Acetic Acid → 7-[3-(tert-butyldimethylsilyloxy)propylamino]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162911Notes

Reaction equation

HRID 1162911 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.[Si:23]([O:30][CH2:31][CH2:32][CH2:33]O)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C(O)(=O)C.C(=O)(O)[O-].[Na+]>CO>[Si:23]([O:30][CH2:31][CH2:32][CH2:33][NH: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:20])[F:21])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1)([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-olHCID 231567387-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Product 1

HCID 575581017-[3-(tert-butyldimethylsilyloxy)propylamino]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (300 mg, 0.986 mmol) obtained in step C of Example 1-1 was dissolved in methanol (10 ml). Thereafter, 3-[(tert-butyldimethylsilyl)oxy]-1-propanol (186 mg, 0.986 mmol), acetic acid (0.339 ml), and a 1 M sodium cyanoborohydride THF solution (2.96 ml, 2.96 mmol) were added at 0° C. to the obtained solution, and the obtained mixture was stirred at a room temperature for 1 hour. Thereafter, a saturated sodium bicarbonate solution was added to the reaction mixture, and the obtained mixture was then extracted with methylene chloride. The extract was dried over magnesium sulfate, and was then concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=1:3), so as to obtain 7-[3-(tert-butyldimethylsilyloxy)propylamino]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (376 mg, 80%).

Workup

  1. extractionthe obtained mixture was then extracted with methylene chloride
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationwas then concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-37c21897418d49c98735a71c6f0c5cb6
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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