Triethylamine → 1,2-Dihydro-3-methyl-1-[4-(propan-1-ylsulfonamido)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 619453Notes

Reaction equation

HRID 619453 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[N:9]3[C:10](=[N:15][C:16]([CH3:17])=[C:8]3[C:7]1=[O:18])[CH:11]=[CH:12][CH:13]=2.C(N(CC)CC)C.[CH2:26]([S:29](Cl)(=[O:31])=[O:30])[CH2:27][CH3:28]>C(Cl)Cl>[CH3:17][C:16]1[N:15]=[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[N:9]2[C:8]=1[C:7](=[O:18])[N:6]3[CH2:5][CH2:4][CH2:3][CH2:2][NH:1][S:29]([CH2:26][CH2:27][CH3:28])(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 211902113-Methyl-1-[4-(amino)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-one

Product 1

HCID 211902631,2-Dihydro-3-methyl-1-[4-(propan-1-ylsulfonamido)butan-1-yl]-1,4,7b-triazacyclopent[cd]inden-2-oneYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.22 g (5.0 mmol) of 1-[4-(amino) butan-1-yl]-1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-one and 1.1 ml (7.9 mmol) of triethylamine in 40 ml of methylene chloride was added, while stirring under ice-cooling, 0.73 ml (6.5 mmol) of propan-1-ylsulfonyl chloride. The mixture was stirred for 0.5 hour at room 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 recrystallized from methylene chloride-methanol-ether to give 1.313 g of the desired compound (75.0%, pale brown crystals), m.p.150.0-151.0° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 0.5 hour at room 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 recrystallized from methylene chloride-methanol-ether

Sources & evidence

ORD record
ord-7c836d3092384e5d87d89887c1556c36
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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