Water → 4-(4-Phenyl-1,3-thiazol-2-yl)-N-pyridin-4-ylpiperazine-1-carboxamide

HRID 2263032Notes

Reaction equation

HRID 2263032 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:23]=[C:24]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[S:25][CH:26]=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:23]=[C:24]([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:25][CH:26]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 142572942,2,2-Trichloroethyl pyridin-4-ylcarbamate

Product 1

HCID 687764124-(4-Phenyl-1,3-thiazol-2-yl)-N-pyridin-4-ylpiperazine-1-carboxamideYield 19.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl pyridin-4-ylcarbamate (360 mg, 1.33 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (360 mg, 1.47 mmol) and diisopropylethylamine (0.256 ml, 1.47 mmol) in dimethyl sulfoxide (4.4 ml) was stirred at 70° C. for 8 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 (ethyl acetate) and recrystallized from a mixed solvent of hexane and ethyl acetate to give 93.7 mg (19.2%) 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 (ethyl acetate)
  6. customrecrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-e62032abe9d94bde81300e80b41e6cd7
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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