WO2010006704 Oxazolopyrimidines as EDG-1 receptor agonists

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Biological target:

sphingosine-1-phosphate receptor 1: S1P1 or EDG-1
Activity:

Agonist

Steps Conditions Reactions
a Et3N / DCM Amide synthesis (coupling reaction)
b Sodium methoxide / EtOH Cyclisation
c PCl5 / CHCl3  Cyclisation 
d 1-bromo-propane / K2CO3 / DMF  Ether synthesis (nucleophilic substitution) 
e NBS / AIBN / CCl4  Bromination
f K2CO3 / DMF  Tertiary amine synthesis (nucleophilic substitution) 
Steps Conditions Reactions
a Et3N / DCM Amide synthesis (coupling reaction)
b MeONa / EtOH Cyclisation
c MeI / NaOH / NMP S-Methylation
d POCl3   Cyclisation 
e 1-Bromo-propane / K2CO3 / DMF  Ether synthesis (nucleophilic substitution) 
f m-CPBA / DCM  Oxidation 
g 3,4-dichloro-benzyl bromide / Mg / Et2O / Dioxane Coupling reaction
Steps Conditions Reactions
a BBr3 / DCM Hydroxyl synthesis (methoxy deprotection)
b (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol / DEAD / polystyrene-bound triphenylphosphine / THF Ether synthesis (Mitsunobu reaction)
c TFA / DCM  Dihydroxyl deprotection 

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