Triethylamine → HCID 90412169, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-bromo-1H-spiro[[1,8]naphthyridine-3,4′-piperidin]-2(4H)-one 2,2,2-trifluoroacetate (Intermediate-14) (600 mg, 1.47 mmol) in DMSO (5 mL) was added triethylamine (0.60 mL, 4.40 mmol) at 0° C. and the mixture was stirred at the same temperature for 15 min. Then phenyl azetidine-1-carboxylate (J) (520 mg, 2.93 mmol) was added and the reaction mixture was allowed to stir at 100° C. for 24 h. The reaction mixture was cooled to 20-35° C., diluted with ice cold water (30 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated under vacuum to get residue; which was purified by column chromatography using mixture of 3% MeOH/DCM as an eluent to get the desired compound as a brown solid (180 mg, 32%); 1H NMR (400 MHz, DMSO-d6) δ 10.70 (s, 1H), 8.22 (d. J=1.5 Hz, 1H), 7.86 (d, J=1.9 Hz, 1H), 3.86 (t, J=7.8 Hz, 4H), 3.43-3.36 (m, 2H), 3.21-3.13 (m, 2H), 2.96 (s, 2H), 2.18-2.10 (m, 2H), 1.73-1.67 (m, 2H), 1.34-1.23 (m, 2H).

Provenance & Evidence