Triethylamine → HCID 90410866, 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) (100 mg, 0.24 mmol) in DCM (3 mL) were added triethylamine (0.1 mL, 0.72 mmol) and pivaloyl chloride (40 mg, 0.32 mmol) at 20-35° C. and the reaction mixture was allowed to stir at 20-35° C. for 16 h. Then the reaction mixture was diluted with water (30 mL) and extracted with DCM (2×30 mL). The organic layer was washed with brine (50 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 60% ethyl acetate/hexane as an eluent to get the desired compound as a creamy white solid (50 mg, 55%); 1H NMR (400 MHz, DMSO-d6) δ 10.73 (s, 1H), 8.23 (d, J=1.9 Hz, 1H), 7.85 (d, J=1.5 Hz, 1H), 3.79-3.74 (m, 2H), 3.44 (t, J=10.1 Hz, 2H), 2.99 (s, 2H), 1.75-1.68 (m, 2H), 1.35-1.29 (m, 2H), 1.18 (s, 9H); ES-MS: 380.2 (M+1)+.

Provenance & Evidence