Potassium Carbonate → HCID 86591304, compound

HRID 1267129Notes

Reaction equation

HRID 1267129 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[C:17]([C:23]4[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=4)=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:39][C:40]([NH2:42])=[O:41]>CC(C)=O>[C:40]([CH2:39][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]([C:16]3[C:17]([C:23]4[CH:24]=[CH:25][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:27][CH:28]=4)=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)=[O:15])=[CH:11][CH:12]=2)[CH2:6][CH2:5]1)(=[O:41])[NH2:42]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 53808214HCID 53808214, compound

Product 1

HCID 86591304HCID 86591304, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4′-isopropyl-6-methyl-biphenyl-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amide (206 mg) in acetone (20 mL) containing K2CO3 (206 mg) was added 2-bromo-acetamide (100 mg) and the mixture was heated at reflux for 16 hours. After cooling at room temperature the salts were removed by filtration, washed with acetone and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography eluting with CH2Cl2/MeOH (93/7) and the solid obtained was recrystallized from CH2Cl2/diisopropyl ether to give the title compound (190 mg) as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customwere removed by filtration
  4. washwashed with acetone
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with CH2Cl2/MeOH (93/7)
  8. customthe solid obtained
  9. customwas recrystallized from CH2Cl2/diisopropyl ether

Sources & evidence

ORD record
ord-1c986ec4d45e4d9498bb779691f5b639
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

Loading…