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

HRID 1794741Notes

Reaction equation

HRID 1794741 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].[F: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]>>[O:27]=[C:25]1[NH:24][C:23](=[O:28])[C:22](=[CH:21][C:20]2[CH:29]=[CH:30][C:31]([N:32]3[CH2:37][CH2:36][CH:35]([NH:1][CH2:2][CH:3]([C:5]4[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=4)[OH:4])[CH2:34][CH2:33]3)=[C:18]([F:17])[CH:19]=2)[S:26]1

Participants

3

Reactant 2

HCID 9837752N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamideHCID 738767205-[3-Fluoro-4-(4-oxo-piperidin-1-yl)-benzylidene]-thiazolidine-2,4-dione

Product 1

HCID 85327344N-[5-(2-{1-[4-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-2-fluoro-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-fluoro-4-(4-oxo-piperidin-1-yl)-benzylidene]-thiazolidine-2,4-dione (which was obtained in Example 62) according to the procedure of Example 63 as a yellow solid; mp>225° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.62–1.71 (m, 2H), 2.03–2.12 (m, 2H), 2.70–2.83 (m, 3H), 2.95 (s, 3H), 3.12–3.33 (m, 2H), 3.49–3.52 (m, 2H), 4.72–4.75 (m 1H), 5.96 (brs, 1H), 6.89 (d, J=8.1 Hz, 1H), 7.05–7.13 (m, 3H), 7.25–7.38 (m, 3H), 8.70 (brs, 1H), 9.8 (brs, 1H); MS (ES) m/z: 551.0 (MH+); HRMS for C24H27FN4O6S2 (MH+): 551.1434. Found: 551.1438.

Sources & evidence

ORD record
ord-12c962c67f224f7c9928a55183d5f810
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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