Tetrahydrofuran → HCID 135848671, compound

HRID 254441Notes

Reaction equation

HRID 254441 reaction equation
[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:26][C:25](=[O:27])[O:24][N:23]=3)=[CH:12][CH:11]=2)[C:7]2[C:28]([C:32]([OH:34])=[O:33])=[CH:29][CH:30]=[CH:31][C:6]=2[N:5]=1)[CH3:2].C(N(CC)CC)C.ClC1C=C(Cl)[CH:49]=[C:48](Cl)[C:44]=1[C:45](Cl)=[O:46].C1C[O:57]CC1>>[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:26][C:25](=[O:27])[O:24][N:23]=3)=[CH:14][CH:15]=2)[C:7]2[C:28]([C:32]([O:34][CH:49]3[CH2:48][CH2:44][C:45](=[O:46])[O:57]3)=[O:33])=[CH:29][CH:30]=[CH:31][C:6]=2[N:5]=1)[CH3:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 135415867Azilsartan

Product 1

HCID 135848671HCID 135848671, compoundYield 3.3%

Procedure

To a solution of 2-ethoxy-1-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylic acid (4.0 g) and triethylamine (1.3 mL) in THF (50 mL) was added dropwise 2,4,6-trichlorobenzoyl chloride (1.4 mL) under ice-cooling. After stirring at room temperature for 12 hrs., insoluble material was filtered off and the filtrate was concentrated. The residue was dissolved in methylene chloride (50 mL) and 5-oxotetrahydro-2-furanyl (0.67 g) and N,N-dimethylaminopyridine (1.0 g) were added under ice-cooling. After stirring at room temperature for 4 hrs., the reaction mixture was diluted with chloroform (150 mL), washed with water, saturated aqueous sodium hydrogen carbonate, 1 N hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound (0.16 g, 3.3%) as a colorless solid.

Workup

  1. temperaturecooling
  2. filtration, insoluble material was filtered off
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in methylene chloride (50 mL)
  5. addition5-oxotetrahydro-2-furanyl (0.67 g) and N,N-dimethylaminopyridine (1.0 g) were added under ice-
  6. temperaturecooling
  7. stirringAfter stirring at room temperature for 4 hrs
  8. addition, the reaction mixture was diluted with chloroform (150 mL)
  9. washwashed with water, saturated aqueous sodium hydrogen carbonate, 1 N hydrochloric acid and saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ad5ff181277f4417b42e3c6262a4527b
Source dataset
uspto-grants-2011_01
Patent number
US07875637B2

Reaction notes

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