Triethylamine → N-[4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]naphthalene-2-carboxamide

HRID 412370

Reaktionsgleichung

Reaktionsgleichung von HRID 412370
C(N(CC)CC)C.[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:18](Cl)=[O:19].Cl.Cl.[NH2:23][C:24]1[CH:56]=[CH:55][C:27]([O:28][C:29]2[CH:30]=[CH:31][C:32]3[N:36]=[C:35]([CH2:37][O:38][C:39]4[CH:52]=[CH:51][C:42]([CH2:43][CH:44]5[S:48][C:47](=[O:49])[NH:46][C:45]5=[O:50])=[CH:41][CH:40]=4)[N:34]([CH3:53])[C:33]=3[CH:54]=2)=[CH:26][CH:25]=1>CN(C)C=O>[O:49]=[C:47]1[NH:46][C:45](=[O:50])[CH:44]([CH2:43][C:42]2[CH:41]=[CH:40][C:39]([O:38][CH2:37][C:35]3[N:34]([CH3:53])[C:33]4[CH:54]=[C:29]([O:28][C:27]5[CH:55]=[CH:56][C:24]([NH:23][C:18]([C:9]6[CH:10]=[CH:11][C:12]7[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=7)[CH:8]=6)=[O:19])=[CH:25][CH:26]=5)[CH:30]=[CH:31][C:32]=4[N:36]=3)=[CH:52][CH:51]=2)[S:48]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Produkt 1

HCID 10145908N-[4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]naphthalene-2-carboxamideAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A reaction was conducted by a similar procedure to that described in Example 52 using triethylamine (0.32 ml), 2-naphthoyl chloride (153 mg), 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg) and anhydrous N,N-dimethylformamide (8 ml). The reaction mixture was concentrated under reduced pressure. To the residue was added ethyl acetate and water. The precipitate was isolated by filtration to afford the title compound (337 mg, white powder, mp 221-223° C.).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added ethyl acetate and water
  3. customThe precipitate was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-30fc791967ed4708876ca7c2b0f5afde
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562849B1

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