benzyl 4-(6-oxo-6,7-dihydro-5H-imidazo[4,5-c]pyridazin-5-yl)piperidine-1-carboxylate → 5-Piperidin-4-yl-5,7-dihydro-6H-imidazo[4,5-c]pyridazin-6-one

HRID 501083Notes

Reaction equation

HRID 501083 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2[N:6]=[N:7][CH:8]=[CH:9][C:4]=2[N:3]1[CH:11]1[CH2:16][CH2:15][N:14](C(OCC2C=CC=CC=2)=O)[CH2:13][CH2:12]1>CCO.[Pd]>[NH:14]1[CH2:15][CH2:16][CH:11]([N:3]2[C:4]3[CH:9]=[CH:8][N:7]=[N:6][C:5]=3[NH:10][C:2]2=[O:1])[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 22293218benzyl 4-(6-oxo-6,7-dihydro-5H-imidazo[4,5-c]pyridazin-5-yl)piperidine-1-carboxylate

Product 1

HCID 222933035-Piperidin-4-yl-5,7-dihydro-6H-imidazo[4,5-c]pyridazin-6-oneYield 119.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of benzyl 4-(6-oxo-6,7-dihydro-5H-imidazo[4,5-c]pyridazin-5-yl)piperidine-1-carboxylate (35 mg, 0.099 mmol) and 10% Pd/C (50 mg) in EtOH (5 mL), was hydrogenated under a balloon overnight. The reaction was filtered through Celite with more EtOH and concentrated to afford the title compound (26 mg). MS 220.2 (M+1).

Workup

  1. customwas hydrogenated under a balloon overnight
  2. filtrationThe reaction was filtered through Celite with more EtOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6dd1a0e04dde41d7b4a1c56e47ac6468
Source dataset
uspto-grants-2010_08
Patent number
US07772224B2

Reaction notes

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