Diisopropylethylamine → N-ethyl-N-(2-phenoxybenzylamino)-pyridazine-3-carboxamide

HRID 355770Notes

Reaction equation

HRID 355770 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]([NH2:10])=[O:9])=[CH:6][CH:7]=1.C([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)C.[CH:28](N(C(C)C)CC)(C)[CH3:29]>CN(C=O)C>[CH2:28]([N:10]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:8]([C:5]1[N:4]=[N:3][CH:2]=[CH:7][CH:6]=1)=[O:9])[CH3:29]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 125775576-Chloropyridazine-3-carboxamideHCID 22675571N-ethyl-N-(2-(phenoxy)benzyl)amine

Product 1

HCID 86588794N-ethyl-N-(2-phenoxybenzylamino)-pyridazine-3-carboxamideYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chloro-pyridazine-6-carboxamide (1.53, 9.69 mmol), N-ethyl-N-(2-(phenoxy)benzyl)amine (2.2 g, 9.69 mmol) and di-isopropylethylamine (3.87 g, 30 mmol) in DMF (19 ml) was heated to 135° C. for 20 hours. The reaction was cooled to ambient temperature and allowed to stand for 48 hours. It was partitioned between ethyl acetate/H2O, the aqueous layer extracted with ethyl acetate and the organic layers washed with water (4×), dried (MgSO4) and evaporated. The residue was subjected to chromatography (eluant: ethyl acetate/hexane) to give 6-(N-ethyl-N-(2-phenoxybenzylamino)-pyridazine-3-carboxamide as a brown solid (1.53 g, 43%).

Workup

  1. customIt was partitioned between ethyl acetate/H2O
  2. extractionthe aqueous layer extracted with ethyl acetate
  3. washthe organic layers washed with water (4×)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-aabaa4545fcf40809f7c4f121747005e
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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