Triethylamine → (R)-(1-(2-(6-(3-Hydroxyoxetan-3-yl)pyridin-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

Temperature

110 °C

Into a flask was added 6-(3-hydroxyoxetan-3-yl)picolinaldehyde (54 mg, 0.30 mmol), (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (Intermediate 1, Step 3) (76 mg, 0.24 mmol) and ethanol (1.2 mL). Then sodium dithionate (0.20 g, 1.2 mmol), triethylamine (82 μL, 0.59 mmol) and water (1.0 mL) were added. The solution was heated to 110° C. for 18 h. The mixture was cooled to room temperature and diluted with ethyl acetate. The mixture was washed with water, washed with a saturated aqueous solution of ammonium chloride, washed with a saturated aqueous solution of sodium bicarbonate and washed with brine. The organics were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was dried under high vacuum to give a green oil which was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 448.9; HPLC retention time 1.89 min (Method A).

1. temperatureThe mixture was cooled to room temperature
2. washThe mixture was washed with water
3. washwashed with a saturated aqueous solution of ammonium chloride
4. washwashed with a saturated aqueous solution of sodium bicarbonate
5. washwashed with brine
6. dry with materialThe organics were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was dried under high vacuum
10. customto give a green oil which
11. customwas purified via HPLC

ORD record

ord-f881a111a9e14922b9d4cbfd0d41c688

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296745B2