Ethyl Acetate → Tert-butyl (r)-1-(6-(3-chlorophenylamino)pyridazin-3-ylaminocarbamoyl)ethylcarbamate

Participants

Reaction Steps

(Step 1-iii) N-(3-chlorophenyl)-6-hydrazinylpyridazin-3-amine (2.4 g, 10 mmol) was combined with Boc-D-Ala-OH (2.0 g, 10.5 mmol), HBTU (4.4 g, 11.6 mmol) in DMF and DIEA (2.0 mL (11.5 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours and poured into ethyl acetate/saturated sodium bicarbonate. The organic layer was dried over sodium sulfate, concentrated to an oil, and purified by silica gel column chromatography (EtOAc to 10% MeOH/EtOAc), to give the product, tert-butyl (R)-1-(6-(3-chlorophenylamino)pyridazin-3-ylaminocarbamoyl)ethylcarbamate (1.38 g, 3.4 mmol, 34%).

Provenance & Evidence