Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 58851436, compound

HRID 1696462Notes

Reaction equation

HRID 1696462 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][CH2:7][NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[NH2:2].[C:18]([CH2:24][C:25]#[N:26])(=O)[C:19]([CH3:22])([CH3:21])[CH3:20].Cl.CCO>CCO>[NH2:26][C:25]1[N:1]([C:3]2[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:7][NH:8][C:9](=[O:14])[C:10]([F:11])([F:12])[F:13])[N:2]=[C:18]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:24]=1

Participants

5

Reactant 3

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 21887872Ethanol hydrochlorideHCID 58011019HCID 58011019, compound

Product 1

HCID 58851436HCID 58851436, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
77.5 °C

Procedure

To a stirring solution of N-(3-hydrazinophenethyl)-2,2,2-trifluoroacetamide (0.18 g, 0.73 mmol) in absolute EtOH (5 ml) at RT was added pivaloylacetonitrile (0.11 g, 0.87 mmol) and saturated HCl/EtOH (3 drops from a pipet). The resulting solution was stirred at 75-80° C. overnight, then cooled to RT and concentrated. The residue was dissolved in Et2O and washed with saturated. NaHCO3. The aqueous was extracted with Et2O (1×). The combined organics were washed with brine (1×), dried (MgSO4), filtered, concentrated and purified via flash chromatography to provide N-[3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)phenethyl]-2,2,2-trifluoroacetamide as an orange glass (0.18 g, 70% yield). 1H NMR (300 MHz, CDCl3): δ 7.47-7.46 (m, 2H), 7.43-7.39 (m, 1H), 7.14-7.12 (m, 1H), 5.51 (s, 1H), 3.67 (q, J=6.6 Hz, 2H), 2.95 (t, J=6.6 Hz, 2H), 1.33 (s, 9H); MS (ESI) m/z: 355.2 (M+H+).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in Et2O
  4. washwashed with saturated
  5. extractionThe aqueous was extracted with Et2O (1×)
  6. washThe combined organics were washed with brine (1×)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified via flash chromatography

Sources & evidence

ORD record
ord-260c89904a3142dcb7ca3bae490ed770
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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