Cesium carbonate → HCID 68865751, compound

HRID 494102Notes

Reaction equation

HRID 494102 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[C:16](=[O:18])[NH:15][N:14]=[CH:13][C:12]=2[N:11]2[CH:19]([CH3:25])[CH2:20][N:21]([CH3:24])[C:22](=[O:23])[C:10]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:31][C:30]3[CH:33]=[CH:34][C:27]([F:26])=[CH:28][CH:29]=3)[N:14]=[CH:13][C:12]=2[N:11]2[CH:19]([CH3:25])[CH2:20][N:21]([CH3:24])[C:22](=[O:23])[C:10]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 68864550HCID 68864550, compound

Product 1

HCID 68865751HCID 68865751, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10-(benzyloxy)-6,8-dimethyl-7,8-dihydropyrazino[1′,2′:1,5]-pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.12 g, 0.34 mmol), 4-fluorobenzyl bromide (63 μL, 0.34 mmol), and cesium carbonate (0.22 g, 0.68 mmol) in anhydrous DMF (1 mL) was stirred at room temperature for 2 hours. The reaction mixture was concentrated under vacuum and the residue partitioned between ethyl acetate and aqueous citric acid. The organic extract was washed with brine, dried over MgSO4, filtered, and concentrated to provide the titled dione. The residue was subjected to column chromatography on silica gel eluted with a methanol-chloroform gradient to provide the titled product.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue partitioned between ethyl acetate and aqueous citric acid
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto provide the titled dione
  9. washeluted with a methanol-chloroform gradient

Sources & evidence

ORD record
ord-1b193c5dacd84149b43af1d6dbca01ea
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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