2-Cyanoethyl 3-aminocrotonate → HCID 69063213, compound

HRID 1727931Notes

Reaction equation

HRID 1727931 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:28])[C:15]([C:25](=O)[CH3:26])=[CH:16][C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:29]([CH2:31][CH2:32][O:33][C:34](=[O:39])/[CH:35]=[C:36](\[NH2:38])/[CH3:37])#[N:30]>CC(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:15]2[CH:16]([C:17]3[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=3)[C:35]([C:34]([O:33][CH2:32][CH2:31][C:29]#[N:30])=[O:39])=[C:36]([CH3:37])[NH:38][C:25]=2[CH3:26])=[O:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 136714102-Cyanoethyl 3-aminocrotonateHCID 86590786HCID 86590786, compound

Product 1

HCID 69063213HCID 69063213, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

1.66 g (3.88 mmol) of 4-[2-acetyl-3-(3,5-dichlorophenyl)-2-propenoyl] piperazine-1-carboxylic acid t-butyl ester and 598 mg (3.88 mmol) of 3-aminocrotonate 2-cyanoethyl ester were stirred in 30 ml of 2-propanol at 80° C. overnight and then stirred at 120° C. for 2 hours. After concentration under reduced pressure, ethyl acetate was added and the residue was washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol =100/1 to 30/1) to obtain the title compound.

Workup

  1. concentrationAfter concentration under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe residue was washed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by the silica gel chromatography (dichloromethane/methanol =100/1 to 30/1)

Sources & evidence

ORD record
ord-e472bac759e94a3a8943a25ecdf751b4
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

Loading…