Acetic Acid → HCID 178424646, compound

Participants

Reaction Steps

138.8 mg (0.51 mmol) 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridine×2HCl (60% pure) are dissolved in 3.9 mL NMP. 0.15 mL (1.08 mmol) triethylamine are added and the reaction mixture is stirred for one hour. 200 mg (0.46 mmol) 4-(7-Isopropylamino-6-phenyl-2-pyridine-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 0.05 mL (0.83 mmol) acetic acid are added. The reaction mixture is stirred over night at room temperature. 107 mg (0.51 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature over night. The reaction mixture is treated with NaHCO3 and the formed precipitate has been filtered off. The filtrate is extracted with methyl-tert.butylether. The organic phase is washed with water, dried (Na2SO4) and the solvent removed. This residue and the precipitate are combined and purified by column chromatography (silicagel, eluents: dichloromethane/methanol) and additionally by HPLC yielding 7.4 mg (2.54%) of the desired compound.

Provenance & Evidence