HCID 58945794, compound → HCID 24742810, compound

HRID 2242808Notes

Reaction equation

HRID 2242808 reaction equation
[NH2:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]=1[N:9]([C:18]1[C:23](=[O:24])[CH2:22][CH2:21][CH2:20][C:19]=1O)[C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14]>C1COCC1>[O:24]=[C:23]1[C:18]2[N:9]([C:10]3[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=3)[C:13]#[N:14])[C:3]3[C:4](=[O:8])[CH2:5][CH2:6][CH2:7][C:2]=3[NH:1][C:19]=2[CH2:20][CH2:21][CH2:22]1

Participants

3

Reactant 1

HCID 58945794HCID 58945794, compound

Product 1

HCID 24742810HCID 24742810, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[(2-Amino-6-oxo-cyclohex-1-enyl)-(2-hydroxy-6-oxo-cyclohex-1-enyl)-amino]-benzonitrile (0.4 mmoL) in THF (5 mL) was treated with NaNH2 (1 mmoL) at 70° C. for 6 h. The solvent was removed and the residue was partitioned between DCM and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude material, which was then purified by silica gel column chromatography to give the title compound as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between DCM and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude material, which
  8. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-066e8f4aafc54e8fa6e0244242f65db6
Source dataset
uspto-grants-2010_03
Patent number
US07674793B2

Reaction notes

Loading…