Triethylamine → HCID 21190206, compound

HRID 619438Notes

Reaction equation

HRID 619438 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:18](=[O:19])[C:17]2[N:20]3[C:10](=[CH:11][N:12]=[C:13]3[CH:14]=[CH:15][CH:16]=2)[C:9]1=[O:21].C(N(CC)CC)C.[F:29][C:30]([F:37])([F:36])[CH2:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[F:29][C:30]([F:37])([F:36])[CH2:31][S:32]([NH:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:18](=[O:19])[C:17]2[N:20]3[C:10](=[CH:11][N:12]=[C:13]3[CH:14]=[CH:15][CH:16]=2)[C:9]1=[O:21])(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 21190223HCID 21190223, compound

Product 1

HCID 21190206HCID 21190206, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 994 mg (3.0 mmol) of 4,5-dihydro-4-[4-(amino)butan-1-yl]-3H-1,4,8b-triazaacenaphthylene-3,5-dione-dihydrochloride in 50 ml of methylene chloride was added, while stirring under ice-cooling, 1.47 ml (10.5 mmol) of triethylamine. The mixture was stirred for 5 minutes, to which was added dropwise 0.66 g (3.6 mmol) of 2,2,2-trifluoroethanesulfonyl chloride. The reaction mixture was cooled with ice for one hour, which was stirred for 19 hours at room temperature. The reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate, which was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate), followed by washing with ether and dried to give 470 mg of the desired compound (38.7%, colorless solid), m.p.154.0-155.0° C. NMR(200 MHz,CDCl3 -DMSO-d6) δ: 1.58-1.90(4H,m), 3.17(2H,m), 3.84(2H,q,J=9.2 Hz), 4.19(2H,t,J=7.0 Hz), 7.45(1H,br), 7.83(1H,dd,J=8.6,7.6 Hz), 8.17(1H,d,J=7.6 Hz), 8.18(1H,d,J=8.6 Hz), 8.61(1H,s).

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringThe mixture was stirred for 5 minutes, to which
  4. temperatureThe reaction mixture was cooled with ice for one hour
  5. stirringwhich was stirred for 19 hours at room temperature
  6. washThe reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate, which
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by column chromatography (eluent: ethyl acetate)
  10. washby washing with ether
  11. customdried

Sources & evidence

ORD record
ord-8f3e20970c11489399be6284466d86e4
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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