Ammonia → Aminobenzodiazepine

温度

-78 °C

Ammonia (500 mL) was condensed with a dry ice condenser and maintained at −78° C. To this was added a solution of 6 (35 g, 91 mmol) in CH2Cl2 (600 mL). After 8 h, the dry ice condenser was removed and the reaction was warmed to room temperature allowing the ammonia to evaporate. The remaining solution was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a white solid. This solid was dissolved in EtOH (500 mL) and AcOH (15 mL), and the resulting solution was refluxed for 24 h, and concentrated to yield a yellow-red oil. Addition of Et2O (300 mL) to this oil resulted in the precipitation of 8 (13 g, 47%) as a white powder: 1H NMR (300 MHz, CDCl3) δ 9.32 (s, 1H), 7.83-7.05 (m, 8H), 4.39 (s, 2H); ESI MS m/z=305 [C15H11F3N2O+H]+.

1. customcondensed with a dry ice condenser
2. customthe dry ice condenser was removed
3. temperaturethe reaction was warmed to room temperature
4. customto evaporate
5. washThe remaining solution was washed with brine
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customto yield a white solid
10. concentrationconcentrated
11. customto yield a yellow-red oil

ORDレコード

ord-67b8c49e26864c489a8ef105cd7d10f5

出典データセット

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07456278B2