Benzamide, N-(cyclopropylmethoxy)-3,4,5-trifluoro-2-((4-iodo-2-methylphenyl)amino)-

Base Information

• Chemical Name: Benzamide, N-(cyclopropylmethoxy)-3,4,5-trifluoro-2-((4-iodo-2-methylphenyl)amino)-
• CAS No.: 212631-61-3
• Molecular Formula: C18H16F3IN2O2
• Molecular Weight: 476.23200
• UNII: WQ5121ZGT3
• DSSTox Substance ID: DTXSID70433306
• Wikidata: Q27165235
• ChEMBL ID: CHEMBL1474985
• Mol file: 212631-61-3.mol

Synonyms:PD 198306;PD198306

Chemical Property of Benzamide, N-(cyclopropylmethoxy)-3,4,5-trifluoro-2-((4-iodo-2-methylphenyl)amino)-

Chemical Property:

• Melting Point: 125-127 °C
• PKA: -3.95±0.50(Predicted)
• PSA: 50.36000
• Density: 1.686g/cm3
• LogP: 5.29580
• Storage Temp.: Store at +4°C
• Solubility.: Soluble in DMSO
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 476.02086
• Heavy Atom Count: 26
• Complexity: 497

Purity/Quality:

≥98% by HPLC ^*data from raw suppliers

PD 198306 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)I)NC2=C(C(=C(C=C2C(=O)NOCC3CC3)F)F)F
• Description: PD 198306 is an orally bioavailable and potent inhibitor of MAPK kinase 1/2 (MEK1/2; IC50 = 8 nM). It is selective for MEK1/2 over ERK, c-Src, PI3Kγ, and cyclin-dependent kinases (IC50s = >1 μM). PD 198306 (3-100 μM) reduces ERK1/2 phosphorylation and inhibits growth of HL-60 cells in vitro. In vivo, PD 198306 (10-30 mg/kg) reduces ERK1/2 phosphorylation and matrix metalloproteinase-1 (MMP-1) expression in a dose-dependent manner in a rabbit model of osteoarthritis. It also reduces ERK1/2 activity in the lumbar spinal cord and blocks static allodynia in rat models of neuropathic pain induced by streptozotocin or chronic constriction injury.
• Uses: PD 198306 is a cell-permeable and highly selective potent inhibitor of MEK 1/2.

Technology Process of Benzamide, N-(cyclopropylmethoxy)-3,4,5-trifluoro-2-((4-iodo-2-methylphenyl)amino)-

There total 3 articles about Benzamide, N-(cyclopropylmethoxy)-3,4,5-trifluoro-2-((4-iodo-2-methylphenyl)amino)- 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: 61.0%

3,4,5-Trifluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid + O-(cyclopropylmethyl)hydroxylamine hydrochloride → N-cyclopropylmethoxy-3,4,5-trifluoro-2-(4-iodo-2-methyl-phenylamino)-benzamide (212631-61-3)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2008.10.054

Reference yield:

2-(4-iodo-2-methylamino)-3,4,5-trifluorobenzoic acid + O-cyclopropylmethyl-hydroxylamine (75647-90-4) + Diphenylphosphinic chloride (1499-21-4) → N-cyclopropylmethoxy-3,4,5-trifluoro-2-(4-iodo-2-methyl-phenylamino)-benzamide (212631-61-3)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; ethyl acetate;

Reference yield:

→ N-cyclopropylmethoxy-3,4,5-trifluoro-2-(4-iodo-2-methyl-phenylamino)-benzamide (212631-61-3)

Guidance literature:

upstream raw materials:

O-cyclopropylmethyl-hydroxylamine

Diphenylphosphinic chloride