1-(1H-Imidazol-1-yl)ethanone → HCID 178475390, compound

HRID 1822238Notes

Reaction equation

HRID 1822238 reaction equation
[OH:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][C:7]2[C:11]3[C:12](=[O:26])[N:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:14]4[N:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]=3[NH:9][N:8]=2)=[CH:4][CH:3]=1.[C:29](N1C=CN=C1)(=[O:31])[CH3:30]>CN(C=O)C.C(=O)([O-])O.[Na+]>[C:29]([O:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][C:7]2[C:11]3[C:12](=[O:26])[N:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:14]4[N:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]=3[NH:9][N:8]=2)=[CH:4][CH:3]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 2

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 178514896HCID 178514896, compound

Product 1

HCID 178475390HCID 178475390, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-(4-hydroxybenzyl)-5-phenyl-1H-pyrazolo [4,3-c][1,8]naphthyridin-4 (5H)-one (192 mg, 0.52 mmol, prepared in Example 41) in DMF (2 ml) was added a solution of 1-acetylimidazole (114 mg, 1.04 mmol, 2 eq.) in DMF (2 ml) while ice-cooling, and the mixture was stirred overnight at room temperature, and then diluted with aqueous sodium hydrogen carbonate. Precipitates were filtered off, and the mixture was dried and purified by flash column chromatography to afford 3-(4-acetoxybenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (128 mg, 60%).

Workup

  1. temperaturecooling
  2. customPrecipitates
  3. filtrationwere filtered off
  4. customthe mixture was dried
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-754f6ecfd952413fb8b93cc2cfe0ae65
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

Loading…