Sodium Iodide → 1-(Cyclopropylmethyl)-5-(2-(2,3-Dihydro-1h-Imidazo[1,2-A]benzimidazol-1-Yl)ethoxy)-3-(1-Phenyl-1h-Pyrazol-5-Yl)pyridazin-4(1h)-One

HRID 333733Notes

Reaction equation

[CH:1]1([CH2:4][N:5]2[CH:10]=[C:9]([OH:11])[C:8](=[O:12])[C:7]([C:13]3[N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:16]=[CH:15][CH:14]=3)=[N:6]2)[CH2:3][CH2:2]1.Cl[CH2:25][CH2:26][N:27]1[C:31]2=[N:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[N:30]2[CH2:29][CH2:28]1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CC(N(C)C)=O>[CH:1]1([CH2:4][N:5]2[CH:10]=[C:9]([O:11][CH2:25][CH2:26][N:27]3[C:31]4=[N:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=5[N:30]4[CH2:29][CH2:28]3)[C:8](=[O:12])[C:7]([C:13]3[N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:16]=[CH:15][CH:14]=3)=[N:6]2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 1-(cyclopropylmethyl)-5-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (231 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 and an insoluble material was separated and washed with ethyl acetate. The filtrate and the washing were combined, and concentrated under reduced pressure to dryness. The residue was purified by NH silica gel column chromatography (ethyl acetate/methanol) to give the title compound (231 mg) as a white amorphous powder.

Workup

filtrationThe reaction mixture was filtered
customan insoluble material was separated
washwashed with ethyl acetate
concentrationconcentrated under reduced pressure to dryness
customThe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record: ord-9509177f140b41a781c4c27e390e6b49
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883788B2

Reaction notes

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