WO2010013161 Fluorinated heteroaryls

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Scaffold: Pyridin-2-one and Pyrimidone

Biological target:

Glucokinase enzyme

Activity:

Modulator

Steps Conditions Reactions
a  1M H2SO4 / NaNO2 / H2O Hydroxyl synthesis (Diazonium / Hydrolysis)
b  SOCl2 / MeOH Ester synthesis (Esterification)
c Triflic anhydride / 2,6-lutidine / DCM Triflic synthesis
d LiHMDS / THF Nucleophilic Substitution
e AlMe3 / Toluene Amide synthesis (coupling reaction)
Steps Conditions Reactions
a Zn / PdCl2(PPh3)2 / DMF Neghisi coupling
b H2 / Pd-C / MeOH Alkene reduction
c HCl 6N Carboxylic acid synthesis (Ester hydrolysis)
d 1N H2SO4 / NaNO2 / H2O Hydroxyl synthesis (Diazonium / Hydrolysis)
e HCl /MeOH Ester synthesis (Esterification)
f Triflic anhydride / lutidine / DCM Triflic synthesis

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