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

HRID 2263018Notes

Reaction equation

HRID 2263018 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.[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:2]=[CH:3][C:4]([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:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 142572942,2,2-Trichloroethyl pyridin-4-ylcarbamateHCID 687780931-(3-Pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine

Product 1

HCID 68778017N-pyridin-4-yl-4-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideYield 23%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl pyridin-4-ylcarbamate (198 mg, 0.735 mmol), 1-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.809 mmol) and diisopropylethylamine (0.139 ml, 0.809 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 a mixed solution of ethyl acetate/tetrahydrofuran (1:1). 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:methanol=9:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 62.1 mg (23.0%) of the desired product as a solid.

Workup

  1. extractionthe resulting solution was extracted with a mixed solution of ethyl acetate/tetrahydrofuran (1:1)
  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:methanol=9:1)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-2c37bade6558433a88e7f25d21d40baf
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

Loading…