Water → HCID 86595188, compound

HRID 856576Notes

Reaction equation

HRID 856576 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[C:4]([C:12]([NH2:14])=[O:13])[CH2:3][CH2:2]1.O>CN(C=O)C>[CH2:3]([N:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[C:4]([C:12]([NH2:14])=[O:13])[CH2:3][CH2:2]1)[CH:4]([CH3:12])[CH3:5]

Participants

4

Reactant 2

HCID 962WaterHCID 69521870HCID 69521870, compound

Product 1

HCID 86595188HCID 86595188, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[(1-trityl-1H-imidazol-4-yl)methyl]thio]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (0.50 g) in DMF (10 ml), 2-iodinated ethanol (0.25 ml) was added at room temperature, and the mixture was stirred at 50° C. for 4 days. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (basic silica gel, ethanol:ethyl acetate 1:49→1:19), to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[1-(2-hydroxyethyl)-1H-imidazol-5-yl]methyl]thio]phenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 438) (124.6 mg) as yellow amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was separated
  6. custompurified by column chromatography (basic silica gel, ethanol:ethyl acetate 1:49→1:19)

Sources & evidence

ORD record
ord-edf63da113e04fc598ba9e6d6b556614
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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