Sodium Iodide → 5-[2-(2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl)ethoxy]-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 333729Notes

Reaction equation

[OH:1][C:2]1[C:3](=[O:20])[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[N:5][N:6]([CH3:8])[CH:7]=1.Cl[CH2:22][CH2:23][N:24]1[C:28]2=[N:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:27]2[CH2:26][CH2:25]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CC(N(C)C)=O>[N:24]1([CH2:23][CH2:22][O:1][C:2]2[C:3](=[O:20])[C:4]([C:9]3[N:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:12]=[CH:11][CH:10]=3)=[N:5][N:6]([CH3:8])[CH:7]=2)[C:28]2=[N:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[N:27]2[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 5-hydroxy-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (201 mg), 1-(2-chloroethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (249 mg), cesium carbonate (428 mg) and sodium iodide (253 mg) in dimethylacetamide (10 mL) was stirred at 80° C. for 13 hr. The reaction mixture was filtered to separate an insoluble material, which was washed with ethyl acetate. The filtrate and washing were combined, and the mixture was concentrated under reduced pressure to dryness. The residue was purified by NH silica gel column chromatography (ethyl acetate/methanol) to give the title compound (227 mg) as a white solid.

Workup

filtrationThe reaction mixture was filtered
customto separate an insoluble material, which
washwas washed with ethyl acetate
washThe filtrate and washing
concentrationthe mixture was concentrated under reduced pressure to dryness
customThe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record: ord-b17b7a1c89c044c99d5b74bf888da079
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883788B2

Reaction notes

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