HCID 18422180, compound → HCID 18422168, compound

HRID 649956Notes

Reaction equation

HRID 649956 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]2[N:6]=[C:7]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[C:8]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[S:11][C:9]=3[NH:10][C:4]=2[CH:3]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:32]=[CH:31][C:5]2[N:6]=[C:7]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:8]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[S:11][C:9]=3[NH:10][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 18422180HCID 18422180, compound

Product 1

HCID 18422168HCID 18422168, compoundYield 136.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

8-Fluoro-12-(4-tert-butoxycarbonylpiperazin-1-yl)-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine (1.6 g) was dissolved in trifluoroacetic acid (8 ml) and the mixture was stirred at room temperature for 3 hours. Trifluoroacetic acid was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and saturated aqueous sodium hydrogencarbonate solution was added. The mixture was stirred at room temperature for 2 hours and the ethyl acetate layer was dried over magnesium sulfate. After natural filtration, the solvent was evaporated and the residue was separated and purified by silica gel column chromatography (chloroform:methanol=4:1) to give 8-fluoro-12-(piperazin-1-yl)-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine (1.7 g), which was treated with maleic acid to give 8-fluoro-12-(piperazin-1-yl)-6H-[1]betzothieno[2,3-b][1,5]benzodiazepine.{fraction (3/2)} maleate.½ hydrate (347 mg).

Workup

  1. customTrifluoroacetic acid was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. additionsaturated aqueous sodium hydrogencarbonate solution was added
  4. stirringThe mixture was stirred at room temperature for 2 hours
  5. dry with materialthe ethyl acetate layer was dried over magnesium sulfate
  6. filtrationAfter natural filtration
  7. customthe solvent was evaporated
  8. customthe residue was separated
  9. custompurified by silica gel column chromatography (chloroform:methanol=4:1)

Sources & evidence

ORD record
ord-03b8f21e4bcd441cbbcfac6f73c97ae2
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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