Hydrazine → HCID 20300086, compound
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.[NH2:16][NH2:17]>>[NH:16]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1)[NH2:17]Participants
Procedure
Compounds of this invention can be prepared as illustrated by the exemplary reaction in Scheme 2. Coupling of a 2,5-dihalopyridine, such as 5-bromo-2-chloropyridine, with a substituted phenylboronic acid, such as 4-methoxyphenylboronic acid, in the presence of a palladium catalyst, such as tetrakis(triphenylphosphine)palladium, produced 2-chloro-5-(4-methoxyphenyl)pyridine. Reaction of 2-chloro-5-(4-methoxyphenyl)pyridine with hydrazine produced 2-hydrazinyl-5-(4-methoxyphenyl)pyridine. Reaction of 2-hydrazinyl-5-(4-methoxyphenyl)pyridine with a substituted benzoic acid, such as 4-chloro-2-methoxybenzoic acid, in the presence of coupling agents, such as BOP (benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate) and NMM (N-methylmorpholine), produced 4-chloro-2-methoxy-N-(5-(4-methoxyphenyl)pyridin-2-yl)-benzohydrazide. Treatment of 4-chloro-2-methoxy-N-(5-(4-methoxyphenyl)pyridin-2-yl)-benzohydrazide with phosphorus oxychloride produced the cyclized product 3-(4-chloro-2-methoxyphenyl)-6-(4-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine, which can be converted into a salt by treatment with HCl in ethyl acetate.
Sources & evidence
- ORD record
- ord-3dd5ece677f04ff9b50afe0f88356c05
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199983B2
Reaction notes
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