Sodium Bicarbonate → 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[hydroxy-(1-oxidopyridin-1-ium-2-yl)methyl]-3-methyl-phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 856393Notes

Reaction equation

HRID 856393 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[NH:24][CH2:23][CH2:22][C:21]([C:25]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([CH:34]([OH:42])[C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][N+:36]=5[O-:41])=[C:30]([CH3:43])[CH:29]=4)=[O:26])=[CH:20][C:19]=3[CH:44]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].C(=O)(O)[O-].[Na+]>ClCCCl>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:11][CH:12]([CH3:15])[CH3:13])[CH2:23][CH2:22][C:21]([C:25]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([CH:34]([OH:42])[C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][N+:36]=5[O-:41])=[C:30]([CH3:43])[CH:29]=4)=[O:26])=[CH:20][C:19]=3[CH:44]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 114674547-[4-(2-butoxyethoxy)phenyl]-N-[4-[hydroxy(1-oxidopyridin-2-yl)methyl]-3-methylphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

Product 1

HCID 30134227-[4-(2-butoxyethoxy)phenyl]-N-[4-[hydroxy-(1-oxidopyridin-1-ium-2-yl)methyl]-3-methyl-phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxamideYield 182.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

7-[4-(2-butoxyethoxy)phenyl]-N-[4-[hydroxy(1-oxidopyridin-2-yl)methyl]-3-methylphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (0.6 g) and isobutylaldehyde (0.46 ml) were dissolved in 1,2-dichloroethane (50 ml), and to the solution, triacetoxy sodium borohydride (0.64 g) was added under ice-cooling and the mixture was stirred overnight at room temperature. To the mixture, isobutylaldehyde (0.46 ml) and triacetoxy sodium borohydride (0.64 g) were further added, and the mixture was stirred overnight at room temperature. The mixture was neutralized with solution of sodium bicarbonate, concentrated, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol/triethylamine) to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[hydroxy(1-oxidopyridin-2-yl)methyl]-3-methylphenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (compound 8) (0.6 g) as pale yellow amorphous.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight at room temperature
  3. concentrationconcentrated
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol/triethylamine)

Sources & evidence

ORD record
ord-b0376853f6ce484093ddf52bedcb6e9f
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…