Methyl iodide → 4-({2-[(4-bromophenyl)amino]-1-methyl-1H-1,3-benzodiazol-6-yl}oxy)-N-methylpyridine-2-carboxamide

HRID 2070288

Reaktionsgleichung

Reaktionsgleichung von HRID 2070288
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]([NH:15][CH3:16])=[O:14])[CH:8]=2)=[CH:4][C:3]=1[NH:19][CH3:20].[Br:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=S)=[CH:24][CH:23]=1.IC>CO>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]2[N:19]([CH3:20])[C:3]3[CH:4]=[C:5]([O:6][C:7]4[CH:12]=[CH:11][N:10]=[C:9]([C:13]([NH:15][CH3:16])=[O:14])[CH:8]=4)[CH:17]=[CH:18][C:2]=3[N:1]=2)=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 161334-Bromophenyl isothiocyanateHCID 58385469HCID 58385469, Verbindung

Produkt 1

HCID 220409784-({2-[(4-bromophenyl)amino]-1-methyl-1H-1,3-benzodiazol-6-yl}oxy)-N-methylpyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of the {4-[4-amino-3-(methylamino)phenoxy](2-pyridyl)}-N-methylcarboxamide (1 eq) in methanol was treated with 4-bromophenylisothiocyanate (1 eq) and stirred at 60° C. for 2 hours. The reaction mixture was cooled down to room temperature and iodomethane (1 eq) was added and stirred overnight at 60° C. The reaction was concentrated and preparative chromatography gave (4-{2-[(4-bromophenyl)amino]-1-methylbenzimidazol-6-yloxy)-(2-pyridyl)-N-methylcarboxamide. MS: MH+=452.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringstirred overnight at 60° C
  3. concentrationThe reaction was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-6ddbcf52b2e1440b9b19a2490d919581
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299108B2

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