Pentanenitrile, 4,4-dimethyl-3-oxo- → ethyl 3-(3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl)propanoate

HRID 1696467Notes

Reaction equation

HRID 1696467 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][NH2:14])[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:9]2[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH:12]=[CH:11][CH:10]=2)[N:14]=1)([CH3:24])([CH3:23])[CH3:16]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 588429213-(3-Hydrazinophenyl)propionic acid ethyl ester

Product 1

HCID 58842892ethyl 3-(3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl)propanoateYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(3-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-(3-(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 7.50-7.42 (m, 4H), 5.63 (s, 1H), 5.14 (s, 2H), 4.04 (q, J=6.9 Hz, 2H), 2.92 (t, J=7.5 Hz, 2H), 2.66 (t, J=7.5 Hz, 2H), 1.27 (s, 9H), 1.16 (t, J=7.5 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-cf5eaac8bc654cf9ad1aea6097cf39b9
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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