4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol → 5-(4-{4-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

HRID 1061247Notes

Reaction equation

HRID 1061247 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]([OH:34])[CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1>>[OH:34][C@H:24]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)[CH2:23][NH:22][CH: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

Participants

3

Reactant 2

HCID 98775474-((2S)-3-Amino-2-hydroxy-propoxy)-phenolHCID 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione

Product 1

HCID 102989685-(4-{4-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

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 4-[(2S)-3-amino-2-hydroxy-propoxy]-phenol (which was obtained in Example 5) according to the procedure of Example 73 as a pale yellowish solid; mp >160° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.35-1.60 (m, 2H), 1.85-2.05 (m, 2H), 2.60-3.50 (m, 7H), 3.67 (brd, J=12.1 Hz, 2H), 3.75-3.95 (m, 3H), 4.57 (dd, J=9.6, 3.8 Hz, 1H), 6.66 (d, J=8.9 Hz, 2H), 6.77 (d, J=8.9 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 7.03 (d, J=8.6 Hz, 2H), 8.92 (brs, 1H); MS (ES) m/z: 472.0 (MH+); HRMS Calcd. for C24H30N3O5S(MH+): 472.1906. Found: 472.1898.

Sources & evidence

ORD record
ord-d75abf184cc24220bc6e694a2f239b5d
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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