Diisopropylethylamine → 5-Neopentyl-7-(2-oxo-2-(4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidin-1-yl)ethyl)-7,8-dihydro-1H-pyrazolo[3,4-g]quinolin-6(5H)-one

Participants

Reaction Steps

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (116 mg, 0.3 mmol) was added to a solution of 2-(1-neopentyl-2-oxo-2,3,4,7-tetrahydro-1H-pyrazolo[3,4-h]quinolin-3-yl)acetic acid (95 mg, 0.3 mmol) and N,N-diisopropylethylamine (158 μL, 0.9 mmol) in dichloromethane (5.0 mL). Mixture was stirred at room temperature for 45 minutes. 4-(2-Oxo-1,4-dihydro-2H-quinazolin-3-yl) piperidine (70 mg, 0.3 mmol) was then added to the mixture. After 3 h stirring at room temperature, the crude reaction mixture was purified by prep HPLC starting from 30% methanol in water to 90% methanol in water over a period of 8 min and at a flow rate of 40 ml/min. Removal of solvent furnished the desired. MS (ESI) 529 (M+H); Rf=1.57.

Provenance & Evidence