Hydrochloric Acid → HCID 54760983, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of N-(4-(3-(5-(tert-butyl)isoxazol-3-yl)ureido)phenyl)-6-((1,3-dioxoisoindolin-2-yl)methyl)picolinamide (60 mg, 0.11 mmol) from Step 1 of this example in ethanol was heated at 70° C. until a clear solution was observed. Hydrazine hydrate (0.1 mL) was then added, the resulting mixture was heated at 70° C. for 1 h. The reaction mixture was cooled to 0° C. and filtered through celite. The filtrate was concentrated under reduced pressure, and the crude residue was purified by preparative TLC, eluting with MeOH in DCM (10:1, v:v). The compound obtained was treated with 2N HCl in Et2O to form the corresponding hydrochloric acid salt. The salt was washed with cold water and dried in a vacuum oven to afford 6-(aminomethyl)-N-(4-(3-(5-(tert-butyl)isoxazol-3-yl)ureido)phenyl)picolinamide hydrochloride (8 mg, 16%). LC-MS (ESI) m/z 409 (M+H)+.

Provenance & Evidence