Water → HCID 11508866, compound

HRID 2262989Notes

Reaction equation

HRID 2262989 reaction equation
ClC(Cl)(Cl)COC([N:7]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C:8]([O:10]CC(Cl)(Cl)Cl)=O)=O.[C:24]1([C:30]2[N:31]=[C:32]([N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[S:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:24]1([C:30]2[N:31]=[C:32]([N:35]3[CH2:40][CH2:39][N:38]([C:8]([NH:7][C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)=[O:10])[CH2:37][CH2:36]3)[S:33][CH:34]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineHCID 86625475HCID 86625475, compound

Product 1

HCID 11508866HCID 11508866, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of bis(2,2,2-trichloroethyl)pyridin-3-ylimidodicarbonate (359 mg, 0.810 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (396 mg, 1.62 mmol) and diisopropylethylamine (0.281 ml, 1.62 mmol) in dimethyl sulfoxide (2.7 ml) was stirred at 70° 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 (100% ethyl acetate) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 82.0 mg (27.8%) of the desired product as a solid. mp 74-75° C.

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 (100% ethyl acetate)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-95e5a8d44e0149fba1464ed0223be0a4
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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