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

HRID 412334

Reaktionsgleichung

Reaktionsgleichung von HRID 412334
Cl.Cl.[NH2:3][C:4]1[CH:36]=[CH:35][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:32]=[CH:31][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:21][CH:20]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:6][CH:5]=1.[C:37]12([N:47]=[C:48]=S)[CH2:46][CH:41]3[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]3)[CH2:38]1)[CH2:44]2.C(N(CC)CC)C.CN(C)C=[O:60]>>[C:37]12([NH:47][C:48]([NH:3][C:4]3[CH:36]=[CH:35][C:7]([O:8][C:9]4[CH:10]=[CH:11][C:12]5[N:16]=[C:15]([CH2:17][O:18][C:19]6[CH:32]=[CH:31][C:22]([CH2:23][CH:24]7[S:28][C:27](=[O:29])[NH:26][C:25]7=[O:30])=[CH:21][CH:20]=6)[N:14]([CH3:33])[C:13]=5[CH:34]=4)=[CH:6][CH:5]=3)=[O:60])[CH2:46][CH:41]3[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]3)[CH2:38]1)[CH2:44]2

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 107279Adamantyl isothiocyanateHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Produkt 1

HCID 101223331-(Adamant-1-yl)-3-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)urea

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg), 1-adamantyl isothiocyanate (284 mg), triethylamine (153 mg) and anhydrous N,N-dimethylformamide (8 ml) was stirred at room temperature for 4.5 hours, at 50° C. for 2.5 hours and then at 80° C. for 4.5 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=1:1→2:1→3:1 as the eluant and the product was recrystallized from ethyl acetate to afford the title compound (192 mg, mp 164.0-166.6° C.).

Aufarbeitung

  1. waitat 80° C. for 4.5 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. customn-hexane=1:1→2:1→3:1 as the eluant and the product was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-55abd78f2e8243ba8bb97b31de87291e
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562849B1

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