3-Cyclopentyl-3-oxopropanenitrile → HCID 58851804, compound

HRID 1696521Notes

Reaction equation

HRID 1696521 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7][CH2:6]2)[NH2:2].[CH:14]1([C:19](=O)[CH2:20][C:21]#[N:22])[CH2:18][CH2:17][CH2:16][CH2:15]1>CCO>[NH2:22][C:21]1[N:1]([C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8](=[O:13])[CH2:7][CH2:6]3)[N:2]=[C:19]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:20]=1

Participants

4

Reactant 2

HCID 135921183-Cyclopentyl-3-oxopropanenitrileHCID 55281213HCID 55281213, compound

Product 1

HCID 58851804HCID 58851804, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

6-Hydrazinyl-3,4-dihydroquinolin-2(1H)-one (1.00 g, 4.68 mmol, available from Example A35) was dissolved in EtOH (10 mL) and 3-cyclopentyl-3-oxopropanenitrile (0.706 g, 5.15 mmol) was added. The reaction mixture was heated at 80° C. for 22 h. The reaction mixture was concentrated and the residue was suspended in EtOAc (30 mL) and treated slowly with satd. Na2CO3 (30 mL). The solution was extracted with EtOAc (3×), and the combined organics were washed H2O and dried (Na2SO4), filtered, concentrated and dried to yield 6-(5-amino-3-cyclopentyl-1H-pyrazol-1-yl)-3,4-dihydroquinolin-2(1H)-one (1.2 g, 87% yield) which was used without further purification. LC-MS (EI) m/z: 297.2 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiontreated slowly with satd
  3. extractionThe solution was extracted with EtOAc (3×)
  4. washthe combined organics were washed H2O
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried

Sources & evidence

ORD record
ord-1acbcd0c3b414a17ba4282200a8e4e28
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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