Triethylamine → 3-Methyl-1-[4-(pentafluoropropanoylamino)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 1068751Notes

Reaction equation

HRID 1068751 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7](=[O:18])[N:8]3[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17].C(N(CC)CC)C.[F:26][C:27]([F:35])([F:34])[C:28]([F:33])([F:32])[C:29](O)=[O:30]>C(#N)C>[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7](=[O:18])[N:8]3[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:29](=[O:30])[C:28]([F:33])([F:32])[C:27]([F:35])([F:34])[F:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62356Pentafluoropropionic acidHCID 211902113-Methyl-1-[4-(amino)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

Product 1

HCID 211902893-Methyl-1-[4-(pentafluoropropanoylamino)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.44 g (10.0 mmol) of 3-methyl-1-[4-(amino)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one and 1.81 ml (13.0 mmol) of triethylamine in 100 ml of acetonitrile was added, while stirring at room temperature, 2.31 g (12.0 mmol) of ethyl ester of pentafluoropropionic acid. The mixture was stirred for 14 hours at the same temperature. The solvent was distilled off. To the residue was added methylene chloride. The mixture was washed with water, which was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent:ethyl acetate), and recrystallized from ethyl acetate—hexane to afford 1.53 g (39.1%, a colorless crystals) of the desired compound.

Workup

  1. stirringThe mixture was stirred for 14 hours at the same temperature
  2. distillationThe solvent was distilled off
  3. additionTo the residue was added methylene chloride
  4. washThe mixture was washed with water, which
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent:ethyl acetate)
  8. customrecrystallized from ethyl acetate—hexane
  9. customto afford 1.53 g (39.1%

Sources & evidence

ORD record
ord-644d23f4e7ef45a9953dd5fa6791577a
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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