Methanol → HCID 117925890, compound
Reaction equation
N1C=CC=C([C:7]([O:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=O)C=1.[Li].[CH3:19][OH:20]>>[N:12]1[CH:13]=[CH:14][CH:15]=[C:16]([C:19]([C:16]2[C:11]([C:10]([O:9][CH3:7])=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:20])[CH:11]=1Participants
Procedure
Synthetic Scheme 6 is yet another method of regiospecific synthesis of the methyl 3-picolinoylpicolinate 7 and 5-(pyridin-2-yl)pyrido[2,3-d]pyridazin-8(7H)-one 9. N,N-diethylpicolinamide 14, prepared as in Synthetic Scheme 5, is reacted with 1 equiv of sec-butyl lithium, and, without isolation of the lithiated intermediate, a second equivalent of N,N-diethylpicolinamide 14 is added to the reaction mixture, resulting in the condensation reaction yielding lithium 3-picolinoylpicolinate 16. Lithium 3-picolinoylpicolinate 16 is reacted with methanol to yield the methyl ester, methyl 3-picolinoylpicolinate 7, which is then reacted with hydrazine to yield 5-(pyridin-2-yl)pyrido[2,3-d]pyridazin-8(7H)-one 9. The pyridazinone 9 can be converted to the various ketone-Rilyazines 11, and then to the corresponding thione-Rilyazines 13 similarly to the methods shown in Scheme 4.
Sources & evidence
- ORD record
- ord-844bf245029f44fd9d0b0a126f0625fb
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394299B2
Reaction notes
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