Acetic Acid → 3-(2-trifluoromethylphenyl)-7-((2S,3R)-2,3,4-trihydroxybutylamino)-2H-isoquinolin-1-one

HRID 1162908Notes

Reaction equation

HRID 1162908 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[O:23]=[CH:24][C@@H:25]([C@@H:27]([CH2:29]O)[OH:28])[OH:26].C(O)(=O)C>CO>[F:21][C:19]([F:22])([F:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:7]1[NH:8][C:9](=[O:12])[C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([NH:1][CH2:29][C@H:27]([OH:28])[C@H:25]([OH:26])[CH2:24][OH:23])[CH:11]=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 94176D-ErythroseHCID 231567387-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Product 1

HCID 575580323-(2-trifluoromethylphenyl)-7-((2S,3R)-2,3,4-trihydroxybutylamino)-2H-isoquinolin-1-oneYield 285.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (2.04 g, 0.986 mmol) obtained in step C of Example 1-1 and D-(−)-erythrose (807 mg, 6.72 mmol) were dissolved in methanol (40 ml). Thereafter, acetic acid (2.31 ml, 40.3 mmol) and a 1 M sodium cyanoborohydride THF solution (20.2 ml, 20.2 mmol) were added at 0° C. to the obtained solution, and the obtained mixture was then stirred at a room temperature for 4 hours. Thereafter, the reaction mixture was concentrated under reduced pressure, and water was then added to the concentrate, followed by extraction with methylene chloride. The extract was washed with a saturated saline solution, and was then dried over sodium sulfate, followed by concentration under reduced pressure. The obtained residue was purified by silica gel chromatography (methylene chloride:methanol=15:1 to 10:1), so as to obtain 3-(2-trifluoromethylphenyl)-7-((2S,3R)-2,3,4-trihydroxybutylamino)-2H-isoquinolin-1-one (1.15 g, 42%).

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure, and water
  2. additionwas then added to the concentrate
  3. extractionfollowed by extraction with methylene chloride
  4. washThe extract was washed with a saturated saline solution
  5. dry with materialwas then dried over sodium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe obtained residue was purified by silica gel chromatography (methylene chloride:methanol=15:1 to 10:1)

Sources & evidence

ORD record
ord-dce5b31a9a65475abe339b2109a3380e
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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