Water → HCID 68779058, compound

HRID 2262934Notes

Reaction equation

HRID 2262934 reaction equation
ClC(Cl)(Cl)CO[C:5]([NH:7][C:8]1[O:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:9]=1)=[O:6].[C:19]1([C:25]2[N:29]=[C:28]([N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[S:27][N:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:19]1([C:25]2[N:29]=[C:28]([N:30]3[CH2:35][CH2:34][N:33]([C:5]([NH:7][C:8]4[O:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:9]=4)=[O:6])[CH2:32][CH2:31]3)[S:27][N:26]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 68779576HCID 68779576, compound

Product 1

HCID 68779058HCID 68779058, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of methyl 5-{[(2,2,2-trichloroethoxy)carbonyl]amino}-2-furancarboxylate (321 mg, 1.01 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and diisopropylethylamine (0.177 ml, 1.01 mmol) in dimethyl sulfoxide (3.4 ml) was stirred at 70° C. for 5 hours. Water was poured to the reaction mixture, and the resulting solution 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=1:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 71.7 mg (17.1%) of the desired product as a solid.

Workup

  1. extractionthe resulting solution 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=1:1)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-99aa3dbc9a0f4973934f9f50af19d0cc
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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