Water → HCID 68777882, compound

HRID 2263150Notes

Reaction equation

[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10](=[O:17])OCC(Cl)(Cl)Cl)=[CH:5][CH:4]=1)#[N:2].[C:18]1([C:24]2[N:28]=[C:27]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[S:26][N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:1]([C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]([N:32]2[CH2:33][CH2:34][N:29]([C:27]3[S:26][N:25]=[C:24]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:28]=3)[CH2:30][CH2:31]2)=[O:17])=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,2,2-trichloroethyl (6-cyanopyridin-3-yl)carbamate (263 mg, 0.893 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and diisopropylethylamine (0.156 ml, 0.893 mmol) in dimethylsulfoxide (2.7 ml) was stirred at 70° C. for 3 hours. Water was poured into 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=3:7) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to obtain the desired product (26.1 mg, 8.2%) 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 (hexane:ethyl acetate=3:7)
customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record: ord-17c4a1646c864d0483c1a9a55f8ea543
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

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