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

HRID 16955

Reaktionsgleichung

Reaktionsgleichung von HRID 16955
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 58842892ethyl 3-(3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl)propanoateAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-07529dbc42134ba2b0775176156d04e0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737283B2

Verknüpfte Notizen

Wird geladen…