5-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione → HCID 86584557, compound

HRID 1061265Notes

Reaction equation

HRID 1061265 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH:6]=1)[OH:4].O=[C:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:38]=[CH:37][C:28]([CH2:29][CH:30]3[S:34][C:33](=[O:35])[NH:32][C:31]3=[O:36])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1>>[Cl:17][C:12]1[CH:11]=[C:10]([C:7]2[CH:6]=[C:5]([C@@H:3]([OH:4])[CH2:2][NH:1][CH:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:38]=[CH:37][C:28]([CH2:29][CH:30]5[S:34][C:33](=[O:35])[NH:32][C:31]5=[O:36])=[CH:27][CH:26]=4)[CH2:23][CH2:24]3)[O:9][N:8]=2)[CH:15]=[CH:14][C:13]=1[Cl:16]

Participants

3

Reactant 2

HCID 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dioneHCID 69654860HCID 69654860, compound

Product 1

HCID 86584557HCID 86584557, compound

Procedure

The title compound was prepared from (1S)-2-amino-1-[3-(3,4-dichloro-phenyl)isoxazol-5-yl]ethanol (which was obtained in Example 109) and 5-[4-(4-oxopiperidine-1-yl)benzyl]-1,3-thiazolidine-2,4-dione (which was obtained in Example 38) in substantially the same manner, as described in Example 106 and was obtained as a white solid (0.22 g, 48% yield), mp 110° C.; MS (ES) m/z: 561 (MH+); 1H NMR (400 MHz, DMSO-d6) δ 1.38 (m, 2H), 1.89 (m, 2H), 3.32-2.67 (m, 7H), 3.60 (m, 2H), 4.74 (m. 1H), 4.85 (m, 1H), 6.85 (d, 1H), 7.02 (d, 1H), 7.11 (s, 1H), 7.79 (d, 1H), 7.86 (d, 1H), 8.13 (s, 1H).

Sources & evidence

ORD record
ord-ec68cc95b39a4e0cb0a3153d2f90bd42
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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