Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 18449924, compound

HRID 1696471Notes

Reaction equation

HRID 1696471 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][NH2:14])=[CH:9][CH:8]=1)[CH3:2].[CH3:16][C:17]([CH3:24])([CH3:23])[C:18](=O)[CH2:19][C:20]#[N:21]>CCO>[C:17]([C:18]1[CH:19]=[C:20]([NH2:21])[N:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])=[CH:8][CH:9]=2)[N:14]=1)([CH3:24])([CH3:23])[CH3:16]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 10375773HCID 10375773, compound

Product 1

HCID 18449924HCID 18449924, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(4-hydrazinophenyl)propionic acid ethyl ester (13 g, 53.3 mmol) and 4,4-dimethyl-3-oxopentanenitrile (6.9 g, 55 mol) in EtOH (150 mL) was heated at reflux overnight. The reaction solution was evaporated under vacuum. The residue was purified by column chromatography to yield ethyl 3-(4-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl)propanoate (14.3 g, 85% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6); δ 7.44 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.7 Hz, 2H), 5.34 (s, 1H), 5.11 (s, 2H), 4.04 (q, J=7.2 Hz, 2H), 2.86 (t, J=7.5 Hz, 2H), 2.61 (t, J=7.5 Hz, 2H), 1.19 (s, 9H), 1.15 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 316 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe reaction solution was evaporated under vacuum
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6dde2c6d13f14e1781a00bafd1b79af7
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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