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

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Reaction Steps

A solution of 1,1-dimethylethyl {1-[(3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-piperidinyl}carbamate (13.35 g, containing about 12.5% dichloromethane) in dichloromethane (125 ml) was ice-cooled, treated with TFA (100 ml), stirred at room temperature for 1 hour and evaporated. The residue was shaken with aqueous sodium bicarbonate (excess) and 15% methanol/dichloromethane, separated and the aqueous extracted about 50 times with 15% methanol/dichloromethane. The combined organic phases were dried and evaporated and the residue chromatographed using dichloromethane/methanol/0.88 ammonia 9:1:0.1 to give the product (8.1 g).

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