Triethylamine → HCID 18537586, compound

HRID 412371Notes

Reaction equation

HRID 412371 reaction equation
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]([C:41]1[CH:42]=[C:43]([CH:47]=[C:48]([C:51]([CH3:54])([CH3:53])[CH3:52])[C:49]=1[OH:50])[C:44](O)=[O:45])([CH3:40])([CH3:39])[CH3:38].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[C:51]([C:48]1[CH:47]=[C:43]([CH:42]=[C:41]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:49]=1[OH:50])[C:44]([NH: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)=[O:45])([CH3:54])([CH3:53])[CH3:52]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Product 1

HCID 18537586HCID 18537586, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg) and 3,5-di-t-butyl-4-hydroxybenzoic acid (204 mg) in anhydrous N,N-dimethylformamide (8 ml) were added triethylamine (0.32 ml) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (153 mg). The mixture was stirred at room temperature for 1 hour and then allowed to stand at room temperature overnight. To the reaction mixture was further added triethylamine (0.10 ml) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (134 mg) and this mixture was stirred at room temperature for 8 hours and allowed to stand at room temperature overnight. The reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=2:1→3:1 as the eluant to afford the title compound (176 mg, mp 160-162° C.).

Workup

  1. waitto stand at room temperature overnight
  2. stirringthis mixture was stirred at room temperature for 8 hours
  3. waitto stand at room temperature overnight
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. custompartitioned between ethyl acetate and water
  6. washThe extract was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-28e394ab9afb4626931905d3acaa50c7
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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