Diisopropylethylamine → N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-{[(2-methoxyethyl)(methyl)amino]methyl}benzamide

Participants

Reaction Steps

To a reaction vessel containing 4-chloromethyl-N-(5-cyclohexylamino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-benzamide ((B8), 90 mg, 0.23 mmol, 1 eq.) and N,N-diisopropylethylamine (0.35 mmol, 61 μL, 1.5 eq.) in dioxane (3 mL) was added N-(2-methoxyethyl)methylamine (0.28 mmol, 25 μL, 1.2 eq.) dropwise. The vessel was capped and the reaction stirred at room temperature for 1 hour and heated to 80° C. for a further 15 hours. The solvent was removed in vacuo and the residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a light yellow solid (3.9 mg, 4%). HPLC, Rt: 3.46 min (purity: 93%). LC/MS M+(ESI): 437.2, M−(ESI) 435.2.

Provenance & Evidence