Trifluoroacetic acid → 4-(2-carboxyethyl)-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one

HRID 982812

Reaction equation

HRID 982812 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH2:11][N:12]2[C:17](=[O:18])[C:16]([CH2:19][CH:20](C(OC(C)(C)C)=O)[C:21]([O:23]C(C)(C)C)=[O:22])=[CH:15][C:14]([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([F:43])[CH:36]=3)=[N:13]2)[CH2:10][CH2:9]1>>[C:21]([CH2:20][CH2:19][C:16]1[C:17](=[O:18])[N:12]([CH2:11][CH:8]2[CH2:9][CH2:10]2)[N:13]=[C:14]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([F:43])[CH:36]=2)[CH:15]=1)([OH:23])=[O:22]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 219916102-cyclopropylmethyl-4-[2,2-di(tert-butoxycarbonyl)ethyl]-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one

Product 1

HCID 219914104-(2-carboxyethyl)-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-oneYield 94.7%

Procedure

Trifluoroacetic acid (21 mL) was added to 2-cyclopropylmethyl-4-[2,2-di(tert-butoxycarbonyl)ethyl]-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one (1.39 g, 2.77 mmol), and the mixture was stirred at room temperature for 30 minutes. The solvent was distilled off under reduced pressure, and toluene was added further, followed by azeotropic boiling. The residue was heated at 190 to 200° C. for 30 minutes under a nitrogen atmosphere to yield the title compound as a pale brown powder (yield: 907 mg, 94.7%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and toluene
  2. additionwas added further
  3. temperatureThe residue was heated at 190 to 200° C. for 30 minutes under a nitrogen atmosphere

Sources & evidence

ORD record
ord-2bc8009a003c453186649f2b170bf1e6
Source dataset
uspto-grants-2005_03
Patent number
US06861428B2

Linked notes

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