Stannous Chloride → 3-[3-(2-Benzo[1,3]dioxol-5-yl-2H-pyrazol-3-yl)-4-oxo-4H-pyridazin-1-yl]-N,N-dimethyl-benzenesulfonamide

HRID 1924584Notes

Reaction equation

CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:15]=[C:16]([S:20]([N:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=2)[N:8]=1)=O.[O:27]1[C:31]2[CH:32]=[CH:33][C:34]([NH:36][NH2:37])=[CH:35][C:30]=2[O:29][CH2:28]1.N([O-])=O.[Na+].[Sn](Cl)Cl>>[O:27]1[C:31]2[CH:32]=[CH:33][C:34]([N:36]3[C:5]([C:7]4[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]5[CH:15]=[C:16]([S:20]([N:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=5)[N:8]=4)=[CH:4][CH:3]=[N:37]3)=[CH:35][C:30]=2[O:29][CH2:28]1

Participants

Reactant 4

HCID 24479Stannous Chloride

HCID 126584411,3-Benzodioxol-5-ylhydrazine

HCID 23668193Sodium Nitrite

HCID 593701633-[3-((E)-3-Dimethylamino-acryloyl)-4-oxo-4H-pyridazin-1-yl]-N,N-dimethyl-benzenesulfonamide

Product 1

HCID 593699973-[3-(2-Benzo[1,3]dioxol-5-yl-2H-pyrazol-3-yl)-4-oxo-4H-pyridazin-1-yl]-N,N-dimethyl-benzenesulfonamide

Procedure

The product was obtained starting from 3-[3-((E)-3-Dimethylamino-acryloyl)-4-oxo-4H-pyridazin-1-yl]-N,N-dimethyl-benzenesulfonamide (A-12) 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=466.2 (M+H)+

Workup

customThe product was obtained

Sources & evidence

ORD record: ord-753bb6721d4f4d0f958f5812a581dedd
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178538B2

Reaction notes

Loading…