Potassium Carbonate → HCID 178428217, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with potassium carbonate (0.028 g, 0.200 mmol), methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (0.034 g, 0.200 mmol), 6′-fluoro-4-methyl-N-[4-(trifluoromethyl)pyridin-2-yl]-2,3′-bipyridin-6-amine (0.032 g, 0.1 mmol), NMP (1 mL), and DIEA (0.035 mL, 0.20 mmol). The vial was sealed and heated to 130° C. for 72 hours. Aqueous NaOH (1M, 0.5 mL) was added, and the vial was heated in a microwave for 10 minutes at 110° C. The mixture was filtered through a CELITE cartridge, washing with NMP (3 mL). The residue, dissolved in 3 mL of NMP, was purified by mass triggered reverse phase HPLC (21-55% Acetonitrile/Water with a 0.1% Ammonium Hydroxide modifier on a Waters X-Bridge C18 19 mm×100 mm) to yield trans-4-{[(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)oxy]methyl}cyclohexanecarboxylic acid. MS ESI calcd. for C25H26F3N4O3 [M+H]+ 487. found 487. rhSyk IC50=3 nM.

Provenance & Evidence