5-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione → HCID 131723780, compound

HRID 1061255Notes

Reaction equation

HRID 1061255 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:39])=[C:30]([NH:32][S:33]([CH:36]([CH3:38])[CH3:37])(=[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:39])=[C:30]([NH:32][S:33]([CH:36]([CH3:37])[CH3:38])(=[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 86584574HCID 86584574, compound

Product 1

HCID 131723780HCID 131723780, 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 propane-2-sulfonic acid [5-((1 R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-amide (which was obtained in Example 27) according to the procedure of Example 73 as a white solid; mp >175° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.25 (d, J=6.8 Hz, 6H), 1.30-1.55 (m, 2H), 1.80-2.00 (m, 2H), 2.60-3.70 (m, 9H), 4.47 (dd, J=9.7, 3.9 Hz, 1H), 4.58 (dd, J=8.7, 3.4 Hz, 1H), 6.75-6.90 (m, 3H), 6.90-7.10 (m, 3H), 7.26 (d, J=2.0 Hz, 1H); MS (ES) m/z: 563.0 (MH+, 100%); HRMS Calcd. for C26H35N4O6S2 (MH+): 563.1992. Found: 563.1985.

Sources & evidence

ORD record
ord-92fc6caac9314f6fad7673927e8988aa
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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