Sodium hydride → HCID 57426194, compound

HRID 1094100Notes

Reaction equation

HRID 1094100 reaction equation
[H-].[Na+].[N+:3]([C:6]1[C:14]2[NH:13][C:12](=[O:15])[N:11]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10]=2[CH:9]=[CH:8][CH:7]=1)([O-:5])=[O:4].Br[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29]>CN(C=O)C>[C:20]([O:19][C:17](=[O:18])[CH2:16][N:11]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[C:14]=2[N:13]([CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[C:12]1=[O:15])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 107604Methyl 4-bromobutyrateHCID 57426193HCID 57426193, compound

Product 1

HCID 57426194HCID 57426194, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (26.7 mg of a 60% dispersion in mineral oil, 0.66 mmol) was added to a solution of tert-butyl (4-nitro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate from Step A (96 mg, 0.327 mmol) in DMF (5 mL). After 10 min, methyl 4-bromobutyrate (178 mg, 0.98 mmol) was added and the reaction was stirred at room temperature for 18 h. The mixture was quenched with H2O and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound. MS: m/z=394 (M+1).

Workup

  1. customThe mixture was quenched with H2O
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by HPLC
  9. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-849c32ed8d244567a72a2ced847b95ab
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

Loading…