Ethanol → HCID 178521009, compound

Temperature

110 °C

Into a tube was added 6-(trifluoromethyl)picolinaldehyde (150 mg, 0.47 mmol), (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (Intermediate 1, Step 3) (82.2 mg, 0.47 mmol), sodium dithionite (310.7 mg, 1.78 mmol), ethanol (10 mL) and water (1.5 mL). The vessel was sealed and the reaction mixture was stirred at 110° C. for 16 h. The solvent was evaporated under reduced pressure and water was added to the resulting residue. The mixture was extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified via preparative TLC to afford the title compound (50 mg, 29%) as a yellow solid. MS (ES+APCI) (M+H) 445.2; LCMS retention time 2.657 min (Method G).

1. customThe vessel was sealed
2. customThe solvent was evaporated under reduced pressure and water
3. additionwas added to the resulting residue
4. extractionThe mixture was extracted with ethyl acetate
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe crude material was purified via preparative TLC

ORD record

ord-06039163eacd4e4caa0ef925887c43c4

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296745B2