5-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione → HCID 44377771, compound

HRID 1061257Notes

Reaction equation

HRID 1061257 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][C@@H:24]([C:26]1[CH:27]=[CH:28][C:29]([OH:42])=[C:30]([NH:32][S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH:31]=1)[OH:25]>>[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]([C:26]4[CH:27]=[CH:28][C:29]([OH:42])=[C:30]([NH:32][S:33]([C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)(=[O:35])=[O:34])[CH:31]=4)[OH:25])[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 69654868HCID 69654868, compound

Product 1

HCID 44377771HCID 44377771, compound

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-((R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-phenylsulfonamide (which was obtained in Example 32) according to the procedure of Example 73 as a white solid; mp >150° C. (decomposed); 1H NMR (300 MHz, DMSO- d6) δ 1.39 (m, 4H), 1.85 (m, 4H), 2.64 (m, 2H), 2.89 (s, 3H), 4.48 (m, 1H), 6.67 (d, J=6 Hz, 1H), 6.86 (m, 2H), 7.02 (m, 2H), 7.48 (m, 2H), 7.72 (d, J=6 Hz, 1H); MS (ES) m/z: 597.0 (MH+, 100%); HRMS Calcd. for C29H32N4O6S2 (MH+): 597.1836. Found: 597.1827.

Sources & evidence

ORD record
ord-50ef7bb418a54f938c4018ec8be3a4ef
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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