Water → 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-phthalimidomethyl-2H-pyridazin-3-one

HRID 7927Notes

Reaction equation

HRID 7927 reaction equation
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12]OS(C)(=O)=O)=[CH:8][C:7]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([F:26])[CH:19]=3)=[N:6]2)[CH2:3][CH2:2]1.[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.[K].O>CN(C)C=O>[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12][N:31]3[C:27](=[O:37])[C:28]4=[CH:36][CH:35]=[CH:34][CH:33]=[C:29]4[C:30]3=[O:32])=[CH:8][C:7]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([F:26])[CH:19]=3)=[N:6]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 219916182-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-meth anesulfonyloxymethyl-2H-pyridazin-3-oneHCID 24194345Phthalimide potassium salt

Product 1

HCID 219914002-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-phthalimidomethyl-2H-pyridazin-3-oneYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one (220 mg, 0.57 mmol) in N,N-dimethylformamide (5 mL) was added potassium phthalimide (160 mg, 0.87 mmol), and the mixture was stirred at 80° C. for 2 hours. Water (30 mL) was added to the reaction mixture. After stirring under cooling over ice water, precipitated crystals were collected by filtration, dried in air, and recrystallized from chloroform-hexane to yield the title compound as colorless needles (202 mg, 81.0%).

Workup

  1. stirringAfter stirring
  2. customprecipitated crystals
  3. filtrationwere collected by filtration
  4. customdried in air
  5. customrecrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-238e053add69416583ec29575c2096aa
Source dataset
uspto-grants-2006_08
Patent number
US07087606B2

Reaction notes

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