WO2010008761: Piperidyl Acrylamide Antagonists of CCR2

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Biological target:

Chemokine receptors: CCR2

Activity:

Antagonist

Steps Conditions Reactions
a TFA, CH2Cl2 50/50 Secondary amine formation (Boc-deprotection)
b SOCl2, CH2Cl2 reflux Acid chloride formation
c Et3N, CH2Cl2 N-acylation (amide formation)
Steps Conditions Reactions
a (Boc)2O, K2CO3, THF.H2O Boc-formation (amine protection)
b TsCl, TBAHS, toluene N-acylation (amine protection)
c TFA, CH2Cl2 25/75 Amine formation (Boc-deprotection)
d NaNO2, HCl, CHCl3 N-Nitrosation
e LAH, THF NO-Reduction / Tosyl deprotection
Steps Conditions Reactions
a NaBH(OAc)3, DCE-THF, HOAc Reductive amination
b HCHO (37% in H2O), NaBH(OAc)3, DCE-THF, HOAc Reductive amination
Steps Conditions Reactions
a LiHMDS, TMSCl, Br2, THF Bromination
b LiOH.H2O, THF-MeOH Hydrolysis (ester saponification)
c 2f, Et3N, CH3CN Nucleophilic Substitution

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