Triethylamine → 9-bromo-1-chloro-N-[(1-methyl-1H-pyrazol-3-yl)methyl]benzo[c]-1,6-naphthyridin-6-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 9-bromo-1,6-dichloro-benzo[c][1,6]naphthyridine (0.10 g, 0.31 mMol) in anhydrous CH3CN (4.0 mL) was added C-(1-methyl-1H-pyrazol-3-yl)-methylamine (0.040 g 0.36 mMol) and anhydrous Et3N (0.22 mL, 1.6 mMol). The reaction mixture was heated in a sealed tube at 120° C. After 3 hours the solvent was removed and the solid obtained was re-dissolved in EtOAc (10 mL). The EtOAc layer was washed with water (2×5 mL), brine (1×10 mL), and dried over MgSO4. The filtrate was concentrated and the resulting residue was purified using preparative HPLC to afford 9-bromo-1-chloro-N-[(1-methyl-1H-pyrazol-3-yl)methyl]benzo[c]-1,6-naphthyridin-6-amine. 1H NMR (400 MHz, DMSO-d6) 11.34 (br d, 1H), 10.11 (d, 1H), 8.61 (t, 1H), 8.32 (d, 1H), 7.75-7.73 (dd, 1H), 7.55 (d, 1H), 7.37 (t, 1H), 6.40 (d, 1H), 6.18 (d, 1H), 4.74 (d, 2H), 3.77 (s, 3H). LRMS calculated for C17H14BrClN5 [M+H]+, 404.0; found 403.9.

Provenance & Evidence