HCID 23125017, Verbindung → HCID 23125005, Verbindung

HRID 2223365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223365
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:23]=[CH:22][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:13][C:12]=2[N+:24]([O-])=O)=[O:10])=[N:6][CH:7]=1>O1CCCC1.[Ni]>[NH2:24][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][C:11]=1[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:10])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Komponenten

4

Edukt 1

HCID 23125017HCID 23125017, Verbindung

Produkt 1

HCID 23125005HCID 23125005, VerbindungAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

t-Butyl 4-{[(5-chloropyridin-2-yl)amino]-carbonyl}-3-nitrobenzoate (3.2 g) obtained in Example 2(1) is dissolved in tetrahydrofuran (50 ml) and thereto is added Raney nickel, and the mixture is stirred at room temperature under hydrogen pressure (3 atm.) overnight. The insoluble materials are removed by filtration on Celite and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=20/1) to give t-butyl 3-amino-4-{[(5-chloropyridin-2-yl)amino]carbonyl}benzoate (2.3 g). APCI-MS M/Z: 348[M+H]+

Aufarbeitung

  1. customThe insoluble materials are removed by filtration on Celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-ff84efa0aa3b4308891ee84b171c5d8a
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375119B2

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