Methanol → (R)-N-(6-Chloro-2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamide

HRID 418497Notes

Reaction equation

HRID 418497 reaction equation
C([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:33])[C:14]=2[NH:18][C:19](=[O:32])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[C:23]([F:31])[CH:22]=2)[C:9]1=[O:34])[CH3:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>O>[Cl:33][C:13]1[C:14]([NH:18][C:19](=[O:32])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[C:23]([F:31])[CH:22]=2)=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:34])[N:8]([C@H:6]([CH3:7])[CH2:5][OH:4])[CH:17]=[CH:16]2

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 59515861(R)-2-(6-Chloro-5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 25013762(R)-N-(6-Chloro-2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

A round bottom flask was charged with (R)-2-(6-chloro-5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propyl acetate (1.200 g, 0.002406 mol), potassium carbonate (0.997 g, 0.00722 mol) and methanol (20 mL, 0.5 mol) and 2 drops of water. The reaction was stirred at room temperature for 1 hour and was filtered over sodium sulfate and washed with methanol. the solvent was removed under reduced pressureunder reduced pressure and the residue purified by flash chromatography to afford the product as a white solid.

Workup

  1. filtrationwas filtered over sodium sulfate
  2. washwashed with methanol
  3. customthe solvent was removed
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-7e98572252ba45d1ad7f66970bad8a75
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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