HCID 58495462, compound → HCID 58495574, compound

HRID 1191098Notes

Reaction equation

HRID 1191098 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:9]=[CH:8][C:7]([C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=3)=[N:6]2)[CH2:3][CH2:2]1>CO.Cl.[Pd]>[CH:1]1([CH2:4][N:5]2[CH:9]=[CH:8][C:7]([C:10]3[CH:11]=[CH:12][C:13]([CH2:14][NH2:15])=[CH:16][CH:17]=3)=[N:6]2)[CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 58495462HCID 58495462, compound

Product 1

HCID 58495574HCID 58495574, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Bubble nitrogen into a solution of 4-(1-cyclopropylmethyl-1H-pyrazol-3-yl)-benzonitrile (256 mg, 1.15 mmol) in methanol (48 mL) with 5 drops of concentrated hydrochloric acid for 10 min. Add 10% Pd/C (Degussa type, 48 mg) and submit the mixture to hydrogenation at atmospheric pressure overnight. Filter the mixture over Celite® and concentrate in vacuo. Add saturated aqueous NaHCO3 and extract twice with AcOEt. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to give the title compound as a yellow oil (207 mg, 80%). MS (ES+) m/z: 228 (M+H)+.

Workup

  1. customat atmospheric pressure overnight
  2. filtrationFilter the mixture over Celite®
  3. concentrationconcentrate in vacuo
  4. extractionAdd saturated aqueous NaHCO3 and extract twice with AcOEt
  5. dry with materialDry the combined organic extracts over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-a690fbbb33ef41f7890f87c22ab71c68
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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