Trifluoroacetic acid → HCID 178460809, compound

HRID 1881760Notes

Reaction equation

HRID 1881760 reaction equation
[S:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4](=[O:12])[NH:3]1.[C:13]1([C:19](S)([CH3:21])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(C(F)(F)F)=O>C([O-])(O)=O.[Na+]>[C:13]1([C:19]([S:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[C:4]([OH:12])[N:3]=2)([CH3:21])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2752457HCID 2752457, compoundHCID 99641522-phenylpropane-2-thiol

Product 1

HCID 178460809HCID 178460809, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a 50 mL round bottom flask was added 1-thioxo-1,4-dihydro-2H-isoquinolin-3-one (250 mg, 1.41 mmol), and 2-phenylpropan-2-thiol (192 mg, 1.41) followed by a solution of TFA (10 mL, 20% v/v in DCM). The reaction mixture was stirred under Ar for 1 h, neutralized with NaHCO3 (100 mL, sat. aq.), and then extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4, and then the solvent was removed by rotary evaporation to yield a crude residue. The crude residue was purified via silica gel chromatography to provide the title compound as an orange solid (188 mg, 0.636 mmol, 45%). 1H NMR (400 MHz, CDCl3): δ ppm 8.11 (d, J=8.79 Hz, 1H), 7.55 (t, J=7.47 Hz, 3H), 7.42-7.50 (m, 1H), 7.14-7.29 (m, 5H), 6.74 (s, 1H), 1.95 (s, 6H). LC/MS m/z 296 [M+H].

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed by rotary evaporation
  5. customto yield a crude residue
  6. customThe crude residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-eff410a84bcf47c7bce7f14eacd398a5
Source dataset
uspto-grants-2012_11
Patent number
US08318941B2

Reaction notes

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