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

HRID 2424427Notes

Reaction equation

HRID 2424427 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fc38fe7d8c164fb4981a0b336a5b52ab
Source dataset
uspto-grants-2011_06
Patent number
US07964591B2

Reaction notes

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