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

HRID 2262970Notes

Reaction equation

HRID 2262970 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.[C:16]1([C:22]2[N:26]=[C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[S:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:16]1([C:22]2[N:26]=[C:25]([N:27]3[CH2:32][CH2:31][N:30]([C:8]([NH:7][C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[O:15])[CH2:29][CH2:28]3)[S:24][N:23]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 142572942,2,2-Trichloroethyl pyridin-4-ylcarbamate

Product 1

HCID 159792494-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-(pyridin-4-yl)piperazine-1-carboxamideYield 44.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl pyridin-4-ylcarbamate (271 mg, 0.610 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and diisopropylethylamine (0.129 ml, 0.610 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 (methanol ethyl acetate=1:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 98.3 mg (44.1%) 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 (methanol ethyl acetate=1:1)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-6738c8bcb8244a71a4d7f3c4450f6569
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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