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

HRID 2263242Notes

Reaction equation

HRID 2263242 reaction equation
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:20])OCC(Cl)(Cl)Cl)=[CH:8][CH:7]=1)(=[O:4])[CH2:2][CH3:3].[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[N:32]=[C:31]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[S:30][N:29]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[N:32]=[C:31]([N:33]2[CH2:34][CH2:35][N:36]([C:13]([NH:12][C:9]3[CH:8]=[CH:7][C:6]([NH:5][C:1](=[O:4])[CH2:2][CH3:3])=[CH:11][CH:10]=3)=[O:20])[CH2:37][CH2:38]2)[S:30][N:29]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 687757201-[3-(2-Fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazineHCID 866255132,2,2-Trichloroethyl [4-(propionylamino)phenyl]carbamate

Product 1

HCID 687796564-[3-(2-Fluorophenyl)-1,2,4-thiadiazol-5-yl]-N-[4-(propionylamino)phenyl]piperazine-1-carboxamideYield 22.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl [4-(propionylamino)phenyl]carbamate (200 mg, 0.589 mmol), 1-[3-(2-fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazine (145 mg, 0.589 mmol), diisopropylethylamine (0.206 ml, 1.18 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 60.5 mg (22.6%) 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-315ae979aa334ec7bb55436f67eaf2a7
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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