N-[2-tert-butoxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]-4-but-2-ynyloxybenzamide → 4-but-2-ynyloxy-N-[2-hydroxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]benzamide

HRID 517493Notes

Reaction equation

HRID 517493 reaction equation
C([O:5][NH:6][C:7]([CH:9]([N:25]1[CH2:30][CH2:29][N:28]([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:27][CH2:26]1)[CH2:10][NH:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]#[C:22][CH3:23])=[CH:15][CH:14]=1)=[O:8])(C)(C)C>FC(F)(F)C(O)=O>[CH2:20]([O:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]([NH:11][CH2:10][CH:9]([C:7](=[O:8])[NH:6][OH:5])[N:25]2[CH2:30][CH2:29][N:28]([S:31]([CH3:34])(=[O:32])=[O:33])[CH2:27][CH2:26]2)=[O:24])=[CH:18][CH:17]=1)[C:21]#[C:22][CH3:23]

Participants

3

Reactant 1

HCID 86667905N-[2-tert-butoxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]-4-but-2-ynyloxybenzamide

Product 1

HCID 510298144-but-2-ynyloxy-N-[2-hydroxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]benzamideYield 34.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

100 mg (0.2 mmol) of N-[2-tert-butoxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]-4-but-2-ynyloxybenzamide are placed in 3 ml of trifluoroacetic acid. After stirring for 8 days at ambient temperature, the mixture is concentrated under vacuum then the crude product is purified by chromatography over silica gel eluted with a 9/1 dichloromethane/methanol mixture. 30 mg (34%) of 4-but-2-ynyloxy-N-[2-hydroxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]benzamide are obtained in the form of a beige solid.

Workup

  1. concentrationthe mixture is concentrated under vacuum
  2. customthe crude product is purified by chromatography over silica gel
  3. washeluted with a 9/1 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-cf84b45b95e44c9e9ab7a924a855630f
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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