Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 3-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-hydroxy-acrylamide

HRID 130587Notes

Reaction equation

HRID 130587 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]([NH:20][O:21]C2CCCCO2)=[O:19])[CH:13]=[CH:14][CH:15]=1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>CO>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]([NH:20][OH:21])=[O:19])[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 724240283-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Product 1

HCID 850546673-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-hydroxy-acrylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the appropriate 3-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (11, 0.25 mmol) in MeOH (2 mL) was added CSA (0.28 mmol). The reaction was stirred for 2 hr at ambient temperature and, without further work-up, purified by preparative LCMS to yield the desired 3-[3-(1H-benzoimidazol-2-yl)-phenyl]-N-hydroxy-acrylamide (12).

Workup

  1. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-a1d76e73438d46d1b66b26de2c44c5b6
Source dataset
uspto-grants-2008_06
Patent number
US07381825B2

Reaction notes

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