Diisopropylethylamine → 6-(N-ethyl-N-(2-aminobenzyl)amino)-pyridazine-3-carboxamide

HRID 355775Notes

Reaction equation

HRID 355775 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])[CH3:2].Cl[C:13]1[N:18]=[N:17][C:16]([C:19]([NH2:21])=[O:20])=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:1]([N:3]([C:13]1[N:18]=[N:17][C:16]([C:19]([NH2:21])=[O:20])=[CH:15][CH:14]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10329442N-ethyl-N-(2-aminobenzyl)amineHCID 125775576-Chloropyridazine-3-carboxamide

Product 1

HCID 226754686-(N-ethyl-N-(2-aminobenzyl)amino)-pyridazine-3-carboxamideYield 39.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Ethyl-N-(2-aminobenzyl)amine (707 mg, 4.7 mmol) in DMF (11 ml) was treated with 6-chloropyridazin-3-amide (4.7 mmol) followed by diisopropylethylamine (15.4 mol) and the reaction stirred at 140° under argon for 24 hours. The reaction was evaporated in vacuo (cold-finger) and the residue partitioned between water and ethyl acetate. The combined organic extracts were dried and evaporated to give a brown gum. The gum was purified by medium pressure chromatography to give 6-(N-ethyl-N-(2-aminobenzyl)amino)-pyridazine-3-carboxamide (500 mg, 30%).

Workup

  1. customThe reaction was evaporated in vacuo (cold-finger)
  2. customthe residue partitioned between water and ethyl acetate
  3. customThe combined organic extracts were dried
  4. customevaporated
  5. customto give a brown gum
  6. customThe gum was purified by medium pressure chromatography

Sources & evidence

ORD record
ord-960e14b03a99458ab44528d7a955074e
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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