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

HRID 2354623

반응식

HRID 2354623 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-be4a508a8c1a477dbd13b2f4975a0f44
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754711B2

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