5-(4-chlorophenyl)-N-(3,5-dimethoxyphenyl)furan-2-carboxamide

Base Information

• Chemical Name: 5-(4-chlorophenyl)-N-(3,5-dimethoxyphenyl)furan-2-carboxamide
• CAS No.: 944261-79-4
• Molecular Formula: C19H16ClNO4
• Molecular Weight: 357.793
• Hs Code.: 2932190090
• European Community (EC) Number: 687-382-8
• UNII: 339LBH1395
• ChEMBL ID: CHEMBL250699
• DSSTox Substance ID: DTXSID90241480
• Nikkaji Number: J2.709.423F
• Pharos Ligand ID: S466W7QXCMWQ
• Wikidata: Q27074084
• Mol file: 944261-79-4.mol

Synonyms:A 803467;A-803467;A803467

Chemical Property of 5-(4-chlorophenyl)-N-(3,5-dimethoxyphenyl)furan-2-carboxamide

Chemical Property:

• Vapor Pressure: 2.6E-08mmHg at 25°C
• Melting Point: 128-130?C
• Refractive Index: 1.611
• Boiling Point: 450.6 °C at 760 mmHg
• PKA: 11.72±0.70(Predicted)
• Flash Point: 226.3 °C
• PSA: 60.70000
• Density: 1.294 g/cm³
• LogP: 4.94250
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 357.0767857
• Heavy Atom Count: 25
• Complexity: 429

Purity/Quality:

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

A 803467 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1)NC(=O)C2=CC=C(O2)C3=CC=C(C=C3)Cl)OC
• Description: Nav1.8 is a tetrodotoxin-resistant (TTX-R) sodium channel with high activation threshold and slow inactivating kinetics that is highly expressed in small-diameter sensory neurons and has been implicated in signaling various types of pain. A-803467 is a sodium channel blocker with high-affinity and selectivity for inhibiting human Nav1.8 sodium channels (IC50 = 8 nM when stimulated at half-maximal inactivation and IC50 = 79 nM at a resting state). This compound is unusual in that it blocks hNav1.8 at negative resting membrane potentials (many small molecule sodium channel blockers show a reduced affinity for the resting state) and does not demonstrate significant frequency-dependent block during a 10 Hz pulse train. A-803467 dose-dependently reduces behavioral responses in a variety of neuropathic and inflammatory pain models.
• Uses: A selective NaV1.8 sodium channel blocker, reduces behavioral measures of chronic pain. A selective NaV1.8 sodium channel blocker, reduces behavioral measures of chronic pain. Analgesic.

Technology Process of 5-(4-chlorophenyl)-N-(3,5-dimethoxyphenyl)furan-2-carboxamide

There total 3 articles about 5-(4-chlorophenyl)-N-(3,5-dimethoxyphenyl)furan-2-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: 64.0%

5-(4-chlorophenyl)furan-2-carboxamide (57753-81-8) + 1-bromo-3,5-dimethoxybenzene (20469-65-2) → [3H]-A-803467 (944261-79-4)

Guidance literature:

With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; TPGS-750-M; sodium t-butanolate; tert-butyl XPhos; In water; at 50 ℃; for 16h;

DOI:10.1039/c4gc00853g

Reference yield:

5-(4-chloro-phenyl)-furan-2-carbonyl chloride (57753-80-7) + 3.5-dimethoxyaniline (10272-07-8) → [3H]-A-803467 (944261-79-4)

Guidance literature:

With triethylamine; In dichloromethane; at 23 ℃; for 2h;

DOI:10.1021/jm070637u

Reference yield:

5-bromo-furan-2-carboxylic acid (585-70-6) → [3H]-A-803467 (944261-79-4)

Guidance literature:

Multi-step reaction with 3 steps

1: N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 20 °C

2: TPGS-750-M; triethylamine; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water / 50 °C / Inert atmosphere

3: bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; tert-butyl XPhos; sodium t-butanolate; TPGS-750-M / water / 16 h / 50 °C

With N-hydroxybenzotriazole ammonium salt; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; TPGS-750-M; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium t-butanolate; tert-butyl XPhos; In water; N,N-dimethyl-formamide; 2: |Suzuki-Miyaura Coupling / 3: |Buchwald-Hartwig Coupling;

DOI:10.1039/c4gc00853g

upstream raw materials:

5-(4-chloro-phenyl)-furan-2-carbonyl chloride

3.5-dimethoxyaniline

5-(4-chlorophenyl)furan-2-carboxamide

1-bromo-3,5-dimethoxybenzene

Refernces

• 1、 Kort, Michael E.,Drizin, Irene,Gregg, Robert J.,Scanio, Marc J. C.,Shi, Lei,Gross, Michael F.,Atkinson, Robert N.,Johnson, Matthew S.,Pacofsky, Gregory J.,Thomas, James B.,Carroll, William A.,Krambis, Michael J.,Liu, Dong,Shieh, Char-Chang,Zhang, XuFeng,Hernandez, Gricelda,Mikusa, Joseph P.,Zhong, Chengmin,Joshi, Shailen,Honore, Prisca,Roeloffs, Rosemarie,Marsh, Kennan C.,Murray, Bernard P.,Liu, Jinrong,Werness, Stephen,Faltynek, Connie R.,Krafte, Douglas S.,Jarvis, Michael F.,Chapman, Mark L.,Marron, Brian E.. "Discovery and biological evaluation of 5-aryl-2-furfuramides, potent and selective blockers of the Nav1.8 sodium channel with efficacy in models of neuropathic and inflammatory pain". . p. 407 - 416. Retrieved 2008/09/18.