Potassium Carbonate → HCID 58355468, compound

Temperature

80 °C

6-Methoxy-1-(4-methoxybutyl)-2-(trichloromethyl)-1H-benzimidazole (1.42 g) was dissolved in acetonitrile-water (2:1, 150 ml), 1-tert-butyl 3-methyl (3R,5S)-5-{(2-methylpropyl)amino}piperidine-1,3-dicarboxylate (1.02 g) was added, potassium carbonate (5.5 g) was added and the mixture was stirred at 80° C. for 19 hr. The reaction mixture was concentrated under reduced pressure, acidified (pH3) with 6M hydrochloric acid, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-hexane (5:95)-ethyl acetate-ethyl acetate-methanol (85:15) was concentrated under reduced pressure. The residue was subjected to reversed-phase preparative HPLC, and a fraction eluted with water-acetonitrile (9:1-6:4) was collected, basified (pH 10) with saturated aqueous potassium carbonate solution, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the object product (460 mg).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. extractionextracted with ethyl acetate
3. dry with materialThe extract was dried over anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. washa fraction eluted with ethyl acetate-hexane (5:95)-ethyl acetate-ethyl acetate-methanol (85:15)
6. concentrationwas concentrated under reduced pressure
7. washa fraction eluted with water-acetonitrile (9:1-6:4)
8. customwas collected
9. extractionextracted with ethyl acetate
10. dry with materialThe extract was dried over anhydrous magnesium sulfate
11. concentrationconcentrated under reduced pressure

ORD record

ord-5e8ed090165e4612809c8056ea67a910

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08664380B2