Dimethyl Sulfoxide → 4-(4-Phenylpyridin-2-yl)-N-pyridazin-3-ylpiperazine-1-carboxamide

HRID 1158711

Reaction equation

HRID 1158711 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[N:2]=1.[C:16]1([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:16]1([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([N:28]3[CH2:33][CH2:32][N:31]([C:8]([NH:7][C:3]4[N:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:15])[CH2:30][CH2:29]3)[CH:23]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 22640117HCID 22640117, compoundHCID 685766982,2,2-Trichloroethyl pyridazin-3-ylcarbamate

Product 1

HCID 161139284-(4-Phenylpyridin-2-yl)-N-pyridazin-3-ylpiperazine-1-carboxamideYield 46.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl pyridazin-3-ylcarbamate (113 mg, 0.418 mmol), 1-(4-phenylpyridin-2-yl)piperazine (75.0 mg, 0.313 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 52.0 mg (46.0%) 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-b9f66ac5b406430fb3098a300e5cd3f2
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Linked notes

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