Methanesulfonyl chloride → Methyl 3-cyanopyridine-2-carboxylate
Reaction equation
N1C2C=NNC(=O)C=2C=C[CH:2]=1.[C:12]([C:15]1[C:16]([C:21]([OH:23])=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1)(=O)[NH2:13].CS(Cl)(=O)=O>>[C:12]([C:15]1[C:16]([C:21]([O:23][CH3:2])=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1)#[N:13]Participants
4
Procedure
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.
Sources & evidence
- ORD record
- ord-cf851168bb56480c8f65c0bd05527a21
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06924284B2
Reaction notes
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