WO2010045309 Inhibitors of AKT activity

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Biological target:

AKT

Activity:

Inhibitor

Steps Conditions Reactions
a H2SO4 cat / MeOH Ester synthesis (Esterification)
b AlCl3 / Br2 / CHCl3 Bromination
Steps Conditions Reactions
a NaH / THF Nucleophilic substitution
b HCl / AcOH Decarboxylation
c Boc2O / NaOH / Dioxane / H2O Boc protection
Steps Conditions Reactions
a 1. pivaloyl chloride / THF 2. n-BuLi / (4R)-4-(phenylmethyl)-1,3-oxazolidin-2-one / THF 
b Phenylmethyl [(methyloxy)methyl]carbamate / TiCl4 / DIPEA / DCM
c H2O2 / LiOH / THF / H2
Steps Conditions Reactions
a H2SO4 cat / MeOH Ester synthesis (Esterification)
b Bis(tri-t-butylphosphine)palladium (0) / K2CO3 / dioxane / H2O Suzuki reaction
c NaOH 6N / THF Carboxylic acid synthesis (Ester hydrolysis)
d

1. NaN3 / methyl chloroformate / Et3N / Acetone

2. TBuOH / dioxane

Curtius rearrangement
e NCS / DMF Chlorination       
f HCl 4N (dioxane)  / MeOH Boc deprotection 
g PyBrop / DIPEA / DCM Amide synthesis (PyBrop coupling)
h TFA / DCM Boc deprotection

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