Triethylamine → HCID 21190163, compound

HRID 1068750Notes

Reaction equation

HRID 1068750 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:19])[N:8]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18].C(N(CC)CC)C.C([O:29][C:30](=O)[C:31]([F:34])([F:33])[F:32])C>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:19])[N:8]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:30](=[O:29])[C:31]([F:34])([F:33])[F:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 211901113-Methyl-1-[5-(amino)pentyl]-1,4,7b-triazacyclopent[cd]inden-2-one

Product 1

HCID 21190163HCID 21190163, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.58 g (10.0 mmol) of 3-methyl-1-[5-(amino)pentyl]-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 under ice-cooling, 1.43 ml (12.0 mmol) of trifluoroacetic acid ethyl ester. The mixture was stirred for one hour at the same temperature. The solvent was distilled off. To the residue was added ethyl acetate—tetrahydrofuran. The mixture was washed with an aqueous saline solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate), which was recrystallized from ethyl acetate—n-hexane to afford 2.57 g (72.6%, a pale yellow crystals) of the desired compound.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for one hour at the same temperature
  3. distillationThe solvent was distilled off
  4. additionTo the residue was added ethyl acetate—tetrahydrofuran
  5. washThe mixture was washed with an aqueous saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent: ethyl acetate), which
  9. customwas recrystallized from ethyl acetate—n-hexane
  10. customto afford 2.57 g (72.6%

Sources & evidence

ORD record
ord-c8df865b3bd44697bec210c97ff390ed
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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