Methanol → HCID 77106562, Verbindung

BF3Et2O in THF (47-49%) (0.70 mL, 2.34 mmol) was added to a solution of [3-[6-amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-5-chloro-phenyl]-morpholino-methanone (200 mg, 0.46 mmol) in THF (10.0 mL) at 0° C., then reaction mixture was stirred for 30 min, added NaBH4 (89 mg, 2.36 mmol) at 0° C., reaction mixture was slowly warmed to RT, stirred for 16 h. Reaction mixture was cooled to 0° C., added MeOH (5.0 mL) to the reaction mixture, heated to 70° C. for 2 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×30 mL). Combined organic layers was dried over Na2SO4 and concentrated under reduced pressure. Crude product was purified by silica (100-200 mesh) column eluted with 2% MeOH in DCM to afford 39 mg (Yield: 20.2%) of the title compound. This was converted to its HCl salt by using HCl in ether (2M) to afford 45 mg as a pale gray solid.

1. customreaction mixture
2. customreaction mixture
3. stirringstirred for 16 h
4. customReaction mixture
5. temperaturewas cooled to 0° C.
6. temperatureheated to 70° C. for 2 h
7. extractionextracted with ethyl acetate (2×30 mL)
8. dry with materialCombined organic layers was dried over Na2SO4
9. concentrationconcentrated under reduced pressure
10. customCrude product was purified by silica (100-200 mesh) column
11. washeluted with 2% MeOH in DCM

ORD-Eintrag

ord-eecb26df08454409869dab57a917fc90

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09393248B1