Water → N-[6-(Acetylamino)pyridin-3-yl]-4-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide

HRID 2263173

Reaction equation

[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:20][C:21]1[S:25][C:24]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[N:23][C:22]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]([N:29]2[CH2:30][CH2:31][N:26]([C:24]3[S:25][C:21]([CH3:20])=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:23]=3)[CH2:27][CH2:28]2)=[O:19])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,2,2-trichloroethyl [6-(acetylamino)pyridin-3-yl]carbamate (277 mg, 0.848 mmol), 1-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine (200 mg, 0.771 mmol) and diisopropylethylamine (0.148 ml, 0.848 mmol) in dimethylsulfoxide (2.6 ml) was stirred at 70° C. for 18 hours. 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. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 161 mg (47.8%) of the desired product as a solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate)
customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record: ord-37c81f786d24455b9f77d935f0c91186
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Linked notes

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