WO2010056564 Quinolone neuropeptide S receptor antagonists

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Scaffold: quinolone

Biological target:

Neuropeptide S receptor: NPS

Activity:

Antagonist

Steps Conditions Reactions
a NMO / TPAP / DCM / 5A° sieves Ketone synthesis
b ZnI / TMSCN / MeOH Strecker reaction
c LAH / THF Primary amine synthesis (Cyanide reduction)
d Sodium triacetoxyborohydride / 1,2-dichloroethane / AcOH  Secondary amine synthesis (reductive amination)
e Et3N / DCM Amide synthesis (coupling reaction)
f H2 / Pd-C / EtOH Alkene reduction
Steps Conditions Reactions
a DCM
b NH2-NH2 / KOH / Ethylene glycol Methyl carbamate deprotection
c Sodium triacetoxyborohydride / AcOH / DCE Secondary amine synthesis (reductive amination)
d DIEA / DCE Amide synthesis (coupling reaction)
e N-methylmorpholine N-oxide / Osmium tetroxide / t-BuOH / THF Aldehyde synthesis
f Sodium triacetoxyborohydride / AcOH / Sodium acetate / DCE Tertiary amine synthesis (reductive amination)
Steps Conditions Reactions
a n-BuLi / THF Nucleophilic substitution
b SOCl2 / Pyridine  Dehydratation
c H2 / Pd-C / HCl c / EtOH Primary amine synthesis (Cyanide reduction) / Alkene reduction
Steps Conditions Reactions
a NaCN / MeOH / AcOH Strecker reaction
b H2 / Raney-Nickel / NH3 / EtOH   Primary amine synthesis (Cyanide reduction)

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