WO2010070238 Derivatives of 6-cycloamino-2,3-di-pyridinyl-imidazo[1,2-B]-pyridazine, preparation and therapeutic application thereof

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Biological target:

Casein kinase 1: CK1



Steps Conditions Reactions
a Et3N, EtOH reflux Imidazopyridazine formation
b ICl in MeOH, CHCl3 Iodation
c (2-methyl-4-pyridinyl)boronic acid, PdCl2(dppf), Cs2CO3, THF-H2O 9/1 Suzuki coupling reaction
d 2,2-dimethylpiperazine, pentanol, 150oC, 24h SnAr
Steps Conditions Reactions
a ethyl bromoacetate, EtOH reflux, 24h
b POBr3, toluene, 160oC, 3h Imidazopyridazine formation
c 1-isopropylpiperazine, EtOH, 160oC, 8h, scelled tube SnAr
d ICl in MeOH, CHCl3, OoC Iodation
e Pyridin-4-yl-boronic acid, Pd(dppf)Cl2, Cs2CO3 aq, dioxane, 110oC, scelled tube, 30 min microwaves Suzuki coupling reaction
f 2-Fluoropyridine-4-boronic acid Pd(dppf)Cl2, Cs2CO3 aq, dioxane, 120oC, scelled tube, 20 min Suzuki coupling reaction