Reaction equation
[S:1]([NH2:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].[N:12]([O-])=O.[Na+].Cl.[Sn](Cl)[Cl:18]>>[CH:7]1[C:6]([NH:9][NH2:12])=[CH:5][CH:4]=[C:3]([S:1]([NH2:11])(=[O:10])=[O:2])[CH:8]=1.[ClH:18]Participants
Procedure
a Celecoxib Analog: Compound 30c, 3-[1-{p-(Sulfonamido)phenyl}-5-p-tolyl-1H-pyrazol-3-yl]propanoic acid., was synthesized by the method depicted in FIG. 2. Briefly, 4′-methylacetophenone and succinnic hydride were reacted in the presence of lithium diisopropanolamine (LDA) and tetrahydrofuran (THF) for 1 hour at −78° C. to produce p-tolyl-4,6-dioxohexanoic acid as a white solid (66% yield). Also sulfanilamide has reacted with sodium nitrite (NaNO2) and concentrated hydrochloric acid at 0-4° C. for 30 minutes, after which tin(II) chloride (SnCl2) was added and the reaction allowed to continue for an additional 4 hours at 0° C. to produce 4-sulfonamidophenylhydrazine hydrochloride as a pale yellow solid (55% yield). The 4,6,dioxo-6-p-tolylhexanoic acid and the 4-sulfonamidophenylhydrazine hydrochloride were then complexed for 16 hours at room temperature in the presence of triethanolamine (TEA) in methanol to produce Compound 30c as a yellow solid (76% yield).
Sources & evidence
- ORD record
- ord-71dc152e54a64201b2053bf3e0715fa6
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07736624B2
Linked notes
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