Potassium Carbonate → HCID 69489634, Verbindung

HRID 1271845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271845
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:19]=2[CH:18]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:36][CH2:37][N:38]([CH3:40])[CH3:39]>C(OCC)(=O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:36][CH2:37][N:38]([CH3:40])[CH3:39])=[CH:25][C:19]=2[CH:18]=1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 69487009HCID 69487009, Verbindung

Produkt 1

HCID 69489634HCID 69489634, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 77 mg (0.20 mmol) {2-[(5-Hydroxy-benzo[b]thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (4) in 3 ml ethyl acetate was added 120 mg potassium carbonate and 36 mg (0.25 mmol) (2-chloro-ethyl)-dimethyl-amine hydrochloride. The reaction mixture was heated at reflux for 16 h and poured into brine. The aqueous phase was extracted with ethyl acetate and the organic phase was dried over sodium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (dichloromethane/methanol 19:1 and then 9:1). (2-{[5-(2-Dimethylamino-ethoxy)-benzo[b]thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester (5) (72 mg, 0.158 mmol) was obtained as a colorless solid.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-31ae386ed93c4f6d84b885b591790e3c
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208491B2

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