Dimethyl Sulfoxide → 4-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-(pyrazin-2-yl)piperazine-1-carboxamide

HRID 2263072Notes

Reaction equation

HRID 2263072 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl.[C:16]1([C:22]2[N:26]=[C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[S:24][N: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[N:26]=[C:25]([N:27]3[CH2:32][CH2:31][N:30]([C:8]([NH:7][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)=[O:15])[CH2:29][CH2:28]3)[S:24][N:23]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 687774032,2,2-Trichloroethyl pyrazin-2-ylcarbamate

Product 1

HCID 445621834-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-(pyrazin-2-yl)piperazine-1-carboxamideYield 36.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trichloroethyl pyrazin-2-ylcarbamate (150 mg, 0.556 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (137 mg, 0.556 mmol), diisopropylethylamine (0.0968 ml, 0.556 mmol) and dimethylsulfoxide (3 ml) was stirred at 70° C. for 12 hours, the reaction mixture was poured into water and a solid was collected by filtration and washed with water. This was recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate to obtain the desired product (74.3 mg, 36.4%) as a solid.

Workup

  1. filtrationa solid was collected by filtration
  2. washwashed with water
  3. customThis was recrystallized from a mixed solvent of tetrahydrofuran and ethyl acetate

Sources & evidence

ORD record
ord-04b8e660f6a64747a568e25c9ece7002
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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