Ethylene Glycol → HCID 10159761, compound

HRID 644783Notes

Reaction equation

HRID 644783 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2=[N:15][C:16](S(C)(=O)=O)=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])=[C:13]2[CH2:12][NH:11][C:10]1=[O:31].[CH2:32]([OH:35])[CH2:33][OH:34]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2=[N:15][C:16]([O:34][CH2:33][CH2:32][OH:35])=[N:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])=[C:13]2[CH2:12][NH:11][C:10]1=[O:31]

Participants

3

Reactant 2

HCID 174Ethylene GlycolHCID 10160942HCID 10160942, compound

Product 1

HCID 10159761HCID 10159761, compound

Procedure

The product of Example 3 (0.0658 g, 0.147 mmol) was suspended in ethylene glycol (1 mL) and stirred under argon. NaH, dry, 95%, (8.0 mg, 0.32 mmol) was added. After 30 min the solvent was removed in vacuo, and the residue partitioned between EtOAc and H2O. The organic phase was washed with H2O (2×), satd aq NaCl (1×), dried over anhydrous Na2SO4, filtered, and evaporated to give the crude product. Flash chromatography on silica gel eluted with 0-10% EtOAc/CH2Cl2 gave the title compound as a white-amorphous solid. mp 172-175° C., LC MS m/z=431 (MH+) Rt=1.7 min.

Workup

  1. dry with materialNaH, dry
  2. addition95%, (8.0 mg, 0.32 mmol) was added
  3. customAfter 30 min the solvent was removed in vacuo
  4. customthe residue partitioned between EtOAc and H2O
  5. washThe organic phase was washed with H2O (2×)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give the crude product
  10. washFlash chromatography on silica gel eluted with 0-10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-0dd63ddde8144faa9de93480cf80748b
Source dataset
uspto-grants-2010_04
Patent number
US07700768B2

Reaction notes

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