Triethylamine → 6-CHLOROPYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYL-2-HYDROXYETHYL)AMIDE

HRID 2354623ノート

反応式

HRID 2354623 の反応式
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH2:15][CH2:16][CH:17]([CH:19]1[CH2:21][CH2:20]1)[OH:18].C(N(CC)CC)C>O1CCOCC1.O>[CH:19]1([CH:17]([OH:18])[CH2:16][NH:15][C:8]([C:5]2[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:10])[CH2:21][CH2:20]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 64157626-chloropyridazine-3-carboxylic AcidHCID 148520982-Amino-1-cyclopropylethan-1-ol

生成物 1

HCID 632963846-CHLOROPYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYL-2-HYDROXYETHYL)AMIDE収率 10.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

To the solution of 6-chloropyridazine-3-carboxylic acid (375 mg, 2.37 mmol) in 5 mL of dioxane was added thionyl chloride (420 mg, 3.56 mmol). The mixture was refluxed for 4 hours and the solvent was removed in vacuo. 2-Amino-1-cyclopropylethanol (479 mg, 4.73 mmol) in 5 mL of dioxane was added to the residue and followed by the addition of triethylamine (0.2 mL). The mixture was stirred at ambient temperature overnight. Water was added to the mixture and then extracted with ethyl acetate. The organic extract was separated, washed with water and brine; dried over Na2SO4. The residue after removal of solvent was purified by column chromatography eluted with ethyl acetate:hexane (70:30) to yield 58 mg of the white desired product.

後処理

  1. temperatureThe mixture was refluxed for 4 hours
  2. customthe solvent was removed in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. customwas separated
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. customThe residue after removal of solvent
  9. customwas purified by column chromatography
  10. washeluted with ethyl acetate:hexane (70:30)

出典と根拠

ORDレコード
ord-be4a508a8c1a477dbd13b2f4975a0f44
出典データセット
uspto-grants-2010_07
特許番号
US07754711B2

反応ノート

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