Hydrochloric Acid → HCID 178503158, compound

HRID 1882074Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-[3-chloro-4-(methylsulfanyl)phenyl]-1-(4-chloro-2-(pyridin-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-5-yl)-2-(tetrahydro-2H-pyran-4-yl)ethanol (1.47 g) in ethanol (40 mL) was added 3M hydrochloric acid (40 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=30:70-80:20, volume ratio) to give the title compound (1.10 g, yield 100%) as a colorless amorphous solid. MS: 446 (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=30:70-80:20, volume ratio)

Sources & evidence

ORD record: ord-40ee5d3bb2724a11a197ca59a6751716
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318746B2

Reaction notes

Loading…