(2S)-(-)-1-Amino-3-phenoxy-2-propanol → 5-{4-[4-((2S)-2-Hydroxy-3-phenoxy-propylamino)-piperidine-1-yl]-benzylidene}-thiazolidine-2,4-dione

HRID 1794751Notes

Reaction equation

HRID 1794751 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:21]=[CH:20][C:11]([CH:12]=[C:13]2[S:17][C:16](=[O:18])[NH:15][C:14]2=[O:19])=[CH:10][CH:9]=1.[NH2:22][CH2:23][C@H:24]([OH:33])[CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[OH:33][C@H:24]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:23][NH:22][CH:6]1[CH2:5][CH2:4][N:3]([C:8]2[CH:21]=[CH:20][C:11]([CH:12]=[C:13]3[S:17][C:16](=[O:18])[NH:15][C:14]3=[O:19])=[CH:10][CH:9]=2)[CH2:2][CH2:7]1

Participants

3

Reactant 2

HCID 1133101(2S)-(-)-1-Amino-3-phenoxy-2-propanolHCID 738767195-[4-(Oxo-piperidin-1-yl)-benzylidene]-thiazolidine-2,4-dione

Product 1

HCID 865845535-{4-[4-((2S)-2-Hydroxy-3-phenoxy-propylamino)-piperidine-1-yl]-benzylidene}-thiazolidine-2,4-dione

Procedure

The title compound was prepared from 5-[4-(4-oxo-piperidin-1-yl)-benzylidene]-thiazolidine-2,4-dione (which was obtained in Example 36) and (2S)-1-amino-3-phenoxy-propan-2-ol (which was obtained in Example 3) according to the procedure of Example 73 as a pale yellowish solid; mp 208–210° C.; MS (ES) m/z: 454.0 (MH+); HRMS Calcd. for C24H27N3O4S (M+): 453.1723. Found: 453.1710.

Sources & evidence

ORD record
ord-e123f06f3400487daa51c6137c111224
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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