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

HRID 1924631Notes

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]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=2)[N:8]=1)=O.[F:26][C:27]1([F:38])[O:31][C:30]2[CH:32]=[CH:33][CH:34]=[C:35]([NH:36]N)[C:29]=2[O:28]1.N([O-])=O.[Na+].[Sn](Cl)Cl>>[F:38][C:27]1([F:26])[O:31][C:30]2[CH:32]=[CH:33][CH:34]=[C:35]([N:36]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]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=5)[N:8]=4)=[CH:4][CH:3]=[N:2]3)[C:29]=2[O:28]1

Participants

Reactant 4

HCID 24479Stannous Chloride

HCID 23668193Sodium Nitrite

HCID 55279040(2,2-Difluoro-benzo[1,3]dioxol-4-yl)hydrazine

HCID 593701233-((E)-3-Dimethylamino-acryloyl)-1-(3-trifluoromethoxy-phenyl)-1H-pyridazin-4-one

Product 1

HCID 593701743-[2-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-2H-pyrazol-3-yl]-1-(3-trifluoromethoxy-phenyl)-1H-pyridazin-4-one

Procedure

The product was obtained starting from 3-((E)-3-Dimethylamino-acryloyl)-1-(3-trifluoromethoxy-phenyl)-1H-pyridazin-4-one (A-6) 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=479.1 (M+H)+

Workup

customThe product was obtained

Sources & evidence

ORD record: ord-0ed5d642eaeb48ecb945f03e0ae20841
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178538B2

Reaction notes

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