Sodium Bicarbonate → 7-methyl-8-[(4-{[6-(pyrrolidin-1-yl)pyridin-3-yl]methyl}piperazin-1-yl)carbonyl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one

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Reaction Steps

To a mixture of 11.9 mg of 7-methyl-8-(piperazin-1-ylcarbonyl)-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one, 15.9 mg of 6-(1-pyrrolidinyl)nicotinaldehyde, 0.3 mL of 1,2-dichloroethane, and 30 μL of acetic acid was added 19.1 mg of sodium triacetoxyborohydride, followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC (methanol/0.1% aqueous formic acid solution) to obtain 9.7 mg of 7-methyl-8-[(4-{[6-(pyrrolidin-1-yl)pyridin-3-yl]methyl}piperazin-1-yl)carbonyl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one.

Provenance & Evidence