Ethyl bromoacetate → HCID 52911641, compound

HRID 1951609Notes

Reaction equation

HRID 1951609 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[S:7][C:8]=1[CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH3:20])=[CH:15][CH:14]=1)=[O:12])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Br[CH2:41][C:42]([O:44]CC)=[O:43]>CN(C)C=O.O>[CH:1]([C:4]1[N:5]=[C:6]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:26]=2)[S:7][C:8]=1[CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH3:20])[CH2:41][C:42]([OH:44])=[O:43])=[CH:15][CH:14]=1)=[O:12])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 69002841HCID 69002841, compound

Product 1

HCID 52911641HCID 52911641, compoundYield 122.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

The obtained 3-[4-Isopropyl-2-[4-(trifluoromethyl)phenyl]thiazol-5-yl]-1-(4-methylaminophenyl)propan-1-one (40 mg, 0.0931 mmol) and diisopropylethylamine (80 μL, 0.462 mmol) were dissolved in anhydrous dimethylformamide (2 mL). Ethyl bromoacetate (66 mg, 0.393 mmol) was added to the solution. The mixture was stirred at 110° C. for 16 hours. The mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried with anhydrous sodium sulfate to remove the solvent. The obtained residue was purified by silica gel column chromatography with hexane/chloroform (7:3, v/v) to give the desired compound (56 mg) as yellow crystalline product (yield 47%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customto remove the solvent
  6. customThe obtained residue was purified by silica gel column chromatography with hexane/chloroform (7:3

Sources & evidence

ORD record
ord-1db84db0ccaa402a85e7ca617dd0dd67
Source dataset
uspto-grants-2013_03
Patent number
US08404726B2

Reaction notes

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