Dabco → HCID 59699558, compound

Participants

Reaction Conditions

Reaction Steps

1,4-Diazabicyclo[2.2.2]-octane (8.60 g, 77 mmol) was added to a solution of 4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (31) (7.9 g, 38 mmol) and piperazin-1-yl-thiophene-2-yl-methanone (11.30 g, 57 mmol) in dimethylacetamide at room temperature. The solution was heated at 110° C. overnight. The solution was cooled and poured into ice cold 10% NH4Cl solution. The solids formed were filtered, washed by cold water and dried under vacuum at room temperature to yield 7.1 g (51%) of 2-oxo-4-[4-(thiophene-2-carbonyl)-piperazine-1-yl]-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (33) as white solids. MP 320° C.; 1H-NMR (DMSO-d6): δ 3.69 (m, 4H), 3.90 (m, 4H), 7.16 (dd, J=3.6, 4.8 Hz, 1H), 7.30 (dd, J=4.4, 8.0 Hz, 1H), 7.49 (d, J=3.6 Hz, 1H), 7.80 (d, J=4.8 Hz, 1H), 8.20 (dd, J=2.0, 8.0 Hz, 1H), 8.60 (d, J=3.2 Hz, 1H), 12.20 (S, 1H); EIMS: 366 (M+1).

Provenance & Evidence