Pyridine → 3-[bis(methylthio)methylene]-1-(cyclobutylamino)quinoline-2,4(1H,3H)-dione

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(cyclobutylamino)-4-hydroxyquinolin-2(1H)-one (0.115 g, 0.5 mmol) and tris(methylthio)methyl methyl sulfate (prepared using the procedures in SYNTHESIS, 22-25, 1988; M Barbero, S. Cadamuro, 1 Degani, R. Fochi, A. Gatti, V. Regondi) (0.27 g, 1.0 mmol) in pyridine (0.316 g, 4.0 mmol) and dioxane (5.0 mL) was heated at 60° C. for 30 minutes. Additional tris(methylthio)methyl methyl sulfate was added (0.27 g, 1.0 mmol) and heating continued for 30 minutes. The mixture was cooled to 25° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. The crude material was chromatographed on silica gel eluting with 95/5 dichloromethane/ethyl acetate to give 3-[bis(methylthio)methylene]-1-(cyclobutylamino)quinoline-2,4(1H, 3H)-dione (0.146 g, 87% yield). MS (ESI+) m/z 335 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 1.54 (m, 1H) 1.66 (m, 1H) 1.99 (m, 4H) 2.61 (s, 6H) 3.62 (m, 1H) 6.18 (d, J=6.25 Hz, 1H) 7.15 (t, J=7.54 Hz, 1H) 7.63 (m, 1H) 7.72 (d, J=8.09 Hz, 1H) 7.98 (dd, J=7.91, 1.29 Hz, 1H).

Provenance & Evidence