Triethylamine → N-(3-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)-5-(imidazo[1,2-b]pyridazin-2-yl)phenyl)methanesulfonamide

HRID 251832

反応式

HRID 251832 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:6]=[C:7]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[N:13][N:12]3[CH:17]=2)[CH:8]=1)#[N:2].Cl.NO.C([N:28](CC)CC)C.[O:33](C(CCl)=O)[C:34]([CH2:36][Cl:37])=O>CCO>[Cl:37][CH2:36][C:34]1[O:33][N:28]=[C:1]([C:3]2[CH:4]=[C:5]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:6]=[C:7]([C:9]3[N:10]=[C:11]4[CH:16]=[CH:15][CH:14]=[N:13][N:12]4[CH:17]=3)[CH:8]=2)[N:2]=1

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 10946Chloroacetic anhydrideHCID 443297Hydroxyamine hydrochlorideHCID 57686828N-(3-cyano-5-(imidazo[1,2-b]pyridazin-2-yl)phenyl)methanesulfonamide

生成物 1

HCID 57686799N-(3-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)-5-(imidazo[1,2-b]pyridazin-2-yl)phenyl)methanesulfonamide収率 90%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of N-(3-cyano-5-(imidazo[1,2-b]pyridazin-2-yl)phenyl)methanesulfonamide (0.25 mmol), hydroxylamine hydrochloride (0.75 mmol) and triethylamine (1 mmol) in EtOH (12 mL) was refluxed for 4 hours. After removal of the solvent in vacuo, the residue was dissolved in THF (12 mL), added with (ClCH2CO)2O (0.75 mmol) and triethylamine (1 mmol), and stirred at room temperature for 1 hours. Then it was heated to reflux for another 8 hours. After removal of the solvent in vacuo and addition of water, the mixture was extracted with EtOAc. The combined organic layer was washed with water and brine sequentially, dried over anhydrous Na2SO4 and concentrated. The resulting residue was purified by column chromatography to give N-(3-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)-5-(imidazo[1,2-b]pyridazin-2-yl)phenyl)methanesulfonamide in 90% yield.

後処理

  1. temperaturewas refluxed for 4 hours
  2. customAfter removal of the solvent in vacuo
  3. dissolutionthe residue was dissolved in THF (12 mL)
  4. temperatureThen it was heated
  5. temperatureto reflux for another 8 hours
  6. customAfter removal of the solvent
  7. additionin vacuo and addition of water
  8. extractionthe mixture was extracted with EtOAc
  9. washThe combined organic layer was washed with water and brine sequentially
  10. dry with materialdried over anhydrous Na2SO4
  11. concentrationconcentrated
  12. customThe resulting residue was purified by column chromatography

出典と根拠

ORDレコード
ord-dda126cfae6d4940bdf0bb2ae889c104
出典データセット
uspto-grants-2011_01
特許番号
US07868001B2

関連ノート

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