WO2010035166 BENZAMIDE DERIVATIVES

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Scaffold: Sulfamoylbenzamide

Biological target:

Voltage-Gated sodium channels: Nav1.5

Activity:

Antagonist

Steps Conditions Reactions
a KOH / H2O Acid carboxylic synthesis (Cyanide hydrolysis)
b HCl / MeOH Ester synthesis (Esterification)
c

1. NaNO2 / HCl / H2O

2. SO2 / CuCl2 / AcOH

Sulfonyl chloride synthesis 
d NaH / DMF Sulfamide synthesis (Coupling reaction)
e HCl 4N / Dioxane (1/1) Deprotection
f NaOH / THF / MEOH Acid carboxylic synthesis (Ester hydrolysis)
Steps Conditions Reactions
a Cs2CO3 / benzylmercaptan / DMSO Thioether synthesis (aromatic substitution)
b MeOH / H2SO4 cat  Ester synthesis (esterification)
c DCM / HCl 4N / NaOCl Sulfonyl chloride synthesis 
Steps Conditions Reactions
a HBTU / Et3N / DMSO Amide synthesis (HBTU Coupling)
b AcCN / H2O / selectfluor Fluorination
c Ac2O / Et3N / DCM  

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