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

HRID 1924636Notes

Reaction equation

HRID 1924636 reaction equation
[F:1][CH:2]([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([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:6][CH:5]=1.[F:25][C:26]1([F:37])[O:30][C:29]2[CH:31]=[CH:32][CH:33]=[C:34]([NH:35]N)[C:28]=2[O:27]1.N([O-])=O.[Na+].[Sn](Cl)Cl>>[F:37][C:26]1([F:25])[O:30][C:29]2[CH:31]=[CH:32][CH:33]=[C:34]([N:35]3[C:17]([C:12]4[C:13](=[O:16])[CH:14]=[CH:15][N:10]([C:7]5[CH:8]=[CH:9][C:4]([O:3][CH:2]([F:24])[F:1])=[CH:5][CH:6]=5)[N:11]=4)=[CH:18][CH:19]=[N:20]3)[C:28]=2[O:27]1

Participants

5

Reactant 4

HCID 24479Stannous ChlorideHCID 23668193Sodium NitriteHCID 55279040(2,2-Difluoro-benzo[1,3]dioxol-4-yl)hydrazineHCID 593699781-(4-Difluoromethoxy-phenyl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one

Product 1

HCID 593701183-[2-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-2H-pyrazol-3-yl]-1-(4-difluoromethoxy-phenyl)-1H-pyridazin-4-one

Procedure

The product was obtained starting from 1-(4-Difluoromethoxy-phenyl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one (A-9) and 2,2-difluoro-benzo[1,3]dioxol-4-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. MS: M=461.3 (M+H)+

Workup

  1. customThe product was obtained

Sources & evidence

ORD record
ord-2ffda8a806f2470abdc341e2934a1979
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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