Water → HCID 69157289, compound

HRID 750374Notes

Reaction equation

HRID 750374 reaction equation
Br[CH2:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4].[C:33]([NH2:36])(=S)[CH3:34].O>CN(C=O)C>[NH2:36]/[C:33](/[CH3:34])=[CH:2]\[C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 2723949ThioacetamideHCID 86599571HCID 86599571, compound

Product 1

HCID 69157289HCID 69157289, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution (6 ml) of 4-[[3-(2-bromoacetyl)-6-chloro-1-oxo-4-phenyl-1H-isoquinolin-2-yl]methyl]benzoic acid (570 mg) in DMF was added thioacetamide (170 mg), and the mixture was stirred at 70° C. for 24 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound (270 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-48b3e2a1f45d47d6bafa1cf8b388433a
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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