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

HRID 333742Notes

Reaction equation

HRID 333742 reaction equation
[OH:1][C:2]1[C:3](=[O:20])[C:4]([C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[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+]>CN(C)C=O>[N:24]1([CH2:23][CH2:22][O:1][C:2]2[C:3](=[O:20])[C:4]([C:14]3[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=3)=[N:5][N:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[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

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 7619001-(2-chloroethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazoleHCID 895867585-hydroxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one

Product 1

HCID 895864585-[2-(2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl)ethoxy]-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-oneYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 5-hydroxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one (54 mg), 1-(2-chloroethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (49 mg), cesium carbonate (98 mg), and sodium iodide (33 mg) in dimethylformamide (4 mL) was stirred at 70° C. for 15 hr. The reaction mixture was filtered, and the obtained insoluble material was washed with ethyl acetate. The filtrate and washing were combined, and concentrated under reduced pressure to dryness. The residue was purified by silica gel column chromatography (ethyl acetate/methanol). A fraction containing the title compound was again purified by NH silica gel column chromatography (ethyl acetate/methanol) to give the title compound (10 mg) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe obtained insoluble material was washed with ethyl acetate
  3. washThe filtrate and washing
  4. concentrationconcentrated under reduced pressure to dryness
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  6. additionA fraction containing the title compound
  7. customwas again purified by NH silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-f5a2e92d61cb430bba7dca3c37cad703
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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