Diisopropylethylamine → HCID 58015499, compound

Participants

Reaction Conditions

Reaction Steps

(2R)—N′-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide HATU (9.0 g, 24 mmol), (R)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanoic acid hydrochloride and 1-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)hydrazine (3.6 g, 17 mmol) were taken up in acetonitrile (52 ml, 0.3 M) and cooled to 0° C. DIPEA (8.2 ml, 47 mmol) was added dropwise and the reaction was allowed to stir to room temperature for 30 minutes until complete by LCMS. The crude material was concentrated onto silica gel and then purified via MPLC eluting with 100% DCM to 90% DCM:10% MeOH:1% NH4OH to yield (2R)—N′-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide (4.927 g, 77% yield).

Provenance & Evidence