WO2010014593 Chemical compounds and uses

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Biological target:

G protein-coupled receptor 119: GPR119

Activity:

Agonist

Steps Conditions Reactions
a

[N-[(1R,2R)-2-(amino-N)-1,2-diphenylethyl]-2,4,6-trimethylbenzenesulfonamidato-N]chloro[(1,2,3,4,5,6-n-)1-methyl-4-(1-methylethyl)benzene]ruthenium / Et3N / formic acid 

Hydroxyl chiral synthesis (Chiral ketone reduction)
b H2 / PtO2 / AcOH / MeOH Piperidine synthesis (Pyridine reduction)
c

Boc2O / Et3N / DCM

Boc protection
Steps Conditions Reactions
a

1. HNO3 / H2SO4

2. NaOH / H2O

Phenol synthesis
b DIAD / PPh3 / THF Ether synthesis (Mitsunobu reaction)
c

Pd(PPh3)2Cl2 / 4-(tributylstannanyl)pyridazine / dioxane

Stille reaction
d

1. TFA / DCM

2. Isopropyl chloroformate / DIEA / toluene 

Boc deprotection
Steps Conditions Reactions
a

K2CO3 / DMSO

Tertiary amine synthesis (Nucleophilic substitution)