Acetic Acid → 1,4,5,7-Tetramethyl-6-(4-trifluoromethoxy-phenyl)-6H-pyrrolo[3,4-d]pyridazine

HRID 2375384Notes

Reaction equation

HRID 2375384 reaction equation
[C:1]([CH:4]([C:12](=O)[CH3:13])[CH:5]([C:9](=O)[CH3:10])[C:6](=O)[CH3:7])(=O)[CH3:2].[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.CC(O)=O.[NH2:31][NH2:32]>CCO>[CH3:2][C:1]1[C:4]2=[C:12]([CH3:13])[N:22]([C:21]3[CH:23]=[CH:24][C:18]([O:17][C:16]([F:25])([F:26])[F:15])=[CH:19][CH:20]=3)[C:9]([CH3:10])=[C:5]2[C:6]([CH3:7])=[N:32][N:31]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9321HydrazineHCID 787303,4-Diacetyl-2,5-hexanedioneHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 102463271,4,5,7-Tetramethyl-6-(4-trifluoromethoxy-phenyl)-6H-pyrrolo[3,4-d]pyridazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,1,2,2-tetraacetylethane (250 mg, 1.26 mmol) and 4-trifluoromethoxy aniline (170 μL, 1.26 mmol) was refluxed in EtOH (5 mL)/AcOH (1%) for 48 h. Hydrazine (100 μL, 3.15 mmol) was added and the mixture was refluxed for 1 h. The reaction mixture was poured into ice water (50 mL). The resulting precipitate was filtered and dried under vacuum to afford 1,4,5,7-tetramethyl-6-[4-(trifluoromethoxy)phenyl]-6H-pyrrolo[3,4-d]pyridazine as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 7.42 (d, 2H), 7.25 (d, 2H), 2.81 (s, 6H), 2.41 (s, 6H); MS (ESI) 336 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. filtrationThe resulting precipitate was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d230f21a656b482eb928501698728332
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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