HCID 66884043, compound → HCID 66883168, compound

HRID 241382Notes

Reaction equation

HRID 241382 reaction equation
[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=2[S:6][C:5]=1[CH2:17][CH2:18][C:19]1[C:23]2[CH:24]=[C:25]([CH3:32])[C:26]([NH:28]C(=O)C)=[CH:27][C:22]=2[O:21][N:20]=1)([CH3:3])[CH3:2]>Cl.CC(O)=O.[OH-].[Na+]>[NH2:28][C:26]1[C:25]([CH3:32])=[CH:24][C:23]2[C:19]([CH2:18][CH2:17][C:5]3[S:6][C:7]4[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=4[C:4]=3[CH:1]([CH3:3])[CH3:2])=[N:20][O:21][C:22]=2[CH:27]=1

Participants

5

Reactant 1

HCID 66884043HCID 66884043, compound

Product 1

HCID 66883168HCID 66883168, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

The above-mentioned N-[3-[2-[3-Isopropyl-6-(trifluoromethyl)benzothiophen-2-yl]ethyl]-5-methylbenzisoxazol-6-yl]acetamide (326 mg, 0.708 mmol) was dissolved in 1M HCl (3.0 mL) and AcOH (7.0 mL). The solution was heated under reflux for 23 hours. Then reaction mixture was cooled to room temperature, diluted with 4M NaOH, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate. After the solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography (hexane/ethyl acetate, 2:1) to give the title compound as a brown crystal (201 mg, yield: 68%).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 23 hours
  3. customThen reaction mixture
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter the solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-961973e53ac54d8496f6c8c5f2e3fb66
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

Loading…