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

HRID 1061237Notes

Reaction equation

HRID 1061237 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[Br:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][C:31]=1[N:32]1[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]1)[CH:21]=[C:22]1[S:26][C:25](=[O:27])[NH:24][C:23]1=[O:28]>>[Br:17][C:18]1[CH:19]=[C:20]([CH:21]=[C:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])[CH:29]=[CH:30][C:31]=1[N:32]1[CH2:33][CH2:34][CH:35]([NH:1][CH2:2][CH:3]([C:5]2[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=2)[OH:4])[CH2:36][CH2:37]1

Participants

3

Reactant 2

HCID 9837752N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamideHCID 738767165-[3-Bromo-4-(4-oxo-piperidin-1-yl)-benzylidene]-thiazolidine-2,4-dione

Product 1

HCID 86588905N-[5-(2-{1-[2-Bromo-4-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-phenyl]-piperidin-4-ylamino}-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide

Procedure

The title compound was prepared from N-[5-(2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 9) and 5-[3-bromo-4-(4-oxo-piperidine-1-yl)-benzylidene]-thiazolidine-2,4-dione (which was obtained in Example 58) according to the procedure of Example 63 as a dull yellow solid; mp >200° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.70-1.82 (m, 2H), 2.07-2.17 (m, 2H), 2.65-2.73 (m, 3H), 2.95 (s, 3H), 3.07-3.17 (m, 4H), 4.74-4.77 (m, 3H), 6.00 (brs, 1H), 6.89 (d, J=8.3 Hz, 1H), 7.09 (dd, J=8.4, 2.0 Hz, 1H), 7.20 (d, J=8.4 Hz, 1H), 7.26-7.27 (m, 2H), 7.50 (dd, J=8.4, 2.0 Hz, 1H), 7.75 (d, J=2.0 Hz, 1H), 8.7 (brs, 1H), 9.9 (brs, 1H); MS (ES) m/z: 612.8 (MH+).

Sources & evidence

ORD record
ord-000f806694784fa98f1ac7aa516bc04b
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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