3-(4-Benzyl-2-methylpiperazin-1-yl)-6-(4-fluorophenyl)-4,5-dimethylpyridazine → 3-(4-Fluorophenyl)-4,5-dimethyl-6-(2-methylpiperazin-1-yl)pyridazine

HRID 2093366Notes

Reaction equation

HRID 2093366 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[C:18]([CH3:21])[C:19]=2[CH3:20])[CH:10]([CH3:29])[CH2:9]1)C1C=CC=CC=1>CCO.[Pd]>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:17]2[N:16]=[N:15][C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]3[CH3:29])=[C:19]([CH3:20])[C:18]=2[CH3:21])=[CH:27][CH:26]=1

Participants

4

Reactant 1

HCID 583592493-(4-Benzyl-2-methylpiperazin-1-yl)-6-(4-fluorophenyl)-4,5-dimethylpyridazine

Product 1

HCID 583592433-(4-Fluorophenyl)-4,5-dimethyl-6-(2-methylpiperazin-1-yl)pyridazineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Add a solution of 3-(4-benzyl-2-methylpiperazin-1-yl)-6-(4-fluorophenyl)-4,5-dimethylpyridazine (200 mg, 3.25 mmol) in absolute EtOH (15 mL) to 10% Pd/C (46.8 mg) pre-wetted with EtOH (5 mL). Shake the mixture in a Parr bottle pressurized with H2 at 60 psi for 10 h. Filter the reaction mixture, and apply the solution directly to an SCX column (Varian, 2 g). Rinse the column with MeOH and CH2Cl2. Elute the product with a 1:1 mixture of 2 M NH3/MeOH and CH2Cl2. Concentrate the eluent under reduced pressure to afford the title compound as an off-white foam (142 mg, 92%). ES/MS m/z 301.2 (M+1).

Workup

  1. filtrationFilter the reaction mixture
  2. washRinse the column with MeOH and CH2Cl2
  3. washElute the product
  4. additionwith a 1:1 mixture of 2 M NH3/MeOH and CH2Cl2
  5. concentrationConcentrate the eluent under reduced pressure

Sources & evidence

ORD record
ord-b97e5de5fa464da9ae8b1ed96866b4bb
Source dataset
uspto-grants-2013_05
Patent number
US08445493B2

Reaction notes

Loading…