WO2010006191 4-phenoxymethylpiperidines as modulators of GPR119 activity

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Biological target:

G protein-coupled receptor 119: GPR119

Activity:

Modulator

Steps Conditions Reactions
a K2CO3 / DMA Tertiary amine synthesis (Nucleophilic substitution)
b MsCl / Et3N / DCM Mesyl synthesis
c Cs2CO3 / DMF Ether synthesis 
d Bis(pinacolato)diboron / Pd(dppf)Cl2 / AcOK / DMSO Ester boronic synthesis
e Pd(dppf)Cl2 / Cs2CO3 / dioxane Suzuki reaction
Steps Conditions Reactions
a TsCl / Pyridine Tosyl synthesis
b Cs2CO3 / DMF Thioether synthesis
c m-CPBA / DCM Oxidation
d bis(pinacolato)diboron / Pd(dppf)Cl2 / AcOK / DMSO Ester boronic synthesis
Steps Conditions Reactions
a Toluene 
b EtMgBr / Et2O Cyclopropyl synthesis
c 4-nitrophenyl chloroformate / DMAP / 2,4,6-collidine / DCM Carbamate synthesis
d

1. TFA / DCM

2. Et3N / DCM 

Boc deprotection / Nuclephilic substitution
Steps Conditions Reactions
a Sodium methanesulfinate  / [Cu(I)OTf]2Ph / Dimethylethyldiamine / Cs2CO3 / DMSO 
Steps Conditions Reactions
a NaI / AcCl / ACN Iodination
b 1H-1,2,4-triazole / [Cu(I)OTf]2Ph / Dimethylethyldiamine / Cs2CO3 / DMSO
Steps Conditions Reactions
a m-CPBA / AcOEt  N-oxide pyridine synthesis
b Ac2
c MeI / Cs2CO3 / DMF N-Methylation
Steps Conditions Reactions
a Pd(OAc)2 / Ph2P(CH2)3PPh2 / CO / Et3N / DMA:MeOH (1:1) Ester synthesis
Steps Conditions Reactions
a Pd(dppf)Cl2 / Cs2CO3 / dioxane Suzuki reaction
b K2CO3 / MeOH
Steps Conditions Reactions
a

1. ACN

2. NaOH 


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