Triethylamine → HCID 67171641, compound

Participants

Reaction Conditions

Reaction Steps

26.1 mg of hydroxylamine hydrochloride, 62.7 μl of triethylamine and 2.5 mL of EtOH were added to 1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4′-piperidine]-6-carbonitrile (115 mg) obtained in Example 16, and stirred at 60° C. for 24 hours. The reaction mixture was concentrated, and the residue was purified through silica gel column chromatography (2% MeOH/CHCl3) to obtain 83.4 mg of 1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4′-piperidine]-6-carboximidamide. 49.1 mg of the product was dissolved in 1.0 mL of DMF along with 9.7 μl of pyridine therein, and 21.6 μl of 2-ethylhexyl chloroformate was added thereto at 0° C. The mixture was stirred at 0° C. for 30 minutes, then diluted with ethyl acetate (15 mL), washed with water and saturated brine, dried over sodium sulfate, and concentrated. The residue was dissolved in xylene, refluxed for 4 hours, and then concentrated, and the residue was purified through silica gel chromatography (developed with 20% MeOH/EtOAc) to obtain the intended compound. 1H-NMR (CDCl3) δ: 8.50 (1H, d, J=2.4 Hz), 8.11 (1H, dd, J=8.8, 2.4 Hz), 7.78 (1H, dd, J=8.3, 1.0 Hz), 7.47 (1H, dd, J=8.3, 7.8 Hz), 7.21 (1H, s), 7.16 (1H, d, J=8.8 Hz), 7.07 (1H, dd, J=1.0, 7.8 Hz), 4.61-4.53 (1H, m), 4.20-4.12 (1H, m), 4.10 (3H, s), 4.01 (3H, s), 3.71-3.62 (1H, m), 3.40-3.31 (1H, m), 2.95 (2H, s), 2.26-1.86 (4H, m). MS [M+H]+=517.

Provenance & Evidence