1-Hydroxybenzotriazole → HCID 66743834, compound

Participants

Reaction Steps

A mixture of 6′-(pyridin-4-yl)-1′H-spiro[piperidine-4,2′-thieno[3,2-d]pyrimidin]-4′(3′H)-one in DMF (0.16 M, 0.50 mL, 0.080 mmol), N-(tert-butoxycarbonyl)glycine in DMF (0.192 M, 0.50 mL, 0.096 mmol) and a solution of 1-hydroxybenzotriazole and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride in DMF (0.192 M, 0.50 mL, 0.096 mmol for each) was stirred for 16 h at room temperature. The reaction mixture was extracted with EtOAc (3.5 mL) and 2% aqueous sodium hydrogen carbonate (1 mL). After evaporating the organic solvent, 1 M methanesulfonic acid in MeCN (0.5 mL) was added to the residue. The mixture was stirred for 16 h at room temperature. After neutralizing the reaction mixture with 1 M N-ethyl-N-(1-methylethyl)propan-2-amine (0.5 mL), the crude product was chromatographed on preparative HPLC (YMC CombiPrep. Hydrosphere C18, 10 mM NH4HCO3 in water/MeCN) to afford the title compound (0.8 mg, 2.8%):

Provenance & Evidence