Hydrochloric Acid → HCID 178525463, compound

Participants

Reaction Conditions

Reaction Steps

To (Z)-5-((5-(5-chloro-2-fluorophenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)-3-(hydroxymethyl)imidazolidine-2,4-dione (100 mg, 0.218 mmol) in pyridine (4.5 mL) was added glutaric anhydride (125 mg, 1.095 mmol), and DMAP (3 mg, 0.022 mmol). The reaction mixture was stirred at 75° C. overnight after which the reaction was not complete. Added glutaric anhydride (125 mg, 1.095 mmol) and DMAP (3 mg, 0.022 mmol) and stirred an additional 16 hours at 75° C. Cooled to 0° C. in ice bath and added 6M HCl until pH was less than 3 by pH paper. Filtered off the solid and washed with 0.1M HCl. Dried under vacuum to provide 40 mg (32%) of (Z)-5-((4-((5-(5-chloro-2-fluorophenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)-2,5-dioxoimidazolidin-1-yl)methoxy)-5-oxopentanoic acid as a yellow solid. LCMS (ES): >95% pure, m/z 572 [M+1]+.

Provenance & Evidence