Trifluoroacetic acid → HCID 56640367, compound

HRID 1186728Notes

Reaction equation

HRID 1186728 reaction equation
C(OC(NC1C=C([C:15]2[C:24]3[NH:23][C:22](=[O:25])[C:21](=[O:26])[NH:20][C:19]=3[C:18]3[CH2:27][CH2:28][CH2:29][CH2:30][C:17]=3[CH:16]=2)C=CC=1)=O)(C)(C)C.F[C:32](F)(F)[C:33](O)=O>ClCCl>[NH2:20][C:19]1[CH:18]=[C:17]([N:23]2[C:24]3[CH:15]=[CH:16][C:17]4[CH2:30][CH2:29][CH2:28][CH2:27][C:18]=4[C:19]=3[NH:20][C:21](=[O:26])[C:22]2=[O:25])[CH:16]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86689998HCID 86689998, compound

Product 1

HCID 56640367HCID 56640367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane (15 mL) solution of 5-(3-tert-butoxycarbonylaminophenyl)-1,4,7,8,9,10-hexahydrobenzo[f]quinoxaline-2,3-dione (180 mg, 0.440 mmol) was added dropwise a dichloromethane (3 mL) solution of trifluoroacetic acid (2 mL) under cooling in an ice-bath. The mixture was stirred for one hour under cooling in ice-bath. The solvent was removed by evaporation under reduced pressure. The obtained solid was washed with ethyl acetate and water, and dried to obtain 4-(3-aminophenyl)-1,4,7,8,9,10-hexahydrobenzo[f]quinoxaline-2,3-dione (93 mg). The obtained compound was dissolved in dichloromethane (5 mL) and methanol (2 mL). To the solution, a 2M hydrogen chloride/methanol solution (0.15 mL) was added. The solvent was removed by evaporation under reduced pressure. To the obtained residue was added ethyl acetate, and the mixture was stirred at room temperature for 18 hours, filtered, and dried to obtain the titled compound as a white crystal (80 mg, yield 77%).

Workup

  1. temperatureunder cooling in an ice-bath
  2. temperatureunder cooling in ice-bath
  3. customThe solvent was removed by evaporation under reduced pressure
  4. washThe obtained solid was washed with ethyl acetate and water
  5. customdried

Sources & evidence

ORD record
ord-aac32419b5e84d6e85d3d5c981ade1d6
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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