancer cells. AZD 8330 is orally bioavailable, inhibits ERK phosphorylation in vivo, and reduces tumor growth in a Calu-6 nude rat xenograft model.
• Uses: AZD8330 is an orally active and selective MEK inhibitor.

Technology Process of 2-((2-fluoro-4-iodophenyl)amino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide

There total 8 articles about 2-((2-fluoro-4-iodophenyl)amino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

2-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridine-3-carboxamide (934639-06-2) → 2-[(2-fluoro-4-iodoiodophenyl)amino]-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide (869357-68-6)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 17 - 22 ℃; for 1.25h; Product distribution / selectivity;

Reference yield:

2-chloro-6-oxo-1,6-dihydropyridine-3-carboxylic acid (38025-90-0) → 2-[(2-fluoro-4-iodoiodophenyl)amino]-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide (869357-68-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium hydride / N,N-dimethyl-formamide / 0.67 h

1.2: 0.75 h

1.3: pH 6 - 7

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C

3.1: dimethyl zinc(II) / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; toluene / 0.5 h / 100 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 0.42 h / -78 °C

5.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.17 h / 0 - 20 °C

6.1: hydrogenchloride; water / ethanol / 0.75 h / 20 °C

6.2: pH 7

With hydrogenchloride; N-Bromosuccinimide; water; dimethyl zinc(II); lithium hydride; lithium hexamethyldisilazane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; N,N-dimethyl-formamide; toluene;

Reference yield:

methyl 2-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (853109-24-7) → 2-[(2-fluoro-4-iodoiodophenyl)amino]-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide (869357-68-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C

2.1: dimethyl zinc(II) / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; toluene / 0.5 h / 100 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 0.42 h / -78 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.17 h / 0 - 20 °C

5.1: hydrogenchloride; water / ethanol / 0.75 h / 20 °C

5.2: pH 7

With hydrogenchloride; N-Bromosuccinimide; water; dimethyl zinc(II); lithium hexamethyldisilazane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

2-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridine-3-carboxamide

2-chloro-6-oxo-1,6-dihydropyridine-3-carboxylic acid

methyl 2-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

methyl 2-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Refernces

• 1、 -. "COMBINATION OF AN MEK INHIBITOR AND THE SRC KINASE INHIBITOR AZD0530 FOR USE IN THE TREATMENT OF CANCER". Page/Page column 14-15. . Retrieved 2008/12/06.
• 2、 -. "HETEROCYCLIC INHIBITORS OF MEK AND METHODS OF USE THEREOF". Page/Page column 82; 83. . Retrieved 2008/06/13.