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

HRID 491994

Reaction equation

HRID 491994 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]>C(O)C>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:20]([NH2:21])=[CH:19][C:18]([C:17]([CH3:24])([CH3:23])[CH3:16])=[N:14]2)[CH:8]=1)[CH3:2]

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 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example Y (13 g, 53.3 mmol) and 4,4-dimethyl-3-oxo-pentanenitrile (6.9 g, 55 mol) in ethanol (150 mL) was heated to reflux overnight. The reaction solution was evaporated under reduced pressure. The residue was purified by column chromatography to give 3-[3-(5-amino-3-t-butyl-pyrazol-1-yl)-phenyl]-propionic acid ethyl ester (14.3 g, 45.4 mmol) as a white solid. 1H NMR (DMSO-d6): 7.39-7.32 (m, 3H), 7.11 (d, J=6.8 Hz, 1H), 5.34 (s, 1H), 5.16 (s, 2H), 4.03 (q, J=7.2 Hz, 2H), 2.88 (t, J=7.6 Hz, 2H), 2.63 (t, J=7.6 Hz, 2H), 1.19 (s, 9H), 1.15 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureto reflux overnight
  2. customThe reaction solution was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-09cdeaa9159f48b4b9097837414a9823
Source dataset
uspto-grants-2009_05
Patent number
US07531566B2

Linked notes

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