Tetrahydrofuran → 9-Acetyl-8-[4-(1,1-dimethyl-prop-2-ynyl)-piperazin-1-yl]-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61796

Reaction equation

HRID 61796 reaction equation
C1COCC1.[C:6]([C:9]1[C:30]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:29][C:12]2[C:13]([CH3:28])([CH3:27])[C:14]3[NH:15][C:16]4[C:21]([C:22]=3[C:23](=[O:24])[C:11]=2[CH:10]=1)=[CH:20][CH:19]=[C:18]([C:25]#[N:26])[CH:17]=4)(=[O:8])[CH3:7].Cl[C:38]([CH3:42])([CH3:41])[C:39]#[CH:40].C(N(CC)CC)C>[Cu]Cl.O>[C:6]([C:9]1[C:30]([N:31]2[CH2:32][CH2:33][N:34]([C:38]([CH3:42])([CH3:41])[C:39]#[CH:40])[CH2:35][CH2:36]2)=[CH:29][C:12]2[C:13]([CH3:28])([CH3:27])[C:14]3[NH:15][C:16]4[C:21]([C:22]=3[C:23](=[O:24])[C:11]=2[CH:10]=1)=[CH:20][CH:19]=[C:18]([C:25]#[N:26])[CH:17]=4)(=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 706791-Butyne, 3-chloro-3-methyl-HCID 668342259-acetyl-6,6-dimethyl-11-oxo-8-piperazin-1-yl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Product 1

HCID 866638229-Acetyl-8-[4-(1,1-dimethyl-prop-2-ynyl)-piperazin-1-yl]-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileYield 35%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

To the anhydrous THF solution (0.5 mL) of 9-acetyl-6,6-dimethyl-11-oxo-8-piperazin-1-yl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound H8-5, 25 mg, 0.06 mmol), 3-chloro-3-methyl-but-1-yne (0.013 mL, 0.12 mmol), copper (I) chloride (0.6 mg, 0.006 mmol) and triethylamine (0.017 mL, 0.12 mmol) were added at room temperature. After stirring for 30 min, the mixture was added with water and extracted with ethyl acetate. 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 amino silica gel column chromatography (dichloromethane/methanol) to obtain the title compound (white solid, 9.8 mg, 35%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customThe drying agent was removed by filtration
  4. customthe residues obtained
  5. concentrationafter concentration under reduced pressure
  6. customwere purified by amino silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-bd5b2995ffff48a3b42d46972faac34f
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Linked notes

Loading…