Trifluoroacetic acid → N-(2,6-diethylphenyl)-8-({2-methoxy-4-[(1-methylpiperidin-4-yl)amino]phenyl}amino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Participants

Reaction Steps

To a stirred solution of 8-[(4-amino-2-methoxyphenyl)amino]-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (80 mg, 0.158 mmol) in 1.5 ml of CH2Cl2 under argon atmosphere, tetrahydro-4H-pyran-4-one (20 mg, 0.198 mmol), TFA (0.428 mmol; 2.7 eq) and tetramethylammonium triacetoxyborohydride (63 mg, 0.238 mmol) were added. The mixture was stirred at room temperature for 1 h. Saturated aqueous NaHCO3 was added and the organic layer separated, dried on anhydrous Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (97.5/2.5 CH2Cl2/CH3OH) giving the to desired product as a brown foam in a 34% yield.

Provenance & Evidence