Water → 4-[3-(3-Furyl)-1,2,4-thiadiazol-5-yl]-N-pyridin-4-ylpiperazine-1-carboxamide

HRID 2263019Notes

Reaction equation

HRID 2263019 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)=[CH:3][CH:2]=1.[O:16]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[C:24]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[S:23][N:22]=2)=[CH:17]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[O:16]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[C:24]([N:26]3[CH2:27][CH2:28][N:29]([C:8]([NH:7][C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[O:15])[CH2:30][CH2:31]3)[S:23][N:22]=2)=[CH:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 142572942,2,2-Trichloroethyl pyridin-4-ylcarbamateHCID 687778431-[3-(3-Furyl)-1,2,4-thiadiazol-5-yl]piperazine

Product 1

HCID 687820174-[3-(3-Furyl)-1,2,4-thiadiazol-5-yl]-N-pyridin-4-ylpiperazine-1-carboxamideYield 30.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl pyridin-4-ylcarbamate (207 mg, 0.770 mmol), 1-[3-(3-furyl)-1,2,4-thiadiazol-5-yl]piperazine (200 mg, 0.846 mmol) and diisopropylethylamine (0.134 ml, 0.846 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 80° C. for 3 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 (ethyl acetate) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 84.5 mg (30.8%) 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 (ethyl acetate)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-debbd1bacb3747469b526ff26c86f440
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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