4-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]benzene-1-sulfonyl chloride → 4-(2,4-Dioxo-thiazolidin-5-ylmethyl)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide

HRID 1061347Notes

Reaction equation

HRID 1061347 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=2)[S:3]1.Cl.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]2)=[CH:23][CH:22]=1>>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:28][CH2:29][C:30](=[O:33])[CH2:31][CH2:32]4)=[CH:23][CH:22]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)[S:3]1

Participants

3

Reactant 2

HCID 156164324-[(2,4-Dioxo-1,3-thiazolidin-5-yl)methyl]benzene-1-sulfonyl chlorideHCID 222202401-(4-Amino-phenyl)-piperidin-4-one hydrochloride

Product 1

HCID 222205034-(2,4-Dioxo-thiazolidin-5-ylmethyl)-N-[4-(4-oxo-piperidin-1-yl)-phenyl]-benzenesulfonamide

Procedure

The title compound was prepared from 4-(2,4-dioxo-thiazolidin-5-ylmethyl)benzenesulfonylchloride (J. Med. Chem. 1992, 35, 1853) and 1-(4-amino-phenyl)-piperidine-4-one hydrochloride (which was obtained in Example 224) according to the procedure B of Example 225 as a yellowish solid; 1H NMR (300 MHz, DMSO-d6) δ 2.37 (t, J=6.0 Hz, 4H), 3.10-3.60 (m, 2H), 3.44 (t, J=6.0 Hz, 4H), 4.95 (dd, J=12.3, 6.0 Hz, 1H), 6.80-7.00 (m, 4H), 7.27 (d, J=8.1 Hz, 2H), 7.63 (d, J=8.1 Hz, 2H), 9.77 (brs, 1H), 12.09 (brs, 1H); MS (ES) m/z: 459.9 (MH+); HRMS Calcd. for C21H21N3O5S2 M+): 459.0923. Found: 459.0930.

Sources & evidence

ORD record
ord-d0d894570bed49879029776f36510835
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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