WO2010004197 Pyridino-pyridinone derivatives, preparation thereof, and therapeutic use thereof

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Biological target:

Platelet-derived growth factor and fms-like tyrosine kinase receptor-3: PDGF and Flt3

Activity:

Agonist

Steps Conditions Reactions
a EtNH2 / H2O

Secondary amine synthesis (Nucleophilic substitution)

b Cyanuric fluoride / Pyridine / DCM
Fluorination
c NaH / DMF  Nucleophilic substitution 
d n-Butanol  Cyclisation 
e Pd(dppf)Cl2 / Bis(pinacolato)diborane / AcOK / DMSO  Ester boronic synthesis 
Steps Conditions Reactions
a Tr-Cl / Et3N / CHCl3  Amine protection (trityl protection)
b LAH / THF Primary amine synthesis (amide reduction)
c

1. Oxalyl chloride / DMF

2. NaHCO3 / DMF 

Amide synthesis (Coupling reacion)
d 1-iodo-2-fluoroethane / NaHCO3 / DMF   Tertiary amine synthesis (Nucleophilic substitution) 
Steps Conditions Reactions
a Pd(PPh3)4 / NaHCO3sat / DME / EtOH Suzuki reaction

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