Water → N-pyridin-3-yl-4-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2262983Notes

Reaction equation

HRID 2262983 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:2]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[N:26]=[C:25]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[S:24][N:23]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([N:30]2[CH2:29][CH2:28][N:27]([C:25]3[S:24][N:23]=[C:22]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=4)[N:26]=3)[CH2:32][CH2:31]2)=[O:15])[CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 685753802,2,2-Trichloroethyl pyridin-3-ylcarbamateHCID 687780931-(3-Pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine

Product 1

HCID 68777295N-pyridin-3-yl-4-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideYield 38.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (297 mg, 1.10 mmol), 1-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine (300 mg, 1.21 mmol) and diisopropylethylamine (0.211 ml, 1.21 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:hexane=1:1, followed by ethyl acetate:methanol=9:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 156 mg (38.5%) 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:hexane=1:1, followed by ethyl acetate:methanol=9:1)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-d159a85e85cb45a9a50832a5bc27bf46
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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