Dicyclohexylcarbodiimide → HCID 71007254, compound

Participants

Reaction Conditions

Reaction Steps

N-(4-((3S)-3-amino-1-piperidinyl)-3-pyridinyl)-6-(3-fluoro-2-pyridinyl)[1,2,4]triazolo[4,3-b]pyridazin-3-amine. A mixture of (S)-tert-butyl (1-(3-isothiocyanatopyridin-4-yl)piperidin-3-yl)carbamate (193 mg, 0.58 mmol, Preparation XI) and 3-(3-fluoropyridin-2-yl)-6-hydrazinylpyridazine (113 mg, 0.551 mmol) in ACN (2 mL) was heated at 85° C. for 30 min. After the reaction mixture was cooled to RT, it was treated with DCC (125 mg, 0.60 mmol) and heating was resumed at 90° C. for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (50-100% EtOAc in DCM followed by 1-10% MeOH in EtOAc) to provide (S)-tert-butyl (1-(3-((6-(3-fluoropyridin-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)amino)pyridin-4-yl)piperidin-3-yl)carbamate (250 mg, 90% yield) as a dark green crystalline solid. MS (ESI, pos. ion) m/z: 506.0 (M+1).

Provenance & Evidence