5-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione → 5-(4-{4-[(2S)-2-Hydroxy-3-(8-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolin-5-yloxy)-propylamino]-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

HRID 1061253Notes

Reaction equation

HRID 1061253 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:39])[CH2:25][O:26][C:27]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]2[C:28]=1[CH2:29][CH2:30][C:31](=[O:38])[NH:32]2>>[OH:39][C@H:24]([CH2:25][O:26][C:27]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]2[C:28]=1[CH2:29][CH2:30][C:31](=[O:38])[NH:32]2)[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 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dioneHCID 69655051(S)-5-(3-amino-2-hydroxy-propoxy)-8-hydroxy-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 865845555-(4-{4-[(2S)-2-Hydroxy-3-(8-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolin-5-yloxy)-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 (S)-5-(3-amino-2-hydroxy-propoxy)-8-hydroxy-3,4-dihydro-1H-quinolin-2-one) (which was obtained in Example 12) according to the procedure of Example 73 as a pale yellowish solid; mp >140° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.55 (m, 2H), 1.85-2.00 (m, 2H), 2.40 (t, J=8.0 Hz, 2H), 2.60-3.00 (m, 8H), 3.25 (dd, J=15.9, 3.9 Hz, 1H), 3.50-3.70 (m, 2H), 3.80-4.00 (m, 3H), 4.50 (dd, J=9.7, 3.9 Hz, 1H), 6.34 (d, J=8.9 Hz, 1H), 6.61 (d, J=8.9 Hz, 1H), 6.85 (d, J=8.6 Hz, 2H), 7.05 (d, J=8.6 Hz, 2H), 8.76 (s, 1H), 9.24 (brs, 1H); MS (ES) m/z: 541.1 (MH+); HRMS Calcd. for C27H33N4O6S(MH+): 541.2121. Found: 541.2148.

Workup

  1. custom(which was obtained in Example 12)

Sources & evidence

ORD record
ord-4594061dcde24062980ff04ac33fffa9
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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