Ethanol → HCID 178521014, compound

Temperature

120 °C

To a solution of (R)-(1-(4-amino-5-nitropyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (0.5 g, 1.5 mmol) in a mixture of ethanol and water were added 5-bromonicotinaldehyde (0.35 g, 1.6 mmol) and sodium dithionate (1.1 g, 5.9 mmol). The reaction mixture was heated to 120° C. for 16 h. The reaction mixture was concentrated and partitioned between water and ethyl acetate. The organics were concentrated under reduced pressure and the resulting crude was purified via preparative TLC to afford (R)-(1-(2-(5-bromopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (400 mg, 60%).

1. concentrationThe reaction mixture was concentrated
2. custompartitioned between water and ethyl acetate
3. concentrationThe organics were concentrated under reduced pressure
4. customthe resulting crude was purified via preparative TLC

ORD record

ord-e8fd26ce69f34352b461988a968b53c9

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296745B2