4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one → HCID 10301188, compound

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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 (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 173–175° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.45–1.60 (m, 2 H), 1.90–2.15 (m, 2 H), 2.10–2.95 (m, 5 H), 3.03 (brd, J=10.5 Hz, 1 H), 3.26 (dd, J=14.1, 3.8 Hz, 1 H), 3.68 (brd, J=12.4 Hz, 2 H), 3.95–4.05 (m, 3 H), 4.51 (dd, J=10.0, 4.0 Hz, 1 H), 6.58 (d, J=7.8 Hz, 1 H), 6.63 (d, J=8.1 Hz, 1 H), 6.75–6.95 (m, 3 H), 7.05 (d, J=8.7 Hz, 2 H), 11.60 (s, 1 H), 11.85 (brs, 1 H); MS (ES) m/z: 512.0 (MH+); HRMS Calcd. for C25H30N5O5S (MH+): 512.1968. Found: 512.1982.

Provenance & Evidence