Diethyl Ether → HCID 10290989, Verbindung

HRID 1435767

Reaktionsgleichung

Reaktionsgleichung von HRID 1435767
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=2)[N:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+:30]1C=CC=CC=1.C(OCC)C>ClCCl>[NH2:30][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][CH:18]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 86588970{4-[4-Chloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazin-2-ylamino]-phenyl}-methanolHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 10290989HCID 10290989, VerbindungAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of the title compound of Example 41 (375 mg, 1.1 mmol) in dichloromethane (100 ml) was added pyridinium chlorochromate (810 mg, 2.7 mmol) and crushed molecular sieves (1.25 g, 3A). After stirring for 6 hours, diethyl ether (150 ml) was added and the mixture was filtered through a pad of silica gel under suction. The filtrate was concentrated under reduced pressure and purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3 followed by 1:2 followed by 1:1) to provide the title compound (25 mg, 7% yield). 1H NMR (DMSO-d6) 10.10 (s, 1H), 9.86 (s, 1H), 8.07 (d, J=8.6 Hz, 2H), 7.84 (d, J=8.6 Hz, 2H), 7.79 (s, 1H), 7.43 (m, 2H), 7.34 (m, 2H), 2.53 (s, 3H).

Aufarbeitung

  1. filtrationthe mixture was filtered through a pad of silica gel under suction
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. custompurified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3 followed by 1:2 followed by 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c375d4849178412b8077f89cf867ce6e
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618968B2

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