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

HRID 1870750ノート

反応式

HRID 1870750 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:19]=[N:20][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[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:19]=[N:20][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1)[CH2:1][CH3:2]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 186932346-Chloropyridazine-3-sulfonamideHCID 18693239N-Ethyl 5-chloro-2-(2-methylprop-2-en-1-yloxy)benzylamine

生成物 1

HCID 186932626-[N-(5-Chloro-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-sulphonamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

A mixture of N-ethyl-5-chloro-2-(2-methylprop-2-en-1-yloxy)benzylamine (2.76 g, 10 mmol), 3-chloro-pyridazine-6-sulphonamide [Archiv der Pharmazie (1966) 299, 646-650 and EP patent no 96,004] (1.5 g, 7.8 mmol) and ethyl di-isopropylamine (10 ml, 57 mM) in DMF (50 ml) was stirred at 130° C. for 16 hours under a reflux condenser. The solvent was evaporated at reduced pressure and the residue partitioned between dichloromethane (100 ml) and water (100 ml). The organic layer was separated, dried over anhydrous magnesium sulphate, filtered and evaporated to give a brown gum (2.5 g). The brown gum was purified by chromatography on silica, eluting with a gradient of 0→20% ethyl acetate in dichloromethane to give the title compound as a yellow solid (600 mg).

後処理

  1. customThe solvent was evaporated at reduced pressure
  2. customthe residue partitioned between dichloromethane (100 ml) and water (100 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-2b55a7a92bba4d43b90f9c0df0d36d3a
出典データセット
uspto-grants-2000_08
特許番号
US06100258

反応ノート

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