2-Chloroacetophenone → HCID 59702107, compound

Participants

Reaction Steps

A solution of 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (5) (750 mg, 1.79 mmol), Cs2CO3 (1.76 g, 5.40 mmol), 2-chloroacetophenone (0.333 g, 2.15 mmol) in dry NMP was heated overnight at 90° C. The solution was poured into ice water and the solids formed were filtered, washed by cold water, and dried. The crude product was purified by recrystallization with acetone. MP 240° C. 1H-NMR (DMSO-d6) δ 1.26 (t, J=7.2 Hz, 3H), 3.39 (m, 4H), 3.83 (m, 4H), 4.23 (q, J=7.2 Hz, 2H), 4.23 (q, J=7.2 Hz, 2H), 5.75 (s, 2H), 7.16 (m, 1H), 7.34 (d, J=5.6 Hz, 1H), 7.50 (dd, J=1.2, 3.6 Hz, 1H), 7.61 (t, J=7.6 Hz, 2H), 7.74 (m, 1H), 7.80 (dd, J=1.2, 5.2 Hz, 1H), 8.01 (d, J=7.0 Hz, 1H), 8.10 (m, 2H); EIMS m/z 536(M+1).

Provenance & Evidence