Diisopropylethylamine → 6-[N-(5-Chloro-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxamide

HRID 1870744

Reaction equation

HRID 1870744 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[O:12][CH2:13][C:14]([CH3:16])=[CH2:15])[CH3:2].Cl[C:18]1[N:23]=[N:22][C:21]([C:24]([NH2:26])=[O:25])=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:11][C:9]1[CH:8]=[CH:7][C:6]([O:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:5]([CH:10]=1)[CH2:4][N:3]([C:18]1[N:23]=[N:22][C:21]([C:24]([NH2:26])=[O:25])=[CH:20][CH:19]=1)[CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 125775576-Chloropyridazine-3-carboxamideHCID 18693239N-Ethyl 5-chloro-2-(2-methylprop-2-en-1-yloxy)benzylamine

Product 1

HCID 186932586-[N-(5-Chloro-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxamideYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-ethyl-5-chloro-2-(2-methylprop-2-en-1-yloxy)benzylamine (reference example 16) (13.8 g, 50 mM), 6-chloropyridazine-3-carboxamide (7.9 g, 50 mM) and di-isopropylethylamine (20.0 ml, 115 mM) in DMF (50 ml) was stirred at reflux for 16 hours. The mixture was cooled and diluted with water (200 ml) giving an oil which was allowed to settle out (1 hour). The supernatant liquor was decanted and the residual brown gum dissolved in dichloromethane (250 ml) and washed with 2N hydrochloric acid (100 ml). The product was obtained by eluting the organic layer through silica, adjusting the solvent to dichloromethane/isopropanol (19:1) and collecting relevant fractions, which were combined and evaporated to give the title compound as a gum (10.5 g, 58%).

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureThe mixture was cooled
  3. customgiving an oil which
  4. custom(1 hour)
  5. customThe supernatant liquor was decanted
  6. dissolutionthe residual brown gum dissolved in dichloromethane (250 ml)
  7. washwashed with 2N hydrochloric acid (100 ml)
  8. customThe product was obtained
  9. washby eluting the organic layer through silica
  10. customcollecting relevant fractions, which
  11. customevaporated

Sources & evidence

ORD record
ord-a8bc73af172c49169e86b91fd96c8325
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Linked notes

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