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

HRID 1924587Notes

Reaction equation

HRID 1924587 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N:10]3[CH:15]=[CH:14][C:13](=[O:16])[C:12]([C:17](=O)/[CH:18]=[CH:19]/[N:20](C)C)=[N:11]3)[C:4]=2[O:3][CH2:2]1.[O:24]1[C:28]2[CH:29]=[CH:30][C:31]([NH:33]N)=[CH:32][C:27]=2[O:26][CH2:25]1.N([O-])=O.[Na+].[Sn](Cl)Cl>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N:10]3[CH:15]=[CH:14][C:13](=[O:16])[C:12]([C:17]4[N:33]([C:31]5[CH:30]=[CH:29][C:28]6[O:24][CH2:25][O:26][C:27]=6[CH:32]=5)[N:20]=[CH:19][CH:18]=4)=[N:11]3)[C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 4

HCID 24479Stannous ChlorideHCID 126584411,3-Benzodioxol-5-ylhydrazineHCID 23668193Sodium NitriteHCID 593700051-Benzo[1,3]dioxol-4-yl-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one

Product 1

HCID 462202551-Benzo[1,3]dioxol-4-yl-3-(2-benzo[1,3]dioxol-5-yl-2H-pyrazol-3-yl)-1H-pyridazin-4-one

Procedure

The product was obtained starting from 1-Benzo[1,3]dioxol-4-yl-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one (A-14) 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. MS: M=403.2 (M+H)+

Workup

  1. customThe product was obtained

Sources & evidence

ORD record
ord-03cb6be4a6a44f7db67a35f3e981b455
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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