WO2010032200 Amide compounds useful in therapy

WO2010032200.pdf
Adobe Acrobat Document 6.1 MB

Scaffold: 3-phenylpyrazole

Biological target:

Progesterone receptor (nuclear receptor): PR

Activity:

Antagonist

Steps Conditions Reactions
a  n-BuLi / isopropylamine / THF Ketone synthesis
b  EtOH / AcOH Cyclisation
c KI / Tert-butyl nitrite / ACN / H2O Iodination (Sandmeyer reaction)
d 1,1'-Bis(diphenylphosphino)ferrocene dichloropalladium (II) / CO / Et3N / MeOH Ester synthesis
e NaOH / H2O Carboxylic acid synthesis (Ester hydrolysis) 
Methodes  Conditions Reactions
A ZnCN / 1,1'-Bis(diphenylphosphino)ferrocene / tris-(dibenzylideneacetone) dipalladium / DMF Cyanide synthesis
B  K4[Fe(CN)6],3H2O / Palladium acetate / K2CO3 / DMA Cyanide synthesis
Steps Conditions Reactions
a

1. SOCl2 / Isopropylacetate

2. Et3N / Isopropylacetate

Amide synthesis
b HBTU / Pyridine / 2-Methyl tetrahydrofuran Amide synthesis (HBTU coupling)
Steps Conditions Reactions
a

THF

Grignard reaction
b HCl 4N / Dioxane / DCM  Boc deprotection
Steps Conditions Reactions
a

DAST / DCM

Fluorination
b LAH / Et2 Hydroxyl synthesis (Ester reduction)
c TsCl / pyridine Tosyl synthesis
d NaCN / DMSO Cyanide synthesis

Site Search