Dimethyl Sulfoxide → HCID 68779157, compound

HRID 2262917Notes

Reaction equation

HRID 2262917 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:18]1[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[C:20]([N:27](C(OCC(Cl)(Cl)Cl)=O)[C:28](OCC(Cl)(Cl)Cl)=[O:29])=[N:19]1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[O:18]1[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[C:20]([NH:27][C:28]([N:15]2[CH2:16][CH2:17][N:12]([C:10]3[S:9][N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:11]=3)[CH2:13][CH2:14]2)=[O:29])=[N:19]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 86625474HCID 86625474, compound

Product 1

HCID 68779157HCID 68779157, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (738 mg, 3.00 mmol), bis(2,2,2-trichloroethyl) isoxazolo[5,4-b]pyridin-3-ylimidodicarbonate (486 mg, 1.00 mmol), diisopropylethylamine (0.348 ml, 2.00 mmol) and dimethyl sulfoxide (5 ml) was stirred at 70° C. for 5 hours. The reaction mixture was poured to water and 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 tetrahydrofuran to yield 240 mg (59.0%) of the desired product.

Workup

  1. extractionextracted 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 tetrahydrofuran

Sources & evidence

ORD record
ord-51b932dbe961430da6b99828b9daadd3
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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