N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → N-[5-(2-{1-[4-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-phenyl]-piperidine-4-ylamino}-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide
Reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:21]=[CH:20][C:11]([CH:12]=[C:13]2[S:17][C:16](=[O:18])[NH:15][C:14]2=[O:19])=[CH:10][CH:9]=1.[NH2:22][CH2:23][CH:24]([C:26]1[CH:27]=[CH:28][C:29]([OH:37])=[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:31]=1)[OH:25]>>[O:18]=[C:16]1[NH:15][C:14](=[O:19])[C:13](=[CH:12][C:11]2[CH:20]=[CH:21][C:8]([N:3]3[CH2:4][CH2:5][CH:6]([NH:22][CH2:23][CH:24]([C:26]4[CH:27]=[CH:28][C:29]([OH:37])=[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:31]=4)[OH:25])[CH2:7][CH2:2]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)-benzylidene]-thiazolidine-2,4-dione (which was obtained in Example 36) 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>200° C. (decomposed); 1H NMR (300 MHz, DMSO-d6), δ 1.45–1.60 (m, 2 H), 1.90–2.05 (m, 2 H), 2.70–3.50 (m, 5 H), 2.94 (s, 3 H), 3.88 (brd, J=9.9 Hz, 2 H), 4.67 (dd, J=7.2, 2.1 Hz, 1 H), 6.87 (d, J=6.3 Hz, 1 H), 7.00 (d, J=6.8 Hz, 2 H), 7.06 (dd, J=6.3, 1.5 Hz, 1 H), 7.23 (d, J=1.5 Hz, 1 H), 7.33 (s, 1 H), 7.38 (d, J=6.8 Hz, 2 H); MS (ES) m/z: 533.0 (MH+); HRMS Calcd. for C24H29N4O6S2 (MH+): 533.1529. Found: 533.1544.
Sources & evidence
- ORD record
- ord-67c4f462beba44babe1c7ade79beccd4
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022716B2
Reaction notes
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