Triethylamine → 1-(3-Cyanophenyl)-3-(3-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)urea

HRID 412342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412342
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([CH:34]=[CH:35][CH:36]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:15]=[C:14]([CH2:16][O:17][C:18]3[CH:31]=[CH:30][C:21]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])=[CH:20][CH:19]=3)[N:13]([CH3:32])[C:12]=2[CH:33]=1.[C:37]([C:39]1[CH:40]=[C:41]([N:45]=[C:46]=[O:47])[CH:42]=[CH:43][CH:44]=1)#[N:38].C(N(CC)CC)C>CN(C)C=O>[C:37]([C:39]1[CH:40]=[C:41]([NH:45][C:46]([NH:3][C:4]2[CH:36]=[CH:35][CH:34]=[C:6]([O:7][C:8]3[CH:9]=[CH:10][C:11]4[N:15]=[C:14]([CH2:16][O:17][C:18]5[CH:31]=[CH:30][C:21]([CH2:22][CH:23]6[S:27][C:26](=[O:28])[NH:25][C:24]6=[O:29])=[CH:20][CH:19]=5)[N:13]([CH3:32])[C:12]=4[CH:33]=3)[CH:5]=2)=[O:47])[CH:42]=[CH:43][CH:44]=1)#[N:38]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27333153-IsocyanatobenzonitrileHCID 865877725-[4-[6-(3-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Produkt 1

HCID 185375681-(3-Cyanophenyl)-3-(3-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ureaAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-[4-[6-(3-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg), 3-cyanophenyl isocyanate (260 mg), triethylamine (153 mg) and anhydrous N,N-dimethylformamide (8 ml) was stirred at room temperature for 4 hours and then at 50° C. for 2.5 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=3:1→ethyl acetate as the eluant. The product was recrystallized from methanol to afford the title compound (260 mg, mp 148.4-154.0° C.).

Aufarbeitung

  1. waitat 50° C. for 2.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column
  8. customThe product was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-3502b868f21e498fabfeff0ed8e1001f
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562849B1

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