Sodium Iodide → HCID 58790424, compound

HRID 2193802Notes

Reaction equation

HRID 2193802 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17](=[O:20])[NH:18][CH:19]=3)[S:13][C:6]=12.Cl[CH2:29][CH2:30][N:31]([CH3:33])[CH3:32].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CN(C=O)C.ClCCl.C(O)(=O)C.CO>[CH3:32][N:31]([CH3:33])[CH2:30][CH2:29][N:18]1[CH:19]=[C:14]([C:12]2[S:13][C:6]3[C:7](=[N:8][CH:9]=[CH:10][C:5]=3[O:4][C:3]3[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:2]=3[F:1])[CH:11]=2)[CH:15]=[CH:16][C:17]1=[O:20]

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 79012-Chloro-N,N-dimethylethylamine2×HCID 10796Cesium carbonate2×HCID 66649247HCID 66649247, compound

Product 1

HCID 58790424HCID 58790424, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The pyridinone 420 (0.283 g, 0.739 mmol), 2-chloro-N,N-dimethylethanamine (0.128 g, 0.887 mmol), cesium carbonate (0.547 g, 1.68 mmol) and sodium iodide (0.132 g, 0.88 mmol) were heated in DMF (10 mL) at 70° C. for 3 days. An additional portion of 2-chloro-N,N-dimethylethanamine (64 mg, 0.44 mmol) and cesium carbonate (0.289 g, 0.887 mmol) were added. The reaction mixture was heated for additional 8 hours, cooled to room temperature and evaporated under reduced pressure. The residue was partitioned between water (50 mL) and 5% ethanol/dichloromethane. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The residue was then purified by silica gel chromatography using a 25M Biotage column and a gradient of 3 to 20% methanol in dichloromethane with 1% acetic acid, to provide title compound 421 as a solid material (0.108 g, 32% yield). MS (m/z): 228.0 ([M+2H]/2), 455.0 (M+H), 477.0 (M+Na).

Workup

  1. temperatureThe reaction mixture was heated for additional 8 hours
  2. customevaporated under reduced pressure
  3. customThe residue was partitioned between water (50 mL) and 5% ethanol/dichloromethane
  4. customThe organic phase was collected
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-235d638e220f4571b25ac5616fac6b8c
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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