Water → HCID 178522347, compound

HRID 2263137Notes

Reaction equation

HRID 2263137 reaction equation
[NH:1]1[C:5]([N:6]([C:15]([O:17]CC(Cl)(Cl)Cl)=O)C(OCC(Cl)(Cl)Cl)=O)=[CH:4][CH:3]=[N:2]1.[C:23]1([C:29]2[N:33]=[C:32]([N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[S:31][N:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:23]1([C:29]2[N:33]=[C:32]([N:34]3[CH2:39][CH2:38][N:37]([C:15]([NH:6][C:5]4[CH:4]=[CH:3][NH:2][N:1]=4)=[O:17])[CH2:36][CH2:35]3)[S:31][N:30]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 86245086HCID 86245086, compound

Product 1

HCID 178522347HCID 178522347, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of bis(2,2,2-trichloroethyl) 1H-pyrazol-5-ylimidodicarbonate (264 mg, 0.609 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (300 mg, 1.22 mmol) and diisopropylethylamine (0.106 ml, 0.609 mmol) in dimethylsulfoxide (4.0 ml) was stirred at 70° C. for 8 hours. Water was poured into the reaction mixture and the mixture 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 high performance liquid chromatography (YMC HPLC column, A solution 0.1% trifluoroacetic acid solution in acetonitrile, B solution 0.1% trifluoroacetic acid solution in water, eluted with 10% A solution to 100% A solution) and aqueous saturated sodium hydrogen carbonate solution was added thereto and the mixture 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 recrystallized from a mixed solvent of hexane and tetrahydrofuran to obtain the desired product (22.7 mg, 10.5%) 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 high performance liquid chromatography (YMC HPLC column
  6. washA solution 0.1% trifluoroacetic acid solution in acetonitrile, B solution 0.1% trifluoroacetic acid solution in water, eluted with 10% A solution to 100% A solution) and aqueous saturated sodium hydrogen carbonate solution
  7. additionwas added
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-ccb5c1db283f4513b5a841c39d3ae009
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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