3-Amino-3-(4-chlorophenyl)prop-2-enenitrile → HCID 68338293, Verbindung

HRID 1910665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910665
[C:1]([C:3]([C:23](=O)[CH3:24])=[CH:4][C:5]1[O:13][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[CH:6]=1)#[N:2].[NH2:26][C:27]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)=[CH:28][C:29]#[N:30]>C(O)(=O)C>[C:29]([C:28]1[CH:4]([C:5]2[O:13][C:12]3[CH:11]=[CH:10][N:9]=[C:8]([NH:14][C:15](=[O:22])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:7]=3[CH:6]=2)[C:3]([C:1]#[N:2])=[C:23]([CH3:24])[NH:26][C:27]=1[C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1)#[N:30]

Komponenten

4

Edukt 2

HCID 14848883-Amino-3-(4-chlorophenyl)prop-2-enenitrileHCID 67154537HCID 67154537, Verbindung

Produkt 1

HCID 68338293HCID 68338293, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 200 mg (0.604 mmol) N-{2-(2-cyano-3-oxobut-1-en-1-yl)furo[3,2-c]pyridin-4-yl}benzamide (Example 4A) and 129 mg (0.724 mmol) 3-amino-3-(4-chlorophenyl)prop-2-enenitrile (Example 6A) in acetic acid (2 ml) was stirred for 30 min at 110° C. Upon cooling, the mixture was concentrated under reduced pressure, and the residue was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient, final mixture 90:10 v/v) to yield 197 mg (64% of th.) of the racemic title compound.

Aufarbeitung

  1. temperatureUpon cooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe residue was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient, final mixture 90:10 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-d43f3b0750bb450fbea155be1f6f1782
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604028B2

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