Methanol → [[4-Chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoyl]-(2-methoxy-phenyl)-amino]-acetic acid methyl ester

HRID 1848602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848602
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[O:7])=[CH:4][C:3]=1[C:19]1[C:24]([Cl:25])=[CH:23][C:22]([Cl:26])=[CH:21][N:20]=1.[H-].[Na+].Br[CH2:30][O:31][C:32](=[O:34])[CH3:33].CO>CN(C=O)C>[CH3:30][O:31][C:32](=[O:34])[CH2:33][N:8]([C:6](=[O:7])[C:5]1[CH:17]=[CH:18][C:2]([Cl:1])=[C:3]([C:19]2[C:24]([Cl:25])=[CH:23][C:22]([Cl:26])=[CH:21][N:20]=2)[CH:4]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 68536Bromomethyl acetateHCID 686027194-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-methoxy-phenyl)-benzamide

Produkt 1

HCID 59370363[[4-Chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoyl]-(2-methoxy-phenyl)-amino]-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-methoxy-phenyl)-benzamide (40 mg, 0.1 mmol) in DMF (0.6 mL) at 0-5° C., NaH (8 mg, 0.2 mmol, 60% in mineral oil) was added and the mixture was stirred for 25 min at rt. Upon addition of bromomethylacetate (21 μL, 0.2 mmol), the mixture was stirred at room temperature for 12 hrs. Addition of MeOH (0.3 mL) was followed by filtration and purification on preparative HPLC to afford [[4-chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoyl]-(2-methoxy-phenyl)-amino]-acetic acid methyl ester 17-1.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 12 hrs
  2. filtrationwas followed by filtration and purification on preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-54dcee41d488407d9a92c615064a6437
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952161B2

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