Cesium carbonate → HCID 57426193, compound

HRID 2426187Notes

Reaction equation

HRID 2426187 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[N+:7]([C:10]1[C:18]2[NH:17][C:16](=[O:19])[NH:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)([O-:9])=[O:8].Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>CN(C=O)C>[N+:7]([C:10]1[C:18]2[NH:17][C:16](=[O:19])[N:15]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:14]=2[CH:13]=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 41498284-Nitro-1H-benzo[d]imidazol-2(3H)-one2×

Product 1

HCID 57426193HCID 57426193, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (1.75 g, 5.4 mmol) was added to a solution of 4-nitro-1,3-dihydro-2H-benzimidazol-2-one (800 mg, 4.5 mmol, described in Intermediate 31) and tert-butyl bromoacetate (0.791 mL, 5.4 mmol) in DMF (15 mL). After 18 h, the reaction was quenched with H2O (100 mL) and the solid precipitate was collected by filtration. The crude product was purified by silica gel chromatography, eluting with CH2Cl2:MeOH—95:5, to give the title compound. MS: m/z=294 (M+1).

Workup

  1. customthe reaction was quenched with H2O (100 mL)
  2. filtrationthe solid precipitate was collected by filtration
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-cb91515598b747338a24976a0f7dbdac
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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