Cesium carbonate → HCID 67006628, compound

HRID 564058Notes

Reaction equation

HRID 564058 reaction equation
[CH2:1]([O:8][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+].[CH3:22][O:23][C:24]([C:26]1[S:27][C:28]([CH2:31][CH2:32]OS(C)(=O)=O)=[CH:29][CH:30]=1)=[O:25]>CN(C=O)C>[CH3:22][O:23][C:24]([C:26]1[S:27][C:28]([CH2:31][CH2:32][N:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]2=[O:15])=[CH:29][CH:30]=1)=[O:25]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 19856070HCID 19856070, compound

Product 1

HCID 67006628HCID 67006628, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.20 g (5.96 mmol) 4-benzyloxy-1H-pyridin-2-one in DMF is added subsequently 3.89 g (11.9 mmol) cesium carbonate and 1.58 g (5.96 mmol) 5-(2-methanesulfonyloxy-ethyl)thiophene-2-carboxylic acid methyl ester (preparation 11a). The reaction mixture is stirred overnight at RT. After filtration, the residue is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).

Workup

  1. filtrationAfter filtration
  2. customthe residue is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90)

Sources & evidence

ORD record
ord-bf3df5b442744c068f6e23b904da4743
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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