HCID 10160942, compound → HCID 21114423, compound

HRID 1866774Notes

Reaction equation

HRID 1866774 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-cf55b658d450472eab24f04a8542664b
Source dataset
uspto-grants-2009_12
Patent number
US07629462B2

Reaction notes

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