Acetonitrile → 9-fluoro-6-(1-methyl-2-morpholin-4-ylethyl)benzo[c]-1,6-naphthyridin-1(2H)-one

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Reaction Conditions

Reaction Steps

A suspension of 6-(2-bromo-1-methylethyl)-9-fluorobenzo[c]-1,6-naphthyridin-1(2H)-one (HBr salt) (25 mg, 0.060 mmol) in morpholine (1.0 mL) was stirred at 100° C. for 1 h. After cooling to room temperature, acetonitrile was added, and the resulting solution was concentrated to a crude residue. The resulting crude residue was purified by preparative reverse phase HPLC eluting with an acetonitrile/water (with 0.05% TFA as a modifier) gradient to afford 9-fluoro-6-(1-methyl-2-morpholin-4-ylethyl)benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (500 MHz, DMSO-D6). δ 11.86 (br d, 1H), 9.76 (dd, 1H), 8.63 (dd, 1H), 7.62 (br t, 1H), 7.57 (br t, 1H), 6.76 (d, 1H), 4.20 (br m, 1H), 3.47 (br s, 4H), 2.80 (br dd, 1H), 2.65 (br m, 1H), 2.43 (br s, 4H), 1.33 (d, 3H). LRMS (ESI) calc'd for (C19H20FN3O2) [M+H]+, 342.2; found 342.1.

Provenance & Evidence