Water → HCID 86655381, compound

HRID 2190432Notes

Reaction equation

HRID 2190432 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=3)[C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)=[O:16])[CH:8]=[CH:7][C:5]=2[N:6]=1.C([O:34][CH2:35][C:36](Cl)=[O:37])(=O)C.O>CN(C)C=O>[C:35]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=3)[C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=3)=[O:16])[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:34])[CH2:36][OH:37]

Participants

5

Reactant 3

HCID 962WaterHCID 26297Acetoxyacetyl chlorideHCID 86655379HCID 86655379, compound

Product 1

HCID 86655381HCID 86655381, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-N-[3-(trifluoromethyl)phenyl]benzamide (429 mg, 1.0 mmol) produced in Example A29(v) and 2-chloro-2-oxoethyl acetate (546 mg, 4.0 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 6 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (5 mL)/tetrahydrofuran (5 mL), 8N aqueous sodium hydroxide solution (1 mL) was added under ice-cooling, and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1), and triturated with diethyl ether to give the title compound (300 mg, 62%) as a pale-yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (5 mL)/tetrahydrofuran (5 mL), 8N aqueous sodium hydroxide solution (1 mL)
  5. additionwas added under ice-
  6. temperaturecooling
  7. stirringthe mixture was stirred at room temperature for 30 min
  8. additionThe reaction mixture was poured into water
  9. extractionthe mixture was extracted with ethyl acetate
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1)
  13. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-5c405e6239dc499792d386354385aa36
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

Loading…