Dicyclohexylcarbodiimide → HCID 86732191, Verbindung

(2S,4S)-4-amino-4-(5-bromo-2-fluoropyridin-3-yl)-1,1,1,5-tetrafluoropentan-2-ol (2.83 g, 8.11 mmol) in MeCN (70 mL) was added benzoyl isothiocyanate (1.20 ml, 8.92 mmol) and the mixture was stirred at room temperature for 1 h. N,N′-dicyclohexylcarbodiimide (1.840 g, 8.92 mmol) and diisopropylethylamine (2.82 ml, 16.21 mmol) were added. The mixture was stirred at 50° C. for 7 h. The reaction was worked up with water and EtOAc. The separated organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography using a gradient of 0-25% EtOAc/hexane to give N-((4S,6S)-4-(5-bromo-2-fluoropyridin-3-yl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (2.27 g, 4.75 mmol, 58.6% yield). MS m/z=479.8 [M+H]+. Calculated for C18H13BrF5N3O2: 478.2.

1. stirringThe mixture was stirred at 50° C. for 7 h
2. washThe separated organic layer was washed with brine
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude material was purified by column chromatography

ORD-Eintrag

ord-bbdd2d1e83284f80ac2517ebe6f5ef7c

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09296734B2