WO2010022307 Propyl hydroxylase inhibitors

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Biological target:

HIF prolyl-hydroxylase

Activity:

Inhibitor

Steps Conditions Reactions
a 1,2-dichlorobenzene Cyclisation
b Glycine / Na / 2-methoxyethanol Amide synthesis (nucleophilic substitution)
Steps Conditions Reactions
a toluene Cyclisation
b DBU / EtOH Amide synthesis (nucleophilic substitution)
Steps Conditions Reactions
a

1. NaH / THF

2. NaOH / EtOH

Nucleophilic substitution
b 1,2-dichlorobenzene Cyclisation
Steps Conditions Reactions
a APTS / Toluene Primary amine protection (Pyrrole protection)
b NaH / CuI / DMF / 2-propanol Ether synthesis (Nucleophilic substitution)
c NH2-OH / Et3N / EtOH / H2O Primary Amine synthesis (Pyrrole deprotection)
d 1,2-dichlorobenzene Cyclisation