Diisopropylethylamine → 6,6-Dimethyl-11-oxo-8-[2-(3-oxo-piperazin-1-yl)-ethoxy]-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2275095Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:20](=[O:21])[C:19]3[C:18]4[C:13](=[CH:14][C:15]([C:22]#[N:23])=[CH:16][CH:17]=4)[NH:12][C:11]=3[C:10]([CH3:25])([CH3:24])[C:9]=2[CH:26]=1.[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][C:28]1=[O:33].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:25][C:10]1([CH3:24])[C:11]2[NH:12][C:13]3[C:18](=[CH:17][CH:16]=[C:15]([C:22]#[N:23])[CH:14]=3)[C:19]=2[C:20](=[O:21])[C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][N:30]3[CH2:31][CH2:32][NH:27][C:28](=[O:33])[CH2:29]3)=[CH:26][C:9]1=2

Participants

Conditions

Temperature: 80 °C

Procedure

To DMF solution (5 mL) of 8-(2-bromo-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A7-24, 30 mg, 0.07 mmol), piperazin-2-one (44.9 mg, 0.35 mmol) and N,N-diisopropylethylamine (0.061 mL, 0.35 mmol) were added at room temperature and stirred at 80° C. for 18 hr. After cooling to room temperature, the mixture was extracted with ethyl acetate washed with saturated brine. The organic layer was dried over magnesium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by preparative TLC (dichloromethane/methanol) to obtain the title compound (white solid, 24 mg, 80%).

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted with ethyl acetate
washwashed with saturated brine
dry with materialThe organic layer was dried over magnesium sulfate
customThe drying agent was removed by filtration
customthe residues obtained
concentrationafter concentration under reduced pressure
customwere purified by preparative TLC (dichloromethane/methanol)

Sources & evidence

ORD record: ord-233292df729344f59e7b2141ceb07867
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126931B2

Reaction notes

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