Stannous Chloride → 3-(2-Benzo[1,3]dioxol-5-yl-2H-pyrazol-3-yl)-1-(3-fluoro-phenyl)-1H-pyridazin-4-one

HRID 1924585Notes

Reaction equation

HRID 1924585 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[N:8]=1)=O.[O:22]1[C:26]2[CH:27]=[CH:28][C:29]([NH:31]N)=[CH:30][C:25]=2[O:24][CH2:23]1.N([O-])=O.[Na+].[Sn](Cl)Cl>>[O:22]1[C:26]2[CH:27]=[CH:28][C:29]([N:31]3[C:5]([C:7]4[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]5[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=5)[N:8]=4)=[CH:4][CH:3]=[N:2]3)=[CH:30][C:25]=2[O:24][CH2:23]1

Participants

5

Reactant 4

HCID 24479Stannous ChlorideHCID 126584411,3-Benzodioxol-5-ylhydrazineHCID 23668193Sodium NitriteHCID 593699513-((E)-3-Dimethylamino-acryloyl)-1-(3-fluoro-phenyl)-1H-pyridazin-4-one

Product 1

HCID 593701103-(2-Benzo[1,3]dioxol-5-yl-2H-pyrazol-3-yl)-1-(3-fluoro-phenyl)-1H-pyridazin-4-one

Procedure

The product was obtained starting from 3-((E)-3-Dimethylamino-acryloyl)-1-(3-fluoro-phenyl)-1H-pyridazin-4-one (A-13) and benzo[1,3]dioxol-5-yl-hydrazine (prepared from the corresponding amino derivative using sodium nitrite and tin(II) chloride as described in J. Med. Chem. 2003, 46, 4676-4686) according to the method described for example 91.

Workup

  1. customThe product was obtained

Sources & evidence

ORD record
ord-d435778fce2649ee97e3b5594586c4c4
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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