Ethanolamine → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 548813Notes

Reaction equation

HRID 548813 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[N:20]=[N:19][C:18]([C:21]([OH:23])=O)=[CH:17][CH:16]=1.[CH2:24]([CH2:26][NH2:27])[OH:25].O>CN(C=O)C>[OH:25][CH2:24][CH2:26][NH:27][C:21]([C:18]1[N:19]=[N:20][C:15]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:16][CH:17]=1)=[O:23]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 962WaterHCID 665989756-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid

Product 1

HCID 426301336-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (2-hydroxy-ethyl)-amideYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (200 mg, 0.64 mmol) in DMF (8 mL) was added 1,1-carbonyl-diimidazole (135 mg, 0.83 mmol) and the mixture was stirred for 4 h at room temperature. Ethanolamine (0.27 mL, 4.50 mmol) was added and stirring was continued for 1 h. Water (20 mL) was added and the mixture was extracted with ethyl acetate (90 mL). The combined organic layers were washed with water (60 mL) and dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 30:70) afforded the title compound (215 mg, 94%) as a white foam. MS: m/e=355.2 [M+H]+.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. extractionthe mixture was extracted with ethyl acetate (90 mL)
  4. washThe combined organic layers were washed with water (60 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 30:70)

Sources & evidence

ORD record
ord-1572a912655246c7917d143e4a0f1b17
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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