Methanesulfonyl chloride → Methyl 3-cyanopyridine-2-carboxylate

Participants

Reaction Steps

Using a procedure similar to that described for 6H-pyrido[2,3-d]pyridazin-5-one derivatives (Examples 5), 3-carbamoylpicolinic acid (1.5 mmol) was reacted with excess MsCl (4.0 mmol) to yield methyl 3-cyanopicolinate (1.2 mmol). Methyl 3-cyanopicolinate (1.2 mmol), Sc(OTf)3 (0.02 mmol), and diaminopropane (3.0 mmol) were combined and heated at 80° C. for 1 h to yield 7.8-dihydro-6H-1,5,8a-triaza-fluoren-9-one, which was treated with excess hydrazine hydrate (5.0 mmol) in EtOH at RT to yield compound 5-(3-amino-propylamino)-7H-pyrido[2,3-d]pyrido[2,3-d]pyridazin-8-one (0.75 mmol) as a yellow solid.

Provenance & Evidence