Water → HCID 68776217, compound

HRID 2263252Notes

Reaction equation

HRID 2263252 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=2[F:14])[N:6]=1.[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:14][C:8]1[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=1[C:5]1[N:6]=[C:2]([N:18]2[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]2)[S:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 534409702-Bromo-4-(2,4-difluorophenyl)-1,3-thiazole

Product 1

HCID 68776217HCID 68776217, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-4-(2,4-difluorophenyl)-1,3-thiazole (3.23 mg, 11.7 mmol), tert-butyl piperazine-1-carboxylate (4.36 g, 23.4 mmol) and potassium carbonate (1.62 g, 11.7 mmol) in dimethylformamide (40 ml) was stirred at 120° C. for 12 hours. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 3.83 g (85.9%) of the desired product as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-b26e6147280a456f8c4ace4859902633
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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