HCID 11238707, compound → HCID 3013419, compound

HRID 856387Notes

Reaction equation

HRID 856387 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:43])[C:35]5[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][N+:36]=5[O-:42])=[CH:30][CH:29]=4)=[O:26])=[CH:20][C:19]=3[CH:44]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]>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:43])[C:35]5[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][N+:36]=5[O-:42])=[CH:30][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

3

Reactant 1

HCID 11238707HCID 11238707, compound

Product 1

HCID 3013419HCID 3013419, compoundYield 146.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

7-[4-(2-butoxyethoxy)phenyl]-N-[4-[hydroxy(4-methyl-1-oxidopyridin-2-yl)methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (0.25 g) and isobutylaldehyde (0.15 ml) were dissolved in 1,2-dichloroethane (80 ml), and to the solution, triacetoxy sodium borohydride (0.27 g) was added under ice-cooling and the mixture was stirred overnight at room temperature. To the mixture, isobutylaldehyde (1 ml) and triacetoxy sodium borohydride (1.3 g) were further added, and the mixture was stirred overnight at room temperature. The mixture was washed with sodium bicarbonate solution and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, to give 7-[4-(2-butoxyethoxy)phenyl]-N-[4-[hydroxy(4-methyl-1-oxidopyridin-2-yl)methyl]phenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (compound 2) (0.2 g) as yellow amorphous.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight at room temperature
  3. washThe mixture was washed with sodium bicarbonate solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-c78f7329aa8241b69e90be87bd17242b
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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