WO2010001169 Chemical compounds 251

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Biological target:

Proto-oncogene serine/threonine-protein kinase: Pim-1, Pim-2

Activity:

Inhibitor

Steps Conditions Reactions
a

m-CPBA / DCM

Epoxide synthesis
b NaN3 / DMF / Acetone / H2O Azido synthesis                  
c

PPh3 / H2O / THF 

Primary amine synthesis (Staudinger reaction)
d

Boc2O / Et3N / DCM 

Boc protection
e H2 / Pd-C / MeOH Cbz deprotection                               
Steps Conditions Reactions
a

NaH / DMF

Ether synthesis
b DIBAL-H / toluene Aldehyde synthesis  
Steps Conditions Reactions
a

K2CO3 / DMSO

Tertiary amine substitution (Aromatic subtitution)
Steps Conditions Reactions
a

Pd(dppf)Cl2 / Na2CO3 / dioxane / H2O

Suzuki reaction
b Pd(PPh3)4 / Cs2CO3 / Dioxane / H2O Suzuki reaction
Steps Conditions Reactions
a

Fe / HCl / H2O / MeOH

Primary amine synthesis (nitro reduction)
Steps Conditions Reactions
a

Piperidine / EtOH


Steps Conditions Reactions
a

NH2-NH2 / EtOH

Primary amine synthesis (Gabriel reaction)
Steps Conditions Reactions
a

HCl 1.25N / MeOH

TBDMS deprotection
Steps Conditions Reactions
a

NaBH(OAc)3 / DCM

Secondary amine synthesis (Reductive amination)
Steps Conditions Reactions
a

HATU / DIEA / DCM

Amide synthesis (HATU coupling)

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