5-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione → 5-{4-[4-((2R)-2-Hydroxy-2-pyridin-3-yl-ethylamino)-piperidin-1-yl]-benzyl}-thiazolidine-2,4-dione

HRID 1794790Notes

Reaction equation

HRID 1794790 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[OH:4].O=[C:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:31]=[CH:30][C:21]([CH2:22][CH:23]3[S:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1>>[OH:4][C@H:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[CH2:2][NH:1][CH:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:31]=[CH:30][C:21]([CH2:22][CH:23]3[S:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])=[CH:20][CH:19]=2)[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dioneHCID 23556080(R)-2-amino-1-(pyridin-3-yl)ethanol

Product 1

HCID 443775365-{4-[4-((2R)-2-Hydroxy-2-pyridin-3-yl-ethylamino)-piperidin-1-yl]-benzyl}-thiazolidine-2,4-dione

Procedure

The title compound was prepared from (1R)-2-amino-1-(3-pyridinyl)-1-ethanol (which was obtained in Example 135) and 5-[4-(4-oxo-1-piperidinyl)benzyl]-1,3-thiazolidine-2,4-dione (which was obtained in Example 38) in substantially the same manner, as described in Example 125. The product was obtained as a yellow solid; mp 87° C. (decomposed); 1H NMR (400 MHz, DMSO-d6) δ 1.38–1.43 (m, 2 H), 1.89–1.91 (m, 2 H), 2.62–2.71 (t, 2), 2.71–2.91 (m, 4 H), 3.23–3.27 (m, 1 H), 3.60–3.63 (m, 2 H), 4.58–4.61 (m, 1 H), 4.72–4.75 (m, 1 H), 6.38–6.85 (d, 2 H), 7.02–7.05 (d, 2 H), 7.34–7.37 (m, 1 H), 7.75–7.78 (m, 1 H), 8.45–8.46 (m, 1 H), 8.56–8.57 (m, 1 H); MS (ES) m/z: 427 (MH+).

Workup

  1. customThe product was obtained as a yellow solid

Sources & evidence

ORD record
ord-c9494111d2a34b16a29b105d12b3a803
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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