Stannous Chloride → 1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-3-[2-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2H-pyrazol-3-yl]-1H-pyridazin-4-one

HRID 1924643Notes

Reaction equation

HRID 1924643 reaction equation
[F:1][C:2]1([F:25])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]3[CH:16]=[CH:15][C:14](=[O:17])[C:13]([C:18](=O)/[CH:19]=[CH:20]/N(C)C)=[N:12]3)=[CH:10][C:4]=2[O:3]1.[F:26][C:27]1([F:38])[O:31][C:30]2[CH:32]=[CH:33][CH:34]=[C:35]([NH:36][NH2:37])[C:29]=2[O:28]1.N([O-])=O.[Na+].[Sn](Cl)Cl>>[F:25][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]3[CH:16]=[CH:15][C:14](=[O:17])[C:13]([C:18]4[N:36]([C:35]5[C:29]6[O:28][C:27]([F:26])([F:38])[O:31][C:30]=6[CH:32]=[CH:33][CH:34]=5)[N:37]=[CH:20][CH:19]=4)=[N:12]3)=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 4

HCID 24479Stannous ChlorideHCID 23668193Sodium NitriteHCID 55279040(2,2-Difluoro-benzo[1,3]dioxol-4-yl)hydrazineHCID 593701531-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one

Product 1

HCID 593699901-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-3-[2-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2H-pyrazol-3-yl]-1H-pyridazin-4-one

Procedure

The product was obtained starting from 1-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one (A-11) 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=475.0 (M+H)+

Workup

  1. customThe product was obtained

Sources & evidence

ORD record
ord-f31472b0190f41b9af675ffde91679b3
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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