Potassium Carbonate → 6-(5-{4-[(Cyclopropylmethoxy)methyl]piperidin-1-yl}-1,2,4-oxadiazol-3-yl)-2-N-methyl-2-N-phenyl-1,3,5-triazine-2,4-diamine

Participants

Reaction Steps

Potassium carbonate (0.107 g, 0.776 mmol) and 2-N-methyl-2-N-phenyl-6-[5-(trichloromethyl)-1,2,4-oxadiazol-3-yl]-1,3,5-triazine-2,4-diamine (prepared in an analogous manner to Intermediate 60, 0.150 g, 0.388 mmol) were added to a solution of 4-[(cyclopropylmethoxy)methyl]piperidine hydrochloride salt (Intermediate 198, 0.160 g, 0.776 mmol) in DMF (5 mL) at room temperature. The reaction mixture was stirred at room temperature for 18 h and then evaporated under vacuum to remove the DMF. The crude residue was dissolved in EtOAc (5 mL) and washed with water (3×3 mL). The aqueous washes were combined, re-extracted with EtOAc (2×3 mL). The organic extracts were combined, dried over sodium sulfate, filtered and evaporated to provide a crude brown residue which was purified by preparative HPLC, Method B, to afford the title compound as an off-white solid (28 mg, 16%).

Provenance & Evidence