Aniline → N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

Participants

Reaction Conditions

Reaction Steps

Step (i): To a 0.1M solution of 3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carbonyl chloride (0.5 mL, 0.050 mmol) in anhydrous DMF was added a 0.1M solution of aniline (0.75 mL, 0.075 mmol) in anhydrous DMF. The reaction mixture allowed shaken at 80° C. for 16 hours. The solvent was removed under reduced pressure and to give the desired product, 3-(4-methoxybenzyl)-N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide as a solid, which was used in the next step without any further purification. Step (ii): To the product obtained in Step 2(i) was added trifluoroacetic acid (1 mL). The reaction mixture was heated at 70° C. for 16 hours. On the completion of the reaction, toluene (3 mL) was added and the solvent removed under reduced pressure. The crude product was purified using reverse phase HPLC to give the desired product, N-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide as a white solid. LCMS [M+H]: 294.

Provenance & Evidence