Cesium carbonate → 4-(Benzyl-methyl-amino)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

HRID 564061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564061
[CH2:1]([N:8]([CH3:16])[C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][CH:27]=1>CN(C=O)C>[CH2:1]([N:8]([CH3:16])[C:9]1[CH:14]=[CH:13][N:12]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][CH:27]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 18402547[4-(2-Iodo-ethyl)-phenyl]-methanolHCID 670068384-(Benzyl-methyl-amino)-1H-pyridin-2-one

Produkt 1

HCID 670066464-(Benzyl-methyl-amino)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 500 mg (2.33 mmol) 4-(benzyl-methyl-amino)-1H-pyridin-2-one (preparation 14b) and 1.52 g (4.67 mmol) cesium carbonate in 2.3 mL of DMF is stirred 15 min at RT and then 1.22 g (4.67 mmol) [4-(2-iodo-ethyl)-phenyl]-methanol (preparation 1b) is added. The mixture is stirred overnight at RT and the solvent is evaporated. The residue is dissolved in MeOH and is purified by reverse HPLC (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Aufarbeitung

  1. stirringThe mixture is stirred overnight at RT
  2. customthe solvent is evaporated
  3. dissolutionThe residue is dissolved in MeOH
  4. customis purified by reverse HPLC (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90)

Quellen und Nachweise

ORD-Eintrag
ord-f980080131a64721abaa99503a17531a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067590B2

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