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

HRID 2263166Notes

Reaction equation

[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([NH:10][C:11](=[O:18])OCC(Cl)(Cl)Cl)=[N:5]2.[C:19]1([C:25]2[N:26]=[C:27]([N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[S:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O.C(OCC)(=O)C>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([NH:10][C:11]([N:33]1[CH2:34][CH2:35][N:30]([C:27]3[S:28][CH:29]=[C:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:26]=3)[CH2:31][CH2:32]1)=[O:18])=[N:5]2

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,2,2-trichloroethyl imidazo[1,2-b]pyridazin-6-ylcarbamate (198 mg, 0.408 mmol), 1-(4-phenyl-1,3-thiazol-2-yl)piperazine (200 mg, 0.815 mmol) and diisopropylethylamine (0.076 ml, 0.408 mmol) in dimethylsulfoxide (2.7 ml) was stirred at 70° C. for 15 hours. Water was poured into the reaction solution, and the mixture was exacted 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 recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 110 mg (66.5%) of the desired product as a solid.

Workup

washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record: ord-18d5184949fa4b83b40c7825b7ab8da9
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

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