Hydrochloric Acid → HCID 67141245, compound

HRID 1445093Notes

Reaction equation

HRID 1445093 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[N:12]=C(C#N)[CH:14]=[C:15]2[C:19]([CH3:20])=[C:18]([CH3:21])[N:17]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:16]=12.[OH-:32].[K+].Cl.[CH2:35]([OH:37])[CH3:36]>O>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[N:12]=[C:36]([C:35]([OH:32])=[O:37])[CH:14]=[C:15]2[C:19]([CH3:20])=[C:18]([CH3:21])[N:17]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:16]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 67142121HCID 67142121, compound

Product 1

HCID 67141245HCID 67141245, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(4-fluorobenzyl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbonitrile (300 mg, 0.73 mmol) prepared in Example 690 was diluted with a mixture of ethanol (7 ml) and water (1 ml). Potassium hydroxide (410 mg, 7.3 mmol) was added to the solution, which was then refluxed for 72 hours. 1N hydrochloric acid 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 250 mg of the titled compound as a white solid. (Yield: 81%)

Workup

  1. temperaturewas then refluxed for 72 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-79bf16c9996f4ec1a77071fd39134389
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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