(+)-Glycidol → HCID 59520049, compound

HRID 1098301Notes

Reaction equation

HRID 1098301 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 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

132.6 μl (20 mmol) of (R)-glycidol was added to an ethanol solution (10 ml) containing 608.5 mg (2.0 mmol) of the 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Example 38. The obtained mixture was stirred under heating to reflux overnight. The residue obtained by concentration of the reaction solution was purified by silica gel column chromatography (methylene chloride:methanol=20:1), so as to obtain 514.3 mg (68%) of 7-((S)-2,3-dihydroxypropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one in the form of a light yellow amorphous substance.

Workup

  1. temperatureunder heating
  2. temperatureto reflux overnight
  3. customThe residue obtained by concentration of the reaction solution
  4. customwas purified by silica gel column chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-ae625b8bc66c441cbaa3ec0b5390b53f
Source dataset
uspto-grants-2012_03
Patent number
US08143274B2

Reaction notes

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