4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → 5-(4-{4-[(2S)-2-Hydroxy-3-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-propylamino]-piperidin-1-yl}-benzylidene)-thiazolidine-2,4-dione

Participants

Reaction Steps

The title compound was prepared from 5-[4-(4-oxo-piperidine-1-yl)-benzylidene]-thiazolidine-2,4-dione (which was obtained in Example 36) and (S)-4-[2-hydroxy-3-aminopropoxy]-1,3-dihydro-2H-benzimidazol-2-one (U.S. Pat. No. 5,786,356/1998) according to the procedure of Example 73 as a pale yellowish solid; mp >240° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.45-1.60 (m, 2H), 2.00-2.15 (m, 2H), 2.86 (brt, J=9.0 Hz, 2H), 2.90-3.60 (m, 3H), 3.91 (brd, J=9.4 Hz, 1H), 3.93-4.10 (m, 3H), 5.40 (brs, 1H), 6.59 (d, J=6.0 Hz, 1H), 6.63 (d, J=6.0 Hz, 1H), 6.86 (t, J=6.0 Hz, 1H), 7.02 (d, J=6.6 Hz, 2H), 7.36 (s, 1H), 7.40 (d, J=6.6 Hz, 2H), 11.60 (s, 1H), 11.70 (brs, 1H); MS (ES) m/z: 509.9 (MH+); HRMS Calcd. for C25H28N5O5S(MH+): 510.1811. Found: 510.1861.

Provenance & Evidence