HCID 10160942, compound → HCID 21114423, compound

HRID 644781Notes

Reaction equation

HRID 644781 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].[CH3:32][O-:33].[Na+]>CO>[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:33][CH3:32])=[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

4

Reactant 2

HCID 10160942HCID 10160942, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 21114423HCID 21114423, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product of Example 3 (0.102 g, 0.22 mmol) was suspended in MeOH (2 mL) and stirred under argon. A 1 Molar solution of NaOMe in methanol (0.44 mL, 0.44 mmol) was added. After 10 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. Recrystallization from EtOAc/hexane gave the title compound as a white-crystalline solid. mp 210-211° C., LC MS m/z=401 (MH+) Rt=2.0 min.

Workup

  1. customAfter 10 min the solvent was removed in vacuo
  2. customthe residue partitioned between EtOAc and H2O
  3. washThe organic phase was washed with H2O (2×)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product
  8. customRecrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-a34bcdbc866d4cadb13672445f95cd50
Source dataset
uspto-grants-2010_04
Patent number
US07700768B2

Reaction notes

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