4-Methylmorpholine → HCID 67211349, compound

(E)-[2-(2-Propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetic acid (80 mg, 0.189 mmol) obtained in Example 2 was dissolved in 1,2-dimethoxyethane (0.7 mL), N-methylmorpholine (62 μL, 0.567 mmol) and isobutyl chlorocarbonate (49 μL, 0.378 mmol) were added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered, and the filtrate was added to a solution (0.6 mL) of sodium borohydride (36 mg, 0.945 mmol) in water at 0° C., and the mixture was stirred for 10 min. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=95/5) to give the title compound (compound 13) (43 mg, 55%).

1. filtrationThe reaction mixture was filtered
2. stirringthe mixture was stirred for 10 min
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=95/5)

ORD record

ord-76dc073a0116482483f33c1eef30e71b

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486980B2