Hydrochloric Acid → HCID 178503159, compound

HRID 1882072Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([C:19]2[N:23](COCC[Si](C)(C)C)[C:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[N:21][C:20]=2[I:38])(O)[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].Cl.C(=O)([O-])O.[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4](/[C:10](/[C:19]2[NH:23][C:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[N:21][C:20]=2[I:38])=[CH:11]\[CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH:5]=[CH:6][C:7]=1[S:8][CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-[3-chloro-4-(methylsulfanyl)phenyl]-1-(4-iodo-2-(pyridin-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-5-yl)-2-(tetrahydro-2H-pyran-4-yl)ethanol (0.520 g) in ethanol (10 mL) was added 3M hydrochloric acid (10 mL), and the mixture was stirred at 80° C. for 1.5 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-60:40, volume ratio) to give the title compound (0.343 g, yield 84%) as a colorless oil. MS: 358 (MH+).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed successively with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-60:40, volume ratio)

Sources & evidence

ORD record: ord-29e02711b2464dcd8d9a3e86cf253e1b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318746B2

Reaction notes

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