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

Participants

Reaction Conditions

Reaction Steps

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+).

Provenance & Evidence