N-(2-(4-fluorophenyl)-2-methylpropyl)-6-vinylpyridazin-3-amine → 6-ethyl-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridazin-3-amine

HRID 869145Notes

Reaction equation

HRID 869145 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[CH2:9][NH:10][C:11]2[N:12]=[N:13][C:14]([CH:17]=[CH2:18])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[CH2:17]([C:14]1[N:13]=[N:12][C:11]([NH:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)([CH3:20])[CH3:19])=[CH:16][CH:15]=1)[CH3:18]

Participants

5

Reactant 2

HCID 67451769N-(2-(4-fluorophenyl)-2-methylpropyl)-6-vinylpyridazin-3-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 674521136-ethyl-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridazin-3-amineYield 10%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The isolated product from Step 1 was dissolved in ethanol (10 mL) and transferred to a 20 dram vial. Palladium (10% on carbon, 10 mg) was then added, and the reaction was stirred under 60 psi of hydrogen for 3 days. The reaction was then filtered, concentrated, and purified by reverse phase column chromatography to afford 3 mg (10%) of 6-ethyl-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridazin-3-amine as a clear oil, m/z=274 [M+H].

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationconcentrated
  3. custompurified by reverse phase column chromatography

Sources & evidence

ORD record
ord-66f9108007514cb5a39e5b753c665f80
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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