Hydrochloric Acid → HCID 178442240, compound

HRID 216413Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

Hydrogen chloride (4 M in 1,4-dioxane) (1 mL, 4 mmol) was added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-{2-fluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (ca. 10 mg, 0.02 mmol) in methanol (2 mL). After stirring at 70° C. for 1 h, volatiles were removed. The residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride then with 0-100% ethyl acetate/hexane afforded the title compound. LCMS: 386 (M+H).

Workup

customvolatiles were removed
customThe residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide
extractionThe aqueous phase was extracted with ethyl acetate
dry with materialThe combined organic extracts were dried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e48424847c6a4f0b9b038ea96c0b8e0f
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193228B2

Reaction notes

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