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

HRID 8040

Reaction equation

HRID 8040 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-acc6327e872d44b5954e4f6a3294ed3c
Source dataset
uspto-grants-2006_08
Patent number
US07087606B2

Linked notes

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