Dabco → HCID 59702095, compound

Participants

Reaction Conditions

Reaction Steps

1,4-Diazabicyclo[2.2.2]octane (224 mg, 2 mmol) was added to a solution of 7-chloro-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (4) (240 mg, 1 mmol) and piperazin-1-yl-thiophene-2-yl-methanone (215 mg, 1.1 mmol) in dry DMA. The solution was heated at 120° C. for 2 h. The solution was cooled and poured into ice water. The solids formed were filtered, washed by water, and dried to yield 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (400 mg, 96%) as white solids. MP 252° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.27 (t, J=7.2 Hz, 3H), 3.31 (m, 4H), 3.77 (m, 4H), 4.24 (q, J=7.2 Hz, 2H), 6.97 (d, J=5.6 Hz, 1H), 7.15 (dd, J=3.6, 4.8 Hz, 1H), 7.47 (dd, J=1.2, 3.6 Hz, 1H), 7.80 (dd, J=1.2, 4.8 Hz, 1H), 7.96 (d, J=5.6 Hz, 1H), 12.10 (s, 1H) ppm; MS m/z=418 amu (M++1).

Provenance & Evidence