(+)-Glycidol → HCID 59520049, compound

HRID 1162895Notes

Reaction equation

HRID 1162895 reaction equation
[CH2:1]1[O:3][C@@H:2]1[CH2:4][OH:5].[NH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[NH:13][C:14]2=[O:17])=[CH:9][CH:8]=1>C(O)C>[OH:3][C@H:2]([CH2:4][OH:5])[CH2:1][NH:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:25])[F:26])[NH:13][C:14]2=[O:17])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 5460455(+)-GlycidolHCID 231567387-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Product 1

HCID 59520049HCID 59520049, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-Glycidol (78.3 μl, 1.18 mmol) was added to an ethanol solution (4 ml) that contained the 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in step C of Example 1-1, and the obtained mixture was stirred under heating to reflux for 3 days. Thereafter, the reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1), so as to obtain 7-((S)-2,3-dihydroxypropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (281.9 mg; yield: 63%) in the form of a pale yellow amorphous substance.

Workup

  1. temperatureunder heating
  2. temperatureto reflux for 3 days
  3. concentrationThereafter, the reaction solution was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-daa60292596b4a3aa6df18ddac1d90b4
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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