Ammonium Chloride → HCID 118078852, compound

Temperature

80 °C

Iron powder (0.101 g, 1.811 mmol) was added to a solution of (S)-2-(6-bromo-4-nitropyridin-3-ylamino)propane-1-ol (0.050 g, 0.181 mmol) and ammonium chloride (2.422 mg, 0.045 mmol) in ethanol (2.0 mL) and water (0.7 mL). The reaction mixture was heated at 80° C. for 2 h. The mixture was cooled to room temperature and filtered through celite (washing with methanol). The filtrate was concentrated and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford (S)-2-(4-amino-6-bromopyridin-3-ylamino)propane-1-ol (0.028 g, 63%) as a purple solid. MS (ESI, pos. ion) m/z 246, 248.

1. temperatureThe mixture was cooled to room temperature
2. filtrationfiltered through celite (washing with methanol)
3. concentrationThe filtrate was concentrated
4. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
5. customThe aqueous phase was separated
6. extractionextracted with ethyl acetate
7. washThe combined organic phases were washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-5ef49d1cefb04426bffe5b82a55e45cd

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422281B2