Water → HCID 68778085, compound

HRID 2262950Notes

Reaction equation

HRID 2262950 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:11][C:10]([NH:12][C:13](=[O:20])OCC(Cl)(Cl)Cl)=[N:9][N:8]=2)[CH:2]=1.[C:21]1([C:27]2[N:31]=[C:30]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[S:29][N:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:21]1([C:27]2[N:31]=[C:30]([N:32]3[CH2:37][CH2:36][N:35]([C:13]([NH:12][C:10]4[O:11][C:7]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)=[N:8][N:9]=4)=[O:20])[CH2:34][CH2:33]3)[S:29][N:28]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 86625479HCID 86625479, compound

Product 1

HCID 68778085HCID 68778085, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl (5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)carbamate (249 mg, 0.738 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and diisopropylethylamine (0.129 ml, 0.728 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 70° C. for 3 hours and half. 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. Hexane was poured to the residue, and crystals were separated by filtration, which was recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 110 mg (34.2%) 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. additionHexane was poured to the residue, and crystals
  6. customwere separated by filtration, which
  7. customwas recrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-7e144247ba0c4c0c953c4f9f7910cf3e
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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