WO2010007561 Novel compounds active as Muscarinic receptor antagonists

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Scaffold: Piperidine

Biological target:

G-Protein coupled receptor of the muscarinic receptor family: M3

Activity:

Antagonist

Steps Conditions Reactions
a Palladium acetate / tri-o-tolylphosphine / DIEA / ACN   Heck reaction
b Ammonium formate / Pd(OH)2 / EtOH:AcOH (1:1) Alkene reduction
c Phophorus tribromide / toluene Appel reaction
d K2CO3 / DMF Secondary amine synthesis (nucleophilic substitution)
e NH2-NH2.H2O / EtOH Primary amine synthesis (Gabriel synthesis)
Steps Conditions Reactions
a HBTU / Et3N / DMF   Amide synthesis (HBTU coupling)
b EDCI / HOBt / DIEA / THF Amide synthesis (EDCI coupling)
Steps Conditions Reactions
a Titanium tetra-isopropoxide / NaBH4 / EtOH  Secondary amine synthesis (Reductive amination)                  
b Sodium tri(acetoxy)borohydride / DCE Secondary amine synthesis (Reductive amination)