Dabco → HCID 11165828, compound

Participants

Reaction Conditions

Reaction Steps

DABCO (0.57 g, 5.14 mmol) was added to a solution of 4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (15) (0.65 g, 2.57 mmol) and piperazine-1-yl-thiophene-2-yl-methanone (0.60 g, 3.08 mmol) in dimethylacetamide at room temperature. The solution was heated overnight at 110° C. The solution was cooled and poured into ice water. The solids formed were filtered, washed by water, and dried to yield 420 mg (39%) of 2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (16) as white solids. MP: 239° C.; 1H-NMR (DMSO-d6): δ 1.30 (t, J=7.0 Hz, 3H), 3.13 (m, 4H), 3.87 (m, 4H), 4.30 (q, J=7.0 Hz, 2H), 7.15 (dd, J=3.5, 4.8 Hz, 1H), 7.40 (dd, J=4.8, 8.0 Hz, 1H), 7.45 (d, J=3.6 Hz, 1H), 7.80 (d, J=4.8 Hz, 1H), 8.24 (dd, J=1.5, 7.5 Hz, 1H), 8.56 (dd, J=1.5, 7.5 Hz, 1H) 12.25 (s, 1H); EIMS: 413 (M+1).

Provenance & Evidence