Hydrazine hydrate (1:1) → (4-(4-fluoro-phenoxy)-6-(pyridin-3-yloxy)-1H-benzimidazol-2-yl)-hydrazine

HRID 13251Notes

Reaction equation

O.[NH2:2][NH2:3].[F:4][C:5]1[CH:28]=[CH:27][C:8]([O:9][C:10]2[C:18]3[N:17]=[C:16](S)[NH:15][C:14]=3[CH:13]=[C:12]([O:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:11]=2)=[CH:7][CH:6]=1>C(OCC)(=O)C>[F:4][C:5]1[CH:28]=[CH:27][C:8]([O:9][C:10]2[C:18]3[N:17]=[C:16]([NH:2][NH2:3])[NH:15][C:14]=3[CH:13]=[C:12]([O:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:11]=2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 130 °C

Procedure

1.0 ml of hydrazine monohydrate was added to 130 mg of 4-(4-fluoro-phenoxy)-6-(pyridin-3-yloxy)-1H-benzimidazole-2-thiol, and the reaction liquid was stirred overnight at 130° C. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), hexane/ethyl acetate=1/1) to obtain the entitled compound.

Workup

customthe reaction liquid
customThe reaction liquid
washwashed with water and saturated saline in order
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated away under reduced pressure
customthe resulting residue was purified
customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), hexane/ethyl acetate=1/1)
customto obtain the entitled compound

Sources & evidence

ORD record: ord-12857ac82c7d493aadeffb817d916421
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728025B2

Reaction notes

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