Sodium Iodide → HCID 57771961, compound

HRID 561984Notes

Reaction equation

HRID 561984 reaction equation
C([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[NH:19][C:18](=[O:20])[N:17]([C@H:21]([C:30]3[NH:31][C:32]([C:35]4[CH:40]=[CH:39][C:38]([C:41]#[CH:42])=[CH:37][C:36]=4[F:43])=[CH:33][N:34]=3)[C@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:23])[C:16]2=[O:44])=[CH:11][CH:10]=1)(C)(C)C.ClCCl.C(#N)C.[I-].[Na+].Cl[Si](C)(C)C>C(OCC)(=O)C>[C:41]([C:38]1[CH:39]=[CH:40][C:35]([C:32]2[NH:31][C:30]([C@@H:21]([N:17]3[C:16](=[O:44])[C@@H:15]([C:12]4[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][OH:5])=[CH:14][CH:13]=4)[NH:19][C:18]3=[O:20])[C@H:22]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH3:23])=[N:34][CH:33]=2)=[C:36]([F:43])[CH:37]=1)#[CH:42]

Participants

6

Reactant 4

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 21877088Acetonitrile methylene chlorideHCID 86632277HCID 86632277, compound

Product 1

HCID 57771961HCID 57771961, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-5-[4-(2-tert-butoxy-ethoxy)-phenyl]-3-{(1S,2S)-1-[5-(4-ethynyl-2-fluoro-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-imidazolidine-2,4-dione (293 mg, 0.49 mmol) in 1:1 v/v dichloromethane/acetonitrile (10 mL) at 0° C. under an atmosphere of nitrogen was added sodium iodide (148 mg, 0.99 mmol) followed by chlorotrimethylsilane (184 μL, 1.45 mmol) and the resulting mixture was allowed to stir for 30 minutes. Additional sodium iodide (148 mg, 0.99 mmol) followed by chlorotrimethylsilane (184 μL, 1.45 mmol) was added and stirring continued for 45 minutes. The reaction was then poured into ethyl acetate (30 mL) and washed with 10% w/v aqueous sodium thiosulfate solution. The organic extract was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography over silica gel eluted with 80 to 100% v/v ethyl acetate in hexanes to give (R)-3-{(1S,2S)-1-[5-(4-ethynyl-2-fluoro-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-5-[4-(2-hydroxy-ethoxy)-phenyl]-imidazolidine-2,4-dione (59 mg, 22%). HR-MS: calcd for C31H27FN4O4 [M+H+] 539.2089. Found 539.2086.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitcontinued for 45 minutes
  4. washwashed with 10% w/v aqueous sodium thiosulfate solution
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by chromatography over silica gel
  11. washeluted with 80 to 100% v/v ethyl acetate in hexanes

Sources & evidence

ORD record
ord-63edaec778054ab9b1837319a83dbe68
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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