n-(4-Fluoro-2-(n,n-dimethylsulfamoyl)benzyl)-6-benzyloxy-1-isopropyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamide → n-(4-Fluoro-2-(n,n-dimethylsulfamoyl)benzyl)-6-hydroxy-1-isopropyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamide

HRID 1726895Notes

Reaction equation

HRID 1726895 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[N:27]([CH:28]([CH3:30])[CH3:29])[CH2:26][CH2:25][N:13]3[C:14](=[O:24])[C:15]=2[O:16]CC2C=CC=CC=2)=[O:9])=[C:4]([S:33](=[O:38])(=[O:37])[N:34]([CH3:36])[CH3:35])[CH:3]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[N:27]([CH:28]([CH3:30])[CH3:29])[CH2:26][CH2:25][N:13]3[C:14](=[O:24])[C:15]=2[OH:16])=[O:9])=[C:4]([S:33](=[O:37])(=[O:38])[N:34]([CH3:36])[CH3:35])[CH:3]=1

Participants

3

Reactant 1

HCID 57565020n-(4-Fluoro-2-(n,n-dimethylsulfamoyl)benzyl)-6-benzyloxy-1-isopropyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamide

Product 1

HCID 54707365n-(4-Fluoro-2-(n,n-dimethylsulfamoyl)benzyl)-6-hydroxy-1-isopropyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamideYield 82.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(4-fluoro-2-(N,N-dimethylsulfamoyl)benzyl)-6-benzyloxy-1-isopropyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamide (0.155 g, 0.28 mmol) in trifluoroacetic acid (10 ml) was stirred at 25° C. for 72 h. The solvent was then evaporated under reduced pressure and the residue was purified by preparative HPLC (column YMC Pack C-18, 5μ, 20×250 mm, elution gradient acetonitrile-water 0.1% trifluoroacetic acid) to give 0.105 g (81% yield) of the title amide as a white solid.

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. customthe residue was purified by preparative HPLC (column YMC Pack C-18, 5μ, 20×250 mm, elution gradient acetonitrile-water 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-e708ff890e024279beccca319d847ffd
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

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