2-(2-chloro-4-iodophenylamino)-N-cyclopropylmethoxy-3,4-difluorobenzamide

Base Information

• Chemical Name: 2-(2-chloro-4-iodophenylamino)-N-cyclopropylmethoxy-3,4-difluorobenzamide
• CAS No.: 212631-79-3
• Molecular Formula: C₁₇H₁₄ClF₂IN₂O₂
• Molecular Weight: 478.665
• Hs Code.: 2924299090
• European Community (EC) Number: 695-548-6
• UNII: R3K9Y00J04
• DSSTox Substance ID: DTXSID8048945
• Nikkaji Number: J1.154.409F
• Wikidata: Q27076005
• NCI Thesaurus Code: C2670
• Pharos Ligand ID: 4TTWZVD5S7PC
• Metabolomics Workbench ID: 153419
• ChEMBL ID: CHEMBL105442
• Mol file: 212631-79-3.mol

Synonyms:2-(2-chloro-4-iodophenylamino)-N-cyclopropylmethoxy-3,4-difluorobenzamide;CI 1040;CI-1040;PD 184352;PD-184352;PD184352

Chemical Property of 2-(2-chloro-4-iodophenylamino)-N-cyclopropylmethoxy-3,4-difluorobenzamide

Chemical Property:

• Appearance/Colour: Off-white to pale beige solid
• Melting Point: 166-169 °C
• Refractive Index: 1.656
• PKA: -5.58±0.50(Predicted)
• PSA: 50.36000
• Density: 1.748 g/cm³
• LogP: 5.50170
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: ≥30mg/mL
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 477.97566
• Heavy Atom Count: 25
• Complexity: 472

Purity/Quality:

98%,99%, ^*data from raw suppliers

PD 184352 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1CONC(=O)C2=C(C(=C(C=C2)F)F)NC3=C(C=C(C=C3)I)Cl
• Recent ClinicalTrials: CI-1040 in Treating Patients With Advanced Breast, Colon, Pancreatic, or Non-Small Cell Lung Cancer
• Uses: An inhibitor of ERK signaling pathway. A MAP kinase inhibitor. Potent MEK inhibitor. An inhibitor of ERK signaling pathway. A MAP kinase inhibitor

Technology Process of 2-(2-chloro-4-iodophenylamino)-N-cyclopropylmethoxy-3,4-difluorobenzamide

There total 5 articles about 2-(2-chloro-4-iodophenylamino)-N-cyclopropylmethoxy-3,4-difluorobenzamide 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: 73.0%

3,4-difluoro-2-(2-chloro-4-iodophenylamino)-benzoic acid (303175-44-2) + O-(cyclopropylmethyl)hydroxylamine hydrochloride → 2-(2-chloro-4-iodophenylamino)-N-(cyclopropylmethoxy)-3,4-difluorobenzamide (212631-79-3)

Guidance literature:

3,4-difluoro-2-(2-chloro-4-iodophenylamino)-benzoic acid; With dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; for 0.25h;

With dmap; 1-hydroxybenzotriazol-hydrate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 1.5h;

O-(cyclopropylmethyl)hydroxylamine hydrochloride; With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 48h;

DOI:10.1080/00397910500184909

Reference yield: 39.0%

3,4-difluoro-2-(2-chloro-4-iodophenylamino)-benzoic acid (303175-44-2) + benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate (128625-52-5) + O-(cyclopropylmethyl)hydroxylamine hydrochloride → 2-(2-chloro-4-iodophenylamino)-N-(cyclopropylmethoxy)-3,4-difluorobenzamide (212631-79-3) + [2-(2-chloro-4-iodo-phenylamino)-3,4-difluoro-phenyl]-pyrrolidin-1-yl-methanone

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; for 16h; Heating;

DOI:10.1080/00397910500184909

Reference yield:

2-chloro-4-iodoaniline (42016-93-3) → 2-(2-chloro-4-iodophenylamino)-N-(cyclopropylmethoxy)-3,4-difluorobenzamide (212631-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; heptane; ethylbenzene / 0.25 h / -78 °C

1.2: 43 percent / tetrahydrofuran; heptane; ethylbenzene / 96 h / 20 °C

2.1: dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 0.25 h

2.2: 1-hydroxybenzotriazole hydrate; 4-dimethylaminopyridine / tetrahydrofuran; dimethylformamide / 1.5 h / 20 °C

2.3: 73 percent / diisopropyl ethyl amine / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

With dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; N,N-dimethyl-formamide;

DOI:10.1080/00397910500184909

upstream raw materials:

3,4-difluoro-2-(2-chloro-4-iodophenylamino)-benzoic acid

benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate

2-chloro-4-iodoaniline

2,3,4,-trifluorobenzoic acid

Refernces

• 1、 Hamza, Hazem,Koch-Heier, Julia,Laure, Martin,Ludwig, Stephan,Planz, Oliver,Pleschka, Stephan,Quernheim, Martin,Schreiber, Andre,Müller, Christin,Müller, Gerhard. "Antiviral efficacy against influenza virus and pharmacokinetic analysis of a novel MEK-inhibitor, ATR-002, in cell culture and in the mouse model". . . Retrieved 2020.
• 2、 -. "5-SUBSTITUTED-2-PHENYLAMINO-BENZAMIDE AS MEK INHIBITOR". Page/Page column 149. . Retrieved 2008/06/13.