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

HRID 1924570Notes

Reaction equation

HRID 1924570 reaction equation
[F:1][CH:2]([F:24])[O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[C:12]([C:17](=O)/[CH:18]=[CH:19]/[N:20](C)C)=[N:11]2)[CH:7]=[CH:8][CH:9]=1.[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([NH:34]N)=[CH:33][C:28]=2[O:27][CH2:26]1.N([O-])=O.[Na+].[Sn](Cl)Cl>>[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([N:34]3[C:17]([C:12]4[C:13](=[O:16])[CH:14]=[CH:15][N:10]([C:6]5[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH:2]([F:24])[F:1])[CH:5]=5)[N:11]=4)=[CH:18][CH:19]=[N:20]3)=[CH:33][C:28]=2[O:27][CH2:26]1

Participants

5

Reactant 4

HCID 24479Stannous ChlorideHCID 126584411,3-Benzodioxol-5-ylhydrazineHCID 23668193Sodium NitriteHCID 593700141-(3-Difluoromethoxy-phenyl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one

Product 1

HCID 593701723-(2-Benzo[1,3]dioxol-5-yl-2H-pyrazol-3-yl)-1-(3-difluoromethoxy-phenyl)-1H-pyridazin-4-oneYield 16%

Procedure

The product was obtained starting from 1-(3-Difluoromethoxy-phenyl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one (A-10) 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 in 16% yield. MS: M=425.2 (M+H)+

Workup

  1. customThe product was obtained

Sources & evidence

ORD record
ord-fe605f22d3804a54a919b127e1a3b22d
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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