Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 66644209, compound

HRID 2064499Notes

Reaction equation

HRID 2064499 reaction equation
[ClH:1].Cl.[CH:3]1([CH2:6][NH:7][NH2:8])[CH2:5][CH2:4]1.[CH3:9][C:10]([CH3:17])([CH3:16])[C:11](=O)[CH2:12][C:13]#[N:14]>C(O)C>[ClH:1].[C:10]([C:11]1[CH:12]=[C:13]([NH2:14])[N:7]([CH2:6][CH:3]2[CH2:5][CH2:4]2)[N:8]=1)([CH3:17])([CH3:16])[CH3:9]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 43810474(Cyclopropylmethyl)hydrazine--hydrogen chloride (1/2)

Product 1

HCID 66644209HCID 66644209, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of Example 9B (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.69 g, 93 mmol) in ethanol (100 mL) was heated at reflux (oil bath temperature of 90° C.) for 6 hours. The mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate (20 mL). The resulting white solid was collected by filtration (Et2O wash) and dried to provide 17.5 g (90%) of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4H), 1.16-1.27 (m, 1H), 1.28 (s, 9H), 4.02 (d, J=7.12 Hz, 2H), 5.53 (s, 1H), 6.91 (s, 2H), 14.05 (s, 1H); MS (DCI) m/z 294 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate (20 mL)
  4. filtrationThe resulting white solid was collected by filtration (Et2O wash)
  5. customdried

Sources & evidence

ORD record
ord-58a6c67390c14971bfcd427a2c250346
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

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