Water → HCID 11683189, compound

Temperature

55 °C

The compound (250.4 mg, 0.62 mmol) prepared in Example 35 was treated with a saturated sodium bicarbonate solution to obtain 1-benzyl-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-c]pyridine (216.8 mg, 0.59 mmol). A mmonium cerium (IV) nitrate (973 mg, 1.77 mmol) was added at room temperature to a solution of 1-benzyl-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-c]pyridine (216.8 mg, 0.59 mmol) in acetic acid (3 ml) and then stirred for 4 hours at 55° C. The reaction mixture was cooled to room temperature, added to water, and then extracted with ethyl acetate. The separated organic layer was washed with a saturated sodium chloride solution, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was dissolved in methanol (10 ml). 2N Lithium hydroxide (2.5 ml) was added to the reaction mixture, which was then stirred for 1 hour at room temperature. The reaction mixture was neutralized with IN hydrochloride, concentrated under reduced pressure, and then extracted with ethyl acetate. The separated organic layer was dried on anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography to give 1-benzyl-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-3-hydroxymethyl-2-methyl-1H -pyrrolo[3,2-c]pyridine, which was then dissolved in 10 ml of ethyl acetate and saturated with hydrochloric acid gas. The resulting precipitate was filtered to give the titled compound as a white solid (200 mg, 76.8%).

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionextracted with ethyl acetate
3. washThe separated organic layer was washed with a saturated sodium chloride solution
4. dry with materialdried on anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe resulting residue was dissolved in methanol (10 ml)
7. addition2N Lithium hydroxide (2.5 ml) was added to the reaction mixture, which
8. stirringwas then stirred for 1 hour at room temperature
9. concentrationconcentrated under reduced pressure
10. extractionextracted with ethyl acetate
11. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customThe resulting residue was purified with silica gel column chromatography

ORD record

ord-55b9ea77748c4a93a6cd63e2f57c0a9c

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07541366B2