Water → HCID 11597600, compound

HRID 2263309Notes

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.[F:17][C:18]([F:37])([F:36])[C:19]1[CH:20]=[C:21]([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:22]=[CH:23][CH:24]=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:33]2[CH2:34][CH2:35][N:30]([C:27]3[S:28][CH:29]=[C:25]([C:21]4[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:37])([F:17])[F:36])[CH:20]=4)[N:26]=3)[CH2:31][CH2:32]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 (154 mg, 0.536 mmol), 1-[4-(3-trifluoromethylphenyl)-1,3-thiazol-2-yl]piperazine (150 mg, 0.487 mmol) and diisopropylethylamine (0.170 ml, 0.974 mmol) in dimethyl sulfoxide (2.0 ml) was stirred at 70° C. for 15 hours. 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 (hexane:ethyl acetate=1:1), and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 94.8 mg (43.1%) of the desired product as a solid. mp 230-231° 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 (hexane:ethyl acetate=1:1)
customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record: ord-ba6fc75c42e14ef090278ee029cbb25f
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

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