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

HRID 2263244Notes

Reaction equation

HRID 2263244 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:20])OCC(Cl)(Cl)Cl)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.F[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>[C:23]1([C:28]2[N:32]=[C:31]([N:33]3[CH2:38][CH2:37][N:36]([C:13]([NH:12][C:9]4[CH:8]=[CH:7][C:6]([N:1]5[CH:5]=[CH:4][CH:3]=[N:2]5)=[CH:11][CH:10]=4)=[O:20])[CH2:35][CH2:34]3)[S:30][N:29]=2)[CH:22]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 687757201-[3-(2-Fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazineHCID 862452022,2,2-Trichloroethyl [4-(1H-pyrazol-1-yl)phenyl]carbamate

Product 1

HCID 687763734-(3-Phenyl-1,2,4-thiadiazol-5-yl)-N-[4-(1H-pyrazol-1-yl)phenyl]piperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl [4-(1H-pyrazol-1-yl)phenyl]carbamate (200 mg, 0.598 mmol), 1-[3-(2-fluorophenyl)-1,2,4-thiadiazol-5-yl]piperazine (147 mg, 0.598 mmol), diisopropylethylamine (0.208 ml, 1.20 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 purified by silica gel column chromatography (ethyl acetate) to give the desired product as a solid. The solid was recrystallized from ethyl acetate to give 63.7 mg (24.7%) 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 purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ebd64d3764084d729889c50b509fed72
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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