Trifluoroacetic acid → 4-[(4-Amino-1-piperidinyl)methyl]-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

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Reaction Steps

A suspension of 1,1-dimethylethyl{1-[(3-chloro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}carbamate (1.475 g, 4.63 mmol) in dichloromethane (15 ml) was treated with trifluoroacetic acid (12 ml) and stirred at room temperature for 1 h. The reaction mixture was evaporated and then treated with aqueous sodium bicarbonate solution and a 4:1 dichloromethane:methanol solution. The aqueous phase was extracted about 15 times with a 4:1 dichloromethane:methanol solution and then the combined organic phases were dried and the solvent was removed. The residue was subjected to column chromatography on silica gel using a dichloromethane, methanol and aqueous ammonia gradient to provide the desired compound (0.94 g, 84%).

Provenance & Evidence