Potassium Carbonate → 1-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-2-[4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenoxy]-ethanone

HRID 220915Notes

Reaction equation

HRID 220915 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:13][CH2:12]1)=[O:10].[OH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([N:32]2[CH2:41][C:40]3[CH:39]=[N:38][N:37]([CH3:42])[C:36]=3[NH:35][C:34]3[CH:43]=[CH:44][CH:45]=[CH:46][C:33]2=3)=[O:31])=[CH:26][CH:25]=1>C(#N)C>[CH3:20][C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][N:11]([C:9](=[O:10])[CH2:8][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([N:32]3[CH2:41][C:40]4[CH:39]=[N:38][N:37]([CH3:42])[C:36]=4[NH:35][C:34]4[CH:43]=[CH:44][CH:45]=[CH:46][C:33]3=4)=[O:31])=[CH:26][CH:25]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 575551982-Bromo-1-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-ethanoneHCID 136128422(4-Hydroxy-phenyl)-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone

Product 1

HCID 1357360171-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-2-[4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenoxy]-ethanoneYield 11%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (104 mg, 0.76 mmol) was added to a mixture of 2-bromo-1-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-ethanone from Example E37 (110 mg, 0.38 mmol) and (4-hydroxy-phenyl)-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone from Example E75.2 (90 mg, 0.28 mmol) in acetonitrile (5 ml). The mixture was heated at reflux for 20 h then concentrated in vacuo. The residue was dissolved in dichloromethane, washed with 5% KHCO3 solution, dried and concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloro-methane) to give a white powder identified as the title compound (21 mg, 11%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 h
  3. concentrationthen concentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with 5% KHCO3 solution
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloro-methane)
  9. customto give a white powder

Sources & evidence

ORD record
ord-1b72a38866974dacb82cc95523a551ca
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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