Acetic Acid → 5-(4-{4-[(2S)-2-Hydroxy-3-(pyridin-3-yloxy)-propylamino]-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

HRID 1061275Notes

Reaction equation

HRID 1061275 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:12])[CH2:4][O:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.O=[C:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:33]=[CH:32][C:23]([CH2:24][CH:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>CN(C)C=O>[OH:12][C@H:3]([CH2:4][O:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH2:2][NH:1][CH:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:33]=[CH:32][C:23]([CH2:24][CH:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:21]=2)[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 129659555-[4-(4-Oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dioneHCID 69654939(2S)-1-Amino-3-(3-pyridinyloxy)-2-propanol

Product 1

HCID 865845605-(4-{4-[(2S)-2-Hydroxy-3-(pyridin-3-yloxy)-propylamino]-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dioneYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S)-1-Amino-3-(3-pyridinyloxy)-2-propanol (0.21 g, 1.25 mmol) (which was obtained in Example 124) and 5-[4-(4-oxo-1-piperidineyl)benzyl]-1,3-thiazolidine-2,4-dione (which was obtained in Example 38) (0.413, 1.25 mmol) were mixed in N,N-dimethylformamide (12 mL) and then treated with sodium triacetoxyborohydride (0.56 g, 2.5 mmol) and acetic acid (0.26 mL). After stirring at room temperature under a nitrogen atmosphere for one day, the mixture was purified by column chromatography (dichloromethane/methyl alcohol 85/5) to give the title compound as a yellow solid (0.25 g, 56% yield); mp: 130-132° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.20-1.54 (m, 2H), 1.90-2.02 (m, 2H), 2.67 (t, 2H), 2.78-2.97 (m, 4H), 3.22-3.26 (m, 1 H), 3.35 (brs, 2H), 3.64-3.70 (d, 2H), 3.97-4.08 (m, 3H), 4.60-4.63 (m, 1H), 6.84-6.86 (m, 2 H), 7.03-7.05 (m, 2H), 730-7.36 (m, 1H), 7.38-7.40 (m, 1H), 8.16-8.17 (m, 1H), 8.8.29-8.30 (m, 1H); MS (ES) m/z: 457 (MH+).

Workup

  1. customthe mixture was purified by column chromatography (dichloromethane/methyl alcohol 85/5)

Sources & evidence

ORD record
ord-0e74183c6e294ec8b0cd8a287e4e20ea
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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