(4-Methoxyphenyl)hydrazine → HCID 21919803, compound

HRID 1244541Notes

Reaction equation

HRID 1244541 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[O:11]=[C:12]1[C:17](=O)[CH:16]([C:19](=O)[C:20]([F:23])([F:22])[F:21])[CH2:15][CH2:14][N:13]1[C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[O:11])[N:13]([C:25]4[CH:26]=[CH:27][C:28]([C:29]#[N:30])=[CH:31][CH:32]=4)[CH2:14][CH2:15][C:16]=3[C:19]([C:20]([F:23])([F:21])[F:22])=[N:10]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 77023(4-Methoxyphenyl)hydrazineHCID 21919788HCID 21919788, compound

Product 1

HCID 21919803HCID 21919803, compound

Procedure

Condensation of 4-methoxyphenylhydrazine with 4-[2,3-dioxo-4-(2,2,2-trifluoro-acetyl)-piperidin-1-yl]-benzonitrile afforded the desired intermediate 4-[1-(4-methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-benzonitrile. This intermediate was dissolved in anhydrous methanol and HCl gas was bubbled through for 15 min. The reaction mixture was stirred at room temperature for 18 h and concentrated. The residue was re-dissolved in methanol and 2 equivalents of N-methyl-ethylenediamine were added. The reaction mixture was stirred at room temperature for 18 h and concentrated. Pure product was obtained via reverse phase HPLC. ESI mass spectrum 470 (M+H)+.

Sources & evidence

ORD record
ord-824ff51d0f05441aa1dcfbd828746bb5
Source dataset
uspto-grants-2006_10
Patent number
US07122557B2

Reaction notes

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