WO2009158431 Compounds and compositions as kinase inhibitors

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Biological target:

Anaplastic lymphoma kinase: ALK

Insulin-like growth factor: IGF-1

Activity:

Inhibitor

Steps Conditions Reactions
a Na2CO2 / EtOH Secondary amine synthesis (Nucleophilic substitution)
Steps Conditions Reactions
a Tributyl-(1-ethoxyvinyl)tin / Pd(PPh3)4 / DMF Stille reaction
b 1,1-dimethoxy-N,N-dimethylethanamine
c

1. hydroxylamine monohydrochloride / EtOH

2. H2 / Pd-C / MeOH

Cylisation / Primary amine synthesis (nitro reduction)
Steps Conditions Reactions
a Hydrazine / EtOH Cyclisation
b H2 / Pd-C / EtOH Primary amine synthesis (Nitro reduction)
Steps Conditions Reactions
a Pyridin-3-ylboronic acid / Pd2(dba)3 / Na2CO3 / butanol Suzuki reaction
Steps Conditions Reactions
a Br2 / HBr 48% / MeOH Bromination
b Ethanethioamide / EtOH Cyclisation
Steps Conditions Reactions
a Xantphos / Pd(AcO)2 / Cs2CO3 / THF Buchwald-Hartwig amination
Steps Conditions Reactions
a Pd(PPh3)4 / Cs2CO3 / 1,2-dimethoxyethane / MeOH Suzuki reaction
b H2 / Pd-C / MeOH Primary amine synthesis (Nitro reduction)

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