Triethylamine → 1,2-Dihydro-3-methyl-1-[5-[(2,2,2-trifluoro)ethanesulfonamido]pentan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 619446Notes

Reaction equation

HRID 619446 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[N:10]3[C:11](=[N:16][C:17]([CH3:18])=[C:9]3[C:8]1=[O:19])[CH:12]=[CH:13][CH:14]=2.C(N(CC)CC)C.[F:27][C:28]([F:35])([F:34])[CH2:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH3:18][C:17]1[N:16]=[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[N:10]2[C:9]=1[C:8](=[O:19])[N:7]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][S:30]([CH2:29][C:28]([F:35])([F:34])[F:27])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 211901113-Methyl-1-[5-(amino)pentyl]-1,4,7b-triazacyclopent[cd]inden-2-one

Product 1

HCID 702131321,2-Dihydro-3-methyl-1-[5-[(2,2,2-trifluoro)ethanesulfonamido]pentan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-oneYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.630 g (6.31 mmol) of 1-[5-(amino)pentyl]-1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-one and 1.32 ml (9.47 mmol) of triethylamine in 30 ml of methylene chloride was added, while stirring under ice-cooling, 1.38 g (7.56 mmol) of 2,2,2-trifluoroethanesulfonylchloride. The mixture was stirred for 30 minutes at the same temperature. The reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate, which was then dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate) to give 1.669 g of the desired compound (65.4%, pale brown solid substance).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 30 minutes at the same temperature
  3. washThe reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate, which
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-f3d65b665741489a8a56260a8721f360
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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