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

HRID 412370

Reaction equation

HRID 412370 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 10145908N-[4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]naphthalene-2-carboxamideYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-30fc791967ed4708876ca7c2b0f5afde
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Linked notes

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