WO2010011818 Chemical compounds

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Biological target:

HIV integrase 

Activity:

Inhibitor

Steps Conditions Reactions
a BnBr / K2CO3 / ACN  O-Benzyl protection
b LHMDS / PhCHO / THF
c

1. MsCl / Et3N / THF

2. DBU / NMP / THF 

Alkene synthesis                  
d

1. RuCl3 / NaIO4 / ACN / AcOEt / H2O

2. NaClO2                                      

             
e EtOH                   Cyclisation
f MeI / NaHCO3 / NMP                   Ester synthesis (Esterification)
g NBS / DMF                   Bromination                  
h NaIO4 / H2O                   Aldehyde synthesis
Steps Conditions Reactions
a ACN Cyclisation
b Palladium (II) trifluoroacetate / CO / DIEA / dppf / DMSO Amide synthesis
c H2 / Pd-C / EtOH / NH4OH   O-Benzyl deprotection
d NaOH 50% / EtOH                    
Steps Conditions Reactions
a Chloromethyl chloridocarbonate / NMP / DCM
b NaI / acetone Iodination
c K2CO3 / tetrabutylammonium hydrogen sulfate / H2O / DCM Nucleophilic substitution
d DMAP / Et3N / ACN Amide synthesis

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