Sodium hydride → (2-{3-Chloro-5-[(propyl)-(3,5-difluoro-phenyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester

HRID 2268586Notes

Reaction equation

HRID 2268586 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([OH:22])[CH:21]=1)[C:5]([N:7]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)[CH2:8][CH2:9][CH3:10])=[O:6].[H-].[Na+].[C:25]([O:29][C:30]([N:32]([C:46]1[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=1)[CH2:33][CH2:34]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:31])([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[C:25]([O:29][C:30](=[O:31])[N:32]([CH2:33][CH2:34][O:22][C:20]1[CH:19]=[C:4]([C:5](=[O:6])[N:7]([CH2:8][CH2:9][CH3:10])[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)[CH:3]=[C:2]([Cl:1])[CH:21]=1)[C:46]1[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 183488623-Chloro-N-(3,5-difluoro-phenyl)-5-hydroxy-N-propyl-benzamideHCID 54393691Toluene-4-sulfonic acid 2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethyl ester

Product 1

HCID 69949249(2-{3-Chloro-5-[(propyl)-(3,5-difluoro-phenyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl esterYield 34.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloro-N-(3,5-difluoro-phenyl)-5-hydroxy-N-propyl-benzamide (0.050 g) in DMF (0.5 ml) stirred at room temperature under nitrogen was added sodium hydride (60% dispersion in oil, 0.007 g) and after 10 min was added toluene-4-sulfonic acid 2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethyl ester (0.060 g). The reaction was stirred for 66 h, quenched with water and then concentrated in vacuo. and the residue subjected to preparative hplc. The title compound (0.029 g) was obtained as an colourless gum by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile.

Workup

  1. customquenched with water
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6d74e1735f24f408d5249205455d771
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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