Methanol → HCID 51042061, compound

HRID 1875825Notes

Reaction equation

HRID 1875825 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]2[N:22]([CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[N:19]=2)=[C:6]([CH2:8][CH2:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#N)=[CH:12][CH:11]=2)[CH:7]=1.[OH-:34].[K+].C[OH:37]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]2[N:22]([CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[N:19]=2)=[C:6]([CH2:8][CH2:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]([OH:37])=[O:34])=[CH:12][CH:11]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 67049806HCID 67049806, compound

Product 1

HCID 51042061HCID 51042061, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-[2-[5-chloro-2-(1-cyclohexylmethyl-1H-benzoimidazol-2-yl)-phenyl]-ethyl]-benzonitrile (64 mg, 0.14 mmol; Example 74, intermediate a) in methanol (10 ml) was added a solution of potassium hydroxide (78 mg, 1.39 mmol) in water (5 ml) and the mixture was heated to reflux for 12 h. Solvents were removed under reduced pressure and the residue was diluted with water (10 ml) and acidified to pH 4 with 2M aqueous hydrochloric acid solution. It was then extracted three times with ethyl acetate (20 ml each), the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography over silica gel (65% ethyl acetate/n-hexane) to give the desired final product as a colorless powder (31%). MS (Turbo Spray): m/z=473.3 (M+H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 12 h
  3. customSolvents were removed under reduced pressure
  4. additionthe residue was diluted with water (10 ml)
  5. extractionIt was then extracted three times with ethyl acetate (20 ml each)
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure
  10. customThe crude product was purified by column chromatography over silica gel (65% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-2076edc1ba154d5d9470f0da8bd6f503
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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