5-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione → 5-(4-{4-[2-(3-Chloro-phenyl)-(2R)-2-hydroxyethylamino}-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

HRID 1061245Notes

Reaction equation

HRID 1061245 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.Cl.[NH2:23][CH2:24][C@@H:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1)[OH:26]>>[Cl:33][C:29]1[CH:28]=[C:27]([C@@H:25]([OH:26])[CH2:24][NH:23][CH:2]2[CH2:7][CH2:6][N:5]([C:8]3[CH:21]=[CH:20][C:11]([CH2:12][CH:13]4[S:17][C:16](=[O:18])[NH:15][C:14]4=[O:19])=[CH:10][CH:9]=3)[CH2:4][CH2:3]2)[CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dioneHCID 56846012(1R)-2-amino-1-(3-chlorophenyl)ethan-1-ol hydrochloride

Product 1

HCID 101154625-(4-{4-[2-(3-Chloro-phenyl)-(2R)-2-hydroxyethylamino}-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 (1R)-2-amino-1-(3-chloro-phenyl)-ethanol (which was obtained in Example 1) according to the procedure of Example 73 as a pale yellowish solid; mp >195-198° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.60 (m, 2H), 1.85-2.10 (m, 2H), 2.60-3.50 (m, 7H), 3.65 (brd, J=12.5 Hz, 2H), 4.63 (dd, J=9.5, 4.1 Hz, 1H), 4.74 (dd, J=8.8, 3.1 Hz, 1H), 6.86 (d, J=8.7 Hz, 2H), 7.05 (d, J=8.7 Hz, 2H), 7.20-7.50 (m, 4H); MS (ES) m/z: 460.0 (MH+); HRMS Calcd. for C23H26ClN3O3S(M+): 459.1383. Found: 459.1376.

Sources & evidence

ORD record
ord-d48dd2ae8f4a4355bae8f0faa6c5f4a1
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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