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]-benzenesulfonamide

HRID 1061254Notes

Reaction equation

HRID 1061254 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][CH:24]([OH:44])[CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([OH:43])=[C:31]([NH:33][S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[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:44])[CH2:25][O:26][C:27]4[CH:28]=[CH:29][C:30]([OH:43])=[C:31]([NH:33][S:34]([C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)(=[O:35])=[O:36])[CH:32]=4)[CH2:3][CH2:4]3)=[CH:9][CH:10]=2)[S:17]1

Participants

3

Reactant 2

HCID 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dioneHCID 22220361N-[5-(3-Amino-2-hydroxy-propoxy)-2-hydroxy-phenyl]-benzenesulfonamide

Product 1

HCID 10121958N-[5-((2S)-3-{1-[4-(2,4-Dioxo-thiazolidin-5-ylmethyl)-phenyl]-piperidin-4-ylamino}-2-hydroxy-propoxy)-2-hydroxy-phenyl]-benzenesulfonamide

Procedure

The title compound was prepared from 5-[4-(4-oxo-piperidine-1-yl)-benzyl]-thiazolidine-2,4-dione (which was obtained in Example 38) and N-[5-(3-amino-2-hydroxy-propoxy)-2-hydroxy-phenyl]-benzenesulfonamide (which was obtained in Example 21) according to the procedure of Example 73 as an off-white solid; mp >120° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.30-1.55 (m, 2H), 1.80-2.00 (m, 2H), 2.50-4.00 (m, 12H), 4.55 (dd, J=9.6, 4.0 Hz, 1H), 6.49 (dd, J=8.7, 2.9 Hz, 1H), 6.61 (d, J=8.7 Hz, 1H), 6.77 (d, J=2.9 Hz, 1H), 6.86 (d, J=8.7 Hz, 2H), 7.05 (d, J=8.7 Hz, 2H), 7.40-7.60 (m, 3H), 7.70-7.80 (m, 2H); MS (ES) m/z: 627.0 (MH+, 100%); HRMS Calcd. for C30H35N4O7S2 (MH+): 627.1941. Found: 627.1954.

Sources & evidence

ORD record
ord-aeed01af28594224b4d05ae27e8ec4c6
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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