Dimethyl Sulfoxide → N-[4-(2-oxopyrrolidin-1-yl)phenyl]-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2263232Notes

Reaction equation

HRID 2263232 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([N:13]([C:22]([O:24]CC(Cl)(Cl)Cl)=O)C(OCC(Cl)(Cl)Cl)=O)=[CH:9][CH:8]=1.[C:30]1([C:36]2[N:40]=[C:39]([N:41]3[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)[S:38][N:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:22]([N:44]2[CH2:45][CH2:46][N:41]([C:39]3[S:38][N:37]=[C:36]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:40]=3)[CH2:42][CH2:43]2)=[O:24])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 86625512Bis(2,2,2-trichloroethyl) [4-(2-oxopyrrolidin-1-yl)phenyl]imidodicarbonate

Product 1

HCID 68779934N-[4-(2-oxopyrrolidin-1-yl)phenyl]-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of bis(2,2,2-trichloroethyl) [4-(2-oxopyrrolidin-1-yl)phenyl]imidodicarbonate (200 mg, 0.380 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (140 mg, 0.569 mmol), diisopropylethylamine (0.198 ml, 1.14 mmol) and dimethyl sulfoxide (4 ml) was stirred at 70° C. for 24 hours, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl acetate to give 51.0 mg (30.0%) of the desired product as a solid.

Workup

  1. extractionthe mixture 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 recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6d63d1358f014738b7d1baba3084be18
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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