N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → N-[5-(2-{1-[4-(2,4-Dioxo-thiazolidin-5-ylmethyl)-phenyl]-piperidin-4-ylamino}-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide

Participants

Reaction Steps

The title compound was prepared from 5-[4-(4-oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione (which was obtained in Example 38) and N-[5-(2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 9) according to the procedure of Example 73 as a pale yellowish solid; mp>150° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.40–1.60 (m, 2 H), 1.90–2.10 (m, 2 H), 2.55–3.60 (m, 7 H), 2.93 (s, 3 H), 3.67 (brd, J=12.8 Hz, 2 H), 4.56 (dd, J=9.6, 4.0 Hz, 1 H), 4.64 (brd, J=6.5 Hz, 1 H), 6.70–6.95 (m, 3 H), 6.95–7.15 (m, 3 H), 7.22 (d, J=2.1 Hz, 1 H); MS (ES) m/z: 535.0 (MH+); HRMS Calcd. for C24H31N4O6S2 (MH+): 535.1685. Found: 535.1720.

Provenance & Evidence