Hydrochloric Acid → HCID 57785957, compound
Reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23](C(O[Si](C(C)(C)C)(C)C)C([O-])=O)[CH2:24][CH3:25])=[CH:4][CH:3]=1.Cl.[C:39](=[O:42])([O-])[OH:40].[Na+].[O:44]1CCC[CH2:45]1>>[OH:44][CH2:45][C:39]([O:40][CH:23]([C:5]1[C:6]2[N:7]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[C:8]3=[N:9][C:10]=2[C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:24][CH3:25])=[O:42]Participants
Procedure
To a solution of 1-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propyl{[tert-butyl(dimethyl)silyl]oxy}acetate (137.1 mg, 0.235 mmol) in tetrahydrofuran (5.0 mL) was added 1N hydrogen chloride (1.0 mL, 1.0 mmol) at room temperature. The mixture was stirred at room temperature for 1 hr. Aqueous sodium hydrogen carbonate (4.0 mL) was added to the reaction mixture at room temperature and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture and recrystallization from ethyl acetate/n-hexane to give the title compound (88.0 mg, 0.188 mmol, 80%) as colorless crystals.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture and recrystallization from ethyl acetate/n-hexane
Sources & evidence
- ORD record
- ord-fafb3428eadf4cacb3836c8c7fc18077
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901141B2
Reaction notes
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