Water → N-(3,4-Dimethylisoxazol-5-yl)-4-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide

HRID 2263171Notes

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

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,2,2-trichloroethyl (3,4-dimethylisoxazol-5-yl)carbamate (244 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 5 hours. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and ethyl acetate to give 186 mg (60.8%) of the desired product as a solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and dried anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was recrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record: ord-562fafa39af545aeba84c65415fdb8fc
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

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