5-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione → N-[5-((2S)-3-{1-[4-(2,4-Dioxo-thiazolidin-5-ylmethyl)-phenyl]-piperidin-4-ylamino}-2-hydroxy-propoxy)-2-hydroxy-phenyl]-methanesulfonamide
Reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:21]=[CH:20][C:11]([CH2:12][CH:13]3[S:17][C:16](=[O:18])[NH:15][C:14]3=[O:19])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:22][CH2:23][C@H:24]([OH:39])[CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([OH:38])=[C:31]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:32]=1>>[O:18]=[C:16]1[NH:15][C:14](=[O:19])[CH:13]([CH2:12][C:11]2[CH:20]=[CH:21][C:8]([N:5]3[CH2:6][CH2:7][CH:2]([NH:22][CH2:23][C@H:24]([OH:39])[CH2:25][O:26][C:27]4[CH:28]=[CH:29][C:30]([OH:38])=[C:31]([NH:33][S:34]([CH3:37])(=[O:35])=[O:36])[CH:32]=4)[CH2:3][CH2:4]3)=[CH:9][CH:10]=2)[S:17]1Participants
3
Reactant 2
Product 1
Procedure
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-((2S)-3-amino-2-hydroxy-propoxy)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 14) according to the procedure of Example 73 as a grey solid; mp>70° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.45–1.55 (m, 2 H), 1.85–2.00 (m, 2 H), 2.60–2.90 (m, 6 H), 2.94 (s, 3 H), 3.23 (dd, J=14.0, 3.8 Hz, 1 H), 3.60–4.00 (m, 5 H), 4.49 (dd, J=8.8, 3.9 Hz, 1 H), 6.64 (dd, J=8.8, 3.0 Hz, 1 H), 6.75–6.90 (m, 4 H), 7.04 (d, J=8.6 Hz, 2 H); MS (ES) m/z: 564.8 (MH+, 100%); HRMS Calcd. for C25H33N4O7S2 (MH+): 565.1791. Found: 565.1783.
Sources & evidence
- ORD record
- ord-5abce407214940fbb8c745e73362d6c3
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022716B2
Reaction notes
Loading…