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

HRID 1061279Notes

Reaction equation

HRID 1061279 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.O>C(Cl)Cl>[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

5

Reactant 3

HCID 962WaterHCID 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dioneHCID 40480581(S)-2-amino-1-(pyridin-3-yl)ethanol

Product 1

HCID 865845615-{4-[4-((2S)-2-Hydroxy-2-pyridin-3-yl-ethylamino)-piperidin-1-yl]-benzyl}-thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from (1S)-2-amino-1-(3-pyridinyl)-1-ethanol (which was obtained in Example 130) and 5-[4-(4-oxo-1-piperidineyl)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: >88° C. decomposed; 1H NMR (400 MHz, DMSO-d6) δ 1.38-1.50 (m, 2H), 1.90-1.98 (m, 2H), 2.63-2.71 (t, 2H), 2.78-2.96 (m, 4H), 3.23-3.27 (m, 1H), 3.62-3.65 (m, 2H), 4.62-4.67 (m, 1H), 4.76-4.79 (m, 1H), 6.83-6.86 (d, 2H), 7.03-7.05 (d, 2H), 7.36-7.38 (m, 1H), 7.76-7.79 (m, 1H), 8.46-8.48 (m, 1H), 8.57-8.58 (m, 1H); MS (ES) m/z: 427 (MH+); Anal. Calcd. for C22H36N4O2×0.3 H2O×0.3 CH2Cl2: C, 55.87; H, 5.51; N, 11.69. Found: C, 55.92; H, 5.80; N, 11.45.

Workup

  1. customThe product was obtained as a yellow solid

Sources & evidence

ORD record
ord-cb753704541c4a8dbc24439ee4210514
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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