5-Chloro-2-benzoxazolamine → HCID 59758893, compound

HRID 914398Notes

Reaction equation

HRID 914398 reaction equation
C([O:5][C:6](=[O:20])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17](O)=O)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]2[O:29][C:28]([NH2:30])=[N:27][C:26]=2[CH:31]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]2[O:29][C:28]([NH:30][CH2:17][CH2:16][C:14]3[N:15]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:5])=[O:20])[S:12][CH:13]=3)=[N:27][C:26]=2[CH:31]=1

Participants

5

Reactant 3

HCID 61035-Chloro-2-benzoxazolamineHCID 6422Trifluoroacetic acidHCID 59759443{2-[(2-Tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acid

Product 1

HCID 59758893HCID 59758893, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound obtained using {2-[(2-tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acid synthesized in Example 3 and 5-chloro-1,3-benzoxazol-2-amine as starting materials and by operations similar to those of Example 242-1 and Example 242-2 was treated with dichloromethane and trifluoroacetic acid, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=20:1). Ethyl acetate was added, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution (the objective compound was extracted in the ethyl acetate layer). The ethyl acetate layer was washed with aqueous 10% citric acid solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound.

Workup

  1. customThe compound obtained
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=20:1)
  4. additionEthyl acetate was added
  5. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution (the objective compound
  6. extractionwas extracted in the ethyl acetate layer)
  7. washThe ethyl acetate layer was washed with aqueous 10% citric acid solution and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-87d53667543f42ae943605e8059e25d7
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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