Dimethyl Sulfoxide → N-(3,4-Dimethylisoxazol-5-yl)-4-(4-phenylpyridin-2-yl)piperazine-1-carboxamide

HRID 1158710Notes

Reaction equation

HRID 1158710 reaction equation
ClC(Cl)(Cl)CO[C:5](=[O:14])[NH:6][C:7]1[O:11][N:10]=[C:9]([CH3:12])[C:8]=1[CH3:13].[C:17]1([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[CH3:12][C:9]1[C:8]([CH3:13])=[C:7]([NH:6][C:5]([N:32]2[CH2:33][CH2:34][N:29]([C:25]3[CH:24]=[C:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:28]=[CH:27][N:26]=3)[CH2:30][CH2:31]2)=[O:14])[O:11][N:10]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 226401171-(4-Phenylpyridin-2-yl)piperazineHCID 86245257HCID 86245257, compound

Product 1

HCID 16113829N-(3,4-Dimethylisoxazol-5-yl)-4-(4-phenylpyridin-2-yl)piperazine-1-carboxamideYield 36.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl(3,4-dimethylisoxazol-5-yl)carbamate (120 mg, 0.418 mmol), 1-(4-phenylpyridin-2-yl)piperazine (100 mg, 0.418 mmol), diisopropylethylamine (0.146 ml, 0.836 mmol) and dimethylsulfoxide (2 ml) was stirred at 70° C. for 3 hours, then the reaction solution was poured into water, and extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduce pressure, and the residue was recrystallized from ethyl acetate to give the titled compound 58.0 mg (36.7%) as solid 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 away
  5. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-08f17b958e9048cdad5f8a7e894c92fa
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Reaction notes

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