Water → HCID 178521818, compound

HRID 2263031Notes

Reaction equation

HRID 2263031 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([NH:12][C:13](=[O:20])OCC(Cl)(Cl)Cl)=[CH:11][C:5]=2[N:4]=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:13]([NH:12][C:10]4[CH:9]=[CH:8][C:6]5[NH:7][C:3]([C:2]([F:1])([F:21])[F:22])=[N:4][C:5]=5[CH:11]=4)=[O:20])[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 178521819HCID 178521819, compound

Product 1

HCID 178521818HCID 178521818, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixed solution of 2,2,2-trichloroethyl [2-(trifluoromethyl)-1H-benzimidazol-5-yl]carbamate (278 mg, 0.738 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.811 mmol) and diisopropylethylamine (0.129 ml, 0.738 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. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 115 mg (32.8%) 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 (hexane: ethyl acetate=1:1)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-7e9287cc7ae44464b370c3bc73644aba
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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