1,4-Dioxane → 6-[(2,2-dimethylpropyl)amino]-9-fluorobenzo[c]-1,6-naphthyridin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,6-dichloro-9-fluorobenzo[c]-1,6-naphthyridine (20 mg, 0.075 mmol) in dioxane (1.5 mL) was added 2,2-dimethylpropan-1-amine (39 mg, 0.45 mmol) and heated in a microwave reactor at 100° C. for 30 to 50 min. The solution was concentrated and converted to 6-[(2,2-dimethylpropyl)amino]-9-fluorobenzo[c]-1,6-naphthyridin-1(2H)-one in a similar manner exemplified in the synthesis of 9-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one (Method A, Step 2). 1H NMR (600 MHz, CD3OD) δ 9.65 (dd, 1H), 8.60 (dd, 1H), 7.60 (d, 1H), 7.58 (m, 1H), 6.95 (d, 1H), 3.70 (s, 2H), 1.10 (s, 9H). LRMS (ESI) calc'd for (C17H19FN3O) [M+H]+, 300.15; found 300.1.

Provenance & Evidence