Water → HCID 10128859, compound

HRID 750372Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[C:6]([C:24](=[O:27])[CH2:25]Br)=[C:5]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:34]([NH2:37])(=S)[CH3:35].O.C(=O)([O-])O.[Na+]>CN(C=O)C>[NH2:37]/[C:34](/[CH3:35])=[CH:25]\[C:24]([C:6]1[N:7]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=2)[C:8](=[O:12])[C:9]2[C:4]([C:5]=1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)=[O:27]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution (44 ml) of 6-bromo-3-(2-bromoacetyl)-2-(4-methanesulfonylbenzyl)-4-phenyl-2H-isoquinolin-1-one (4.41 g) in DMF was added thioacetamide (1.1 g) and the mixture was stirred at 70° C. for 24 hrs. Water and saturated aqueous sodium hydrogen carbonate were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crystals were washed with methanol and recrystallized (ethyl acetate) to give the title compound (1.31 g).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
washThe obtained crystals were washed with methanol
customrecrystallized (ethyl acetate)

Sources & evidence

ORD record: ord-5eeae1e3ba3847d0b212a0aff7391412
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402595B2

Reaction notes

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