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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence