Benzimidazole → HCID 76281866, compound

HRID 929816Notes

Reaction equation

[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:28]=[C:27]([C:29]([NH2:31])=[O:30])[O:26][N:25]=2)=[CH:20][CH:19]=1>CC#N>[N:1]1([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:28]=[C:27]([C:29]([NH2:31])=[O:30])[O:26][N:25]=3)=[CH:22][CH:23]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of benzimidazole (24 mg, 0.20 mmol), K2CO3 (0.2 mmol), and 3-(4-bromomethyl-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 14; 25 mg, 0.09 mmol) in CH3CN (1 mL) was heated overnight at 60° C. The mixture was filtered and the solvent was evaporated from the filtrate. The residue was purified by chromatography to give 3-(4-benzoimidazol-1-ylmethyl-phenyl)-isoxazole-5-carboxylic acid amide (13.6 mg, 48%). Based on the NMR, the purity was estimated as 80%.

Workup

filtrationThe mixture was filtered
customthe solvent was evaporated from the filtrate
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-9a8aa1820cc24462b23baf5ff3ac21a1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296711B2

Reaction notes

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