Dabco → HCID 59702104, compound

Participants

Reaction Conditions

Reaction Steps

1,4-Diazabicyclo[2.2.2]octane (2.07 g, 10.16 mmol) was added to a solution of 7-chloro-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester (39) (2.4 g, 9.24 mmol) and piperazin-1-yl-thiophene-2-yl-methanone (1.99 g, 10.16 mmol) in dry DMA. The solution was heated at 110° C. for 3 h. The solution was cooled and the solvent was distilled. The residue was suspended in water, sonicated briefly, and filtered. The solids were washed by excess water and dried to yield 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester (3.47 g, 90%) as white solids. MP 282° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.27 (t, J=7.2 Hz, 3H), 3.27 (m, 4H), 3.77 (m, 4H), 4.24 (q, J=7.2 Hz, 2H), 6.86 (d, J=3.6 Hz, 1H), 7.15 (dd, J=3.6, 5.2 Hz, 1H), 7.46 (dd, J=1.2, 3.6 Hz, 1H), 7.80 (dd, J=1.2, 4.8 Hz, 1H), 8.02 (d, J=3.2 Hz, 1H), 11.30 (s, 1H) ppm; MS m/z=418 amu (M++1).

Provenance & Evidence