Dabco → HCID 59699675, compound

Participants

Reaction Conditions

Reaction Steps

DABCO (0.57 g, 5.0 mmol) was added to a solution of 1-benzyl-4-chloro-3-(methylsulfonyl)-[1,8]-naphthyridin-2(1H)-one (115) (0.88 g, 2.5 mmol) and piperazine-1-yl-thiophene-2-yl-methanone (0.60 g, 3.08 mmol) in N-methylpyrrolidone at room temperature. The solution was heated at 110° C. for 15 min. The solution was cooled and poured into ice cold 10% ammonium chloride solution in water. The solids formed were filtered, washed by water, and dried to yield 0.95 g (74%) of 1-benzyl-3-methanesulfonyl-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1H-[1,8]-naphthyridin-2-one (116) as yellow solids MP: 223° C.; 1H-NMR (DMSO-d6): δ 3.37 (s, 3H), 3.59 (m, 4H), 3.93 (b, 4H), 5.59 (s, 2H), 7.2 (m, 6H), 7.38 (m, 1H), 7.47 (dd, J=1.2, 3.6 Hz, 1H), 7.81 (dd, J=1.2, 5.2 Hz, 1H), 8.46 (dd, J=1.6, 8.0 Hz, 1H), 8.70 (dd, J=1.6, 4.4 Hz, 1H); EIMS m/z 509 (M+1).

Provenance & Evidence