Dimethylformamide → 2-(3-tert-Butyl-phenoxy)-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

HRID 2363077Notes

Reaction equation

HRID 2363077 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21](Cl)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].C([O-])([O-])=O.[K+].[K+].[C:31]([C:35]1[CH:36]=[C:37]([OH:41])[CH:38]=[CH:39][CH:40]=1)([CH3:34])([CH3:33])[CH3:32].CN(C=O)C>CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21]([O:41][C:37]3[CH:38]=[CH:39][CH:40]=[C:35]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:36]=3)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 446029352-(3-tert-Butyl-phenoxy)-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amideYield 182.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 5 ml glass tube were placed 2-chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (40 mg, 0.10 mmol), K2CO3(17 mg, 0.12 mmol), 3-tert-butyl phenol (18 mg, 0.12 mmol), DMF (1 mL), and a magnetic stir bar. The vial was sealed with septum and placed into the Microwave cavity. The vial was irradiated in a Microwave synthesizer at 130° C. for 10 min. The reaction mixture was diluted with EtOAc, and washed with saturated ammonium chloride and water. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane) to give title compound (90 mg, 80%).

Workup

  1. customIn a 5 ml glass tube were placed
  2. customThe vial was sealed with septum
  3. customThe vial was irradiated in a Microwave synthesizer at 130° C. for 10 min
  4. washwashed with saturated ammonium chloride and water
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-4d275b45ecf44cdc8bcb3864aff2b4f3
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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