5-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione → 5-(4-{4-[(2S)-2-Hydroxy-3-(8-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolin-5-yloxy)-propylamino]-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

Participants

Reaction Steps

The title compound was prepared from 5-[4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dione (which was obtained in Example 38) and (S)-5-(3-amino-2-hydroxy-propoxy)-8-hydroxy-3,4-dihydro-1H-quinolin-2-one) (which was obtained in Example 12) according to the procedure of Example 73 as a pale yellowish solid; mp >140° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.55 (m, 2H), 1.85-2.00 (m, 2H), 2.40 (t, J=8.0 Hz, 2H), 2.60-3.00 (m, 8H), 3.25 (dd, J=15.9, 3.9 Hz, 1H), 3.50-3.70 (m, 2H), 3.80-4.00 (m, 3H), 4.50 (dd, J=9.7, 3.9 Hz, 1H), 6.34 (d, J=8.9 Hz, 1H), 6.61 (d, J=8.9 Hz, 1H), 6.85 (d, J=8.6 Hz, 2H), 7.05 (d, J=8.6 Hz, 2H), 8.76 (s, 1H), 9.24 (brs, 1H); MS (ES) m/z: 541.1 (MH+); HRMS Calcd. for C27H33N4O6S(MH+): 541.2121. Found: 541.2148.

Provenance & Evidence