Acetic Acid → 6-((cis-2,6-Dimethylmorpholino)methyl)-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

Participants

Reaction Steps

A solution of compound G (10 mg, 0.032 mmol), cis-2,6-dimethylmorpholine (5 μL, 0.039 mmol), and acetic acid (4.6 μL, 0.081 mmol) in dichloromethane (1 mL) were stirred for one hour. To this mixture was added sodium triacetoxyborohydride (10.2 mg, 0.048 mmol). After 16 hours, the reaction was concentrated to dryness. Purification by reverse phase HPLC afforded 5 mg (38%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.23 (d, J=4.4 Hz, 1H), 8.55 (s, 1H), 8.26 (d, J=1.8 Hz, 1H), 7.77-7.73 (m, 2H), 7.65 (dd, J=8.7, 2 Hz, 1H), 7.59 (d, J=4.4 Hz, 1H), 7.52 (t, J=8.68, 8.76, 2H), 7.03 (d, J=8.68, 1H), 3.57-3.52 (m, 4H), 2.65 (d, J=10.2 Hz, 2H), 1.01 (d, J=6.3 Hz, 6H); ES-MS [M+1]+: 410.3.

Provenance & Evidence