Water → N-(6-Chloroimidazo[1,2-b]pyridazin-2-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2263152Notes

Reaction equation

HRID 2263152 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)[N:10]=2)[N:7]=1.[C:20]1([C:26]2[N:30]=[C:29]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[S:28][N:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([N:34]3[CH2:35][CH2:36][N:31]([C:29]4[S:28][N:27]=[C:26]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[N:30]=4)[CH2:32][CH2:33]3)=[O:19])[N:10]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 866255022,2,2-Trichloroethyl (6-chloroimidazo[1,2-b]pyridazin-2-yl)carbamate

Product 1

HCID 86625503N-(6-Chloroimidazo[1,2-b]pyridazin-2-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideYield 46.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,2,2-trichloroethyl (6-chloroimidazo[1,2-b]pyridazin-2-yl)carbamate (700 mg, 2.04 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (456 mg, 1.85 mmol) and diisopropylethylamine (0.355 ml, 2.04 mmol) in dimethylsulfoxide (6.2 ml) was stirred at 70° C. for 1 day. Water was poured into the reaction solution, and the mixture 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 added to the residue, and a solid was separated by filtration, which was recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 380 mg (42.3%) of the desired product as a solid.

Workup

  1. extractionthe mixture 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 added to the residue
  6. customa solid was separated by filtration, which
  7. customwas recrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-f05635d9559b4c6bbeaa95bba1176a69
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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