Triethylamine → 8-Amino-9-fluoro-7-oxo-10-(3-(pyridin-3-yl)propylamino)-2,7-dihydrospiro [[1,4]oxazino[2,3,4-ij]quinoline-3,1'-cyclopropane]-6-carbonitrile

Participants

Reaction Steps

A solution of 8-amino-9,10-difluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino-[2,3,4-ij]quinoline-3,1′-cyclopropane]-6-carbonitrile (150 mg, 0.52 mmol), 3-(pyridine-3-yl)propan-1-amine (176 mg, 1.3 mmol), and triethylamine (108 μL, 1.3 mmol) in DMSO (3 mL) was stirred at 120° C. for 15 hr. The reaction mixture was cooled and concentrated. The crude product was taken up in acetonitrile and purified by preparative HPLC to yield the title compound as a yellow solid (52.9 mg). MS (EP) m/z: 406.2 (M++1). (Calcd for C22H20FN5O2, 405.42). 1H NMR (400 MHz, D2O) δ 1.20 (2H, t), 1.50 (2H, t), 2.00 (2H, m,), 2.94 (2H, m,), 3.51 (2H, m), 4.14 (2H, s), 7.86 (1H, m), 8.03 (1H, m), 8.41 (1H, m), 8.52 (1H, m), 8.58 (1H, s)

Provenance & Evidence