Potassium Hydroxide → 5-Chloro-2-[8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl]benzamide

HRID 1399136Notes

Reaction equation

HRID 1399136 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[C:14]3=[N:15][C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[C:17]=4[N:13]3[CH2:12][CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[OH-:28].[K+]>C(O)(C)(C)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[C:14]3=[N:15][C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[C:17]=4[N:13]3[CH2:12][CH2:11]2)=[C:6]([CH:9]=1)[C:7]([NH2:8])=[O:28]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 577861665-Chloro-2-[8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl]benzonitrile

Product 1

HCID 577863505-Chloro-2-[8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl]benzamideYield 63.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-chloro-2-[8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl]benzonitrile (55.0 mg, 0.138 mmol) in tert-butyl alcohol (1.5 mL) was added potassium hydroxide (30.9 mg, 0.551 mmol). The reaction mixture was stirred at 80° C. for 15 min. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 10-60% ethyl acetate/n-hexane gradient mixture. The resulting solid was recrystallized from methanol to give the title compound as a colorless powder (24.6 mg, 0.0872 mmol, 43%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with brine (×1)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a 10-60% ethyl acetate/n-hexane gradient mixture
  9. customThe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-ad4ec65bc27d441abfcfe41c49a6914b
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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