Potassium Hydroxide → HCID 22181285, compound

HRID 1796515Notes

Reaction equation

HRID 1796515 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([N:14](C)[C:15](=O)C)=[CH:13][C:8]=3[N:7]=[C:6]2[CH:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=2)[CH3:20])[CH2:3][CH2:2]1.[OH-].[K+]>CCO>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([NH:14][CH3:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH:19]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH3:29])=[CH:25][CH:26]=2)[CH3:20])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69595825HCID 69595825, compound

Product 1

HCID 22181285HCID 22181285, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[1-(cyclopropylmethyl)-2-[1-(4-ethoxyphenyl)ethyl]-1H-benzimidazol-5-yl]-N-methyl acetamide (2.43 g, 5.64 mmol) and 40% KOH (50 ml) in EtOH was heated for 20 h at reflux. After being cooled down, the mixture was concentrated to a small volume (50 mL) and diluted with H2O (50 mL) which was extracted with dichloromethane (4×50 mL). The combined organic phases were dried with Na2SO4. After filtration and evaporation of the solvent, the residue was purified by MPLC using EtOAc on silica gel to give 1.93 g (99%) of the title compound as an off-white solid. MS (ESI) (M+H)+=350.37.

Workup

  1. temperaturewas heated for 20 h
  2. temperatureat reflux
  3. temperatureAfter being cooled down
  4. concentrationthe mixture was concentrated to a small volume (50 mL)
  5. additiondiluted with H2O (50 mL) which
  6. extractionwas extracted with dichloromethane (4×50 mL)
  7. dry with materialThe combined organic phases were dried with Na2SO4
  8. filtrationAfter filtration and evaporation of the solvent
  9. customthe residue was purified by MPLC

Sources & evidence

ORD record
ord-c4dfc82da22e4efba7a041015781728c
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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