Ethyl Acetate → HCID 70345096, compound

HRID 1738910Notes

Reaction equation

HRID 1738910 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][CH2:14][CH2:15]I)[C:10](=[O:17])[C@@H:9]([CH2:18][C:19]#[N:20])[O:8][C@H:7]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[C:6]=2[CH:31]=1.[CH3:32][C:33]1[NH:34][CH:35]=[CH:36][N:37]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][N:34]3[CH:35]=[CH:36][N:37]=[C:33]3[CH3:32])[C:10](=[O:17])[C@@H:9]([CH2:18][C:19]#[N:20])[O:8][C@H:7]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[C:6]=2[CH:31]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 70345157HCID 70345157, compound

Product 1

HCID 70345096HCID 70345096, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Trans-7-chloro-5-(1 -naphthyl)-1 -(4-iodobutyl)-2-oxo-1,2,3,5-tetrahydro-4,1 -benzoxazepine-3-acetonitrile (575 mg, 1.06 mmol), 2-methylimidazole (87 mg, 1.06 mmol) and potassium carbonate (146 mg, 1.06 mmol) were dissolved in DMF (5 ml) and the resulting solution stirred at 25° C. for 72 hours. Ethyl acetate was added and the solution washed with water (4×). The organic layer was dried (MgSO4), concentrated under reduced pressure and purified by flash column chromatography (ethyl acetate/diethylamine 95:5) to give the title compound (250 mg, 47%) as a colorless foam.

Workup

  1. washthe solution washed with water (4×)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash column chromatography (ethyl acetate/diethylamine 95:5)

Sources & evidence

ORD record
ord-e6d6cf4a172747488bf7ae8e6a161e0e
Source dataset
uspto-grants-1999_10
Patent number
US05965553

Reaction notes

Loading…