Ethanol → HCID 178490314, compound

HRID 2253316Notes

Reaction equation

HRID 2253316 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH2:21][CH2:22][CH2:23][N:24]2[C:33](=[O:34])[CH2:32][C:31]3[CH:30]=[CH:29][C:28]4[N:35]=[C:36]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=5[O:44][CH3:45])[NH:37][C:27]=4[C:26]=3[C:25]2=[O:46])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Br[CH2:48][CH2:49][CH2:50]Br.[OH-].[Na+].[CH3:54][CH2:55]O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH2:21][CH2:22][CH2:23][N:24]2[C:33](=[O:34])[C:32]3([CH2:55][CH2:54][CH2:50][CH2:49][CH2:48]3)[C:31]3[CH:30]=[CH:29][C:28]4[N:35]=[C:36]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=5[O:44][CH3:45])[NH:37][C:27]=4[C:26]=3[C:25]2=[O:46])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 178490316HCID 178490316, compound

Product 1

HCID 178490314HCID 178490314, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of tert-butyl [2-(3,4-dimethoxyphenyl)ethyl]{3-[2-(2-methoxyphenyl)-7,9-dioxo-1,6,7,9-tetrahydro-8H-imidazo[4,5-h]isoquinolin-8-yl]propyl}carbamate (100.0 mg, 0.159 mmol), 1,3-dibromopropane (43.9 mg, 0.19 mmol) and aqueous 1 N NaOH solution (0.32 mL, 0.32 mmol) in water (1.0 mL) and EtOH (1 mL) was heated at 80° C. for 2 h. The cooled mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (40-63μ silica gel; hexane:EtOAc 1:1) to yield the title compound (47 mg, 43% yield) as a white foam.

Workup

  1. customThe cooled mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (40-63μ silica gel; hexane:EtOAc 1:1)

Sources & evidence

ORD record
ord-b8438e10330a46d0a12ae387f03b26c2
Source dataset
uspto-grants-2008_01
Patent number
US07323567B2

Reaction notes

Loading…