Potassium Hydroxide → HCID 67142301, compound

HRID 1932382Notes

Reaction equation

HRID 1932382 reaction equation
[CH2:1]([N:8]1[C:12]2=[C:13]([N:19]3[CH2:28][CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)[N:14]=[C:15]([C:17]#[N:18])[CH:16]=[C:11]2[C:10]([CH3:29])=[C:9]1[CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:31].[K+]>C(O)C.O>[CH2:1]([N:8]1[C:12]2=[C:13]([N:19]3[CH2:28][CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)[N:14]=[C:15]([C:17]([NH2:18])=[O:31])[CH:16]=[C:11]2[C:10]([CH3:29])=[C:9]1[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67142062HCID 67142062, compound

Product 1

HCID 67142301HCID 67142301, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1-Benzyl-7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbonitrile (300 mg, 0.76 mmol) prepared in Example 686 was diluted with a mixture of ethanol (7 ml) and water (1 ml). Potassium hydroxide (426 mg, 7.6 mmol) was added to the solution, which was then refluxed for 2 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, v/v) to give 260 mg of the titled compound as a white solid. (Yield: 84%)

Workup

  1. temperaturewas then refluxed for 2 hours
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1

Sources & evidence

ORD record
ord-963213b71c0e4bb99c1e42ccbfe693e5
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

Loading…