Cesium carbonate → HCID 86628006, compound

HRID 1442875Notes

Reaction equation

HRID 1442875 reaction equation
[O:1]=[C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][N:3]1[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[CH:21]1([CH2:24]Br)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH:21]1([CH2:24][N:6]2[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:4][N:3]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]2=[O:1])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 86606173HCID 86606173, compound

Product 1

HCID 86628006HCID 86628006, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of tert-butyl (2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)acetate from Step B (107 mg, 0.39 mmol), cyclopropylmethyl bromide (105 mg, 0.78 mmol), and cesium carbonate (153 mg, 0.47 mmol) in acetone (5 mL) was heated at reflux for 3 days. The reaction mixture was concentrated under reduced pressure, partitioned between brine and CH2Cl2, and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 50:50 to provide the title compound. MS: m/z=273 (M-C4H7).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 days
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompartitioned between brine and CH2Cl2
  5. extractionextracted with CH2Cl2 (3×)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-8b327639b56e45439e7826344961e664
Source dataset
uspto-grants-2010_02
Patent number
US07659300B2

Reaction notes

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