Water → 4-[4-(2,3-Dichlorophenyl)-1,3-thiazol-2-yl]-N-(3,4-dimethylisoxazol-5-yl)piperazine-1-carboxamide

HRID 2263323Notes

Reaction equation

[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][C:9](=[O:16])OCC(Cl)(Cl)Cl)[O:4][N:3]=1.[Cl:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[C:25]1[N:26]=[C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[S:28][CH:29]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[Cl:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[C:25]1[N:26]=[C:27]([N:30]2[CH2:35][CH2:34][N:33]([C:9]([NH:8][C:5]3[O:4][N:3]=[C:2]([CH3:1])[C:6]=3[CH3:7])=[O:16])[CH2:32][CH2:31]2)[S:28][CH:29]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,2,2-trichloroethyl (3,4-dimethylisoxazol-5-yl)carbamate (121 mg, 0.420 mmol), 1-[4-(2,3-dichlorophenyl)-1,3-thiazol-2-yl]piperazine (120 mg, 0.382 mmol) and diisopropylethylamine (0.133 ml, 0.764 mmol) in dimethyl sulfoxide (1.2 ml) was stirred at 70° C. for 3 days. Water was poured to the reaction mixture, 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:hexane=1:1), and recrystallized from a mixed solvent of hexane and ethyl acetate to give 27.0 mg (15.6%) of the desired product as a solid. mp 175-176° C.

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:hexane=1:1)
customrecrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record: ord-390c0a7f7ce6464a9c19ec86e85b21f4
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

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