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

HRID 1870744

反応式

HRID 1870744 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-a8bc73af172c49169e86b91fd96c8325
出典データセット
uspto-grants-2000_08
特許番号
US06100258

関連ノート

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