2-Cyanoethyl 3-aminocrotonate → HCID 69063213, compound

HRID 1182609Notes

Reaction equation

HRID 1182609 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-2d86c16c95274ff28fe73f8377973345
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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